ID: ALA1908008

Max Phase: Preclinical

Molecular Formula: C27H46O2

Molecular Weight: 402.66

Molecule Type: Small molecule

Representations

Synonyms (1): 19-Hydroxycholesterol
Synonyms from Alternative Forms(1):

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

Standard InChI:  InChI=1S/C27H46O2/c1-18(2)6-5-7-19(3)23-10-11-24-22-9-8-20-16-21(29)12-15-27(20,17-28)25(22)13-14-26(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t19-,21+,22+,23-,24+,25+,26-,27-/m1/s1

Standard InChI Key:  YRWIUNJQYGATHV-FTLVODPJSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 402.66

Molecular Weight (Monoisotopic): 402.3498

AlogP: 6.36

#Rotatable Bonds: 6

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: 5.83

CX LogD: 5.83

Aromatic Rings: 0

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: 2.65

References

1. Tukey RH, Strassburg CP..  (2000)  Human UDP-glucuronosyltransferases: metabolism, expression, and disease.,  40  (1): [PMID:10836148] [10.1146/annurev.pharmtox.40.1.581]

2. 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]

3. 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]

4. Sagimori I, Yoshioka H, Hashimoto Y, Ohgane K..  (2020)  Luciferase-based HMG-CoA reductase degradation assay for activity and selectivity profiling of oxy(lano)sterols.,  28  (3): [PMID:31902650] [10.1016/j.bmc.2019.115298]

Source

Source(1):

• Scientific Literature