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

ID: ALA360685

Chembl Id: CHEMBL360685

PubChem CID: 44387937

Max Phase: Preclinical

Molecular Formula: C39H50N2O9S

Molecular Weight: 722.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C[C@@]2(N=C(N)CS2)C2(O)O[C@@H]3C[C@@]4(COC(=O)c5ccccc5)[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/C39H50N2O9S/c1-22-16-38(41-31(40)19-51-38)39(45)34(48-22)49-29-15-25-8-9-28-27(36(25,17-30(29)50-39)21-47-33(44)23-6-4-3-5-7-23)10-12-35(2)26(11-13-37(28,35)20-42)24-14-32(43)46-18-24/h3-7,14,22,25-30,34,42,45H,8-13,15-21H2,1-2H3,(H2,40,41)/t22-,25+,26-,27+,28-,29-,30-,34+,35-,36-,37+,38+,39?/m1/s1

Standard InChI Key:  VXEFGARJQIVEOL-YKCQPAHQSA-N

Alternative Forms

1. Parent:

   

   ALA360685

   [(1S,3R,5S,7R,9S,12R,14R,15S,18R,19S,22S,23R)-4'-amino-10-hydroxy-22-(hydroxymethyl)-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-yl]methyl benzoate

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: 722.90

Molecular Weight (Monoisotopic): 722.3237

AlogP: 4.35

#Rotatable Bonds: 5

Polar Surface Area: 159.13

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.21

CX Basic pKa: 6.75

CX LogP: 4.39

CX LogD: 4.33

Aromatic Rings: 1

Heavy Atoms: 51

QED Weighted: 0.29

Np Likeness Score: 2.33

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