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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H50O4
Molecular Weight 498.737
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-ACETYL-.BETA.-BOSWELLIC ACID

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@]5(C)CC[C@@]34C)[C@@]1(C)CC[C@@H](OC(C)=O)[C@]2(C)C(O)=O

InChI

InChIKey=YJBVHJIKNLBFDX-MQURJEHKSA-N
InChI=1S/C32H50O4/c1-19-11-14-28(4)17-18-30(6)22(26(28)20(19)2)9-10-23-29(5)15-13-25(36-21(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23-,24-,25-,26+,28-,29-,30-,31-,32-/m1/s1

HIDE SMILES / InChI

Molecular Formula C32H50O4
Molecular Weight 498.737
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Acetyl-β-boswellic acid (or 3-O-acetyl-β-BA or AβBA) is a cytotoxic compound, which can be isolated from the gum resins of various Boswellia species. It was studied the mechanism of action of this compound on prostate cancer cells and was revealed, that AβBA inhibits IκB kinase (IKK) activity, leading to subsequent inhibition of the antiapoptotic proteins Bcl-2 and Bcl-xL and also cyclin D1, a crucial regulator of cell proliferation. This mechanism finally promote apoptosis of the androgen-independent prostate cancer cells. In addition was shown, that AβBA directly interacts with the antimicrobial peptide LL-37. This binding resulted in an inhibition of the functionality of LL-37, that might be a relevant mechanism underlying the anti-inflammatory properties of AβBA and suggested this compound as suitable chemical tools or potential agent for intervention with the antimicrobial peptide LL-37 and related disorders

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P49913
Gene ID: 820.0
Gene Symbol: CAMP
Target Organism: Homo sapiens (Human)
0.2 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory activity of boswellic acids from Boswellia serrata against human leukemia HL-60 cells in culture.
1998 May
Inhibition of IkappaB kinase activity by acetyl-boswellic acids promotes apoptosis in androgen-independent PC-3 prostate cancer cells in vitro and in vivo.
2005 Feb 18
Two new triterpenoids from the resin of Boswellia carterii.
2011 Mar

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
To determine the cytotoxic activity of acetyl-β-boswellic acid (AβBA) in the PC-3 prostate cancer cells, was measured release of lactate dehydrogenase from cells damaged by exposure to the AβBA (range concentration from 1 to 100 uM) for 12–48 h. Viability in terms of lactate dehydrogenase release decreased in AβBA-treated cells with increasing exposure time. These data shown that AβBA exerted a concentration- and time-dependent cytotoxicity on androgen-independent prostate cancer cells
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:13:15 GMT 2023
Edited
by admin
on Sat Dec 16 05:13:15 GMT 2023
Record UNII
5M3483EOU5
Record Status Validated (UNII)
Record Version
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Name Type Language
3-ACETYL-.BETA.-BOSWELLIC ACID
Common Name English
.BETA.-BOSWELLIC ACID ACETATE
Common Name English
ACETYL-.BETA.-BOSWELLIC ACID
Common Name English
URS-12-EN-24-OIC ACID, 3.ALPHA.-HYDROXY-, ACETATE
Systematic Name English
3-ACETYL-.BETA.-BOSWELLIC ACID (CONSTITUENT OF BOSWELLIA SERRATA) [DSC]
Common Name English
URS-12-EN-23-OIC ACID, 3-(ACETYLOXY)-, (3.ALPHA.,4.BETA.)-
Common Name English
Code System Code Type Description
PUBCHEM
11386458
Created by admin on Sat Dec 16 05:13:15 GMT 2023 , Edited by admin on Sat Dec 16 05:13:15 GMT 2023
PRIMARY
FDA UNII
5M3483EOU5
Created by admin on Sat Dec 16 05:13:15 GMT 2023 , Edited by admin on Sat Dec 16 05:13:15 GMT 2023
PRIMARY
CAS
5968-70-7
Created by admin on Sat Dec 16 05:13:15 GMT 2023 , Edited by admin on Sat Dec 16 05:13:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID7057579
Created by admin on Sat Dec 16 05:13:15 GMT 2023 , Edited by admin on Sat Dec 16 05:13:15 GMT 2023
PRIMARY