(3S,8S,9S,10R,13R,14S,17R)-17-((R)-5-hydroxy-5-methylhexan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

ID: ALA2419157

Chembl Id: CHEMBL2419157

Cas Number: 35882-85-0

PubChem CID: 22215776

Max Phase: Preclinical

Molecular Formula: C26H44O2

Molecular Weight: 388.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](CCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C26H44O2/c1-17(10-13-24(2,3)28)21-8-9-22-20-7-6-18-16-19(27)11-14-25(18,4)23(20)12-15-26(21,22)5/h6,17,19-23,27-28H,7-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,25+,26-/m1/s1

Standard InChI Key:  USOOWRCOYYNZPU-LXVLQKCJSA-N

Alternative Forms

1. Parent:

   

   ALA2419157

   26,27-Dinorergost-5-ene-3,24-diol, (3beta)-

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: 388.64

Molecular Weight (Monoisotopic): 388.3341

AlogP: 6.11

#Rotatable Bonds: 4

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 2.77

References

1. Karaki F, Ohgane K, Dodo K, Hashimoto Y..  (2013)  Structure-activity relationship studies of Niemann-Pick type C1-like 1 (NPC1L1) ligands identified by screening assay monitoring pharmacological chaperone effect.,  21  (17): [PMID:23830695] [10.1016/j.bmc.2013.06.022]

2. Ohgane K, Karaki F, Noguchi-Yachide T, Dodo K, Hashimoto Y..  (2014)  Structure-activity relationships of oxysterol-derived pharmacological chaperones for Niemann-Pick type C1 protein.,  24  (15): [PMID:24928400] [10.1016/j.bmcl.2014.05.064]

3. La DS, Salituro FG, Martinez Botella G, Griffin AM, Bai Z, Ackley MA, Dai J, Doherty JJ, Harrison BL, Hoffmann EC, Kazdoba TM, Lewis MC, Quirk MC, Robichaud AJ..  (2019)  Neuroactive Steroid N-Methyl-d-aspartate Receptor Positive Allosteric Modulators: Synthesis, SAR, and Pharmacological Activity.,  62  (16): [PMID:31390523] [10.1021/acs.jmedchem.9b00591]

Source

Source(1):

• Scientific Literature