4,27-Diacetyl-2,3-dihydrowithaferin A 3-beta-O-Sulfate

ID: ALA3234477

Chembl Id: CHEMBL3234477

PubChem CID: 90670445

Max Phase: Preclinical

Molecular Formula: C32H44O12S

Molecular Weight: 652.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCC1=C(C)C[C@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](OC(C)=O)[C@@H](OS(=O)(=O)O)CC(=O)[C@]6(C)[C@H]4CC[C@]23C)OC1=O

Standard InChI:  InChI=1S/C32H44O12S/c1-15-11-24(42-29(36)20(15)14-40-17(3)33)16(2)21-7-8-22-19-12-27-32(43-27)28(41-18(4)34)25(44-45(37,38)39)13-26(35)31(32,6)23(19)9-10-30(21,22)5/h16,19,21-25,27-28H,7-14H2,1-6H3,(H,37,38,39)/t16-,19-,21+,22-,23-,24+,25-,27+,28-,30+,31-,32-/m0/s1

Standard InChI Key:  OAQGIPDONKQPKI-FENFJIRLSA-N

Alternative Forms

1. Parent:

   

   ALA3234477

   [(2R)-2-[(1S)-1-[(1S,2R,5S,6S,7S,9R,11S,12S,15R,16S)-6-acetyloxy-2,16-dimethyl-3-oxo-5-sulfooxy-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-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: 652.76

Molecular Weight (Monoisotopic): 652.2553

AlogP: 3.52

#Rotatable Bonds: 7

Polar Surface Area: 172.10

Molecular Species: ACID

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.68

CX Basic pKa: ┄

CX LogP: 3.45

CX LogD: 1.07

Aromatic Rings: ┄

Heavy Atoms: 45

QED Weighted: 0.18

Np Likeness Score: 2.99

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