3a,11a-dihydroxy-4''-imino-9,15a-dimethyl-1-(5-oxo-2,5-dihydro-3-furanyl)spiro[perhydrocyclopenta[7,8]phenanthro[2,3-b]pyrano[3,2-e][1,4]dioxine-11,2''-(tetrahydro[1,3]thiazolane)]-13a-carbaldehyde

ID: ALA175806

Chembl Id: CHEMBL175806

PubChem CID: 44387914

Max Phase: Preclinical

Molecular Formula: C31H42N2O8S

Molecular Weight: 602.75

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C31H42N2O8S/c1-16-11-30(33-24(32)14-42-30)31(37)26(39-16)40-22-10-18-3-4-21-20(28(18,15-34)12-23(22)41-31)5-7-27(2)19(6-8-29(21,27)36)17-9-25(35)38-13-17/h9,15-16,18-23,26,36-37H,3-8,10-14H2,1-2H3,(H2,32,33)/t16-,18+,19-,20+,21-,22-,23-,26+,27-,28-,29+,30+,31-/m1/s1

Standard InChI Key:  JHKLDCGHXADNGS-DJHKYUSNSA-N

Alternative Forms

1. Parent:

   

   ALA175806

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

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: 602.75

Molecular Weight (Monoisotopic): 602.2662

AlogP: 2.44

#Rotatable Bonds: 2

Polar Surface Area: 149.90

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.18

CX Basic pKa: 6.74

CX LogP: 2.09

CX LogD: 2.03

Aromatic Rings: ┄

Heavy Atoms: 42

QED Weighted: 0.24

Np Likeness Score: 2.99

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