24,26,30-Tetranoroleana-1(10),3,5,7-tetraene-2,21-dione,3,22-dihydroxy-9,13-dimethyl-, (9beta,13alpha,14beta,20beta,22beta)-(9CI
Basic information
- CAS
50656-68-3- Standard SMILES
CC1=C(O)C(=O)C=C2C1=CC=C1[C@@]2(C)CC[C@@]2(C)C3C[C@@H](C)C(=O)[C@@H](O)[C@]3(C)CC[C@]12C- InChIKey
QIRUFAFQGKOTKA-YKUCPAPWSA-N- Molecular formula
- C28H36O4
- Average molar mass
- 436.6 g/mol
- Monoisotopic mass
- 436.26135963
Names & identifiers
- Preferred name
- 24,26,30-Tetranoroleana-1(10),3,5,7-tetraene-2,21-dione,3,22-dihydroxy-9,13-dimethyl-, (9beta,13alpha,14beta,20beta,22beta)-(9CI
- IUPAC
- (6aS,6bS,8aR,9S,11R,14aR)-3,9-dihydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione
- English name
- tingenin B
- Molecular formula
- C28H36O4
- Molecular weight
- 436.58
Names & synonyms
NSC684506CHEMBL1999709SCHEMBL19604972NSC-684506NCI60_03037824,26,30-Tetranoroleana-1(10),3,5,7-tetraene-2,21-dione,3 ,22-dihydroxy-9,13-dimethyl-, (9.beta.,13.alpha.,14.beta.,20.beta.,22.beta.)- (9CItingenin B22β-Hydroxymaytenin22β-Hydroxytingenone3,22β-Dihydroxy-24,29-dinorfriedela-1(10),3,5,7-tetrene-2,21-dione3,22β-Dihydroxy-24,29-dinor-D:A-friedoolean-1(10),3,5,7-tetrene-2,21-dione24,25,26,30-Tetranoroleana-1(10),3,5,7-tetraene-2,21-dione, 3,22-dihydroxy-9,13-dimethyl-, (9β,13α,14β,20β,22β)-
Database identifiers
- CAS
50656-68-3- PubChem CID
- 389017
- ChEMBL
CHEMBL1999709
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 1,070
Chemistry & industry
Applications
DescriptionTingenin B, the plant-derived triterpenoid tingenin B is a potent anticancer agent due to its cytotoxic activity on cancer stem cells of breast cancer in vitro. This compounds target cancer stem cells (CSCs), Tingenin b was cytotoxic against MCF-7s (IC50 value for 48 h was found to be 2.38 μM) by inducing apoptosis. It was evident by Annexin V staining positivity, decreased mitochondrial membrane potential and Bcl-2 dephosphorylation with a concomitant increase in Bax protein expression. In addition, endoplasmic reticulum stress was also found to be involved in tingenin b-induced cell death.
Related reactions
0 records
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Compound notes
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