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

ID: ALA3746600

Chembl Id: CHEMBL3746600

PubChem CID: 127042881

Max Phase: Preclinical

Molecular Formula: C27H33BrN2O5

Molecular Weight: 545.47

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)c1ccco1

Standard InChI:  InChI=1S/C27H33BrN2O5/c1-16(2)17-13-18-19(14-20(17)28)26(3)8-6-9-27(4,25(32)33)23(26)15-21(18)30-35-12-10-29-24(31)22-7-5-11-34-22/h5,7,11,13-14,16,23H,6,8-10,12,15H2,1-4H3,(H,29,31)(H,32,33)/b30-21+/t23-,26-,27-/m1/s1

Standard InChI Key:  QAVSWMABLIGBNF-BGALOUFYSA-N

Alternative Forms

1. Parent:

   

   ALA3746600

   ---

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: 545.47

Molecular Weight (Monoisotopic): 544.1573

AlogP: 5.87

#Rotatable Bonds: 7

Polar Surface Area: 101.13

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.64

CX Basic pKa: 2.60

CX LogP: 5.44

CX LogD: 2.35

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: 0.52

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