(3beta)-3,N-Dihydroxy-urs-12-en-28-amide

ID: ALA3753400

Chembl Id: CHEMBL3753400

PubChem CID: 127037404

Max Phase: Preclinical

Molecular Formula: C30H49NO3

Molecular Weight: 471.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1[C@H](C)CC[C@]2(C(=O)NO)CC[C@]3(C)C(=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/C30H49NO3/c1-18-10-15-30(25(33)31-34)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(32)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,32,34H,9-17H2,1-7H3,(H,31,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

Standard InChI Key:  DXMDXBIXLLHEFM-GPOJBZKASA-N

Alternative Forms

1. Parent:

   

   ALA3753400

   ---

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: 471.73

Molecular Weight (Monoisotopic): 471.3712

AlogP: 6.51

#Rotatable Bonds: 1

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.83

CX Basic pKa: ┄

CX LogP: 5.77

CX LogD: 5.76

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.23

Np Likeness Score: 2.83

References

1. Wiemann J, Heller L, Csuk R..  (2016)  Targeting cancer cells with oleanolic and ursolic acid derived hydroxamates.,  26  (3): [PMID:26750249] [10.1016/j.bmcl.2015.12.064]

2. Minassi A, Rogati F, Cruz C, Prados ME, Galera N, Jinénez C, Appendino G, Bellido ML, Calzado MA, Caprioglio D, Muñoz E..  (2018)  Triterpenoid Hydroxamates as HIF Prolyl Hydrolase Inhibitors.,  81  (10): [PMID:30350996] [10.1021/acs.jnatprod.8b00514]

Source

Source(1):

• Scientific Literature