4-dehydro-withaferin A

ID: ALA2047415

Chembl Id: CHEMBL2047415

Cas Number: 6850-30-2

PubChem CID: 165541

Max Phase: Preclinical

Molecular Formula: C28H36O6

Molecular Weight: 468.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-Dehydro-Withaferin A | 4-Dehydrowithaferin A|4-oxo Withaferin A|6850-30-2|(1S,2R,7S,9R,11S,12S,15R,16S)-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-ene-3,6-dione|(4aS,5aR,6aS,6bS,9R,9aS,11aS,11bR)-9-((S)-1-((R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxirene-1,4-dione|4-Dehydro-WShow More⌵

Canonical SMILES:  CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56C(=O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1

Standard InChI:  InChI=1S/C28H36O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,24,29H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,24+,26+,27-,28+/m0/s1

Standard InChI Key:  XGPALHIQWWGRFB-TTWUVOALSA-N

Alternative Forms

1. Parent:

   

   ALA2047415

   4-Dehydrowithaferin A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 468.59

Molecular Weight (Monoisotopic): 468.2512

AlogP: 3.56

#Rotatable Bonds: 3

Polar Surface Area: 93.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.35

CX LogD: 4.35

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: 3.26

References

1. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Bazzocchi IL..  (2012)  Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.,  54  [PMID:22705001] [10.1016/j.ejmech.2012.05.032]

2. Wijeratne EM, Xu YM, Scherz-Shouval R, Marron MT, Rocha DD, Liu MX, Costa-Lotufo LV, Santagata S, Lindquist S, Whitesell L, Gunatilaka AA..  (2014)  Structure-activity relationships for withanolides as inducers of the cellular heat-shock response.,  57  (7): [PMID:24625088] [10.1021/jm401279n]

3. Perestelo NR, Llanos GG, Reyes CP, Amesty A, Sooda K, Afshinjavid S, Jiménez IA, Javid F, Bazzocchi IL..  (2019)  Expanding the Chemical Space of Withaferin A by Incorporating Silicon To Improve Its Clinical Potential on Human Ovarian Carcinoma Cells.,  62  (9): [PMID:31008605] [10.1021/acs.jmedchem.9b00146]

Source

Source(1):

• Scientific Literature