ID: ALA1087753

Max Phase: Preclinical

Molecular Formula: C30H49NO2

Molecular Weight: 455.73

Molecule Type: Small molecule

Representations

Synonyms (1): Betulin-28-Oxime
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(/C=N/O)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/C30H49NO2/c1-19(2)20-10-15-30(18-31-33)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32-33H,1,8-17H2,2-7H3/b31-18+/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

Standard InChI Key:  GCYZHONUJBNDJH-UXEVJXGNSA-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: 455.73

Molecular Weight (Monoisotopic): 455.3763

AlogP: 7.46

#Rotatable Bonds: 2

Polar Surface Area: 52.82

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.31

CX Basic pKa: 3.05

CX LogP: 6.49

CX LogD: 6.49

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: 3.00

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. Alcazar W, López AS, Alakurtti S, Tuononen ML, Yli-Kauhaluoma J, Ponte-Sucre A..  (2014)  Betulin derivatives impair Leishmania braziliensis viability and host-parasite interaction.,  22  (21): [PMID:25240731] [10.1016/j.bmc.2014.08.023]

3. Laavola M, Haavikko R, Hämäläinen M, Leppänen T, Nieminen R, Alakurtti S, Moreira VM, Yli-Kauhaluoma J, Moilanen E..  (2016)  Betulin Derivatives Effectively Suppress Inflammation in Vitro and in Vivo.,  79  (2): [PMID:26915998] [10.1021/acs.jnatprod.5b00709]

4. Chen S, Zhang L, Chen Y, Fu L..  (2022)  Inhibiting Sodium Taurocholate Cotransporting Polypeptide in HBV-Related Diseases: From Biological Function to Therapeutic Potential.,  65  (19.0): [PMID:36111355] [10.1021/acs.jmedchem.2c01097]

Source

Source(1):

• Scientific Literature