ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid (CFc000118167)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:41:09 UTC

Chemfont ID

CFc000118167

Molecule Identification

Common Name

3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 4',5,7,8'-tetrahydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-one. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₃H₂₂O₁₃

Average Molecular Weight

506.416

Monoisotopic Molecular Weight

506.106040768

IUPAC Name

3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2H-spiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C2C(=C1)C(O)C21COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C23H22O13/c1-33-11-4-8-9(5-12(11)35-22-17(28)15(26)16(27)18(36-22)21(31)32)23(19(8)29)6-34-13-3-7(24)2-10(25)14(13)20(23)30/h2-5,15-19,22,24-29H,6H2,1H3,(H,31,32)

InChI Key

NLXQGCXAGMBZRU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanol
Isoflavanone
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Benzenoid
Oxane
Pyran
Monosaccharide
Hydroxy acid
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0137758)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.52 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	-0.29	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.65 m³·mol⁻¹	ChemAxon
Polarizability	47.42 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0137758

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid (CFc000118167)

MOL for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

3D MOL for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

3D SDF for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

3D-SDF for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

PDB for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

3D PDB for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

SMILES for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

INCHI for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

Structure for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)

3D Structure for CFc000118167 (3,4,5-trihydroxy-6-{5,7,8'-trihydroxy-3'-methoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1',3',5'-trien-4-oneoxy}oxane-2-carboxylic acid)