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

ID: ALA3747245

Chembl Id: CHEMBL3747245

PubChem CID: 127037963

Max Phase: Preclinical

Molecular Formula: C28H35BrN2O4S

Molecular Weight: 575.57

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\OCCCNC(=O)c1cccs1

Standard InChI:  InChI=1S/C28H35BrN2O4S/c1-17(2)18-14-19-20(15-21(18)29)27(3)9-6-10-28(4,26(33)34)24(27)16-22(19)31-35-12-7-11-30-25(32)23-8-5-13-36-23/h5,8,13-15,17,24H,6-7,9-12,16H2,1-4H3,(H,30,32)(H,33,34)/b31-22+/t24-,27-,28-/m1/s1

Standard InChI Key:  KVKSEVSIFIHAPQ-FSRAXSAZSA-N

Alternative Forms

1. Parent:

   

   ALA3747245

   ---

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: 6.73

#Rotatable Bonds: 8

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: 2.75

CX LogP: 6.29

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: 0.32

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