cis-(1R,3aR,4R,5S,7aR)-1-((R)-1,5-Dimethylhexyl)-3a,7adimethyl-5-(4-methylpiperazine-1-yl)-octahydroinden-4-ol

ID: ALA2336941

PubChem CID: 71718896

Max Phase: Preclinical

Molecular Formula: C25H47NO

Molecular Weight: 377.66

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](N3CCC(C)CC3)CC[C@]12C

Standard InChI:  InChI=1S/C25H47NO/c1-18(2)8-7-9-20(4)21-10-14-25(6)23(27)22(11-15-24(21,25)5)26-16-12-19(3)13-17-26/h18-23,27H,7-17H2,1-6H3/t20-,21-,22+,23+,24-,25+/m1/s1

Standard InChI Key:  HBYGMFZKWCCWDK-LUXCBIKGSA-N

Molfile:  

     RDKit          2D

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   13.1336  -16.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1336  -16.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8457  -17.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8457  -15.7004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5577  -16.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5588  -16.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3428  -17.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8263  -16.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3411  -15.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5504  -15.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5545  -17.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5949  -15.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1629  -15.8587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4017  -14.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0421  -14.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8454  -18.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4198  -17.3556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9546  -15.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7614  -15.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3142  -15.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1210  -15.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0603  -16.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7074  -16.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9957  -17.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9925  -18.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7075  -18.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4254  -18.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2771  -18.5862    0.0000 C   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
 12 14  1  0
 12 15  1  6
  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
 17 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336941

   (1R,3aR,4R,5S,7aR)-3a,7a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-5-(4-methylpiperidin-1-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: 377.66

Molecular Weight (Monoisotopic): 377.3658

AlogP: 6.13

#Rotatable Bonds: 6

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.45

CX LogP: 6.45

CX LogD: 3.52

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 1.58

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