ChemFOnt: Showing chemical card for Gambogic acid (CFc000015174)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:14 UTC

Chemfont ID

CFc000015174

Molecule Identification

Common Name

Gambogic acid

Definition

Gambogic acid is found in fruits. Gambogic acid is isolated from Gamboge resin (exudate of Garcinia morella).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gambogate	Generator
a-Gambogic acid	HMDB
b-Guttiferin	HMDB
b-Guttilactone	HMDB
Guttatic acid	HMDB
Guttic acid	HMDB
Gamboge acid	HMDB
Gambogoic acid	HMDB
(2Z)-4-[12-Hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoate	Generator
Gambogic acid	MeSH

Chemical Formula

C₃₈H₄₄O₈

Average Molecular Weight

628.7512

Monoisotopic Molecular Weight

628.303618384

IUPAC Name

(2Z)-4-[12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4,6(11),9,12,15-pentaen-19-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

2752-65-0

SMILES

CC(C)=CCCC1(C)OC2=C(C=C1)C(O)=C1C(=O)C3=CC4CC5C(C)(C)OC(C\C=C(\C)C(O)=O)(C4=O)C35OC1=C2CC=C(C)C

InChI Identifier

InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-

InChI Key

GEZHEQNLKAOMCA-XKZIYDEJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
Chromone
Aromatic monoterpenoid
Monoterpenoid
Aryl ketone
Alkyl aryl ether
Cyclohexenone
Oxepane
Benzenoid
Vinylogous acid
Tetrahydrofuran
Ketone
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034095)
Cell membrane (HMDB: HMDB0034095)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034095)

Source

Exogenous

Exogenous (HMDB: HMDB0034095)

Food

Food (HMDB: HMDB0034095)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034095)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034095)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00071 g/L	ALOGPS
logP	5.57	ALOGPS
logP	7.78	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	179.16 m³·mol⁻¹	ChemAxon
Polarizability	68.1 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon