(1R,4aS,E)-6-Bromo-7-isopropyl-1,4a-dimethyl-9-((2-(4-(trifluoromethyl)phenylsulfonamido)ethoxy)imino)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid

ID: ALA4227690

PubChem CID: 145970227

Max Phase: Preclinical

Molecular Formula: C29H34BrF3N2O5S

Molecular Weight: 659.57

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\OCCNS(=O)(=O)c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C29H34BrF3N2O5S/c1-17(2)20-14-21-22(15-23(20)30)27(3)10-5-11-28(4,26(36)37)25(27)16-24(21)35-40-13-12-34-41(38,39)19-8-6-18(7-9-19)29(31,32)33/h6-9,14-15,17,25,34H,5,10-13,16H2,1-4H3,(H,36,37)/b35-24+/t25-,27-,28-/m1/s1

Standard InChI Key:  ZYDXJXNZGRTKBV-XUNSIDIHSA-N

Molfile:  

     RDKit          2D

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   33.5838  -18.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.8806  -19.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1730  -18.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   31.4665  -18.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5861  -19.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1643  -20.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4665  -19.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3015  -18.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8692  -20.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2992  -16.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7233  -16.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8759  -20.1065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.2997  -16.0091    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   35.0120  -19.6962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0127  -20.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7208  -20.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4281  -20.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1362  -20.9202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5516  -20.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5485  -21.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   39.9679  -21.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9665  -20.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2577  -20.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6756  -22.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6755  -22.9651    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.3834  -21.7395    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.3796  -22.5553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 39 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4227690

   ---

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: 659.57

Molecular Weight (Monoisotopic): 658.1324

AlogP: 6.84

#Rotatable Bonds: 8

Polar Surface Area: 105.06

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.63

CX Basic pKa: 2.52

CX LogP: 7.04

CX LogD: 3.93

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.24

Np Likeness Score: 0.21

References

1. Zhang WM, Yao Y, Yang T, Wang XY, Zhu ZY, Xu WT, Lin HX, Gao ZB, Zhou H, Yang CG, Cui YM..  (2018)  The synthesis and antistaphylococcal activity of N-sulfonaminoethyloxime derivatives of dehydroabietic acid.,  28  (10): [PMID:29650291] [10.1016/j.bmcl.2018.03.062]

Source

Source(1):

• Scientific Literature