MiMeDB: Showing metabocard for D-Glucuronate 1-phosphate (MMDBc0031602)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:00 UTC

Update Date

2024-04-30 19:51:10 UTC

Metabolite ID

MMDBc0031602

Metabolite Identification

Common Name

D-Glucuronate 1-phosphate

Description

D-glucuronate 1-phosphate is a member of the chemical class known as Glucuronides. These are compounds comprising the glucuronic acid linked to another substance via a glycosidic bond.

Structure

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


  Mrv1652307162000082D          

 17 17  0  0  0  0            999 V2000
10000.4111 9999.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.409810000.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1258 9999.2640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.4107 9998.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9815 9997.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5524 9998.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9811 9999.6758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2667 9999.2633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.2667 9998.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9811 9998.0259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6956 9998.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6956 9999.2633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5524 9999.6759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.552410000.5008    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.377210000.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.834110000.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.964610001.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
 12  1  1  6  0  0  0
 11  4  1  1  0  0  0
 10  5  1  6  0  0  0
  9  6  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 13  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031602

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11O10P/c7-1-2(8)4(5(10)11)15-6(3(1)9)16-17(12,13)14/h1-4,6-9H,(H,10,11)(H2,12,13,14)/t1-,2-,3+,4-,6+/m0/s1

> <INCHI_KEY>
AIQDYKMWENWVQJ-QIUUJYRFSA-N

> <FORMULA>
C6H11O10P

> <MOLECULAR_WEIGHT>
274.1193

> <EXACT_MASS>
274.008983084

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.66396260938168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-1.69

> <JCHEM_LOGP>
-2.7358307113333336

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.306138395499081

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.149939048571916

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6871396416133315

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
46.6637

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-phospho-α-D-glucuronic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-20         0                                  
HETATM    1  C   UNK     0    8667.4348666.063   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8667.4328667.603   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.7688665.293   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.4338662.981   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8664.7668661.441   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.0988662.981   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8664.7658666.061   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8663.4318665.292   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.4318663.751   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.7658662.982   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.0988663.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.0988665.292   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8662.0988666.062   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0    8662.0988667.602   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0    8663.6378667.599   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8660.7578668.376   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    8662.8678668.933   0.000  0.00  0.00           O+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6    9                                                            
CONECT    7    8   12                                                       
CONECT    8    9    7   13                                                  
CONECT    9    8   10    6                                                  
CONECT   10    9   11    5                                                  
CONECT   11   10   12    4                                                  
CONECT   12   11    7    1                                                  
CONECT   13   14    8                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0003976
HETATM    1  O1  UNL     1      -3.280   1.998   0.783  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.126   1.928   0.309  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.314   3.053   0.373  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.582   0.703  -0.320  1.00  0.00           C  
HETATM    5  O3  UNL     1      -0.303   0.886  -0.757  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.655   0.122  -0.157  1.00  0.00           C  
HETATM    7  O4  UNL     1       1.837   0.313  -0.912  1.00  0.00           O  
HETATM    8  P1  UNL     1       3.076   0.954   0.012  1.00  0.00           P  
HETATM    9  O5  UNL     1       2.594   1.738   1.185  1.00  0.00           O  
HETATM   10  O6  UNL     1       3.985   1.978  -1.000  1.00  0.00           O  
HETATM   11  O7  UNL     1       4.140  -0.284   0.506  1.00  0.00           O  
HETATM   12  C4  UNL     1       0.374  -1.368  -0.220  1.00  0.00           C  
HETATM   13  O8  UNL     1       0.904  -1.945  -1.379  1.00  0.00           O  
HETATM   14  C5  UNL     1      -1.105  -1.668  -0.212  1.00  0.00           C  
HETATM   15  O9  UNL     1      -1.420  -2.871   0.376  1.00  0.00           O  
HETATM   16  C6  UNL     1      -1.769  -0.516   0.552  1.00  0.00           C  
HETATM   17  O10 UNL     1      -3.132  -0.789   0.630  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.585   3.934  -0.050  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.222   0.521  -1.234  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.802   0.438   0.889  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.505   2.823  -1.167  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.658  -1.134   0.675  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.798  -1.880   0.691  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.691  -2.478  -1.111  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.493  -1.595  -1.268  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.959  -3.396  -0.296  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.333  -0.410   1.543  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.397  -1.053   1.557  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   16   19
CONECT    5    6
CONECT    6    7   12   20
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   21
CONECT   11   22
CONECT   12   13   14   23
CONECT   13   24
CONECT   14   15   16   25
CONECT   15   26
CONECT   16   17   27
CONECT   17   28
END

Synonyms

Value	Source
1-Phospho-alpha-D-glucuronate	ChEBI, KEGG
1-Phospho-a-D-glucuronate	Generator
1-Phospho-a-D-glucuronic acid	Generator
1-Phospho-alpha-D-glucuronic acid	Generator
1-Phospho-α-D-glucuronate	Generator
1-Phospho-α-D-glucuronic acid	Generator
D-Glucuronic acid 1-phosphoric acid	Generator
alpha-D-Glucopyranuronic acid 1-phosphate	HMDB
alpha-D-Glucuronic acid 1-phosphate	HMDB
α-D-Glucopyranuronic acid 1-phosphate	HMDB
α-D-Glucuronic acid 1-phosphate	HMDB
D-Glucuronate 1-phosphate	HMDB

Molecular Formula

C₆H₁₁O₁₀P

Average Mass

274.1193

Monoisotopic Mass

274.008983084

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid

Traditional Name

1-phospho-α-D-glucuronic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@@H](OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C6H11O10P/c7-1-2(8)4(5(10)11)15-6(3(1)9)16-17(12,13)14/h1-4,6-9H,(H,10,11)(H2,12,13,14)/t1-,2-,3+,4-,6+/m0/s1

InChI Key

AIQDYKMWENWVQJ-QIUUJYRFSA-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
Hexose monosaccharide
Monosaccharide phosphate
Beta-hydroxy acid
Monoalkyl phosphate
Hydroxy acid
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyran
Alkyl phosphate
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Polyol
Carboxylic acid
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucuronic acids (CHEBI:16787 )
D-glucuronic acid 1-phosphate (CHEBI:16787 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	33.8 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.15	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.66 m³·mol⁻¹	ChemAxon
Polarizability	20.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0003976

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023278

KNApSAcK ID

Not Available

Chemspider ID

388541

KEGG Compound ID

C05385

BioCyc ID

CPD-510

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439432

PDB ID

Not Available

ChEBI ID

16787

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Puhakainen E, Hanninen O: Pyrophosphatase and glucuronosyltransferase in microsomal UDPglucuronic-acid metabolism in the rat liver. Eur J Biochem. 1976 Jan 2;61(1):165-9. doi: 10.1111/j.1432-1033.1976.tb10007.x. [PubMed:1276 ]
Watkins JB 3rd, Engles DR, Beck LV: Effect of volatile anesthetics on the hepatic UDP-glucuronic acid pathway in mice. Biochem Pharmacol. 1990 Aug 15;40(4):731-5. doi: 10.1016/0006-2952(90)90308-8. [PubMed:2167093 ]
Linster CL, Van Schaftingen E: Glucuronate, the precursor of vitamin C, is directly formed from UDP-glucuronate in liver. FEBS J. 2006 Apr;273(7):1516-27. doi: 10.1111/j.1742-4658.2006.05172.x. [PubMed:16689937 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for D-Glucuronate 1-phosphate (MMDBc0031602)

MOL for #<Metabolite:0x00007f9238aa6730>

3D MOL for #<Metabolite:0x00007f9238aa6730>

3D SDF for #<Metabolite:0x00007f9238aa6730>

3D-SDF for #<Metabolite:0x00007f9238aa6730>

PDB for #<Metabolite:0x00007f9238aa6730>

3D PDB for #<Metabolite:0x00007f9238aa6730>

SMILES for #<Metabolite:0x00007f9238aa6730>

INCHI for #<Metabolite:0x00007f9238aa6730>

Structure for #<Metabolite:0x00007f9238aa6730>

3D Structure for #<Metabolite:0x00007f9238aa6730>