(1R,4aS,10aR,E)-6-Bromo-7-isopropyl-1,4a-dimethyl-9-(2-(5-methylthiophene-2-carboxamido)ethoxyimino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

ID: ALA3747271

Chembl Id: CHEMBL3747271

PubChem CID: 127037958

Max Phase: Preclinical

Molecular Formula: C28H35BrN2O4S

Molecular Weight: 575.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NCCO/N=C2\C[C@H]3[C@](C)(C(=O)O)CCC[C@]3(C)c3cc(Br)c(C(C)C)cc32)s1

Standard InChI:  InChI=1S/C28H35BrN2O4S/c1-16(2)18-13-19-20(14-21(18)29)27(4)9-6-10-28(5,26(33)34)24(27)15-22(19)31-35-12-11-30-25(32)23-8-7-17(3)36-23/h7-8,13-14,16,24H,6,9-12,15H2,1-5H3,(H,30,32)(H,33,34)/b31-22+/t24-,27-,28-/m1/s1

Standard InChI Key:  ZQTNKIZCVCOWAK-FSRAXSAZSA-N

Alternative Forms

1. Parent:

   

   ALA3747271

   ---

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: 575.57

Molecular Weight (Monoisotopic): 574.1501

AlogP: 6.65

#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: 3.66

CX Basic pKa: 2.78

CX LogP: 6.87

CX LogD: 3.85

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: 0.35

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