Bovine Metabolome Database: Showing metabocard for Mesterolone (BMDB0006036)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:19:50 UTC

Update Date

2020-04-22 15:16:44 UTC

BMDB ID

BMDB0006036

Secondary Accession Numbers

BMDB06036

Metabolite Identification

Common Name

Mesterolone

Description

Mesterolone, also known as proviron or vistimon, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, mesterolone is considered to be a steroid. Based on a literature review a significant number of articles have been published on Mesterolone.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Proviron	MeSH
Vistimon	MeSH
SH-723Mesterolone	ChEMBL, HMDB
(1a,5a,17b)-17-Hydroxy-1-methyl-androstan-3-one	HMDB
17b-Hydroxy-1a-methyl-5a-androstan-3-one	HMDB
1a-Methyl-17b-hydroxy-5a-androstan-3-one	HMDB
1a-Methyl-5a-androstan-17b-ol-3-one	HMDB
1a-Methyl-5a-dihydrotestosterone	HMDB
Androviron	HMDB
Mesteranum	HMDB
Mestoranum	HMDB
Provirone 25	HMDB
SH 723	HMDB
Testiwop	HMDB
Jenapharm brand OF mesterolone	MeSH, HMDB
Schering brand OF mesterolone	MeSH, HMDB
Mesterolone jenapharm brand	MeSH, HMDB
Mesterolone schering brand	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

proviron

CAS Registry Number

1424-00-6

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C

InChI Identifier

InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

InChI Key

UXYRZJKIQKRJCF-TZPFWLJSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxosteroid
3-oxo-5-alpha-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C19 steroids (androgens) and derivatives (LMST02020107 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	204 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.75	ALOGPS
logP	3.7	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.15 m³·mol⁻¹	ChemAxon
Polarizability	36.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-0290000000-6711f2fd4cedd8b8ebe9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03dj-2029000000-d49394c5377c1d882480	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0195000000-44dcd42d89336ba3b750	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0291000000-412b4cbbe59f184a654f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052o-1790000000-09c00b6e9a55d7df2300	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-e48e22f298cdef547931	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-231f9da9a32e84b9b604	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007c-3090000000-69a7d162e0bb3918d70b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-f9d10b76ade80bd401ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-f9d10b76ade80bd401ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udj-0094000000-7cb92f7f18ba37686418	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0079000000-2860312a6cf9370e1957	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0960000000-9c3e64e51c3a7c290a00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3910000000-a9991caf02a89a982090	View in MoNA