Structure Database (LMSD)

Systematic Name
5a-Androstan-3b-ol
Synonyms
LM ID
LMST02020095
Formula
C19H32O
Exact Mass
Calculate m/z
276.245315
Sum Composition
ST 19:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C19 steroids (androgens) and derivatives [ST0202]

Biological Context

5α-Androstan-3β-ol is a steroidal androgen.1 It binds to the androgen receptor in a cell-free assay (IC50 = 1.7 µM) and activates the pregnane X receptor (PXR) in HepG2 cells in a reporter assay (EC50 = 0.8 µM).1,2 5α-Androstan-3β-ol also inhibits the androst-4-ene-3,17-dione hydroxylase activities of 16α- and 6β-hydroxylase but not 16β- or 7α-hydroxylase (IC50s = 70, 110, >150, and >150 µM, respectively).3 It decreases testis weight and sperm production in mice when administered at a dose of 30 mg/kg.4

This information has been provided by Cayman Chemical

References

1. Martinot, E., Baptissart, M., Véga, A., et al. Bile acid homeostasis controls CAR signaling pathways in mouse testis through FXRalpha. Sci. Rep. 7, 42182 (2017).
2. Murray, M., and Mehta, I. Structure-activity relationships in the in vitro modulation of rat hepatic microsomal androst-4-ene-3,17-dione hydroxylase activities by derivatives of 5α- and 5β-androstane. J. Steroid Biochem. 35(3-4), 465-471 (1990).
3. Ekins, S., Chang, C., Mari, S., et al. Human pregnane X receptor antagonists and agonists define molecular requirements for different binding sites. Mol. Pharmacol. 72(3), 592-603 (2007).
4. Fang, H., Tong, W., Branham, W.S., et al. Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. Chem. Res. Toxicol. 16(10), 1338-1358 (2003).

String Representations

InChiKey (Click to copy)
DJTOLSNIKJIDFF-LOVVWNRFSA-N
InChi (Click to copy)
InChI=1S/C19H32O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h13-17,20H,3-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
SMILES (Click to copy)
[C@@]12([H])CC[C@@]3([H])C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)CCC[C@@]21[H]

Other Databases

HMDB ID
HMDB0005830
CHEBI ID
177437
PubChem CID
92877
Cayman ID
34719

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 296.61
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 5.07
Molar Refractivity 82.86

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Created at
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Updated at
9th Jun 2022