Structure Database (LMSD)

Common Name
Androstenediol
Systematic Name
androst-5-en-3β,17β-diol
Synonyms
LM ID
LMST02020005
Formula
C19H30O2
Exact Mass
Calculate m/z
290.22458
Sum Composition
ST 19:1;O2
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

5-Androstenediol is an analytical reference standard categorized as an anabolic androgenic steroid.1 5-Androstenediol is a precursor in the biosynthesis of testosterone (ISO60154 | ISO00154 | 15645).2 5-Androstenediol is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Inaba, M., and Nakao, T. Conversion of 4-androstenediol and 5-androstenediol to testosterone, and conversion of dehydroepiandrosterone to 4-androstenediol by rat testis in vitro. Endocrinol. Jpn. 13(2), 160-172 (1966).
2. Poucke, C.V., Detavernier, C., Van Cauwenberghe, R., et al. Determination of anabolic steroids in dietary supplements by liquid chromatography-tandem mass spectrometry. Anal. Chim. Acta 586(1-2), 35-42 (2007).

String Representations

InChiKey (Click to copy)
QADHLRWLCPCEKT-LOVVWNRFSA-N
InChi (Click to copy)
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

Wikipedia
Androstenediol
KEGG ID
C04295
HMDB ID
HMDB0003818
CHEBI ID
2710
LIPIDBANK ID
SST0026
PubChem CID
10634
SwissLipids ID
SLM:000485341
Cayman ID
34159
PDB ID
B81

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 302.76
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 4.24
Molar Refractivity 84.74

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Updated at
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