(1R,4aS,10aR,E)-9-(2-(1H-pyrrole-2-carboxamido)ethoxyimino)-6-bromo-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

ID: ALA3746830

Chembl Id: CHEMBL3746830

PubChem CID: 127042882

Max Phase: Preclinical

Molecular Formula: C27H34BrN3O4

Molecular Weight: 544.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1cc2c(cc1Br)[C@@]1(C)CCC[C@@](C)(C(=O)O)[C@@H]1C/C2=N\OCCNC(=O)c1ccc[nH]1

Standard InChI:  InChI=1S/C27H34BrN3O4/c1-16(2)17-13-18-19(14-20(17)28)26(3)8-6-9-27(4,25(33)34)23(26)15-22(18)31-35-12-11-30-24(32)21-7-5-10-29-21/h5,7,10,13-14,16,23,29H,6,8-9,11-12,15H2,1-4H3,(H,30,32)(H,33,34)/b31-22+/t23-,26-,27-/m1/s1

Standard InChI Key:  XGSGWMLZPKPSJF-OBDQHKETSA-N

Alternative Forms

1. Parent:

   

   ALA3746830

   ---

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: 544.49

Molecular Weight (Monoisotopic): 543.1733

AlogP: 5.60

#Rotatable Bonds: 7

Polar Surface Area: 103.78

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.68

CX Basic pKa: 2.85

CX LogP: 5.27

CX LogD: 2.29

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: 0.75

References

1. Cui YM, Liu XL, Zhang WM, Lin HX, Ohwada T, Ido K, Sawada K..  (2016)  The synthesis and BK channel-opening activity of N-acylaminoalkyloxime derivatives of dehydroabietic acid.,  26  (2): [PMID:26707391] [10.1016/j.bmcl.2015.12.038]

2. Zhang WM, Yang T, Pan XY, Liu XL, Lin HX, Gao ZB, Yang CG, Cui YM..  (2017)  The synthesis and antistaphylococcal activity of dehydroabietic acid derivatives: modifications at C12 and C7.,  127  [PMID:27837995] [10.1016/j.ejmech.2016.11.002]

Source

Source(1):

• Scientific Literature