11a-hydroxy-3a,13a-di(hydroxymethyl)-9,15a-dimethyl-1-(5-oxo-2,5-dihydro-3-furanyl)-(1S,15aR)-spiro[perhydrocyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-11,2''-(tetrahydro[1,3]thiazolane)]-4''-one

ID: ALA178993

Chembl Id: CHEMBL178993

PubChem CID: 44387916

Max Phase: Preclinical

Molecular Formula: C32H45NO9S

Molecular Weight: 619.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@@]2(NC(=O)CS2)C2(O)O[C@@H]3C[C@@]4(CO)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54CO)C[C@H]3O[C@@H]2O1

Standard InChI:  InChI=1S/C32H45NO9S/c1-17-11-31(33-25(36)14-43-31)32(38)27(40-17)41-23-10-19-3-4-22-21(29(19,15-34)12-24(23)42-32)5-7-28(2)20(6-8-30(22,28)16-35)18-9-26(37)39-13-18/h9,17,19-24,27,34-35,38H,3-8,10-16H2,1-2H3,(H,33,36)/t17-,19+,20-,21+,22-,23-,24-,27+,28-,29-,30+,31+,32?/m1/s1

Standard InChI Key:  GFLITNATXCDEAV-AZGMHVQESA-N

Alternative Forms

1. Parent:

   

   ALA178993

   (1'S,2S,3'R,5'S,7'R,12'R,14'R,15'S,18'R,19'S,22'S,23'R)-10'-hydroxy-14',22'-bis(hydroxymethyl)-7',18'-dimethyl-19'-(5-oxo-2H-furan-3-yl)spiro[1,3-thiazolidine-2,9'-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane]-4-one

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: 619.78

Molecular Weight (Monoisotopic): 619.2815

AlogP: 2.24

#Rotatable Bonds: 3

Polar Surface Area: 143.78

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.21

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 1.89

Aromatic Rings: ┄

Heavy Atoms: 43

QED Weighted: 0.27

Np Likeness Score: 2.94

References

1. Van Quaquebeke E, Simon G, André A, Dewelle J, El Yazidi M, Bruyneel F, Tuti J, Nacoulma O, Guissou P, Decaestecker C, Braekman JC, Kiss R, Darro F..  (2005)  Identification of a novel cardenolide (2''-oxovoruscharin) from Calotropis procera and the hemisynthesis of novel derivatives displaying potent in vitro antitumor activities and high in vivo tolerance: structure-activity relationship analyses.,  48  (3): [PMID:15689169] [10.1021/jm049405a]

Source

Source(1):

• Scientific Literature