19-Hydroxycholesterol

ID: ALA1908008

Cas Number: 561-63-7

PubChem CID: 6453303

Product Number: H345887, Order Now?

Max Phase: Preclinical

Molecular Formula: C27H46O2

Molecular Weight: 402.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 19-Hydroxycholesterol | 19-Hydroxycholesterol|561-63-7|19-Hydroxy Cholesterol|(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol|Cholest-5-en-3beta,19-diol|Cholest-5-ene-3,19-diol, (3beta)-|5-Cholesten-3beta,19-diol|Cholest-5-ene-3,19-diol|SCHEMBL335858|CHEMBL1908008|Cholest-5-ene-3,19-diol #|DTXSID40971482|CHEBI:166800|Cholest-5-en-3.beta.,19-diol|YRWIUNJQYGATHV-FTLVODPJSA-N|Cholest-5-eShow More⌵

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

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
  -13.3252    0.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6107    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8962    0.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8962    1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6107    1.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3252    1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1817    1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4673    1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4673    0.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1818    0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1818    2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4673    3.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7528    2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7528    1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9682    1.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4833    2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9682    3.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6666    3.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6483    0.9502    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6013    1.0322    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0478    2.4447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8962    2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0397    0.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3848    3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5598    3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7006    4.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1473    4.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3223    4.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9098    5.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    5.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3223    5.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6107    2.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9713    2.9461    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  4  7  1  0
  3  4  1  0
 10  3  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
  8  7  1  0
 14  8  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 13 18  1  1
 14 19  1  6
  8 20  1  1
  7 21  1  6
  4 22  1  1
  1 23  1  1
 17 24  1  0
 24 25  1  0
 24 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 22 32  1  0
 17 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1908008

   19-Hydroxy Cholesterol

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

Calculated 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: ┄

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