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

ID: ALA3746008

Chembl Id: CHEMBL3746008

PubChem CID: 127037960

Max Phase: Preclinical

Molecular Formula: C27H32Br2N2O4S

Molecular Weight: 640.44

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(Br)s1

Standard InChI:  InChI=1S/C27H32Br2N2O4S/c1-15(2)16-12-17-18(13-19(16)28)26(3)8-5-9-27(4,25(33)34)22(26)14-20(17)31-35-11-10-30-24(32)21-6-7-23(29)36-21/h6-7,12-13,15,22H,5,8-11,14H2,1-4H3,(H,30,32)(H,33,34)/b31-20+/t22-,26-,27-/m1/s1

Standard InChI Key:  BHMSQXGSSRAHME-KDEBXRSSSA-N

Alternative Forms

1. Parent:

   

   ALA3746008

   ---

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: 640.44

Molecular Weight (Monoisotopic): 638.0450

AlogP: 7.10

#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: 3.62

CX Basic pKa: 2.40

CX LogP: 7.28

CX LogD: 4.14

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: 0.36

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