Bovine Metabolome Database: Showing metabocard for Epitestosterone (BMDB0000628)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:33:50 UTC

Update Date

2020-06-04 20:38:12 UTC

BMDB ID

BMDB0000628

Secondary Accession Numbers

BMDB00628

Metabolite Identification

Common Name

Epitestosterone

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
Epi-testosterone	ChEBI
17-Epitestosterone	HMDB
17a-cis-Testosterone	HMDB
cis-Testosterone	HMDB
Isotestosterone	HMDB
17-alpha-Testosterone	HMDB
17 alpha Testosterone	HMDB
Epitestosterone	MeSH, HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

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

CAS Registry Number

481-30-1

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-KZYORJDKSA-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:42534 )
17alpha-hydroxy steroid (CHEBI:42534 )
androstanoid (CHEBI:42534 )
C19 steroids (androgens) and derivatives (LMST02020051 )

Ontology

Status

Detected and 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	Not Available	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	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	33.93 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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006t-1940000000-716f44b32e61cf34c7b4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006t-1940000000-716f44b32e61cf34c7b4	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-053u-1920200000-db3504f562c54e6e1bbb	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-356ddfa8ddf8e551278d	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0597-7920000000-dde7fba02fcbcec2d665	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05fs-4920000000-ccd839134de79f179f9e	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00ds-0950000000-c65fc8043083ad93d169	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053u-1920200000-db3504f562c54e6e1bbb	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3910000000-356ddfa8ddf8e551278d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-0390000000-09e2a725ebd92c93dc88	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000t-1119000000-bf66038b9de80f6b8aab	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-e1af5f6bcaf571731a2b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-7900000000-581eb9c19ccb29ebac52	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9300000000-37c235bd069ce0c93813	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0690-0190000000-d4814fdc14f2b2818eb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0fk9-1690000000-b39908a52b06c7853085	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0950000000-5ee2f8e5795ea913ebad	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-f4e3ff2bfc8e41de9c54	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-3b8123363e31bc461acf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0190000000-4b469479ef097f60ed90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-8bebba5f70c72e80b630	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5890000000-46ba5a59d051001f2a63	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-3c963477109db1f6b39e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-87d4a2534cd39e8c54a8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-1190000000-abbd0808a06f67c1f6fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-383f8ad782110ec64fbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-383f8ad782110ec64fbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uy0-0090000000-9f1b0a9f20aee057d1dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-7add27947ecc7b5b14bc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ki-0960000000-98c9b1c540f6d162d225	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-2900000000-f5717697f5b4e8b7505f	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-00dv-5940000000-5e22fba0c369374c75df	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adrenal Gland
Milk
Ovary
Prostate Tissue
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Androgen and Estrogen Metabolism		Not Available
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	0.000245 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.000177 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.000344 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Ovary	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000628

DrugBank ID

DB07768

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011544

KNApSAcK ID

Not Available

Chemspider ID

9789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epitestosterone

METLIN ID

5601

PubChem Compound

10204

PDB ID

Not Available

ChEBI ID

42534

References

Synthesis Reference

Alvarez, Francisco. Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation. Steroids (1963), 2(4), 393-8.

Material Safety Data Sheet (MSDS)

Not Available

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 Epitestosterone (BMDB0000628)

Structure for BMDB0000628 (Epitestosterone)