15-beta-Acetoxy-4,27-diacetylwithaferin A

ID: ALA3234490

Chembl Id: CHEMBL3234490

PubChem CID: 90670458

Max Phase: Preclinical

Molecular Formula: C34H44O10

Molecular Weight: 612.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C)C[C@H]([C@@H](C)[C@H]2C[C@@H](OC(C)=O)[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](OC(C)=O)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)OC1=O

Standard InChI:  InChI=1S/C34H44O10/c1-16-12-25(43-31(39)22(16)15-40-18(3)35)17(2)24-14-26(41-19(4)36)30-21-13-29-34(44-29)28(42-20(5)37)9-8-27(38)33(34,7)23(21)10-11-32(24,30)6/h8-9,17,21,23-26,28-30H,10-15H2,1-7H3/t17-,21+,23-,24+,25+,26+,28-,29+,30+,32+,33-,34+/m0/s1

Standard InChI Key:  IGIDPOKUUXWPAJ-DQCBRXESSA-N

Alternative Forms

1. Parent:

   

   ALA3234490

   [(2R)-2-[(1S)-1-[(1S,2R,6S,7S,9R,11R,12S,13R,15R,16R)-6,13-diacetyloxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-15-yl]ethyl]-4-methyl-6-oxo-2,3-dihydropyran-5-yl]methyl acetate

Molecule Features

Natural Product: No

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: 612.72

Molecular Weight (Monoisotopic): 612.2934

AlogP: 4.04

#Rotatable Bonds: 6

Polar Surface Area: 134.80

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.53

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.25

Np Likeness Score: 3.21

References

1. 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]

Source

Source(1):

• Scientific Literature