Milk Composition Database: Showing metabocard for Androstenedione (BMDB0000053)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:01 UTC

Update Date

2020-06-04 23:01:42 UTC

MCDB 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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	170 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.058 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	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 (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000f-8940000000-f2892fe3b281d44164c8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-007d-1960000000-167f1765b095da9d603b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0590000000-502d6b821317a01a1990	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-36e848ba16b141eef47b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-9600000000-712954fc35a84c8217de	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9300000000-f8e9aa16b4b208b69f7b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-000f-8940000000-e12025ea2b7808c64b9c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-6910000000-b616785c86a92f46158e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-9800000000-73e545a1eb2232d55371	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-735473bc44dd70e29259	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-114675a4457063901f2b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-052b-7910000000-f0d8591998137c42f717	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kb-5790000000-f47366cff1ef47253455	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-052b-9800000000-58ced8830fbdd255377e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-00kb-5790000000-4d32bf4d34aaef92de91	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-9700000000-5a645018a15e2dd1adeb	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-70913f3a4e21abdcf9ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-1405c9c7f6ea07c8d1e4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-eec15e6fd9d08b27ef07	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-778071650dcadc3b3069	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00c3-0900000000-faf22b1b9717d889edd8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00ei-0940000000-930c091a3d1471221653	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-0347db9e9578e8d5d6f2	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05pc-0490000000-d4049441f1c172450dc3	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-4790000000-355bc0834a6465ecad30	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-887b6f223b77c683ef99	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-9dafdd780cca012f1fb3	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-2190000000-264074b1eefeed0e3103	2017-07-26	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-059m-3940000000-9cb32ac21e46afb2829a	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.002 +/- 0.0004 uM	PMID: 17852390	details
Detected and Quantified	0.001 +/- 0.0003 uM	PMID: 17852390	details
Detected and Quantified	0.003 +/- 0.001 uM	PMID: 17852390	details
Detected and Quantified	0.00147 uM	PMID: 18412364	details
Detected and Quantified	0.00101 uM	PMID: 18412364	details
Detected and Quantified	0.00306 uM	PMID: 18412364	details

External Links

HMDB ID

HMDB0000053

DrugBank ID

DB01536

Phenol Explorer Compound ID

Not Available

FoodDB 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 ]

Showing metabocard for Androstenedione (BMDB0000053)

Structure for BMDB0000053 (Androstenedione)