MiMeDB: Showing metabocard for 2-Oxoarginine (MMDBc0048345)

Microbial

Human

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:57:36 UTC

Update Date

2024-10-17 04:54:42 UTC

Metabolite ID

MMDBc0048345

Metabolite Identification

Common Name

2-Oxoarginine

Description

2-Oxoarginine is a guanidino compound metabolite of arginine catabolism. 2-Oxoarginine levels are increased in patients with argininemia (OMIM:207800 ). Argininemia, characterized by arginase deficiency (EC 3.5.3.1, catalyzes the last step of the urea cycle) is an autosomal recessive inborn error of metabolism caused by a defect in the final step in the urea cycle, the hydrolysis of arginine to urea and ornithine. Accumulation of arginine metabolites (such as guanidino compounds) especially 2-oxoarginine, may produce the central nervous system damage in argininemia. (PMID: 3433275 , 1588833 , 1690873 , 819629 ). 2-Oxoarginine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8641.2788642.985   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8642.6098642.216   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8643.9458642.985   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8645.2808642.216   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8646.6128642.985   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8646.6128644.525   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0    8647.9488642.216   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8639.9438642.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8638.6098642.985   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8637.2718642.216   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8638.6098644.525   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8639.9438640.676   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

Synonyms

Value	Source
2-oxo-5-Guanidino-pentanoate	ChEBI
2-oxo-5-Guanidinopentanoate	ChEBI
2-oxo-5-Guanidinovaleric acid	ChEBI
5-((Aminoiminomethyl)amino)-2-oxopentanoic acid	ChEBI
5-Guanidino-2-oxo-pentanoate	ChEBI
5-Guanidino-2-oxopentanoate	ChEBI
alpha-Keto-delta-guanidinopentanoic acid	ChEBI
alpha-Keto-delta-guanidinovaleric acid	ChEBI
2-oxo-5-Guanidino-pentanoic acid	Generator
2-oxo-5-Guanidinopentanoic acid	Generator
2-oxo-5-Guanidinovalerate	Generator
5-((Aminoiminomethyl)amino)-2-oxopentanoate	Generator
5-Guanidino-2-oxo-pentanoic acid	Generator
5-Guanidino-2-oxopentanoic acid	Generator
a-Keto-delta-guanidinopentanoate	Generator
a-Keto-delta-guanidinopentanoic acid	Generator
alpha-Keto-delta-guanidinopentanoate	Generator
Α-keto-δ-guanidinopentanoate	Generator
Α-keto-δ-guanidinopentanoic acid	Generator
a-Keto-delta-guanidinovalerate	Generator
a-Keto-delta-guanidinovaleric acid	Generator
alpha-Keto-delta-guanidinovalerate	Generator
Α-keto-δ-guanidinovalerate	Generator
Α-keto-δ-guanidinovaleric acid	Generator
a-Keto-δ-guanidinovalerate	HMDB
a-Keto-δ-guanidinovaleric acid	HMDB
a-Keto-δ-guanidinopentanoate	HMDB
a-Keto-δ-guanidinopentanoic acid	HMDB
5-(Diaminomethylideneamino)-2-oxopentanoate	HMDB
5-(Diaminomethylideneamino)-2-oxopentanoic acid	HMDB
5-Guanidino-2-oxovaleric acid	HMDB
a-Keto-D-guanidinovaleric acid	HMDB
D-Guanidino-a-oxovaleric acid	HMDB
D-Guanido-a-ketovaleric acid	HMDB
delta-Guanidino-alpha-oxovaleric acid	HMDB
delta-Guanido-alpha-ketovaleric acid	HMDB
2-Oxoarginine	ChEBI
5-[(Aminoiminomethyl)amino]-2-oxopentanoic acid	PhytoBank
δ-Guanidino-α-oxovaleric acid	PhytoBank
δ-Guanido-α-ketovaleric acid	PhytoBank

Molecular Formula

C₆H₁₁N₃O₃

Average Mass

173.1698

Monoisotopic Mass

173.080041233

IUPAC Name

5-[(diaminomethylidene)amino]-2-oxopentanoic acid

Traditional Name

5-[(diaminomethylidene)amino]-2-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

NC(=N)NCCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C6H11N3O3/c7-6(8)9-3-1-2-4(10)5(11)12/h1-3H2,(H,11,12)(H4,7,8,9)

InChI Key

ARBHXJXXVVHMET-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Guanidine
Ketone
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:28116 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.97 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.4	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	10.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	41.23 m³·mol⁻¹	ChemAxon
Polarizability	16.72 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9100000000-303513b0b209bca56206	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9710000000-95bf9765fd1fa4c2cd82	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0900000000-4c337e4db09d448ecc63	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0563-9600000000-d97800b4db5ae44aebba	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9200000000-6286bbf95e4a4716e7d4	2012-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-1900000000-05cd70e6e18e08b35be8	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0900-7900000000-aec8a82d0097632e2cc6	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-c27deb914dc894c12d6c	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2900000000-67d1c875d2da6e075630	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9800000000-1a3c6500b4d652bcaadb	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-89a2ffbc759f6a2a5922	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-fcee1bc9a64cc54c8a61	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-9100000000-884cb4184447c0cb50bd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-d71574817dabeaf6e5e0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2900000000-48efdecf4dbd7823ddff	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fu-6900000000-0ca535d235f66409d225	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9000000000-82063658464a6dc17369	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

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	455.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	303.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	40.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	227.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	280.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	288.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	431.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	808.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	626.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	162.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	506.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	174.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	44.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	326.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	813.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	60.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	222.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	630.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	576.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2-Oxoarginine_TMS_1	C[Si](C)(C)OC(=O)C(=O)CCCNC(=N)N	standard non polar	2025-10-24	1746.77
Gas Chromatography	2-Oxoarginine_TMS_2	C[Si](C)(C)OC(=CCCNC(=N)N)C(=O)O	standard non polar	2025-10-24	1722.44
Gas Chromatography	2-Oxoarginine_TMS_3	C[Si](C)(C)NC(=N)NCCCC(=O)C(=O)O	standard non polar	2025-10-24	1890.54
Gas Chromatography	2-Oxoarginine_TMS_4	C[Si](C)(C)N=C(N)NCCCC(=O)C(=O)O	standard non polar	2025-10-24	2156.72
Gas Chromatography	2-Oxoarginine_TMS_5	C[Si](C)(C)N(CCCC(=O)C(=O)O)C(=N)N	standard non polar	2025-10-24	1968.31
Gas Chromatography	2-Oxoarginine_TMS_6	C[Si](C)(C)OC(=O)C(=CCCNC(=N)N)O[Si](C)(C)C	standard non polar	2025-10-24	2055.15
Gas Chromatography	2-Oxoarginine_TMS_7	C[Si](C)(C)NC(=N)NCCCC(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2401.76
Gas Chromatography	2-Oxoarginine_TMS_8	C[Si](C)(C)OC(=O)C(=O)CCCN(C(=N)N)[Si](C)(C)C	standard non polar	2025-10-24	1650.33
Gas Chromatography	2-Oxoarginine_TMS_9	C[Si](C)(C)N=C(N)NCCCC(=O)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1558.99
Gas Chromatography	2-Oxoarginine_TMS_10	C[Si](C)(C)NC(=N)NCCC=C(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2026.87
Gas Chromatography	2-Oxoarginine_TMS_11	C[Si](C)(C)OC(=CCCN(C(=N)N)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2156.77
Gas Chromatography	2-Oxoarginine_TMS_12	C[Si](C)(C)N=C(N)NCCC=C(O[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1458.16
Gas Chromatography	2-Oxoarginine_TMS_13	C[Si](C)(C)N(C(=N)NCCCC(=O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2203.43
Gas Chromatography	2-Oxoarginine_TMS_14	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O)N[Si](C)(C)C	standard non polar	2025-10-24	1911.79
Gas Chromatography	2-Oxoarginine_TMS_15	C[Si](C)(C)NC(=N)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1873.89
Gas Chromatography	2-Oxoarginine_TMS_16	C[Si](C)(C)N=C(N)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2410.98
Gas Chromatography	2-Oxoarginine_TMS_17	C[Si](C)(C)NC(=N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2040.17
Gas Chromatography	2-Oxoarginine_TMS_18	C[Si](C)(C)OC(=O)C(=CCCN(C(=N)N)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1894.84
Gas Chromatography	2-Oxoarginine_TMS_19	C[Si](C)(C)N=C(N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1935.03
Gas Chromatography	2-Oxoarginine_TMS_20	C[Si](C)(C)OC(=O)C(=O)CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2635.65
Gas Chromatography	2-Oxoarginine_TMS_21	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	standard non polar	2025-10-24	2198.14
Gas Chromatography	2-Oxoarginine_TMS_22	C[Si](C)(C)NC(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1928.5
Gas Chromatography	2-Oxoarginine_TMS_23	C[Si](C)(C)N=C(N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1799.9
Gas Chromatography	2-Oxoarginine_TMS_24	C[Si](C)(C)OC(=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1375.21
Gas Chromatography	2-Oxoarginine_TMS_25	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O)N[Si](C)(C)C	standard non polar	2025-10-24	2292.78
Gas Chromatography	2-Oxoarginine_TMS_26	C[Si](C)(C)NC(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1667.98
Gas Chromatography	2-Oxoarginine_TMS_27	C[Si](C)(C)N=C(N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2412.08
Gas Chromatography	2-Oxoarginine_TMS_28	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2079.02
Gas Chromatography	2-Oxoarginine_TMS_29	C[Si](C)(C)N(CCCC(=O)C(=O)O)C(=N)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2192.35
Gas Chromatography	2-Oxoarginine_TMS_30	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1510.88
Gas Chromatography	2-Oxoarginine_TMS_31	C[Si](C)(C)OC(=O)C(=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2254.44
Gas Chromatography	2-Oxoarginine_TMS_32	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	standard non polar	2025-10-24	1523.18
Gas Chromatography	2-Oxoarginine_TMS_33	C[Si](C)(C)NC(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1811.31
Gas Chromatography	2-Oxoarginine_TMS_34	C[Si](C)(C)N=C(N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1357.07
Gas Chromatography	2-Oxoarginine_TMS_35	C[Si](C)(C)OC(=O)C(=O)CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1805.36
Gas Chromatography	2-Oxoarginine_TMS_36	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1919.74
Gas Chromatography	2-Oxoarginine_TMS_37	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1710.4
Gas Chromatography	2-Oxoarginine_TMS_38	C[Si](C)(C)OC(=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1902.0
Gas Chromatography	2-Oxoarginine_TMS_39	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2001.06
Gas Chromatography	2-Oxoarginine_TMS_40	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2366.87
Gas Chromatography	2-Oxoarginine_TMS_41	C[Si](C)(C)N=C(N(CCCC(=O)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2195.09
Gas Chromatography	2-Oxoarginine_TMS_42	C[Si](C)(C)OC(=O)C(=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2773.97
Gas Chromatography	2-Oxoarginine_TMS_43	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1151.1
Gas Chromatography	2-Oxoarginine_TMS_44	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2047.11
Gas Chromatography	2-Oxoarginine_TMS_45	C[Si](C)(C)N=C(N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2124.55
Gas Chromatography	2-Oxoarginine_TMS_46	C[Si](C)(C)N=C(N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2086.36
Gas Chromatography	2-Oxoarginine_TMS_47	C[Si](C)(C)N=C(N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1669.34
Gas Chromatography	2-Oxoarginine_TMS_1	C[Si](C)(C)OC(=O)C(=O)CCCNC(=N)N	standard polar	2025-10-24	2001.2
Gas Chromatography	2-Oxoarginine_TMS_2	C[Si](C)(C)OC(=CCCNC(=N)N)C(=O)O	standard polar	2025-10-24	2394.67
Gas Chromatography	2-Oxoarginine_TMS_3	C[Si](C)(C)NC(=N)NCCCC(=O)C(=O)O	standard polar	2025-10-24	2272.04
Gas Chromatography	2-Oxoarginine_TMS_4	C[Si](C)(C)N=C(N)NCCCC(=O)C(=O)O	standard polar	2025-10-24	2005.48
Gas Chromatography	2-Oxoarginine_TMS_5	C[Si](C)(C)N(CCCC(=O)C(=O)O)C(=N)N	standard polar	2025-10-24	2647.71
Gas Chromatography	2-Oxoarginine_TMS_6	C[Si](C)(C)OC(=O)C(=CCCNC(=N)N)O[Si](C)(C)C	standard polar	2025-10-24	1751.0
Gas Chromatography	2-Oxoarginine_TMS_7	C[Si](C)(C)NC(=N)NCCCC(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2376.87
Gas Chromatography	2-Oxoarginine_TMS_8	C[Si](C)(C)OC(=O)C(=O)CCCN(C(=N)N)[Si](C)(C)C	standard polar	2025-10-24	2070.1
Gas Chromatography	2-Oxoarginine_TMS_9	C[Si](C)(C)N=C(N)NCCCC(=O)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2055.43
Gas Chromatography	2-Oxoarginine_TMS_10	C[Si](C)(C)NC(=N)NCCC=C(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1858.14
Gas Chromatography	2-Oxoarginine_TMS_11	C[Si](C)(C)OC(=CCCN(C(=N)N)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2481.23
Gas Chromatography	2-Oxoarginine_TMS_12	C[Si](C)(C)N=C(N)NCCC=C(O[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1596.3
Gas Chromatography	2-Oxoarginine_TMS_13	C[Si](C)(C)N(C(=N)NCCCC(=O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1715.59
Gas Chromatography	2-Oxoarginine_TMS_14	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O)N[Si](C)(C)C	standard polar	2025-10-24	2633.85
Gas Chromatography	2-Oxoarginine_TMS_15	C[Si](C)(C)NC(=N)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1805.57
Gas Chromatography	2-Oxoarginine_TMS_16	C[Si](C)(C)N=C(N)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2071.35
Gas Chromatography	2-Oxoarginine_TMS_17	C[Si](C)(C)NC(=N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2007.13
Gas Chromatography	2-Oxoarginine_TMS_18	C[Si](C)(C)OC(=O)C(=CCCN(C(=N)N)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2472.78
Gas Chromatography	2-Oxoarginine_TMS_19	C[Si](C)(C)N=C(N)NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2281.71
Gas Chromatography	2-Oxoarginine_TMS_20	C[Si](C)(C)OC(=O)C(=O)CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2036.58
Gas Chromatography	2-Oxoarginine_TMS_21	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	standard polar	2025-10-24	1806.06
Gas Chromatography	2-Oxoarginine_TMS_22	C[Si](C)(C)NC(=N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	980.003
Gas Chromatography	2-Oxoarginine_TMS_23	C[Si](C)(C)N=C(N)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1664.54
Gas Chromatography	2-Oxoarginine_TMS_24	C[Si](C)(C)OC(=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2359.21
Gas Chromatography	2-Oxoarginine_TMS_25	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O)N[Si](C)(C)C	standard polar	2025-10-24	2302.98
Gas Chromatography	2-Oxoarginine_TMS_26	C[Si](C)(C)NC(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1701.28
Gas Chromatography	2-Oxoarginine_TMS_27	C[Si](C)(C)N=C(N)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2405.14
Gas Chromatography	2-Oxoarginine_TMS_28	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1801.58
Gas Chromatography	2-Oxoarginine_TMS_29	C[Si](C)(C)N(CCCC(=O)C(=O)O)C(=N)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1955.16
Gas Chromatography	2-Oxoarginine_TMS_30	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC(=O)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2579.63
Gas Chromatography	2-Oxoarginine_TMS_31	C[Si](C)(C)OC(=O)C(=CCCNC(=N)N([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2125.11
Gas Chromatography	2-Oxoarginine_TMS_32	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N[Si](C)(C)C	standard polar	2025-10-24	2379.02
Gas Chromatography	2-Oxoarginine_TMS_33	C[Si](C)(C)NC(=N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1285.05
Gas Chromatography	2-Oxoarginine_TMS_34	C[Si](C)(C)N=C(N)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2285.34
Gas Chromatography	2-Oxoarginine_TMS_35	C[Si](C)(C)OC(=O)C(=O)CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1885.29
Gas Chromatography	2-Oxoarginine_TMS_36	C[Si](C)(C)N=C(NCCCC(=O)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2463.03
Gas Chromatography	2-Oxoarginine_TMS_37	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2605.49
Gas Chromatography	2-Oxoarginine_TMS_38	C[Si](C)(C)OC(=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1784.76
Gas Chromatography	2-Oxoarginine_TMS_39	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2199.44
Gas Chromatography	2-Oxoarginine_TMS_40	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1688.9
Gas Chromatography	2-Oxoarginine_TMS_41	C[Si](C)(C)N=C(N(CCCC(=O)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2388.89
Gas Chromatography	2-Oxoarginine_TMS_42	C[Si](C)(C)OC(=O)C(=CCCN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2270.62
Gas Chromatography	2-Oxoarginine_TMS_43	C[Si](C)(C)N=C(NCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1548.83
Gas Chromatography	2-Oxoarginine_TMS_44	C[Si](C)(C)N=C(N[Si](C)(C)C)N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1105.88
Gas Chromatography	2-Oxoarginine_TMS_45	C[Si](C)(C)N=C(N(CCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2240.39
Gas Chromatography	2-Oxoarginine_TMS_46	C[Si](C)(C)N=C(N(CCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1956.09
Gas Chromatography	2-Oxoarginine_TMS_47	C[Si](C)(C)N=C(N(CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2051.13

Biological Properties

Cellular Locations

Extracellular
Membrane
Peroxisome

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
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
MMDBp0192057	Amiloride-sensitive amine oxidase [copper-containing]	Unknown	P19801	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

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
MMDBr0025150	D-Arginine	2-Oxoarginine	FAD-dependent catabolic D-arginine dehydrogenase DauA	Dehydrogenation	RHEA	34755880
MMDBr0025436	L-Arginine	2-Oxoarginine	L-amino acid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0026140	2-Oxoarginine	L-Arginine	Ornithine aminotransferase	Amine group addition	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cirrhosis	Slight Decrease	Association	Human Blood	HMDB	7752905
Hyperthyroidism	Slight Increase	Association	Human Blood	HMDB	9284897
Hypothyroidism	Slight Decrease	Association	Human Blood	HMDB	9284897
Uremia	Increased	Association	Human Blood	HMDB	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria/Eubacteria	Proteobacteria	5	Human
Bacteria	Proteobacteria	1	Human
Bacteria	Actinobacteria	1
Bacteria/Eubacteria	Firmicutes	23	Human feces; Human
Eukaryota/Fungi	Ascomycota	4

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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
Human Blood	Detected and Quantified	0.09		0.035	0.150	uM	Adult (>18 years old)	Both	Cirrhosis	HMDB	7752905
Human Blood	Detected and Quantified	0.160	0.009			uM	Adult (>18 years old)	Both	Hyperthyroidism	HMDB	9284897
Human Blood	Detected and Quantified	0.134	0.014			uM	Adult (>18 years old)	Both	Hypothyroidism	HMDB	9284897
Human Blood	Detected and Quantified	0.23		0.18	0.35	uM	Adult (>18 years old)	Both	Uremia	HMDB	22626821
Human Blood	Detected and Quantified	<0.200				uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Blood	Detected and Quantified	0.10		0.035	0.20	uM	Adult (>18 years old)	Both	Normal	HMDB	7752905
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.12 +/- 0.12		0	0.25	uM	Adult (>18 years old)	Both	Normal	HMDB	3433275
Human Blood	Detected and Quantified	0.145	0.007			uM	Adult (>18 years old)	Both	Normal	HMDB	9284897
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0004225

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023338

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

7030

PubChem Compound

558

PDB ID

Not Available

ChEBI ID

28116

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wiechert P, Mortelmans J, Lavinha F, Clara R, Terheggen HG, Lowenthal A: Excretion of guanidino-derivates in urine of hyperargininemic patients. J Genet Hum. 1976 Mar;24(1):61-72. [PubMed:819629 ]
Marescau B, Deshmukh DR, Kockx M, Possemiers I, Qureshi IA, Wiechert P, De Deyn PP: Guanidino compounds in serum, urine, liver, kidney, and brain of man and some ureotelic animals. Metabolism. 1992 May;41(5):526-32. doi: 10.1016/0026-0495(92)90213-t. [PubMed:1588833 ]
Marescau B, De Deyn PP, Lowenthal A, Qureshi IA, Antonozzi I, Bachmann C, Cederbaum SD, Cerone R, Chamoles N, Colombo JP, et al.: Guanidino compound analysis as a complementary diagnostic parameter for hyperargininemia: follow-up of guanidino compound levels during therapy. Pediatr Res. 1990 Mar;27(3):297-303. doi: 10.1203/00006450-199003000-00020. [PubMed:1690873 ]
Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. doi: 10.1620/tjem.153.197. [PubMed:3433275 ]
Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. doi: 10.1016/0009-8981(85)90120-2. [PubMed:3987036 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Showing metabocard for 2-Oxoarginine (MMDBc0048345)

MOL for #<Metabolite:0x00007f9acceb62e8>

3D MOL for #<Metabolite:0x00007f9acceb62e8>

3D SDF for #<Metabolite:0x00007f9acceb62e8>

3D-SDF for #<Metabolite:0x00007f9acceb62e8>

PDB for #<Metabolite:0x00007f9acceb62e8>

3D PDB for #<Metabolite:0x00007f9acceb62e8>

SMILES for #<Metabolite:0x00007f9acceb62e8>

INCHI for #<Metabolite:0x00007f9acceb62e8>

Structure for #<Metabolite:0x00007f9acceb62e8>

3D Structure for #<Metabolite:0x00007f9acceb62e8>