Bovine Metabolome Database: Showing metabocard for Androstenedione (BMDB0000053)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:01 UTC

Update Date

2020-06-04 23:01:42 UTC

BMDB ID

BMDB0000053

Secondary Accession Numbers

BMDB00053

Metabolite Identification

Common Name

Androstenedione

Description

Androstenedione, also known as fecundin, 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, androstenedione is considered to be a steroid lipid molecule. Androstenedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstenedione exists in all living organisms, ranging from bacteria to humans. Androstenedione participates in a number of enzymatic reactions, within cattle. In particular, Androstenedione can be converted into androstanedione through its interaction with the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstenedione can be converted into 19-hydroxyandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In cattle, androstenedione is involved in the metabolic pathway called the androstenedione metabolism pathway. Androstenedione is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Androstene-3,17-dione	ChEBI
4-ANDROSTENE-3-17-dione	ChEBI
delta(4)-Androsten-3,17-dione	ChEBI
delta(4)-Androstene-3,17-dione	ChEBI
Δ(4)-Androsten-3,17-dione	Generator
Δ(4)-Androstene-3,17-dione	Generator
(4)-Androsten-3,17-dione	HMDB
17-Ketotestosterone	HMDB
3,17-Dioxoandrost-4-ene	HMDB
4-Androsten-3,17-dione	HMDB
4-Androstenedione	HMDB
Androst-4-ene-3,17-dione	HMDB, KEGG
Androstendione	HMDB
D4-Androstene-3,17-dione	HMDB
delta4-Androstenedione	HMDB
Fecundin	HMDB
delta 4 Androstenedione	MeSH, HMDB
delta-4-Androstenedione	MeSH, HMDB
4 Androstene 3,17 dione	MeSH, HMDB
Androstenedione	HMDB
delta4-Androstene-3,17-dione	HMDB
Δ4-Androstene-3,17-dione	HMDB

Chemical Formula

C₁₉H₂₆O₂

Average Molecular Weight

286.4085

Monoisotopic Molecular Weight

286.193280076

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

63-05-8

SMILES

Not Available

InChI Identifier

InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

InChI Key

AEMFNILZOJDQLW-QAGGRKNESA-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
Oxosteroid
17-oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16422 )
17-oxo steroid (CHEBI:16422 )
androstanoid (CHEBI:16422 )
androstane (C00280 )
C19 steroids (androgens) and derivatives (C00280 )
Androstane and derivatives (C00280 )
Androgens (C00280 )
C19 steroids (androgens) and derivatives (LMST02020007 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0578 mg/mL	Not Available
LogP	2.75	HANSCH,C ET AL. (1995)

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane
Mitochondria

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Epidermis
Fibroblasts
Kidney
Liver
Milk
Ovary
Placenta
Prostate Tissue
Skeletal Muscle
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
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected and Quantified	<0.000545 uM	Not Specified	Not Specified	Normal	PMID: 21172370	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	0.00186 +/- 0.000354 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.00103 +/- 0.000302 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.00326 +/- 0.000946 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.00147 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.00101 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.00306 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Ovary	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	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
Skeletal Muscle	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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.000545 uM	Not Specified	Not Specified	Treated with estradiol benzoate and progesterone	PMID: 21172370	details
Blood	Detected and Quantified	0.000716 uM	Not Specified	Not Specified	Treated with estradiol benzoate	PMID: 21172370	details

External Links

HMDB ID

HMDB0000053

DrugBank ID

DB01536

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16422

References

Synthesis Reference

Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.

Material Safety Data Sheet (MSDS)

Not Available

General References

Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
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. Aromatase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively. Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid. Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen. Also displays 2-hydroxylase activity toward estrone. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:: CYP19A1
Uniprot ID:: P46194
Molecular weight:: 58090.0

Reactions

Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Water + Oxidized flavoprotein	details

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis. Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol. Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione. Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA. Also 16-alpha hydroxylates androgens, relevant for estriol synthesis. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:: CYP17A1
Uniprot ID:: P05185
Molecular weight:: 57244.0

Reactions

17-Hydroxyprogesterone → Androstenedione	details

Showing metabocard for Androstenedione (BMDB0000053)

Structure for BMDB0000053 (Androstenedione)

Enzymes

Reactions

Reactions