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

ID: ALA2336936

PubChem CID: 71718895

Max Phase: Preclinical

Molecular Formula: C25H45NO

Molecular Weight: 375.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)C(=O)[C@@H](N3CCC(C)CC3)CC[C@]12C

Standard InChI:  InChI=1S/C25H45NO/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/h18-22H,7-17H2,1-6H3/t20-,21-,22+,24-,25+/m1/s1

Standard InChI Key:  MLPIILVXHXMFMC-QZJHCZKLSA-N

Molfile:  

     RDKit          2D

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   13.2278   -2.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2278   -3.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9330   -3.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9330   -2.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6383   -2.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6394   -3.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4159   -3.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8949   -2.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4142   -2.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6310   -1.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6352   -4.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6657   -1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2283   -2.1585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4648   -1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1181   -0.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9328   -4.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5207   -3.6412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0124   -1.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8115   -1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3591   -2.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1582   -2.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1076   -3.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8150   -3.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1100   -3.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1070   -4.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8151   -4.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5263   -4.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3983   -4.8601    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  2  0
  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:

   

   ALA2336936

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

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: 375.64

Molecular Weight (Monoisotopic): 375.3501

AlogP: 6.33

#Rotatable Bonds: 6

Polar Surface Area: 20.31

Molecular Species: BASE

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.69

CX LogP: 7.21

CX LogD: 5.90

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: 1.48

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