ChemFOnt: Showing chemical card for 3alpha-Acetoxy-11-keto-beta-boswellic acid (CFc000017609)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:41 UTC

Chemfont ID

CFc000017609

Molecule Identification

Common Name

3alpha-Acetoxy-11-keto-beta-boswellic acid

Definition

3alpha-Acetoxy-11-keto-beta-boswellic acid is found in herbs and spices. 3alpha-Acetoxy-11-keto-beta-boswellic acid is isolated from Boswellia serrata (Indian olibanum).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3a-Acetoxy-11-keto-b-boswellate	Generator
3a-Acetoxy-11-keto-b-boswellic acid	Generator
3alpha-Acetoxy-11-keto-beta-boswellate	Generator
3Α-acetoxy-11-keto-β-boswellate	Generator
3Α-acetoxy-11-keto-β-boswellic acid	Generator
(3R,4R,6AR,6BS,8ar,11R,12S,12ar,14BS)-3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylate	HMDB

Chemical Formula

C₃₂H₄₈O₅

Average Molecular Weight

512.7205

Monoisotopic Molecular Weight

512.350174646

IUPAC Name

(3R,4R,6aR,6bS,8aR,11R,12S,12aR,14bS)-3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

Traditional Name

(3R,4R,6aR,6bS,8aR,11R,12S,12aR,14bS)-3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid

CAS Registry Number

67416-61-9

SMILES

C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC(=O)C4[C@@]5(C)CC[C@@H](OC(C)=O)[C@@](C)(C5CC[C@@]34C)C(O)=O)[C@@H]2[C@H]1C

InChI Identifier

InChI=1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23?,24-,25+,26?,28-,29+,30-,31-,32-/m1/s1

InChI Key

HMMGKOVEOFBCAU-MFIYSICPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
15-hydroxysteroid
Hydroxysteroid
Steroid
Cyclohexenone
Dicarboxylic acid or derivatives
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036672)

Source

Endogenous

Endogenous (HMDB: HMDB0036672)

Plant

Plant (HMDB: HMDB0036672)

Animal

Animal (HMDB: HMDB0036672)

Exogenous

Food

Food (HMDB: HMDB0036672)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036672)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036672)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036672)

Lipid metabolism pathway (HMDB: HMDB0036672)

Cellular process

Cell signaling (HMDB: HMDB0036672)

Biochemical process

Lipid transport (HMDB: HMDB0036672)

Role

Biological role

Energy source (HMDB: HMDB0036672)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036672)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	5.9	ALOGPS
logP	6.46	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	143.49 m³·mol⁻¹	ChemAxon
Polarizability	59.04 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

HMDB0036672

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015602

KNApSAcK ID

C00054337

Chemspider ID

24022866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45359902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3alpha-Acetoxy-11-keto-beta-boswellic acid (CFc000017609)

MOL for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

3D MOL for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

3D SDF for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

3D-SDF for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

PDB for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

3D PDB for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

SMILES for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

INCHI for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

Structure for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)

3D Structure for CFc000017609 (3alpha-Acetoxy-11-keto-beta-boswellic acid)