ID: ALA1087415

Max Phase: Preclinical

Molecular Formula: C32H52O3

Molecular Weight: 484.77

Molecule Type: Small molecule

Representations

Synonyms (1): 3-O-Acetylbetulin
Synonyms from Alternative Forms(1):

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

Standard InChI:  InChI=1S/C32H52O3/c1-20(2)22-11-16-32(19-33)18-17-30(7)23(27(22)32)9-10-25-29(6)14-13-26(35-21(3)34)28(4,5)24(29)12-15-31(25,30)8/h22-27,33H,1,9-19H2,2-8H3/t22-,23+,24-,25+,26-,27+,29-,30+,31+,32+/m0/s1

Standard InChI Key:  XUDTWJGGQFHXCR-VFUWXHBOSA-N

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

Properties

Molecular Weight: 484.77

Molecular Weight (Monoisotopic): 484.3916

AlogP: 7.57

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.61

CX LogD: 6.61

Aromatic Rings: 0

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: 3.15

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. Lee S, Jung K, Lee D, Lee SR, Lee KR, Kang KS, Kim KH..  (2015)  Protective effect and mechanism of action of lupane triterpenes from Cornus walteri in cisplatin-induced nephrotoxicity.,  25  (23): [PMID:26592171] [10.1016/j.bmcl.2015.10.035]

3. Wiemann J, Heller L, Perl V, Kluge R, Ströhl D, Csuk R..  (2015)  Betulinic acid derived hydroxamates and betulin derived carbamates are interesting scaffolds for the synthesis of novel cytotoxic compounds.,  106  [PMID:26547057] [10.1016/j.ejmech.2015.10.043]

4. Heller L, Perl V, Wiemann J, Al-Harrasi A, Csuk R..  (2016)  Amino(oxo)acetate moiety: A new functional group to improve the cytotoxicity of betulin derived carbamates.,  26  (12): [PMID:27142753] [10.1016/j.bmcl.2016.04.055]

5. Brandes B, Hoenke S, Fischer L, Csuk R..  (2020)  Design, synthesis and cytotoxicity of BODIPY FL labelled triterpenoids.,  185  [PMID:31718946] [10.1016/j.ejmech.2019.111858]

Source

Source(1):

• Scientific Literature