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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1991 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15576374 |
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Target ID: CHEMBL3476 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15576374 |
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Target ID: P49913 Gene ID: 820.0 Gene Symbol: CAMP Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26361729 |
0.2 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibitory activity of boswellic acids from Boswellia serrata against human leukemia HL-60 cells in culture. | 1998 May |
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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 |
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Two new triterpenoids from the resin of Boswellia carterii. | 2011 Mar |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15576374
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
Edited
Sat Dec 16 05:13:15 GMT 2023
by
admin
on
Sat Dec 16 05:13:15 GMT 2023
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Record UNII |
5M3483EOU5
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Record Status |
Validated (UNII)
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Record Version |
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5M3483EOU5
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5968-70-7
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DTXSID7057579
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admin on Sat Dec 16 05:13:15 GMT 2023 , Edited by admin on Sat Dec 16 05:13:15 GMT 2023
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