(1R,3aR,4R,5S,7aR)-1-((R)-1,5-Dimethylhexyl)-5-[(furan-3-ylmethyl)-amino]-3a,7a-dimethyloctahydroinden-4-ol

ID: ALA2336927

PubChem CID: 71583187

Max Phase: Preclinical

Molecular Formula: C24H41NO2

Molecular Weight: 375.60

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](NCc3ccoc3)CC[C@]12C

Standard InChI:  InChI=1S/C24H41NO2/c1-17(2)7-6-8-18(3)20-9-12-24(5)22(26)21(10-13-23(20,24)4)25-15-19-11-14-27-16-19/h11,14,16-18,20-22,25-26H,6-10,12-13,15H2,1-5H3/t18-,20-,21+,22+,23-,24+/m1/s1

Standard InChI Key:  BDZTXNUVDKOFAO-APRANIPNSA-N

Molfile:  

     RDKit          2D

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   21.5483  -23.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -24.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -22.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9588  -22.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9599  -23.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7364  -23.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2154  -23.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7347  -22.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9515  -22.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9556  -24.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9862  -21.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5488  -22.5924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.7853  -21.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4386  -21.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2533  -24.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8411  -24.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3329  -22.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1320  -22.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6796  -22.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4787  -22.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4281  -23.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1328  -23.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4257  -24.0772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6804  -23.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1345  -24.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5441  -25.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3431  -24.8944    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
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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  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336927

   (1R,3aR,4R,5S,7aR)-5-(furan-3-ylmethylamino)-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: 375.60

Molecular Weight (Monoisotopic): 375.3137

AlogP: 5.78

#Rotatable Bonds: 8

Polar Surface Area: 45.40

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.66

CX LogP: 5.79

CX LogD: 4.52

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: 1.54

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