(1R,3aR,4S,5S,7aR)-1-((R)-1,5-Dimethylhexyl)-5-[(5-iodofuran-2-ylmethyl)-amino]-3a,7a-dimethyloctahydroinden-4-ol

ID: ALA2337346

PubChem CID: 71582967

Max Phase: Preclinical

Molecular Formula: C24H40INO2

Molecular Weight: 501.49

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(I)o3)CC[C@]12C

Standard InChI:  InChI=1S/C24H40INO2/c1-16(2)7-6-8-17(3)19-11-13-24(5)22(27)20(12-14-23(19,24)4)26-15-18-9-10-21(25)28-18/h9-10,16-17,19-20,22,26-27H,6-8,11-15H2,1-5H3/t17-,19-,20+,22-,23-,24+/m1/s1

Standard InChI Key:  PWVPUSOWIGEZGE-DHXQKRHUSA-N

Molfile:  

     RDKit          2D

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   23.3188   -2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0241   -3.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0241   -1.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7294   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7304   -2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5070   -2.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9860   -2.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5053   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7221   -1.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7262   -3.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7568   -0.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3193   -1.6468    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.5559   -0.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2091   -0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0239   -3.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6117   -3.1295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1035   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9026   -1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4502   -1.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2493   -1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1987   -2.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9034   -2.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1963   -3.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4510   -2.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9050   -3.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3147   -4.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1137   -3.9487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9835   -4.8670    0.0000 I   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 24  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2337346

   (1R,3aR,4S,5S,7aR)-5-[(5-iodofuran-2-yl)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: 501.49

Molecular Weight (Monoisotopic): 501.2104

AlogP: 6.38

#Rotatable Bonds: 8

Polar Surface Area: 45.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.36

CX LogP: 6.66

CX LogD: 5.65

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: 1.07

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