Bovine Metabolome Database: Showing metabocard for Androstenedione (BMDB0000053)

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

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

Traditional Name

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

CAS Registry Number

63-05-8

SMILES

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

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

Property	Value	Source
logP	2.93	ALOGPS
logP	3.93	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	19.03	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	33.21 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 - GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000f-8940000000-f2892fe3b281d44164c8	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-007d-1960000000-167f1765b095da9d603b	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0590000000-502d6b821317a01a1990	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-36e848ba16b141eef47b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-9600000000-712954fc35a84c8217de	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9300000000-f8e9aa16b4b208b69f7b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-000f-8940000000-e12025ea2b7808c64b9c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-6910000000-b616785c86a92f46158e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-9800000000-73e545a1eb2232d55371	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-735473bc44dd70e29259	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-114675a4457063901f2b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-052b-7910000000-f0d8591998137c42f717	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kb-5790000000-f47366cff1ef47253455	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-052b-9800000000-58ced8830fbdd255377e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-00kb-5790000000-4d32bf4d34aaef92de91	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-9700000000-5a645018a15e2dd1adeb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-70913f3a4e21abdcf9ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-1405c9c7f6ea07c8d1e4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-eec15e6fd9d08b27ef07	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-778071650dcadc3b3069	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00c3-0900000000-faf22b1b9717d889edd8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00ei-0940000000-930c091a3d1471221653	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-0347db9e9578e8d5d6f2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05pc-0490000000-d4049441f1c172450dc3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-4790000000-355bc0834a6465ecad30	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-887b6f223b77c683ef99	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-9dafdd780cca012f1fb3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-2190000000-264074b1eefeed0e3103	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-059m-3940000000-9cb32ac21e46afb2829a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
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
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