(1R,4S,5S,7aR)-5-(3-Chlorobenzylamino)-1-((R)-1,5-dimethylhexyl)-7a-methyloctahydroinden-4-ol

ID: ALA2336920

PubChem CID: 71582968

Max Phase: Preclinical

Molecular Formula: C26H42ClNO

Molecular Weight: 420.08

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](NCc3cccc(Cl)c3)CC[C@]12C

Standard InChI:  InChI=1S/C26H42ClNO/c1-18(2)8-6-9-19(3)22-12-14-26(5)24(29)23(13-15-25(22,26)4)28-17-20-10-7-11-21(27)16-20/h7,10-11,16,18-19,22-24,28-29H,6,8-9,12-15,17H2,1-5H3/t19-,22-,23+,24-,25-,26+/m1/s1

Standard InChI Key:  XLTRIZPFRLTWED-DQTYAKANSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.2387   -8.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387   -9.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -9.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -8.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6492   -8.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6503   -9.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4268   -9.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9058   -9.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251   -8.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6419   -7.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460  -10.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6766   -7.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392   -8.3659    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4757   -7.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290   -6.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9437  -10.6606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5315   -9.8486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0233   -8.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8224   -7.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3700   -8.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1691   -8.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1185   -9.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8232   -9.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161   -9.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104   -9.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038   -9.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045  -10.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178  -11.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1215  -10.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4218  -11.8943    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
 12 14  1  0
 12 15  1  6
  3 16  1  6
  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
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336920

   (1R,3aR,4S,5S,7aR)-5-[(3-chlorophenyl)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: 420.08

Molecular Weight (Monoisotopic): 419.2955

AlogP: 6.84

#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: 9.16

CX LogP: 7.25

CX LogD: 5.50

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: 0.86

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