20S-hydroxyvitamin D3

ID: ALA2036072

Chembl Id: CHEMBL2036072

PubChem CID: 46938678

Max Phase: Preclinical

Molecular Formula: C27H44O2

Molecular Weight: 400.65

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 20S-Hydroxyvitamin D3 | (20S)-hydroxyvitamin D3|(1~{S},3~{Z})-3-[(2~{E})-2-[(1~{S},3~{a}~{S},7~{a}~{S})-7~{a}-methyl-1-[(2~{S})-6-methyl-2-oxidanyl-heptan-2-yl]-2,3,3~{a},5,6,7-hexahydro-1~{H}-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol|20S-Hydroxyvitamin D3|20S-hydroxycholecalciferol|SCHEMBL1892282|CHEMBL2036072|CHEBI:90983|Q27162978|(3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,20-diol|AYT

Canonical SMILES:  C=C1CC[C@H](O)C/C1=C/C=C1\CCC[C@@]2(C)[C@H]1CC[C@@H]2[C@@](C)(O)CCCC(C)C

Standard InChI:  InChI=1S/C27H44O2/c1-19(2)8-6-17-27(5,29)25-15-14-24-21(9-7-16-26(24,25)4)11-12-22-18-23(28)13-10-20(22)3/h11-12,19,23-25,28-29H,3,6-10,13-18H2,1-2,4-5H3/b21-11+,22-12-/t23-,24-,25-,26-,27-/m0/s1

Standard InChI Key:  IQEQEOBGZMEDBQ-LBRHRNEPSA-N

Alternative Forms

1. Parent:

   

   ALA2036072

   (20S)-hydroxyvitamin D3

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: 400.65

Molecular Weight (Monoisotopic): 400.3341

AlogP: 6.73

#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: 5.81

CX LogD: 5.81

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 2.63

References

1. Lu Y, Chen J, Janjetovic Z, Michaels P, Tang EK, Wang J, Tuckey RC, Slominski AT, Li W, Miller DD..  (2012)  Design, synthesis, and biological action of 20R-hydroxyvitamin D3.,  55  (7): [PMID:22404326] [10.1021/jm201478e]

Source

Source(1):

• Scientific Literature