3-(m-nitrophenyl)-lupa-2,20(29)-dien-28-oic acid

ID: ALA5279187

Chembl Id: CHEMBL5279187

Max Phase: Preclinical

Molecular Formula: C36H49NO4

Molecular Weight: 559.79

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC=C(c6cccc([N+](=O)[O-])c6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12

Standard InChI:  InChI=1S/C36H49NO4/c1-22(2)25-13-18-36(31(38)39)20-19-34(6)27(30(25)36)11-12-29-33(5)16-14-26(23-9-8-10-24(21-23)37(40)41)32(3,4)28(33)15-17-35(29,34)7/h8-10,14,21,25,27-30H,1,11-13,15-20H2,2-7H3,(H,38,39)/t25-,27+,28-,29+,30+,33-,34+,35+,36-/m0/s1

Standard InChI Key:  XAURCHLOUKJRSJ-PDVPNEPJSA-N

Alternative Forms

1. Parent:

   

   ALA5279187

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 559.79

Molecular Weight (Monoisotopic): 559.3662

AlogP: 9.33

#Rotatable Bonds: 4

Polar Surface Area: 80.44

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.78

CX Basic pKa:

CX LogP: 8.96

CX LogD: 6.39

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.23

Np Likeness Score: 2.01

References

1. Borková L, Frydrych I, Vránová B, Jakubcová N, Lišková B, Gurská S, Džubák P, Pavliš P, Hajdúch M, Urban M..  (2022)  Lupane derivatives containing various aryl substituents in the position 3 have selective cytostatic effect in leukemic cancer cells including resistant phenotypes.,  244  [PMID:36283179] [10.1016/j.ejmech.2022.114850]

Source

Source(1):

• Scientific Literature