Structure Database (LMSD)

Common Name
6beta-hydroxytestosterone
Systematic Name
6β,17β-dihydroxyandrost-4-en-3-one
Synonyms
LM ID
LMST02020054
Formula
C19H28O3
Exact Mass
Calculate m/z
304.203845
Sum Composition
ST 19:2;O3
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

CYP3A4 and CYP3A5 are cytochrome P450 enzymes whose expression is induced by glucocorticoids and certain xenobiotics, including many drugs and chemical carcinogens.1 They mediate the metabolism of xenobiotics as well as certain endobiotics, including steroid hormones.2 6β-hydroxy Testosterone is a major metabolite produced from testosterone by the actions of CYP3A4 and CYP3A5, accounting for 75-80% of all metabolites formed from testosterone.2,3 The biological effects of 6β-hydroxy testosterone have been poorly studied.

This information has been provided by Cayman Chemical

References

1. Capdevila, J.H., Karara, A., Waxman, D.J., et al. Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. The Journal of Biological Chemisty 265(19), 10865-10871 (1990).
2. Cooper, B.W., Cho, T.M., Thompson, P.M., et al. Phthalate induction of CYP3A4 is dependent on glucocorticoid regulation of PXR expression. Toxicol. Sci. 103(2), 268-277 (2008).
3. Draper, A.J., Madan, A., Smith, K., et al. Development of a non-high pressure liquid chromatography assay to determine testosterone hydroxylase (CYP3A) activity in human liver microsomes. Drug Metab. Dispos. 26(4), 299-304 (1998).

String Representations

InChiKey (Click to copy)
XSEGWEUVSZRCBC-ZVBLRVHNSA-N
InChi (Click to copy)
InChI=1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,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])C[C@@H](O)C2=CC(=O)C1

Other Databases

KEGG ID
C14497
HMDB ID
HMDB0006259
CHEBI ID
34477
PubChem CID
65543
SwissLipids ID
SLM:000485344
Cayman ID
10008519

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 4
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 308.91
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 3.42
Molar Refractivity 85.13

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Updated at
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