ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid (CFc000127485)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:55:23 UTC

Chemfont ID

CFc000127485

Molecule Identification

Common Name

Definition

3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Based on a literature review very few articles have been published on 3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylate	Generator
3,4,5-Trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₇H₂₆O₁₃

Average Molecular Weight

558.492

Monoisotopic Molecular Weight

558.137340897

IUPAC Name

3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)CO)C(O)=CC2=C1C1=C(C3=C(O1)C=C(OC1OC(C(O)C(O)C1O)C(O)=O)C=C3)C(=O)O2

InChI Identifier

InChI=1S/C27H26O13/c1-10(9-28)3-5-12-14(29)8-16-18(22(12)36-2)23-17(26(35)39-16)13-6-4-11(7-15(13)38-23)37-27-21(32)19(30)20(31)24(40-27)25(33)34/h3-4,6-8,19-21,24,27-32H,5,9H2,1-2H3,(H,33,34)

InChI Key

UKQQKEXEGOBCAL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Phenolic glycoside
Angular furanocoumarin
Furanocoumarin
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Coumarin
Benzopyran
1-benzopyran
Furopyran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Beta-hydroxy acid
Monosaccharide
Benzenoid
Hydroxy acid
Pyran
Oxane
Furan
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Polyol
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0147076)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	1.63	ALOGPS
logP	0.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	205.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	134.11 m³·mol⁻¹	ChemAxon
Polarizability	55.38 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0147076

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-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid (CFc000127485)

MOL for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

3D MOL for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

3D SDF for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

PDB for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

3D PDB for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

SMILES for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

INCHI for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

Structure for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)

3D Structure for CFc000127485 (3,4,5-trihydroxy-6-{[5-hydroxy-4-(4-hydroxy-3-methylbut-2-en-1-yl)-3-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic acid)