4,6,27-Triacetyl-2,3-didehydrosomnifericin

ID: ALA3234480

Chembl Id: CHEMBL3234480

PubChem CID: 90670448

Max Phase: Preclinical

Molecular Formula: C34H46O10

Molecular Weight: 614.73

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](OC(C)=O)[C@]5(O)[C@@H](OC(C)=O)C=CC(=O)[C@]5(C)[C@H]4CC[C@]23C)OC1=O

Standard InChI:  InChI=1S/C34H46O10/c1-17-14-27(44-31(39)23(17)16-41-19(3)35)18(2)24-8-9-25-22-15-30(43-21(5)37)34(40)29(42-20(4)36)11-10-28(38)33(34,7)26(22)12-13-32(24,25)6/h10-11,18,22,24-27,29-30,40H,8-9,12-16H2,1-7H3/t18-,22-,24+,25-,26-,27+,29-,30-,32+,33-,34+/m0/s1

Standard InChI Key:  FJKZTNYOFLAYHF-RZVQGYRWSA-N

Alternative Forms

1. Parent:

   

   ALA3234480

   [(2R)-2-[(1S)-1-[(4S,5S,6S,8S,9S,10R,13S,14S,17R)-4,6-diacetyloxy-5-hydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-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: 614.73

Molecular Weight (Monoisotopic): 614.3091

AlogP: 4.02

#Rotatable Bonds: 6

Polar Surface Area: 142.50

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.27

CX Basic pKa: ┄

CX LogP: 3.74

CX LogD: 3.74

Aromatic Rings: ┄

Heavy Atoms: 44

QED Weighted: 0.34

Np Likeness Score: 2.92

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