MiMeDB: Showing metabocard for Dihydrorhizobitoxine (MMDBc0009756)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:11:06 UTC

Update Date

2025-10-07 16:05:39 UTC

Metabolite ID

MMDBc0009756

Metabolite Identification

Common Name

Dihydrorhizobitoxine

Description

Dihydrorhizobitoxine is a secondary metabolite belonging to the class of alkaloids, specifically involved in the biosynthetic pathway leading to rhizobitoxine, which is significant in plant-microbe interactions. This compound is synthesized by certain rhizobial strains, such as Bradyrhizobium elkanii, where the enzyme dihydroxyacetone phosphate aminotransferase/dihydrorhizobitoxine synthase (RtxA) plays a crucial role in its production (PMID:21706173 ). The rtxC gene encodes dihydrorhizobitoxine desaturase, which catalyzes the conversion of dihydrorhizobitoxine into rhizobitoxine, underscoring its importance in the metabolic pathway (PMID:16516430 ). Studies have shown that mutants lacking rtxC produce dihydrorhizobitoxine but not rhizobitoxine, indicating that dihydrorhizobitoxine is an immediate precursor in this biosynthetic process (PMID:14711685 ). Furthermore, the presence of dihydrorhizobitoxine does not distinctly affect the nodulation phenotype in legumes, suggesting its role may be more nuanced in symbiotic interactions (PMID:14711685 ). Overall, dihydrorhizobitoxine serves as a key intermediate in the biosynthesis of rhizobitoxine, contributing to the complex chemistry of plant-associated bacteria.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231519032D          

 13 12  0  0  0  0            999 V2000
    1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0009756

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CO)COC=CC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O4/c8-5(3-10)4-13-2-1-6(9)7(11)12/h1-2,5-6,10H,3-4,8-9H2,(H,11,12)

> <INCHI_KEY>
SLUXPOIDTZWGCG-UHFFFAOYSA-N

> <FORMULA>
C7H14N2O4

> <MOLECULAR_WEIGHT>
190.199

> <EXACT_MASS>
190.095356939

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.826364944244393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-(2-amino-3-hydroxypropoxy)but-3-enoic acid

> <ALOGPS_LOGP>
-3.66

> <JCHEM_LOGP>
-4.653329668402768

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.052483195502681

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.169417478031922

> <JCHEM_PKA_STRONGEST_BASIC>
9.306915321635618

> <JCHEM_POLAR_SURFACE_AREA>
118.8

> <JCHEM_REFRACTIVITY>
45.552600000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-(2-amino-3-hydroxypropoxy)but-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  N   UNK     0       2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       8.978   3.644   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.312   1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.646   2.104   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.312  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
2-Amino-4-(2-amino-3-hydroxypropoxy)but-3-enoate	Generator

Molecular Formula

C₇H₁₄N₂O₄

Average Mass

190.199

Monoisotopic Mass

190.095356939

IUPAC Name

2-amino-4-(2-amino-3-hydroxypropoxy)but-3-enoic acid

Traditional Name

2-amino-4-(2-amino-3-hydroxypropoxy)but-3-enoic acid

CAS Registry Number

Not Available

SMILES

NC(CO)COC=CC(N)C(O)=O

InChI Identifier

InChI=1S/C7H14N2O4/c8-5(3-10)4-13-2-1-6(9)7(11)12/h1-2,5-6,10H,3-4,8-9H2,(H,11,12)

InChI Key

SLUXPOIDTZWGCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
1,2-aminoalcohol
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	17.9 g/L	ALOGPS
logP	-3.7	ALOGPS
logP	-4.7	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	2.17	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	118.8 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.55 m³·mol⁻¹	ChemAxon
Polarizability	18.83 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

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)	2025-10-23	578.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	498.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	46.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	234.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	323.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	305.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	472.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	1056.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	878.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	174.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	698.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	182.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	29.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	442.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	896.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	81.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	269.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	709.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	632.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Dihydrorhizobitoxine_TMS_1	C[Si](C)(C)OCC(N)COC=CC(N)C(=O)O	standard non polar	2025-10-23	1622.52
Gas Chromatography	Dihydrorhizobitoxine_TMS_2	C[Si](C)(C)OC(=O)C(N)C=COCC(N)CO	standard non polar	2025-10-23	1680.73
Gas Chromatography	Dihydrorhizobitoxine_TMS_3	C[Si](C)(C)NC(CO)COC=CC(N)C(=O)O	standard non polar	2025-10-23	2056.21
Gas Chromatography	Dihydrorhizobitoxine_TMS_4	C[Si](C)(C)NC(C=COCC(N)CO)C(=O)O	standard non polar	2025-10-23	2225.38
Gas Chromatography	Dihydrorhizobitoxine_TMS_5	C[Si](C)(C)OCC(N)COC=CC(N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1644.23
Gas Chromatography	Dihydrorhizobitoxine_TMS_6	C[Si](C)(C)NC(COC=CC(N)C(=O)O)CO[Si](C)(C)C	standard non polar	2025-10-23	2096.33
Gas Chromatography	Dihydrorhizobitoxine_TMS_7	C[Si](C)(C)NC(C=COCC(N)CO[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	2056.98
Gas Chromatography	Dihydrorhizobitoxine_TMS_8	C[Si](C)(C)NC(C=COCC(N)CO)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2413.85
Gas Chromatography	Dihydrorhizobitoxine_TMS_9	C[Si](C)(C)NC(CO)COC=CC(N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2050.58
Gas Chromatography	Dihydrorhizobitoxine_TMS_10	C[Si](C)(C)NC(CO)COC=CC(N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1924.17
Gas Chromatography	Dihydrorhizobitoxine_TMS_11	C[Si](C)(C)N(C(CO)COC=CC(N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1684.58
Gas Chromatography	Dihydrorhizobitoxine_TMS_12	C[Si](C)(C)N(C(C=COCC(N)CO)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-23	1774.58
Gas Chromatography	Dihydrorhizobitoxine_TMS_13	C[Si](C)(C)NC(COC=CC(N)C(=O)O[Si](C)(C)C)CO[Si](C)(C)C	standard non polar	2025-10-23	1830.03
Gas Chromatography	Dihydrorhizobitoxine_TMS_14	C[Si](C)(C)NC(C=COCC(N)CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1828.13
Gas Chromatography	Dihydrorhizobitoxine_TMS_15	C[Si](C)(C)NC(COC=CC(N[Si](C)(C)C)C(=O)O)CO[Si](C)(C)C	standard non polar	2025-10-23	1845.11
Gas Chromatography	Dihydrorhizobitoxine_TMS_16	C[Si](C)(C)OCC(COC=CC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2144.32
Gas Chromatography	Dihydrorhizobitoxine_TMS_17	C[Si](C)(C)OCC(N)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2147.43
Gas Chromatography	Dihydrorhizobitoxine_TMS_18	C[Si](C)(C)NC(CO)COC=CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2316.46
Gas Chromatography	Dihydrorhizobitoxine_TMS_19	C[Si](C)(C)OC(=O)C(C=COCC(N)CO)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1621.2
Gas Chromatography	Dihydrorhizobitoxine_TMS_20	C[Si](C)(C)OC(=O)C(N)C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1225.94
Gas Chromatography	Dihydrorhizobitoxine_TMS_21	C[Si](C)(C)NC(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1873.26
Gas Chromatography	Dihydrorhizobitoxine_TMS_22	C[Si](C)(C)NC(CO)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2141.38
Gas Chromatography	Dihydrorhizobitoxine_TMS_23	C[Si](C)(C)NC(COC=CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)CO[Si](C)(C)C	standard non polar	2025-10-23	2017.33
Gas Chromatography	Dihydrorhizobitoxine_TMS_24	C[Si](C)(C)OCC(COC=CC(N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2098.29
Gas Chromatography	Dihydrorhizobitoxine_TMS_25	C[Si](C)(C)OCC(N)COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1174.9
Gas Chromatography	Dihydrorhizobitoxine_TMS_26	C[Si](C)(C)NC(C=COCC(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-23	1510.47
Gas Chromatography	Dihydrorhizobitoxine_TMS_27	C[Si](C)(C)NC(COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	standard non polar	2025-10-23	1541.72
Gas Chromatography	Dihydrorhizobitoxine_TMS_28	C[Si](C)(C)NC(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1941.06
Gas Chromatography	Dihydrorhizobitoxine_TMS_29	C[Si](C)(C)NC(CO)COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1011.78
Gas Chromatography	Dihydrorhizobitoxine_TMS_30	C[Si](C)(C)N(C(CO)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1975.99
Gas Chromatography	Dihydrorhizobitoxine_TMS_31	C[Si](C)(C)NC(C=COCC(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-23	1869.64
Gas Chromatography	Dihydrorhizobitoxine_TMS_32	C[Si](C)(C)NC(COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	standard non polar	2025-10-23	1758.04
Gas Chromatography	Dihydrorhizobitoxine_TMS_33	C[Si](C)(C)OCC(COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2514.58
Gas Chromatography	Dihydrorhizobitoxine_TMS_34	C[Si](C)(C)OC(=O)C(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1558.95
Gas Chromatography	Dihydrorhizobitoxine_TMS_35	C[Si](C)(C)OCC(COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2204.45
Gas Chromatography	Dihydrorhizobitoxine_TMS_1	C[Si](C)(C)OCC(N)COC=CC(N)C(=O)O	standard polar	2025-10-23	1618.41
Gas Chromatography	Dihydrorhizobitoxine_TMS_2	C[Si](C)(C)OC(=O)C(N)C=COCC(N)CO	standard polar	2025-10-23	1852.74
Gas Chromatography	Dihydrorhizobitoxine_TMS_3	C[Si](C)(C)NC(CO)COC=CC(N)C(=O)O	standard polar	2025-10-23	1909.48
Gas Chromatography	Dihydrorhizobitoxine_TMS_4	C[Si](C)(C)NC(C=COCC(N)CO)C(=O)O	standard polar	2025-10-23	1891.08
Gas Chromatography	Dihydrorhizobitoxine_TMS_5	C[Si](C)(C)OCC(N)COC=CC(N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2000.58
Gas Chromatography	Dihydrorhizobitoxine_TMS_6	C[Si](C)(C)NC(COC=CC(N)C(=O)O)CO[Si](C)(C)C	standard polar	2025-10-23	2099.09
Gas Chromatography	Dihydrorhizobitoxine_TMS_7	C[Si](C)(C)NC(C=COCC(N)CO[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	1721.86
Gas Chromatography	Dihydrorhizobitoxine_TMS_8	C[Si](C)(C)NC(C=COCC(N)CO)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2165.42
Gas Chromatography	Dihydrorhizobitoxine_TMS_9	C[Si](C)(C)NC(CO)COC=CC(N)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2404.39
Gas Chromatography	Dihydrorhizobitoxine_TMS_10	C[Si](C)(C)NC(CO)COC=CC(N[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2024.2
Gas Chromatography	Dihydrorhizobitoxine_TMS_11	C[Si](C)(C)N(C(CO)COC=CC(N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	1881.88
Gas Chromatography	Dihydrorhizobitoxine_TMS_12	C[Si](C)(C)N(C(C=COCC(N)CO)C(=O)O)[Si](C)(C)C	standard polar	2025-10-23	2151.98
Gas Chromatography	Dihydrorhizobitoxine_TMS_13	C[Si](C)(C)NC(COC=CC(N)C(=O)O[Si](C)(C)C)CO[Si](C)(C)C	standard polar	2025-10-23	1912.61
Gas Chromatography	Dihydrorhizobitoxine_TMS_14	C[Si](C)(C)NC(C=COCC(N)CO[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2040.14
Gas Chromatography	Dihydrorhizobitoxine_TMS_15	C[Si](C)(C)NC(COC=CC(N[Si](C)(C)C)C(=O)O)CO[Si](C)(C)C	standard polar	2025-10-23	2498.55
Gas Chromatography	Dihydrorhizobitoxine_TMS_16	C[Si](C)(C)OCC(COC=CC(N)C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2307.29
Gas Chromatography	Dihydrorhizobitoxine_TMS_17	C[Si](C)(C)OCC(N)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2119.46
Gas Chromatography	Dihydrorhizobitoxine_TMS_18	C[Si](C)(C)NC(CO)COC=CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	1912.35
Gas Chromatography	Dihydrorhizobitoxine_TMS_19	C[Si](C)(C)OC(=O)C(C=COCC(N)CO)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1980.53
Gas Chromatography	Dihydrorhizobitoxine_TMS_20	C[Si](C)(C)OC(=O)C(N)C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1502.57
Gas Chromatography	Dihydrorhizobitoxine_TMS_21	C[Si](C)(C)NC(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2979.66
Gas Chromatography	Dihydrorhizobitoxine_TMS_22	C[Si](C)(C)NC(CO)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2618.15
Gas Chromatography	Dihydrorhizobitoxine_TMS_23	C[Si](C)(C)NC(COC=CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)CO[Si](C)(C)C	standard polar	2025-10-23	2174.91
Gas Chromatography	Dihydrorhizobitoxine_TMS_24	C[Si](C)(C)OCC(COC=CC(N)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1684.91
Gas Chromatography	Dihydrorhizobitoxine_TMS_25	C[Si](C)(C)OCC(N)COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2168.54
Gas Chromatography	Dihydrorhizobitoxine_TMS_26	C[Si](C)(C)NC(C=COCC(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-23	2148.91
Gas Chromatography	Dihydrorhizobitoxine_TMS_27	C[Si](C)(C)NC(COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	standard polar	2025-10-23	2226.98
Gas Chromatography	Dihydrorhizobitoxine_TMS_28	C[Si](C)(C)NC(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	2141.43
Gas Chromatography	Dihydrorhizobitoxine_TMS_29	C[Si](C)(C)NC(CO)COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2925.34
Gas Chromatography	Dihydrorhizobitoxine_TMS_30	C[Si](C)(C)N(C(CO)COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1606.52
Gas Chromatography	Dihydrorhizobitoxine_TMS_31	C[Si](C)(C)NC(C=COCC(CO[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-23	3027.7
Gas Chromatography	Dihydrorhizobitoxine_TMS_32	C[Si](C)(C)NC(COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)CO[Si](C)(C)C	standard polar	2025-10-23	1818.68
Gas Chromatography	Dihydrorhizobitoxine_TMS_33	C[Si](C)(C)OCC(COC=CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2992.31
Gas Chromatography	Dihydrorhizobitoxine_TMS_34	C[Si](C)(C)OC(=O)C(C=COCC(CO)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2531.38
Gas Chromatography	Dihydrorhizobitoxine_TMS_35	C[Si](C)(C)OCC(COC=CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2494.39

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

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
MMDBr0025618	di-mu-Sulfido-diiron(1+)	di-mu-Sulfido-diiron(2+)	Dihydrorhizobitoxine desaturase	Desaturation	RHEA	34755880

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	1		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

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

54312403

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Dihydrorhizobitoxine (MMDBc0009756)

MOL for #<Metabolite:0x00007f9ab1187e20>

3D MOL for #<Metabolite:0x00007f9ab1187e20>

3D SDF for #<Metabolite:0x00007f9ab1187e20>

3D-SDF for #<Metabolite:0x00007f9ab1187e20>

PDB for #<Metabolite:0x00007f9ab1187e20>

3D PDB for #<Metabolite:0x00007f9ab1187e20>

SMILES for #<Metabolite:0x00007f9ab1187e20>

INCHI for #<Metabolite:0x00007f9ab1187e20>

Structure for #<Metabolite:0x00007f9ab1187e20>

3D Structure for #<Metabolite:0x00007f9ab1187e20>