ID: ALA1076489

Max Phase: Preclinical

Molecular Formula: C39H56O3

Molecular Weight: 572.87

Molecule Type: Small molecule

Representations

Synonyms (1): 28-O-Cinnamoylbetulin
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(COC(=O)/C=C/c3ccccc3)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C39H56O3/c1-26(2)28-17-22-39(25-42-33(41)16-13-27-11-9-8-10-12-27)24-23-37(6)29(34(28)39)14-15-31-36(5)20-19-32(40)35(3,4)30(36)18-21-38(31,37)7/h8-13,16,28-32,34,40H,1,14-15,17-25H2,2-7H3/b16-13+/t28-,29+,30-,31+,32-,34+,36-,37+,38+,39+/m0/s1

Standard InChI Key:  LXCNPSDULNZQOW-RRKSSEBOSA-N

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

Properties

Molecular Weight: 572.87

Molecular Weight (Monoisotopic): 572.4229

AlogP: 9.26

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 9.20

CX LogD: 9.20

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.22

Np Likeness Score: 2.55

References

1. Pohjala L, Alakurtti S, Ahola T, Yli-Kauhaluoma J, Tammela P..  (2009)  Betulin-derived compounds as inhibitors of alphavirus replication.,  72  (11): [PMID:19839605] [10.1021/np9003245]

2. Yang SJ, Liu MC, Xiang HM, Zhao Q, Xue W, Yang S..  (2015)  Synthesis and in vitro antitumor evaluation of betulin acid ester derivatives as novel apoptosis inducers.,  102  [PMID:26280921] [10.1016/j.ejmech.2015.08.004]

Source

Source(1):

• Scientific Literature