ChemFOnt: Showing chemical card for 6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000120536)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:44:44 UTC

Chemfont ID

CFc000120536

Molecule Identification

Common Name

6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 8-hydroxy-12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-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
6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0,.0,]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₅H₂₈O₁₁

Average Molecular Weight

504.488

Monoisotopic Molecular Weight

504.163161722

IUPAC Name

6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0^{2,7}.0^{13,15}]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0^{2,7}.0^{13,15}]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C3OC3C2=C2OC(=O)C=CC2=C1OC1OC(C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C25H28O11/c1-9(2)5-6-11-17(34-24-16(29)14(27)15(28)21(35-24)23(30)31)10-7-8-12(26)32-18(10)13-19(11)36-25(3,4)22-20(13)33-22/h5,7-8,14-16,20-22,24,27-29H,6H2,1-4H3,(H,30,31)

InChI Key

TZGMKXQZUBXKDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-5-o-glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Pyranocoumarin
Angular pyranocoumarin
Phenolic glycoside
Pyranochromene
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
2,2-dimethyl-1-benzopyran
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Chromane
Beta-hydroxy acid
Alkyl aryl ether
Pyranone
Pyran
Monosaccharide
Hydroxy acid
Benzenoid
Fatty acyl
Oxane
Heteroaromatic compound
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Acetal
Ether
Oxirane
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0140127)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.45	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	164.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.27 m³·mol⁻¹	ChemAxon
Polarizability	50.25 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0140127

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 6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000120536)

MOL for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000120536 (6-{[12,12-dimethyl-9-(3-methylbut-2-en-1-yl)-4-oxo-3,11,14-trioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-1,5,7,9-tetraen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)