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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:06:10 UTC

Update Date

2021-09-23 16:06:10 UTC

HMDB ID

HMDB0302222

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-O-Methylglucuronic acid

Description

4-o-methylglucuronic acid belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 4-o-methylglucuronic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 4-o-methylglucuronic acid can be found in cashew nut and european plum, which makes 4-o-methylglucuronic acid a potential biomarker for the consumption of these food products.

Structure

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

  Mrv1533007131513282D          

 18 17  0  0  1  0            999 V2000
    4.6184    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  2  0  0  0  0
  3  9  1  6  0  0  0
  4 10  1  6  0  0  0
  5 11  1  1  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  1  1  0  0  0  0
  6 14  1  6  0  0  0
  3 15  1  6  0  0  0
  4 16  1  6  0  0  0
  5 17  1  1  0  0  0
  6 18  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302222

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(C=O)[C@@]([H])(O)[C@]([H])(OC)[C@]([H])(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O7/c1-14-6(5(11)7(12)13)4(10)3(9)2-8/h2-6,9-11H,1H3,(H,12,13)/t3-,4+,5-,6-/m0/s1

> <INCHI_KEY>
QGGOCWIJGWDKHC-FSIIMWSLSA-N

> <FORMULA>
C7H12O7

> <MOLECULAR_WEIGHT>
208.166

> <EXACT_MASS>
208.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.955739947480517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5R)-2,4,5-trihydroxy-3-methoxy-6-oxohexanoic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-2.604959521333333

> <ALOGPS_LOGS>
-0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.317480333150304

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3671704102727165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6936650655308476

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
41.964200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5R)-2,4,5-trihydroxy-3-methoxy-6-oxohexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       8.621   0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.953   2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       4.620   4.207   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       5.954   1.897   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       8.621   1.897   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       7.287   4.207   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2    3    8                                                       
CONECT    3    2    4    9   15                                             
CONECT    4    3    6   10   16                                             
CONECT    5    6    7   11   17                                             
CONECT    6    4    5   14   18                                             
CONECT    7    5   12   13                                                  
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    1    6                                                       
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-O-Methylglucuronate	Generator
4-O-Methylglucuronic acid, (D)-isomer	MeSH
4-O-Methylglucuronic acid	MeSH

Chemical Formula

C₇H₁₂O₇

Average Molecular Weight

208.166

Monoisotopic Molecular Weight

208.058302726

IUPAC Name

(2S,3S,4R,5R)-2,4,5-trihydroxy-3-methoxy-6-oxohexanoic acid

Traditional Name

(2S,3S,4R,5R)-2,4,5-trihydroxy-3-methoxy-6-oxohexanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C=O)[C@@]([H])(O)[C@]([H])(OC)[C@]([H])(O)C(O)=O

InChI Identifier

InChI=1S/C7H12O7/c1-14-6(5(11)7(12)13)4(10)3(9)2-8/h2-6,9-11H,1H3,(H,12,13)/t3-,4+,5-,6-/m0/s1

InChI Key

QGGOCWIJGWDKHC-FSIIMWSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Monosaccharide
Fatty acid
Alpha-hydroxy acid
Hydroxy acid
Beta-hydroxy aldehyde
Alpha-hydroxyaldehyde
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302222)

Food

Nut

Cashew nut (FooDB: FOOD00011)

Fruit

Drupe

European plum (FooDB: FOOD00147)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-2.6	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	41.96 m³·mol⁻¹	ChemAxon
Polarizability	17.96 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	147.187	32859911
AllCCS	[M+H-H2O]+	143.563	32859911
AllCCS	[M+Na]+	151.522	32859911
AllCCS	[M+NH4]+	150.553	32859911
AllCCS	[M-H]-	138.708	32859911
AllCCS	[M+Na-2H]-	139.672	32859911
AllCCS	[M+HCOO]-	140.809	32859911
DeepCCS	[M+H]+	144.402	30932474
DeepCCS	[M-H]-	142.007	30932474
DeepCCS	[M-2H]-	176.43	30932474
DeepCCS	[M+Na]+	150.853	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-O-Methylglucuronic acid,5TMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	1949.2	Semi standard non polar	33892256
4-O-Methylglucuronic acid,5TMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	1877.2	Standard non polar	33892256
4-O-Methylglucuronic acid,5TMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	2021.8	Standard polar	33892256
4-O-Methylglucuronic acid,5TBDMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2948.2	Semi standard non polar	33892256
4-O-Methylglucuronic acid,5TBDMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2749.6	Standard non polar	33892256
4-O-Methylglucuronic acid,5TBDMS,isomer #1	CO[C@H]([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2574.5	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 10V, Positive-QTOF	splash10-0a4l-2930000000-71ee4fec81ba1a6110be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 20V, Positive-QTOF	splash10-0ab9-9800000000-75e2c292d54a5c62fdb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 40V, Positive-QTOF	splash10-0a4i-9300000000-3f7f5af492558066a38a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 10V, Negative-QTOF	splash10-0551-8910000000-275f12317057b65aecba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 20V, Negative-QTOF	splash10-0pc9-6900000000-b55bfd717a7ce05bb215	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 40V, Negative-QTOF	splash10-05fr-9200000000-9d980548105dad6dbe18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 10V, Positive-QTOF	splash10-06sv-3910000000-6f5202370db16f52e432	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 20V, Positive-QTOF	splash10-0kor-9400000000-5a4254f62ea39e7f7902	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 40V, Positive-QTOF	splash10-0nvm-9200000000-05b4e702a2e049e14e7a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 10V, Negative-QTOF	splash10-004i-9210000000-2e01999a65ff9e9624fa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 20V, Negative-QTOF	splash10-0pi0-9300000000-b9793f937520dec1a4e3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylglucuronic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-e3dd0ec6a9920549ef24	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003760

KNApSAcK ID

Not Available

Chemspider ID

133102

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151010

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-O-Methylglucuronic acid (HMDB0302222)

MOL for HMDB0302222 (4-O-Methylglucuronic acid)

3D MOL for HMDB0302222 (4-O-Methylglucuronic acid)

3D SDF for HMDB0302222 (4-O-Methylglucuronic acid)

3D-SDF for HMDB0302222 (4-O-Methylglucuronic acid)

PDB for HMDB0302222 (4-O-Methylglucuronic acid)

3D PDB for HMDB0302222 (4-O-Methylglucuronic acid)

SMILES for HMDB0302222 (4-O-Methylglucuronic acid)

INCHI for HMDB0302222 (4-O-Methylglucuronic acid)

Structure for HMDB0302222 (4-O-Methylglucuronic acid)

3D Structure for HMDB0302222 (4-O-Methylglucuronic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra