Showing metabocard for Testosterone (BMDB0000234)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:09 UTC
Update Date2020-06-04 23:02:41 UTC
BMDB IDBMDB0000234
Secondary Accession Numbers
  • BMDB00234
Metabolite Identification
Common NameTestosterone
DescriptionTestosterone 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17beta-Hydroxy-4-androsten-3-oneChEBI
4-Androsten-17beta-ol-3-oneChEBI
AndrodermChEBI
TestosteronChEBI
TestosteronaChEBI
TestosteronumChEBI
AndrogelKegg
AxironKegg
StriantKegg
TestimKegg
17b-Hydroxy-4-androsten-3-oneGenerator
17Β-hydroxy-4-androsten-3-oneGenerator
4-Androsten-17b-ol-3-oneGenerator
4-Androsten-17β-ol-3-oneGenerator
(+)-TestosteroneHMDB
(+-)-8-Iso-testosteroneHMDB
(+-)-RetrotestosteroneHMDB
(+-)-TestosteroneHMDB
(17b)-17-Hydroxy-androst-4-en-3-oneHMDB
13-Iso-testosteroneHMDB
17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-oneHMDB
17-Hydroxy-androst-4-en-3-oneHMDB
17-Hydroxy-D4-androsten-3-oneHMDB
17a-Hydroxy-(13a)-androst-4-en-3-oneHMDB
17a-Hydroxy-13a-androst-4-en-3-oneHMDB
17a-Hydroxy-14b-androst-4-en-3-oneHMDB
17a-Hydroxy-androst-4-en-3-oneHMDB
17b-Hydroxy-(10a)-androst-4-en-3-oneHMDB
17b-Hydroxy-(13a)-androst-4-en-3-oneHMDB
17b-Hydroxy-(8a)-androst-4-en-3-oneHMDB
17b-Hydroxy-(8a,10a)-androst-4-en-3-oneHMDB
17b-Hydroxy-(9b)-androst-4-en-3-oneHMDB
17b-Hydroxy-(9b,10a)-androst-4-en-3-oneHMDB
17b-Hydroxy-13a-androst-4-en-3-oneHMDB
17b-Hydroxy-8a-androst-4-en-3-oneHMDB
17b-Hydroxy-androst-4-en-3-ONHMDB
17b-Hydroxy-androst-4-en-3-oneHMDB
17b-Hydroxy-D4-androsten-3-oneHMDB
17b-Hydroxyandrost-4-en-3-oneHMDB
17b-Hydroxyandrost-4-ene-3-oneHMDB
17b-TestosteroneHMDB
4-Androsten-3-one-17b-olHMDB
8-Iso-testosteroneHMDB
9b,10a-TestosteroneHMDB
9b-TestosteroneHMDB
AndrolinHMDB
AndronaqHMDB
AndropatchHMDB
Androst-4-en-17b-ol-3-oneHMDB
Androst-4-ene-17b-ol-3-oneHMDB
AndrusolHMDB
Cristerona THMDB
D4-Androsten-17b-ol-3-oneHMDB
EpitestosteronHMDB
Geno-cristaux gremyHMDB
HomosteronHMDB
HomosteroneHMDB
LumitestosteronHMDB
MertestateHMDB
NeotestisHMDB
OretonHMDB
OrquisteronHMDB
PerandrenHMDB
Percutacrine androgeniqueHMDB
PrimotestHMDB
PrimotestonHMDB
rac-17b-Hydroxy-(13a)androst-4-en-3-oneHMDB
rac-17b-Hydroxy-(8a)-androst-4-en-3-oneHMDB
rac-17b-Hydroxy-(9b,10a)androst-4-en-3-oneHMDB
rac-17b-Hydroxy-androst-4-en-3-oneHMDB
RelibraHMDB
RetrotestosteroneHMDB
SustanonHMDB
SustanoneHMDB
Sustason 250HMDB
Synandrol FHMDB
TeslenHMDB
TestandroneHMDB
TesticulosteroneHMDB
TestobaseHMDB
TestodermHMDB
TestogelHMDB
TestolentHMDB
TestolinHMDB
TestoproponHMDB
TestosteroidHMDB
Testoviron scheringHMDB
Testoviron THMDB
Testro aqHMDB
TestroneHMDB
TestrylHMDB
TostrelleHMDB
TostrexHMDB
ViatrelHMDB
VirormoneHMDB
VirosteroneHMDB
AndrotopHMDB
CEPA brand OF testosteroneHMDB
HisteroneHMDB
SmithKline beecham brand OF testosteroneHMDB
Solvay brand OF testosteroneHMDB
SterotateHMDB
17-beta-Hydroxy-8 alpha-4-androsten-3-oneHMDB
AstraZeneca brand OF testosteroneHMDB
Bartor brand OF testosteroneHMDB
Dr. kade brand OF testosteroneHMDB
Ferring brand OF testosteroneHMDB
Hauck brand OF testosteroneHMDB
Pasadena brand OF testosteroneHMDB
Testosterone sulfateHMDB
Ulmer brand OF testosteroneHMDB
Unimed brand OF testosteroneHMDB
Watson brand OF testosteroneHMDB
17-beta-Hydroxy-4-androsten-3-oneHMDB
8 IsotestosteroneHMDB
8-IsotestosteroneHMDB
Auxilium pharmaceuticals inc. brand OF testosteroneHMDB
Faulding brand OF testosteroneHMDB
Paladin brand OF testosteroneHMDB
Schering brand OF testosteroneHMDB
17 beta Hydroxy 4 androsten 3 oneHMDB
17 beta Hydroxy 8 alpha 4 androsten 3 oneHMDB
GlaxoSmithKline brand OF testosteroneHMDB
Ortho brand OF testosteroneHMDB
TestopelHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
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 Number58-22-0
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 KeyMUMGGOZAMZWBJJ-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0234 mg/mLNot Available
LogP3.32HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.99ALOGPS
logP3.37ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.43 m³·mol⁻¹ChemAxon
Polarizability33.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-d6ace9b7f8aff4dd46d0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-053u-1920200000-db3504f562c54e6e1bbbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-b43cd1ee268a855c8aa0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-356ddfa8ddf8e551278dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0597-7920000000-dde7fba02fcbcec2d665View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fs-4920000000-ccd839134de79f179f9eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ds-0950000000-c65fc8043083ad93d169View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-3910000000-d6ace9b7f8aff4dd46d0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053u-1920200000-db3504f562c54e6e1bbbView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-b43cd1ee268a855c8aa0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-356ddfa8ddf8e551278dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-074i-0390000000-09e2a725ebd92c93dc88View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001j-3349000000-75c3f3e0341bb42eb819View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-914b212f1dbb7fb7b1acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9800000000-d2e38d44d2f16d0a4203View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-6830823fa12b40e784a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0597-7920000000-dde7fba02fcbcec2d665View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-05fs-4920000000-ccd839134de79f179f9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-00ds-0950000000-48c1f79091d708072f30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-6900000000-3d818ffe03ecd499e078View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-7900000000-6db3d23d98d548cbbfaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ukj-2690000000-14b953cb16c53d1e2744View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uka-2790000000-dcd6839af64c3ef6006eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0090000000-b5f0189f1d6f21b90673View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0090000000-21e1bde01931b051a4a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0fe1-0940000000-acd7cb439468ece54d34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00am-0900000000-9f695ef54b7a75aa0ca5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4j-6900000000-cc148be066f76bf120a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4j-8900000000-5a1a78a963c17ee2f26bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0ukj-2690000000-075abfa2a19ae84712fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0uka-2790000000-528f02372cf3ac228b4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-052k-7950000000-7505adc1ceff21713130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-4b469479ef097f60ed90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-8bebba5f70c72e80b630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5890000000-46ba5a59d051001f2a63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-3c963477109db1f6b39eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-87d4a2534cd39e8c54a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-abbd0808a06f67c1f6fcView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00dv-5940000000-5e22fba0c369374c75dfView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100.54 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Brain
  • Milk
  • Ovary
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00167 uMNot SpecifiedNot Specified
Normal		 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.0000343 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.0000270 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.0000312 uMNot SpecifiedNot Specified
Normal		 details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.00115 uMNot SpecifiedNot Specified
Treated with estradiol benzoate		 details
BloodDetected and Quantified0.00171 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone		 details
HMDB IDHMDB0000234
DrugBank IDDB00624
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003675
Chemspider ID5791
KEGG Compound IDC00535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTestosterone
METLIN IDNot Available
PubChem Compound6013
PDB IDNot Available
ChEBI ID17347
References
Synthesis ReferenceErcoli, 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)Not Available
General References
  1. 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 ]

Enzymes

Enzyme Details
1. 17-beta-hydroxysteroid dehydrogenase type 6
General function:
Lipid transport and metabolism
Specific function:
NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids (By similarity).
Gene Name:
HSD17B6
Uniprot ID:
Q3T001
Molecular weight:
36198.0
Enzyme Details
2. UDP-glucuronosyltransferase 3A1
General function:
Carbohydrate transport and metabolism
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds (By similarity).
Gene Name:
UGT3A1
Uniprot ID:
Q1LZI1
Molecular weight:
59682.0
Reactions
Testosterone → Testosterone glucuronidedetails