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

ID: ALA3360785

PubChem CID: 71470821

Max Phase: Preclinical

Molecular Formula: C27H43NO2

Molecular Weight: 413.65

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)CCCNC4CC4)CC[C@@H]23)C[C@H]1O

Standard InChI:  InChI=1S/C27H43NO2/c1-18(6-5-15-28-22-10-11-22)23-12-13-24-21(7-4-14-27(23,24)3)9-8-20-16-25(29)19(2)26(30)17-20/h8-9,18,22-26,28-30H,2,4-7,10-17H2,1,3H3/b21-9+/t18-,23-,24+,25-,26-,27-/m1/s1

Standard InChI Key:  FLEHQRTTWKDNGI-WSGFCWAJSA-N

Molfile:  

     RDKit          2D

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    7.4832  -11.3969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878  -15.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878  -16.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004  -16.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130  -16.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3004  -14.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734  -16.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7275  -16.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0155  -13.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155  -12.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0219  -11.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050  -11.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3014  -12.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5157  -11.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271  -13.1796    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271  -10.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728  -10.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5806  -10.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220   -9.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1313  -10.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9391  -10.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2935  -11.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004  -17.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0767  -11.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9113  -10.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3108  -11.0693    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
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  5  6  1  0
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  3  8  1  6
  5  9  1  1
  7 10  2  0
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 11 12  2  0
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 12 15  1  0
 16 13  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 17 21  1  6
 16 22  1  1
 20 23  1  0
 23 24  1  0
 23 25  1  6
 24 26  1  0
 26 27  1  0
 27  1  1  0
  1 28  1  0
  4 29  2  0
 30 28  1  0
 31 30  1  0
 28 31  1  0
 20 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3360785

   (1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-5-(cyclopropylamino)pentan-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: 413.65

Molecular Weight (Monoisotopic): 413.3294

AlogP: 5.30

#Rotatable Bonds: 7

Polar Surface Area: 52.49

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.30

CX LogP: 4.23

CX LogD: 1.49

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: 1.84

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