Milk Composition Database: Showing metabocard for Testosterone (BMDB0000234)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:09 UTC

Update Date

2020-06-04 23:02:41 UTC

MCDB ID

BMDB0000234

Secondary Accession Numbers

BMDB00234

Metabolite Identification

Common Name

Testosterone

Description

Testosterone 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, testosterone is considered to be a steroid lipid molecule. Testosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Testosterone exists in all living organisms, ranging from bacteria to humans. Testosterone participates in a number of enzymatic reactions, within cattle. In particular, Testosterone can be converted into 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In addition, Testosterone can be converted into androstenedione; which is catalyzed by the enzyme testosterone 17-beta-dehydrogenase 3. In cattle, testosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Testosterone is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17beta-Hydroxy-4-androsten-3-one	ChEBI
4-Androsten-17beta-ol-3-one	ChEBI
Androderm	ChEBI
Testosteron	ChEBI
Testosterona	ChEBI
Testosteronum	ChEBI
Androgel	Kegg
Axiron	Kegg
Striant	Kegg
Testim	Kegg
17b-Hydroxy-4-androsten-3-one	Generator
17Β-hydroxy-4-androsten-3-one	Generator
4-Androsten-17b-ol-3-one	Generator
4-Androsten-17β-ol-3-one	Generator
(+)-Testosterone	HMDB
(+-)-8-Iso-testosterone	HMDB
(+-)-Retrotestosterone	HMDB
(+-)-Testosterone	HMDB
(17b)-17-Hydroxy-androst-4-en-3-one	HMDB
13-Iso-testosterone	HMDB
17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one	HMDB
17-Hydroxy-androst-4-en-3-one	HMDB
17-Hydroxy-D4-androsten-3-one	HMDB
17a-Hydroxy-(13a)-androst-4-en-3-one	HMDB
17a-Hydroxy-13a-androst-4-en-3-one	HMDB
17a-Hydroxy-14b-androst-4-en-3-one	HMDB
17a-Hydroxy-androst-4-en-3-one	HMDB
17b-Hydroxy-(10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(13a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(8a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(8a,10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(9b)-androst-4-en-3-one	HMDB
17b-Hydroxy-(9b,10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-13a-androst-4-en-3-one	HMDB
17b-Hydroxy-8a-androst-4-en-3-one	HMDB
17b-Hydroxy-androst-4-en-3-ON	HMDB
17b-Hydroxy-androst-4-en-3-one	HMDB
17b-Hydroxy-D4-androsten-3-one	HMDB
17b-Hydroxyandrost-4-en-3-one	HMDB
17b-Hydroxyandrost-4-ene-3-one	HMDB
17b-Testosterone	HMDB
4-Androsten-3-one-17b-ol	HMDB
8-Iso-testosterone	HMDB
9b,10a-Testosterone	HMDB
9b-Testosterone	HMDB
Androlin	HMDB
Andronaq	HMDB
Andropatch	HMDB
Androst-4-en-17b-ol-3-one	HMDB
Androst-4-ene-17b-ol-3-one	HMDB
Andrusol	HMDB
Cristerona T	HMDB
D4-Androsten-17b-ol-3-one	HMDB
Epitestosteron	HMDB
Geno-cristaux gremy	HMDB
Homosteron	HMDB
Homosterone	HMDB
Lumitestosteron	HMDB
Mertestate	HMDB
Neotestis	HMDB
Oreton	HMDB
Orquisteron	HMDB
Perandren	HMDB
Percutacrine androgenique	HMDB
Primotest	HMDB
Primoteston	HMDB
rac-17b-Hydroxy-(13a)androst-4-en-3-one	HMDB
rac-17b-Hydroxy-(8a)-androst-4-en-3-one	HMDB
rac-17b-Hydroxy-(9b,10a)androst-4-en-3-one	HMDB
rac-17b-Hydroxy-androst-4-en-3-one	HMDB
Relibra	HMDB
Retrotestosterone	HMDB
Sustanon	HMDB
Sustanone	HMDB
Sustason 250	HMDB
Synandrol F	HMDB
Teslen	HMDB
Testandrone	HMDB
Testiculosterone	HMDB
Testobase	HMDB
Testoderm	HMDB
Testogel	HMDB
Testolent	HMDB
Testolin	HMDB
Testopropon	HMDB
Testosteroid	HMDB
Testoviron schering	HMDB
Testoviron T	HMDB
Testro aq	HMDB
Testrone	HMDB
Testryl	HMDB
Tostrelle	HMDB
Tostrex	HMDB
Viatrel	HMDB
Virormone	HMDB
Virosterone	HMDB
Androtop	HMDB
CEPA brand OF testosterone	HMDB
Histerone	HMDB
SmithKline beecham brand OF testosterone	HMDB
Solvay brand OF testosterone	HMDB
Sterotate	HMDB
17-beta-Hydroxy-8 alpha-4-androsten-3-one	HMDB
AstraZeneca brand OF testosterone	HMDB
Bartor brand OF testosterone	HMDB
Dr. kade brand OF testosterone	HMDB
Ferring brand OF testosterone	HMDB
Hauck brand OF testosterone	HMDB
Pasadena brand OF testosterone	HMDB
Testosterone sulfate	HMDB
Ulmer brand OF testosterone	HMDB
Unimed brand OF testosterone	HMDB
Watson brand OF testosterone	HMDB
17-beta-Hydroxy-4-androsten-3-one	HMDB
8 Isotestosterone	HMDB
8-Isotestosterone	HMDB
Auxilium pharmaceuticals inc. brand OF testosterone	HMDB
Faulding brand OF testosterone	HMDB
Paladin brand OF testosterone	HMDB
Schering brand OF testosterone	HMDB
17 beta Hydroxy 4 androsten 3 one	HMDB
17 beta Hydroxy 8 alpha 4 androsten 3 one	HMDB
GlaxoSmithKline brand OF testosterone	HMDB
Ortho brand OF testosterone	HMDB
Testopel	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

58-22-0

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

MUMGGOZAMZWBJJ-DYKIIFRCSA-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-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:17347 )
17beta-hydroxy steroid (CHEBI:17347 )
androstanoid (CHEBI:17347 )
androstane (C00535 )
C19 steroids (androgens) and derivatives (C00535 )
Androstane and derivatives (C00535 )
Androgens (C00535 )
C19 steroids (androgens) and derivatives (LMST02020002 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 mg/mL	Not Available
LogP	3.32	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.99	ALOGPS
logP	3.37	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.09	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	84.43 m³·mol⁻¹	ChemAxon
Polarizability	33.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0597-7920000000-dde7fba02fcbcec2d665	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fs-4920000000-ccd839134de79f179f9e	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ds-0950000000-c65fc8043083ad93d169	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-0390000000-09e2a725ebd92c93dc88	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001j-3349000000-75c3f3e0341bb42eb819	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-914b212f1dbb7fb7b1ac	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-9800000000-d2e38d44d2f16d0a4203	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9300000000-6830823fa12b40e784a2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-0597-7920000000-dde7fba02fcbcec2d665	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive	splash10-05fs-4920000000-ccd839134de79f179f9e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-00ds-0950000000-48c1f79091d708072f30	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4j-6900000000-3d818ffe03ecd499e078	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4j-7900000000-6db3d23d98d548cbbfaa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ukj-2690000000-14b953cb16c53d1e2744	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0uka-2790000000-dcd6839af64c3ef6006e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0090000000-b5f0189f1d6f21b90673	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0090000000-21e1bde01931b051a4a3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0fe1-0940000000-acd7cb439468ece54d34	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00am-0900000000-9f695ef54b7a75aa0ca5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0a4j-6900000000-cc148be066f76bf120a2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-0a4j-8900000000-5a1a78a963c17ee2f26b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0ukj-2690000000-075abfa2a19ae84712fb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-0uka-2790000000-528f02372cf3ac228b4a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052k-7950000000-7505adc1ceff21713130	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0190000000-4b469479ef097f60ed90	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-8bebba5f70c72e80b630	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5890000000-46ba5a59d051001f2a63	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-3c963477109db1f6b39e	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-87d4a2534cd39e8c54a8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-1190000000-abbd0808a06f67c1f6fc	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dv-5940000000-5e22fba0c369374c75df	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.54 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.00003 uM	PMID: 18412364	details
Detected and Quantified	0.00003 uM	PMID: 18412364	details
Detected and Quantified	0.00003 uM	PMID: 18412364	details

External Links

HMDB ID

HMDB0000234

DrugBank ID

DB00624

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003675

Chemspider ID

5791

KEGG Compound ID

C00535

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Testosterone

METLIN ID

Not Available

PubChem Compound

6013

PDB ID

Not Available

ChEBI ID

17347

References

Synthesis Reference

Ercoli, Alberto; De Ruggieri, Pietro. An improved method of preparing testosterone, dihydrotestosterone, and some of their esters. Journal of the American Chemical Society (1953), 75 650-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]

Showing metabocard for Testosterone (BMDB0000234)

Structure for BMDB0000234 (Testosterone)