2,3-dihydrowithaferin A

ID: ALA1934585

Chembl Id: CHEMBL1934585

PubChem CID: 15411208

Max Phase: Preclinical

Molecular Formula: C28H40O6

Molecular Weight: 472.62

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2,3-Dihydro-Withaferin A | 2,3-Dihydrowithaferin A | Dihydrowithaferin A|2,3-Dihydrowithaferin A|CHEBI:69124|2,3-Dihydro-Withaferin A|CHEMBL1934585|SCHEMBL21164151|HY-N5120|AKOS040760371|MS-28752|CS-0032441|E88629|Q27137464|(22R)-4beta,27-dihydroxy-5beta,6beta:22,26-diepoxyergost-24-ene-1,26-dione|(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-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]octadecan-3-one

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@]56[C@@H](O)CCC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1

Standard InChI:  InChI=1S/C28H40O6/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/h15-16,18-21,23-24,29,31H,5-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

Standard InChI Key:  YRXCLNDPESBJHL-CKNDUULBSA-N

Alternative Forms

1. Parent:

   

   ALA1934585

   2,3-Dihydrowithaferin 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: 472.62

Molecular Weight (Monoisotopic): 472.2825

AlogP: 3.58

#Rotatable Bonds: 3

Polar Surface Area: 96.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.82

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.48

Np Likeness Score: 3.64

References

1. Zhang H, Samadi AK, Gallagher RJ, Araya JJ, Tong X, Day VW, Cohen MS, Kindscher K, Gollapudi R, Timmermann BN..  (2011)  Cytotoxic withanolide constituents of Physalis longifolia.,  74  (12): [PMID:22098611] [10.1021/np200635r]

2. 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]

3. 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]

4. Yoneyama T, Arai MA, Sadhu SK, Ahmed F, Ishibashi M..  (2015)  Hedgehog inhibitors from Withania somnifera.,  25  (17): [PMID:26169123] [10.1016/j.bmcl.2015.06.081]

5. Llanos GG, Araujo LM, Jiménez IA, Moujir LM, Rodríguez J, Jiménez C, Bazzocchi IL..  (2017)  Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.,  140  [PMID:28923386] [10.1016/j.ejmech.2017.09.004]

Source

Source(1):

• Scientific Literature