(R)-4-((1R,3aS,7aR,E)-4-((Z)-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)pentyl 4-methylbenzenesulfonate

ID: ALA3360783

PubChem CID: 102263901

Max Phase: Preclinical

Molecular Formula: C31H44O4S

Molecular Weight: 512.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@]2(C)[C@@H]([C@H](C)CCCOS(=O)(=O)c3ccc(C)cc3)CC[C@@H]12

Standard InChI:  InChI=1S/C31H44O4S/c1-22-9-15-28(16-10-22)36(33,34)35-20-6-7-24(3)29-17-18-30-25(8-5-19-31(29,30)4)12-13-26-21-27(32)14-11-23(26)2/h9-10,12-13,15-16,24,27,29-30,32H,2,5-8,11,14,17-21H2,1,3-4H3/b25-12+,26-13-/t24-,27+,29-,30+,31-/m1/s1

Standard InChI Key:  AZKXCNCXNFDOFT-MXCOKSJOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3360783

   [(4R)-4-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]pentyl] 4-methylbenzenesulfonate

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: 512.76

Molecular Weight (Monoisotopic): 512.2960

AlogP: 7.29

#Rotatable Bonds: 8

Polar Surface Area: 63.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.08

CX LogD: 7.08

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: 1.63

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