ChemFOnt: Showing chemical card for Mycophenolic acid O-acyl-glucuronide (CFc000040931)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:42:40 UTC

Chemfont ID

CFc000040931

Molecule Identification

Common Name

Mycophenolic acid O-acyl-glucuronide

Definition

897

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
AcMPAG	ChEBI
Mycophenolic acid acyl glucuronide	ChEBI
Mycophenolic acid acyl-glucuronide	ChEBI
Mycophenolic acid-O-acyl-beta-D-glucopyranuronoside	ChEBI
Mycophenolate acyl glucuronide	Generator
Mycophenolate acyl-glucuronide	Generator
Mycophenolate-O-acyl-b-D-glucopyranuronoside	Generator
Mycophenolate-O-acyl-beta-D-glucopyranuronoside	Generator
Mycophenolate-O-acyl-β-D-glucopyranuronoside	Generator
Mycophenolic acid-O-acyl-b-D-glucopyranuronoside	Generator
Mycophenolic acid-O-acyl-β-D-glucopyranuronoside	Generator
Mycophenolate O-acyl-glucuronide	Generator

Chemical Formula

C₂₃H₂₈O₁₂

Average Molecular Weight

496.4612

Monoisotopic Molecular Weight

496.15807636

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1

InChI Key

QBMSTEZXAMABFF-UEARNRKISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Isobenzofuranone
Phthalide
Isocoumaran
Tricarboxylic acid or derivatives
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Benzenoid
Monosaccharide
Pyran
Oxane
Vinylogous acid
Secondary alcohol
Lactone
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic ester (CHEBI:64689 )
phenols (CHEBI:64689 )
gamma-lactone (CHEBI:64689 )
beta-D-glucosiduronic acid (CHEBI:64689 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060491)

Organ

Liver (HMDB: HMDB0060491)
Kidney (HMDB: HMDB0060491)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060491)

Cellular substructure

Cytoplasm (HMDB: HMDB0060491)

Source

Endogenous

Endogenous (HMDB: HMDB0060491)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mycophenolic Acid Metabolism Pathway (PathBank: SMP0000652)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	0.91	ALOGPS
logP	1.58	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.53 m³·mol⁻¹	ChemAxon
Polarizability	49.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0060491

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

C20383

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10028772

PDB ID

Not Available

ChEBI ID

64689

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Mycophenolic acid O-acyl-glucuronide (CFc000040931)

MOL for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

3D MOL for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

3D SDF for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

3D-SDF for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

PDB for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

3D PDB for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

SMILES for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

INCHI for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

Structure for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)

3D Structure for CFc000040931 (Mycophenolic acid O-acyl-glucuronide)