17beta-Hydroxycholesterol

ID: ALA1908007

PubChem CID: 57024754

Max Phase: Preclinical

Molecular Formula: C27H46O2

Molecular Weight: 402.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 17Beta-Hydroxycholesterol | 17Beta-Hydroxycholesterol|SCHEMBL6387160|CHEMBL1908007

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C27H46O2/c1-18(2)7-6-8-19(3)27(29)16-13-24-22-10-9-20-17-21(28)11-14-25(20,4)23(22)12-15-26(24,27)5/h9,18-19,21-24,28-29H,6-8,10-17H2,1-5H3/t19-,21+,22-,23+,24+,25+,26+,27-/m1/s1

Standard InChI Key:  JXWKLNIPHOFKQD-CMOCTXKRSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
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  -12.6107    0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -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
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  -10.4673    3.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
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  -10.4673    2.3572    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1817    1.1197    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
   -8.9682    3.8496    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
  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
 16 17  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  1
 17 25  1  0
 25 26  1  0
 25 27  1  6
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1908007

   17Beta-Hydroxycholesterol

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: 402.66

Molecular Weight (Monoisotopic): 402.3498

AlogP: 6.50

#Rotatable Bonds: 5

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: 0.14

CX LogP: 6.03

CX LogD: 6.03

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 2.31

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]

Source

Source(1):

• Scientific Literature