3-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H48O5
Molecular Weight	512.7205
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Structure Search

SMILES

C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC(=O)[C@@H]4[C@@]5(C)CC[C@@H](OC(C)=O)[C@@](C)([C@@H]5CC[C@@]34C)C(O)=O)[C@@H]2[C@H]1C

InChI

InChIKey=HMMGKOVEOFBCAU-BCDBGHSCSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1602379 | https://www.ncbi.nlm.nih.gov/pubmed/9918566 | https://www.ncbi.nlm.nih.gov/pubmed/19567671 | https://www.ncbi.nlm.nih.gov/pubmed/18667054 | http://www.plthealth.com/products/5-loxin | http://www.5-loxin.com/

Acetyl-11-keto-beta-boswellic acid (AKBA), a pentacyclic triterpene, is a component of gum resin of Boswellia serrata. It inhibits 5-lipoxygenase in a selective, enzyme directed, non-redox, and noncompetitive manner. In addition, AKBA inhibited topoisomerase I. It induces apoptosis and exerts antineoplastic properties. 5-LOXIN, a dietary supplement ingredient (Boswellia serrata extract enriched with 30% 3-O-acetyl-11-keto-beta-boswellic acid) is effective in reducing pain and improving physical functioning in osteoarthritis patients.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase I 60 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9918566	Inhibitor 8504
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9760176 \| https://www.ncbi.nlm.nih.gov/pubmed/8646405 \| https://www.ncbi.nlm.nih.gov/pubmed/1602379	Inhibitor 8504	1.5 µM [IC50]
apoptotic process 51 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9918566 \| https://www.ncbi.nlm.nih.gov/pubmed/12507932	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12507932 https://www.ncbi.nlm.nih.gov/pubmed/9918566 https://www.ncbi.nlm.nih.gov/pubmed/19147543 https://www.ncbi.nlm.nih.gov/pubmed/12664615 https://www.ncbi.nlm.nih.gov/pubmed/19567671 https://www.ncbi.nlm.nih.gov/pubmed/25712055	Primary	Preclinical	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18667054 https://www.ncbi.nlm.nih.gov/pubmed/21060724	Primary	Approved 8583	5-LOXIN Approved Use 5-Loxin is a novel Boswellia serrata extract enriched with 30% 3-O-acetyl-11-keto-beta-boswellic acid (AKBA), which exhibits potential anti-inflammatory properties by inhibiting the 5-lipoxygenase enzyme. In human studies, 5-LOXIN® promotes joint health and function and protects against collagen degradation, an important component of connective tissues.
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16480179	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Acetyl-11-keto-beta-boswellic acid induces apoptosis in HL-60 and CCRF-CEM cells and inhibits topoisomerase I.	1999-02	9918566
Acetyl-11-keto-beta-boswellic acid (AKBA): structure requirements for binding and 5-lipoxygenase inhibitory activity.	1996-02	8646405

Patents

Sample Use Guides

In Vivo Use Guide

5-LOXIN, a dietary supplement ingredient (Boswellia serrata extract enriched with 30% 3-O-acetyl-11-keto-beta-boswellic acid): osteoarthritis patients received either 100 mg or 250 mg of 5-Loxin daily or a placebo for 90 days. Significant improvements in pain score and functional ability were recorded in the treatment group supplemented with 250 mg 5-Loxin as early as 7 days after the start of treatment.

Route of Administration: Oral

In Vitro Use Guide

Treatment of meningioma cells by Acetyl-11-Keto-β-Boswellic Acid (AKBA) revealed a potent cytotoxic activity with half-maximal inhibitory concentrations in the range of 2-8 microM. At similar, physiologically achievable concentrations, AKBA rapidly (within minutes) and potently inhibited the phosphorylation of extracellular signal-regulated kinase 1 and 2 (Erk-1 and Erk-2) in meningioma cells stimulated with platelet-derived growth factor BB.

Name

Type

Language

3-ACETYL-11-KETO-BETA-BOSWELLIC ACID

Preferred Name

English

3-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Common Name

English

3-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID (CONSTITUENT OF BOSWELLIA SERRATA) [DSC]

Common Name

English

ACETYL-11-OXO-.BETA.-BOSWELLIC ACID

Common Name

English

3-ACETYL-11-KETO-BETA-BOSWELLIC ACID [USP-RS]

Common Name

English

(3.ALPHA.,4.BETA.)-3-(ACETYLOXY)-11-OXOURS-12-EN-23-OIC ACID

Systematic Name

English

3.ALPHA.-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Common Name

English

11-KETO-.BETA.-BOSWELLIC ACID ACETATE

Common Name

English

3.ALPHA.-ACETOXY-11-OXO-12-URSEN-24-OIC ACID

Common Name

English

3-O-ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Common Name

English

ACETYL-11-KETO-.BETA.-BOSWELLIC ACID

Common Name

English

AKBA

Common Name

English

URS-12-EN-23-OIC ACID, 3-(ACETYLOXY)-11-OXO-, (3.ALPHA.,4.BETA.)-

Systematic Name

English

Code System Code Type Description

CAS

67416-61-9