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

ID: ALA3746174

Chembl Id: CHEMBL3746174

PubChem CID: 127042886

Max Phase: Preclinical

Molecular Formula: C27H33BrN2O4S

Molecular Weight: 561.54

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)c1ccsc1

Standard InChI:  InChI=1S/C27H33BrN2O4S/c1-16(2)18-12-19-20(13-21(18)28)26(3)7-5-8-27(4,25(32)33)23(26)14-22(19)30-34-10-9-29-24(31)17-6-11-35-15-17/h6,11-13,15-16,23H,5,7-10,14H2,1-4H3,(H,29,31)(H,32,33)/b30-22+/t23-,26-,27-/m1/s1

Standard InChI Key:  JGYMVGDMUIQVOM-QWGYIVJJSA-N

Alternative Forms

1. Parent:

   

   ALA3746174

   ---

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: 561.54

Molecular Weight (Monoisotopic): 560.1344

AlogP: 6.34

#Rotatable Bonds: 7

Polar Surface Area: 87.99

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.65

CX Basic pKa: 2.71

CX LogP: 6.12

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: 0.26

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