MiMeDB: Showing metabocard for Dihydroneopterin (MMDBc0049934)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:35 UTC

Update Date

2023-12-14 16:53:09 UTC

Metabolite ID

MMDBc0049934

Metabolite Identification

Common Name

Dihydroneopterin

Description

7,8-Dihydroneopterin, also known as dihydroneopterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are synthesized in several parts of the body, including the pineal gland. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). Within humans, 7,8-dihydroneopterin participates in a number of enzymatic reactions. In particular, 7,8-dihydroneopterin can be biosynthesized from sepiapterin; which is catalyzed by the enzyme sepiapterin reductase or carbonyl reductase [NADPH] 1. In humans, 7,8-dihydroneopterin is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase (PTPS) deficiency. 7,8-Dihydroneopterin is produced by human monocyte-derived macrophages upon stimulation with interferon-gamma. Increased amounts of 7,8-dihydroneopterin in human body fluids are found in many disorders, including viral infections and autoimmune diseases (PMID: 12804528 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₃N₅O₄

Average Mass

255.2306

Monoisotopic Mass

255.096753929

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)/t4-,6+/m1/s1

InChI Key

YQIFAMYNGGOTFB-XINAWCOVSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	521.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	381.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	50.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	255.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	313.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	297.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	449.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	919.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	739.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	165.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	506.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	175.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	31.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	373.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	764.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	67.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	287.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	755.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	633.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Dihydroneopterin_TMS_1	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	1310.22
Gas Chromatography	Dihydroneopterin_TMS_2	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard non polar	2025-10-24	1791.11
Gas Chromatography	Dihydroneopterin_TMS_3	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard non polar	2025-10-24	1259.79
Gas Chromatography	Dihydroneopterin_TMS_4	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)[NH]1	standard non polar	2025-10-24	2364.21
Gas Chromatography	Dihydroneopterin_TMS_5	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1[NH]C(N)=NC2=O	standard non polar	2025-10-24	1702.91
Gas Chromatography	Dihydroneopterin_TMS_6	C[Si](C)(C)N1C(N)=NC(=O)C2=C1NCC([C@H](O)[C@H](O)CO)=N2	standard non polar	2025-10-24	2373.15
Gas Chromatography	Dihydroneopterin_TMS_7	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1751.04
Gas Chromatography	Dihydroneopterin_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard non polar	2025-10-24	1681.51
Gas Chromatography	Dihydroneopterin_TMS_9	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)[NH]1	standard non polar	2025-10-24	1783.84
Gas Chromatography	Dihydroneopterin_TMS_10	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	2033.43
Gas Chromatography	Dihydroneopterin_TMS_11	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1)[C@H](O)CO	standard non polar	2025-10-24	1548.38
Gas Chromatography	Dihydroneopterin_TMS_12	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard non polar	2025-10-24	2104.14
Gas Chromatography	Dihydroneopterin_TMS_13	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2144.39
Gas Chromatography	Dihydroneopterin_TMS_14	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	2272.21
Gas Chromatography	Dihydroneopterin_TMS_15	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1756.87
Gas Chromatography	Dihydroneopterin_TMS_16	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2124.42
Gas Chromatography	Dihydroneopterin_TMS_17	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1283.31
Gas Chromatography	Dihydroneopterin_TMS_18	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	2166.28
Gas Chromatography	Dihydroneopterin_TMS_19	C[Si](C)(C)N(C1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)[NH]1)[Si](C)(C)C	standard non polar	2025-10-24	1927.35
Gas Chromatography	Dihydroneopterin_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1913.77
Gas Chromatography	Dihydroneopterin_TMS_21	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO)=N2	standard non polar	2025-10-24	2299.55
Gas Chromatography	Dihydroneopterin_TMS_22	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	2098.02
Gas Chromatography	Dihydroneopterin_TMS_23	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard non polar	2025-10-24	1911.17
Gas Chromatography	Dihydroneopterin_TMS_24	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2369.46
Gas Chromatography	Dihydroneopterin_TMS_25	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2063.22
Gas Chromatography	Dihydroneopterin_TMS_26	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1978.0
Gas Chromatography	Dihydroneopterin_TMS_27	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2111.23
Gas Chromatography	Dihydroneopterin_TMS_28	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1857.99
Gas Chromatography	Dihydroneopterin_TMS_29	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1520.12
Gas Chromatography	Dihydroneopterin_TMS_30	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	2566.19
Gas Chromatography	Dihydroneopterin_TMS_31	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1261.25
Gas Chromatography	Dihydroneopterin_TMS_32	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2	standard non polar	2025-10-24	1820.99
Gas Chromatography	Dihydroneopterin_TMS_33	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	1860.22
Gas Chromatography	Dihydroneopterin_TMS_34	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2087.48
Gas Chromatography	Dihydroneopterin_TMS_35	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	2201.69
Gas Chromatography	Dihydroneopterin_TMS_36	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1505.45
Gas Chromatography	Dihydroneopterin_TMS_37	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1711.08
Gas Chromatography	Dihydroneopterin_TMS_38	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	2772.84
Gas Chromatography	Dihydroneopterin_TMS_39	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2	standard non polar	2025-10-24	2166.46
Gas Chromatography	Dihydroneopterin_TMS_40	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1134.29
Gas Chromatography	Dihydroneopterin_TMS_41	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1996.31
Gas Chromatography	Dihydroneopterin_TMS_42	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1045.76
Gas Chromatography	Dihydroneopterin_TMS_43	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2	standard non polar	2025-10-24	2365.56
Gas Chromatography	Dihydroneopterin_TMS_44	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1265.42
Gas Chromatography	Dihydroneopterin_TMS_45	C[Si](C)(C)N(C1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2014.29
Gas Chromatography	Dihydroneopterin_TMS_46	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1172.47
Gas Chromatography	Dihydroneopterin_TMS_47	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1899.39
Gas Chromatography	Dihydroneopterin_TMS_48	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)[NH]1	standard non polar	2025-10-24	2055.63
Gas Chromatography	Dihydroneopterin_TMS_49	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1630.33
Gas Chromatography	Dihydroneopterin_TMS_50	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	911.38
Gas Chromatography	Dihydroneopterin_TMS_51	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1070.98
Gas Chromatography	Dihydroneopterin_TMS_52	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	170.592
Gas Chromatography	Dihydroneopterin_TMS_53	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2	standard non polar	2025-10-24	1614.47
Gas Chromatography	Dihydroneopterin_TMS_54	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	2489.6
Gas Chromatography	Dihydroneopterin_TMS_55	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1825.25
Gas Chromatography	Dihydroneopterin_TMS_56	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1861.51
Gas Chromatography	Dihydroneopterin_TMS_57	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2	standard non polar	2025-10-24	2945.97
Gas Chromatography	Dihydroneopterin_TMS_58	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	2853.58
Gas Chromatography	Dihydroneopterin_TMS_59	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	2316.01
Gas Chromatography	Dihydroneopterin_TMS_60	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1)[C@H](O)CO	standard non polar	2025-10-24	1519.22
Gas Chromatography	Dihydroneopterin_TMS_61	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1946.21
Gas Chromatography	Dihydroneopterin_TMS_62	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1764.93
Gas Chromatography	Dihydroneopterin_TMS_63	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1342.01
Gas Chromatography	Dihydroneopterin_TMS_64	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2	standard non polar	2025-10-24	1751.25
Gas Chromatography	Dihydroneopterin_TMS_65	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1220.86
Gas Chromatography	Dihydroneopterin_TMS_66	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1558.89
Gas Chromatography	Dihydroneopterin_TMS_67	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1621.91
Gas Chromatography	Dihydroneopterin_TMS_68	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1664.65
Gas Chromatography	Dihydroneopterin_TMS_69	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	822.736
Gas Chromatography	Dihydroneopterin_TMS_70	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1543.87
Gas Chromatography	Dihydroneopterin_TMS_71	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1301.84
Gas Chromatography	Dihydroneopterin_TMS_72	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	2268.73
Gas Chromatography	Dihydroneopterin_TMS_73	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	3117.15
Gas Chromatography	Dihydroneopterin_TMS_74	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	2391.35
Gas Chromatography	Dihydroneopterin_TMS_75	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2	standard non polar	2025-10-24	2072.46
Gas Chromatography	Dihydroneopterin_TMS_76	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard non polar	2025-10-24	1028.31
Gas Chromatography	Dihydroneopterin_TMS_77	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1956.07
Gas Chromatography	Dihydroneopterin_TMS_78	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	1649.14
Gas Chromatography	Dihydroneopterin_TMS_79	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	2224.39
Gas Chromatography	Dihydroneopterin_TMS_80	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	2026.33
Gas Chromatography	Dihydroneopterin_TMS_81	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	2633.96
Gas Chromatography	Dihydroneopterin_TMS_82	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	882.833
Gas Chromatography	Dihydroneopterin_TMS_83	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard non polar	2025-10-24	2049.64
Gas Chromatography	Dihydroneopterin_TMS_84	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	2849.95
Gas Chromatography	Dihydroneopterin_TMS_85	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	1592.1
Gas Chromatography	Dihydroneopterin_TMS_86	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	1784.16
Gas Chromatography	Dihydroneopterin_TMS_87	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1517.41
Gas Chromatography	Dihydroneopterin_TMS_88	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	2949.1
Gas Chromatography	Dihydroneopterin_TMS_89	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1696.06
Gas Chromatography	Dihydroneopterin_TMS_90	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard non polar	2025-10-24	2402.11
Gas Chromatography	Dihydroneopterin_TMS_91	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard non polar	2025-10-24	2135.63
Gas Chromatography	Dihydroneopterin_TMS_92	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard non polar	2025-10-24	3269.65
Gas Chromatography	Dihydroneopterin_TMS_93	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1664.77
Gas Chromatography	Dihydroneopterin_TMS_94	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	313.079
Gas Chromatography	Dihydroneopterin_TMS_95	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard non polar	2025-10-24	1847.52
Gas Chromatography	Dihydroneopterin_TMS_1	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	1964.11
Gas Chromatography	Dihydroneopterin_TMS_2	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard polar	2025-10-24	1923.28
Gas Chromatography	Dihydroneopterin_TMS_3	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard polar	2025-10-24	2541.37
Gas Chromatography	Dihydroneopterin_TMS_4	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)[NH]1	standard polar	2025-10-24	1866.95
Gas Chromatography	Dihydroneopterin_TMS_5	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1[NH]C(N)=NC2=O	standard polar	2025-10-24	1896.13
Gas Chromatography	Dihydroneopterin_TMS_6	C[Si](C)(C)N1C(N)=NC(=O)C2=C1NCC([C@H](O)[C@H](O)CO)=N2	standard polar	2025-10-24	2133.34
Gas Chromatography	Dihydroneopterin_TMS_7	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2543.19
Gas Chromatography	Dihydroneopterin_TMS_8	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard polar	2025-10-24	2681.12
Gas Chromatography	Dihydroneopterin_TMS_9	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)[NH]1	standard polar	2025-10-24	2093.28
Gas Chromatography	Dihydroneopterin_TMS_10	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	2458.63
Gas Chromatography	Dihydroneopterin_TMS_11	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1)[C@H](O)CO	standard polar	2025-10-24	2245.52
Gas Chromatography	Dihydroneopterin_TMS_12	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard polar	2025-10-24	2047.52
Gas Chromatography	Dihydroneopterin_TMS_13	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	1773.46
Gas Chromatography	Dihydroneopterin_TMS_14	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2457.16
Gas Chromatography	Dihydroneopterin_TMS_15	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	1592.01
Gas Chromatography	Dihydroneopterin_TMS_16	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	1828.45
Gas Chromatography	Dihydroneopterin_TMS_17	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2406.44
Gas Chromatography	Dihydroneopterin_TMS_18	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	1647.43
Gas Chromatography	Dihydroneopterin_TMS_19	C[Si](C)(C)N(C1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)[NH]1)[Si](C)(C)C	standard polar	2025-10-24	1927.3
Gas Chromatography	Dihydroneopterin_TMS_20	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1693.13
Gas Chromatography	Dihydroneopterin_TMS_21	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO)=N2	standard polar	2025-10-24	2396.18
Gas Chromatography	Dihydroneopterin_TMS_22	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1628.46
Gas Chromatography	Dihydroneopterin_TMS_23	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N)=NC2=O	standard polar	2025-10-24	1687.67
Gas Chromatography	Dihydroneopterin_TMS_24	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	1974.35
Gas Chromatography	Dihydroneopterin_TMS_25	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1596.8
Gas Chromatography	Dihydroneopterin_TMS_26	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2586.5
Gas Chromatography	Dihydroneopterin_TMS_27	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	1774.18
Gas Chromatography	Dihydroneopterin_TMS_28	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2805.81
Gas Chromatography	Dihydroneopterin_TMS_29	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2539.52
Gas Chromatography	Dihydroneopterin_TMS_30	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	1662.47
Gas Chromatography	Dihydroneopterin_TMS_31	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	675.729
Gas Chromatography	Dihydroneopterin_TMS_32	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2	standard polar	2025-10-24	2401.49
Gas Chromatography	Dihydroneopterin_TMS_33	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	2271.52
Gas Chromatography	Dihydroneopterin_TMS_34	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	2378.86
Gas Chromatography	Dihydroneopterin_TMS_35	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1439.71
Gas Chromatography	Dihydroneopterin_TMS_36	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	1827.34
Gas Chromatography	Dihydroneopterin_TMS_37	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1853.69
Gas Chromatography	Dihydroneopterin_TMS_38	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2472.37
Gas Chromatography	Dihydroneopterin_TMS_39	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2	standard polar	2025-10-24	1550.23
Gas Chromatography	Dihydroneopterin_TMS_40	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1492.36
Gas Chromatography	Dihydroneopterin_TMS_41	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2208.22
Gas Chromatography	Dihydroneopterin_TMS_42	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1947.36
Gas Chromatography	Dihydroneopterin_TMS_43	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2	standard polar	2025-10-24	1689.47
Gas Chromatography	Dihydroneopterin_TMS_44	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2003.47
Gas Chromatography	Dihydroneopterin_TMS_45	C[Si](C)(C)N(C1=NC(=O)C2=C(NCC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2084.45
Gas Chromatography	Dihydroneopterin_TMS_46	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2417.73
Gas Chromatography	Dihydroneopterin_TMS_47	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2512.64
Gas Chromatography	Dihydroneopterin_TMS_48	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)[NH]1	standard polar	2025-10-24	2000.84
Gas Chromatography	Dihydroneopterin_TMS_49	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2334.18
Gas Chromatography	Dihydroneopterin_TMS_50	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	1336.8
Gas Chromatography	Dihydroneopterin_TMS_51	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1710.29
Gas Chromatography	Dihydroneopterin_TMS_52	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1981.8
Gas Chromatography	Dihydroneopterin_TMS_53	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2	standard polar	2025-10-24	1747.87
Gas Chromatography	Dihydroneopterin_TMS_54	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1987.28
Gas Chromatography	Dihydroneopterin_TMS_55	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2149.18
Gas Chromatography	Dihydroneopterin_TMS_56	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2233.53
Gas Chromatography	Dihydroneopterin_TMS_57	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2	standard polar	2025-10-24	2099.28
Gas Chromatography	Dihydroneopterin_TMS_58	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1746.46
Gas Chromatography	Dihydroneopterin_TMS_59	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	2819.2
Gas Chromatography	Dihydroneopterin_TMS_60	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1)[C@H](O)CO	standard polar	2025-10-24	2156.17
Gas Chromatography	Dihydroneopterin_TMS_61	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1851.73
Gas Chromatography	Dihydroneopterin_TMS_62	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1606.55
Gas Chromatography	Dihydroneopterin_TMS_63	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2125.07
Gas Chromatography	Dihydroneopterin_TMS_64	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2	standard polar	2025-10-24	1914.15
Gas Chromatography	Dihydroneopterin_TMS_65	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	1885.58
Gas Chromatography	Dihydroneopterin_TMS_66	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2202.71
Gas Chromatography	Dihydroneopterin_TMS_67	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2228.17
Gas Chromatography	Dihydroneopterin_TMS_68	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2503.65
Gas Chromatography	Dihydroneopterin_TMS_69	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1666.0
Gas Chromatography	Dihydroneopterin_TMS_70	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2255.87
Gas Chromatography	Dihydroneopterin_TMS_71	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2593.84
Gas Chromatography	Dihydroneopterin_TMS_72	C[Si](C)(C)N1CC([C@H](O)[C@H](O)CO)=NC2=C1N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1748.94
Gas Chromatography	Dihydroneopterin_TMS_73	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)[NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2060.78
Gas Chromatography	Dihydroneopterin_TMS_74	C[Si](C)(C)NC1=NC(=O)C2=C(NCC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2781.08
Gas Chromatography	Dihydroneopterin_TMS_75	C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2	standard polar	2025-10-24	1630.44
Gas Chromatography	Dihydroneopterin_TMS_76	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N)=NC2=O	standard polar	2025-10-24	2923.56
Gas Chromatography	Dihydroneopterin_TMS_77	C[Si](C)(C)O[C@@H](C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	1748.25
Gas Chromatography	Dihydroneopterin_TMS_78	C[Si](C)(C)O[C@@H](C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2562.01
Gas Chromatography	Dihydroneopterin_TMS_79	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1576.2
Gas Chromatography	Dihydroneopterin_TMS_80	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2238.95
Gas Chromatography	Dihydroneopterin_TMS_81	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	1985.06
Gas Chromatography	Dihydroneopterin_TMS_82	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	2821.75
Gas Chromatography	Dihydroneopterin_TMS_83	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)CO	standard polar	2025-10-24	3474.32
Gas Chromatography	Dihydroneopterin_TMS_84	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1980.09
Gas Chromatography	Dihydroneopterin_TMS_85	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2081.11
Gas Chromatography	Dihydroneopterin_TMS_86	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1903.56
Gas Chromatography	Dihydroneopterin_TMS_87	C[Si](C)(C)O[C@H](CO)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1129.87
Gas Chromatography	Dihydroneopterin_TMS_88	C[Si](C)(C)OC[C@@H](O)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2789.67
Gas Chromatography	Dihydroneopterin_TMS_89	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(NC1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	2622.75
Gas Chromatography	Dihydroneopterin_TMS_90	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C([NH]C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)N([Si](C)(C)C)C1	standard polar	2025-10-24	2481.11
Gas Chromatography	Dihydroneopterin_TMS_91	C[Si](C)(C)NC1=NC(=O)C2=C(N([Si](C)(C)C)CC([C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=N2)N1[Si](C)(C)C	standard polar	2025-10-24	1257.23
Gas Chromatography	Dihydroneopterin_TMS_92	C[Si](C)(C)O[C@@H](C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@@H](CO)O[Si](C)(C)C	standard polar	2025-10-24	2863.98
Gas Chromatography	Dihydroneopterin_TMS_93	C[Si](C)(C)OC[C@@H](O)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	1019.91
Gas Chromatography	Dihydroneopterin_TMS_94	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	770.643
Gas Chromatography	Dihydroneopterin_TMS_95	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=NC2=C(N([Si](C)(C)C)C1)N([Si](C)(C)C)C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O	standard polar	2025-10-24	3059.33

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191763	Alkaline phosphatase, placental type	Unknown	P05187	Homo sapiens
MMDBp0191766	Intestinal-type alkaline phosphatase	Unknown	P09923	Homo sapiens
MMDBp0191769	Alkaline phosphatase, tissue-nonspecific isozyme	Unknown	P05186	Homo sapiens
MMDBp0191772	Alkaline phosphatase, placental-like	Unknown	P10696	Homo sapiens
MMDBp0192101	6-pyruvoyl tetrahydrobiopterin synthase	Unknown	Q03393	Homo sapiens
MMDBp0194160	RuvB-like 2	Enzyme	Q9Y230	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Folate Biosynthesis
GTP Degradation and Molybdenum Cofactor Biosynthesis

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	165	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	280	Pig ; Human feces; Human ; Cattle ; Human pleural fluid plaque; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	98	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human urine; Human gastric fluid; Human saliva; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Firmicutes	2	Pig ; Human feces; Human ; Cattle ; Human pleural fluid plaque; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Chlamydiae	3	Human
Bacteria	Proteobacteria	1	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	nah	1
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Fuchs D, Reibnegger G, Werner ER, Wachter H: Increased 7,8-dihydroneopterin and reduced methyl-group metabolism in HIV-1 infection. Lancet. 1990 May 12;335(8698):1167. doi: 10.1016/0140-6736(90)91176-b. [PubMed:1971904 ]
Gieseg SP, Reibnegger G, Wachter H, Esterbauer H: 7,8 Dihydroneopterin inhibits low density lipoprotein oxidation in vitro. Evidence that this macrophage secreted pteridine is an anti-oxidant. Free Radic Res. 1995 Aug;23(2):123-36. doi: 10.3109/10715769509064027. [PubMed:7581810 ]
Baier-Bitterlich G, Baier G, Fuchs D, Bock G, Hausen A, Utermann G, Pavelka M, Wachter H: Role of 7,8-dihydroneopterin in T-cell apoptosis and HTLV-1 transcription in vitro. Oncogene. 1996 Nov 21;13(10):2281-5. [PubMed:8950996 ]
Baier-Bitterlich G, Fuchs D, Zangerle R, Baeuerle PA, Werner ER, Fresser F, Uberall F, Baier G, Wachter H: trans-Activation of the HIV type 1 promoter by 7,8-dihydroneopterin in vitro. AIDS Res Hum Retroviruses. 1997 Jan 20;13(2):173-8. doi: 10.1089/aid.1997.13.173. [PubMed:9007202 ]
Baier-Bitterlich G, Fuchs D, Wachter H: 7,8-Dihydroneopterin upregulates interferon-gamma promoter in T cells. Immunobiology. 1996;196(4):350-5. doi: 10.1016/s0171-2985(96)80057-x. [PubMed:9061375 ]
Wirleitner B, Baier-Bitterlich G, Bock G, Widner B, Fuchs D: 7,8-Dihydroneopterin-induced apoptosis in Jurkat T lymphocytes: a comparison with anti-Fas- and hydrogen peroxide-mediated cell death. Biochem Pharmacol. 1998 Nov 1;56(9):1181-7. doi: 10.1016/s0006-2952(98)00168-3. [PubMed:9802329 ]
Pagel H, Fandrey J, Schobersberger W, Fuchs D, Jelkmann W: Effects of neopterin and 7,8-dihydroneopterin on hypoxia-induced renal erythropoietin production. Eur J Haematol. 1999 May;62(5):341-5. doi: 10.1111/j.1600-0609.1999.tb01913.x. [PubMed:10359064 ]
Speth C, Stockl G, Fuchs D, Wirleitner B, Widner B, Wurzner R, Mohsenipour I, Lass-Florl C, Dierich MP: Inflammation marker 7,8-dihydroneopterin induces apoptosis of neurons and glial cells: a potential contribution to neurodegenerative processes. Immunobiology. 2000 Nov;202(5):460-76. doi: 10.1016/S0171-2985(00)80104-7. [PubMed:11205375 ]
Gieseg SP, Maghzal G, Glubb D: Protection of erythrocytes by the macrophage synthesized antioxidant 7,8 dihydroneopterin. Free Radic Res. 2001 Feb;34(2):123-36. doi: 10.1080/10715760100300121. [PubMed:11264890 ]
Wirleitner B, Czaputa R, Oettl K, Bock G, Widner B, Reibnegger G, Baier G, Fuchs D, Baier-Bitterlich G: Induction of apoptosis by 7,8-dihydroneopterin: involvement of radical formation. Immunobiology. 2001 May;203(4):629-41. doi: 10.1016/s0171-2985(01)80012-7. [PubMed:11402497 ]
Gieseg SP, Whybrow J, Glubb D, Rait C: Protection of U937 cells from free radical damage by the macrophage synthesized antioxidant 7,8-dihydroneopterin. Free Radic Res. 2001 Sep;35(3):311-8. doi: 10.1080/10715760100300841. [PubMed:11697129 ]
Enzinger C, Wirleitner B, Lutz C, Bock G, Tomaselli B, Baier G, Fuchs D, Baier-Bitterlich G: 7,8-Dihydroneopterin induces apoptosis of Jurkat T-lymphocytes via a Bcl-2-sensitive pathway. Eur J Cell Biol. 2002 Apr;81(4):197-202. doi: 10.1078/0171-9335-00236. [PubMed:12018387 ]
Horejsi R, Jung C, Moller R, Tafeit E, Reibnegger G: Generation of carbon monoxide and iron from hemeproteins in the presence of 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Jun 6;1571(2):124-30. doi: 10.1016/s0304-4165(02)00206-4. [PubMed:12049792 ]
Herpfer I, Greilberger J, Ledinski G, Widner B, Fuchs D, Jurgens G: Neopterin and 7,8-dihydroneopterin interfere with low density lipoprotein oxidation mediated by peroxynitrite and/or copper. Free Radic Res. 2002 May;36(5):509-20. doi: 10.1080/10715760290025898. [PubMed:12150539 ]
Duggan S, Rait C, Platt A, Gieseg S: Protein and thiol oxidation in cells exposed to peroxyl radicals is inhibited by the macrophage synthesised pterin 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Aug 19;1591(1-3):139-145. doi: 10.1016/s0167-4889(02)00272-0. [PubMed:12183064 ]
Gieseg SP, Cato S: Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin. Redox Rep. 2003;8(2):113-5. doi: 10.1179/135100003125001396. [PubMed:12804014 ]
Wirleitner B, Obermoser G, Bock G, Neurauter G, Schennach H, Sepp N, Fuchs D: Induction of apoptosis in human blood T cells by 7,8-dihydroneopterin: the difference between healthy controls and patients with systemic lupus erythematosus. Clin Immunol. 2003 Jun;107(3):152-9. doi: 10.1016/s1521-6616(03)00040-8. [PubMed:12804528 ]
Greilberger J, Oettl K, Cvirn G, Reibnegger G, Jurgens G: Modulation of LDL oxidation by 7,8-dihydroneopterin. Free Radic Res. 2004 Jan;38(1):9-17. doi: 10.1080/10715760310001623322. [PubMed:15061649 ]
Baird SK, Reid L, Hampton MB, Gieseg SP: OxLDL induced cell death is inhibited by the macrophage synthesised pterin, 7,8-dihydroneopterin, in U937 cells but not THP-1 cells. Biochim Biophys Acta. 2005 Sep 30;1745(3):361-9. doi: 10.1016/j.bbamcr.2005.07.001. [PubMed:16084608 ]

Showing metabocard for Dihydroneopterin (MMDBc0049934)

MOL for #<Metabolite:0x00007f2e3afdb9b0>

3D MOL for #<Metabolite:0x00007f2e3afdb9b0>

3D SDF for #<Metabolite:0x00007f2e3afdb9b0>

3D-SDF for #<Metabolite:0x00007f2e3afdb9b0>

PDB for #<Metabolite:0x00007f2e3afdb9b0>

3D PDB for #<Metabolite:0x00007f2e3afdb9b0>

SMILES for #<Metabolite:0x00007f2e3afdb9b0>

INCHI for #<Metabolite:0x00007f2e3afdb9b0>

Structure for #<Metabolite:0x00007f2e3afdb9b0>

3D Structure for #<Metabolite:0x00007f2e3afdb9b0>