(1R,3aR,4R,5S,7aR)-5-(2,4-Dichlorobenzylamino)-1-((R)-1,5-dimethylhexyl)-3a,7a-dimethyloctahydroinden-4-ol

ID: ALA2336929

PubChem CID: 71583189

Max Phase: Preclinical

Molecular Formula: C26H41Cl2NO

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H](O)[C@@H](NCc3ccc(Cl)cc3Cl)CC[C@]12C

Standard InChI:  InChI=1S/C26H41Cl2NO/c1-17(2)7-6-8-18(3)21-11-13-26(5)24(30)23(12-14-25(21,26)4)29-16-19-9-10-20(27)15-22(19)28/h9-10,15,17-18,21,23-24,29-30H,6-8,11-14,16H2,1-5H3/t18-,21-,23+,24+,25-,26+/m1/s1

Standard InChI Key:  QLBCKJMQAOAUPS-UBDPOSNJSA-N

Molfile:  

     RDKit          2D

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   12.7408  -29.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4460  -29.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1513  -28.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1524  -29.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9289  -29.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4079  -28.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9272  -27.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1787  -27.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7412  -27.9785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9778  -27.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6311  -26.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4458  -30.2732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0336  -29.4612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5254  -27.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3245  -27.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8721  -28.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6712  -27.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6206  -28.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3253  -29.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6182  -29.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9125  -29.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2058  -29.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2066  -30.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9199  -30.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6236  -30.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3337  -30.6828    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5000  -30.6928    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  5 10  1  1
  6 11  1  6
  9 12  1  0
  9 13  1  6
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  3 16  1  1
  2 17  1  1
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 17 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 29 30  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336929

   (1R,3aR,4R,5S,7aR)-5-[(2,4-dichlorophenyl)methylamino]-3a,7a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7-hexahydro-1H-inden-4-ol

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: 454.53

Molecular Weight (Monoisotopic): 453.2565

AlogP: 7.49

#Rotatable Bonds: 8

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.51

CX LogP: 7.86

CX LogD: 6.71

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: 0.77

References

1. König M, Müller C, Bracher F..  (2013)  Stereoselective synthesis of a new class of potent and selective inhibitors of human Δ8,7-sterol isomerase.,  21  (7): [PMID:23433667] [10.1016/j.bmc.2013.01.041]

Source

Source(1):

• Scientific Literature