(1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1-(1H-imidazol-1-yl)propan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-methylenecyclohexane-1,3-diol

ID: ALA3360784

PubChem CID: 101563630

Max Phase: Preclinical

Molecular Formula: C25H36N2O2

Molecular Weight: 396.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1[C@H](O)CC(=C/C=C2\CCC[C@]3(C)[C@@H]([C@H](C)Cn4ccnc4)CC[C@@H]23)C[C@H]1O

Standard InChI:  InChI=1S/C25H36N2O2/c1-17(15-27-12-11-26-16-27)21-8-9-22-20(5-4-10-25(21,22)3)7-6-19-13-23(28)18(2)24(29)14-19/h6-7,11-12,16-17,21-24,28-29H,2,4-5,8-10,13-15H2,1,3H3/b20-7+/t17-,21-,22+,23-,24-,25-/m1/s1

Standard InChI Key:  FHDAHQFLZOYWQM-QDYAWOJKSA-N

Molfile:  

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   27.1921   -0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1015   -1.6086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2809   -1.7248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2703   -7.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9280   -2.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.2539   -2.2737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 31 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3360784

   (1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2S)-1-imidazol-1-ylpropan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-methylidenecyclohexane-1,3-diol

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: 396.58

Molecular Weight (Monoisotopic): 396.2777

AlogP: 4.66

#Rotatable Bonds: 4

Polar Surface Area: 58.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.53

CX LogP: 3.22

CX LogD: 3.18

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: 1.35

References

1. Ferla S, Aboraia AS, Brancale A, Pepper CJ, Zhu J, Ochalek JT, DeLuca HF, Simons C..  (2014)  Small-molecule inhibitors of 25-hydroxyvitamin D-24-hydroxylase (CYP24A1): synthesis and biological evaluation.,  57  (18): [PMID:25148392] [10.1021/jm5009314]

2. Bruno, Robert D RD and Njar, Vincent C O VC.  2007-08-01  Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.  [PMID:17544277]

3. Taban, Ismail M IM, Zhu, Jinge J, DeLuca, Hector F HF and Simons, Claire C.  2017-08-01  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.  [PMID:28601511]

Source

Source(1):

• Scientific Literature