Livestock Metabolome Database: Showing metabocard for Androstenedione (LMDB00021)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:38 UTC

Update Date

2016-07-19 23:06:50 UTC

Lmdb

LMDB00021

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Androstenedione

Description

Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.

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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	2.93	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	View
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000f-8940000000-f2892fe3b281d44164c8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-007d-1960000000-167f1765b095da9d603b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0590000000-502d6b821317a01a1990	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0090000000-36e848ba16b141eef47b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-052b-9600000000-712954fc35a84c8217de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052b-9300000000-f8e9aa16b4b208b69f7b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-000f-8940000000-e12025ea2b7808c64b9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-6910000000-b616785c86a92f46158e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-052b-9800000000-73e545a1eb2232d55371	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-735473bc44dd70e29259	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00kb-5790000000-114675a4457063901f2b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-052b-7910000000-f0d8591998137c42f717	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00kb-5790000000-f47366cff1ef47253455	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-052b-9800000000-58ced8830fbdd255377e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-00kb-5790000000-4d32bf4d34aaef92de91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-9700000000-5a645018a15e2dd1adeb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-70913f3a4e21abdcf9ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9500000000-1405c9c7f6ea07c8d1e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-eec15e6fd9d08b27ef07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-778071650dcadc3b3069	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00c3-0900000000-faf22b1b9717d889edd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00ei-0940000000-930c091a3d1471221653	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-0347db9e9578e8d5d6f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05pc-0490000000-d4049441f1c172450dc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-4790000000-355bc0834a6465ecad30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-887b6f223b77c683ef99	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-9dafdd780cca012f1fb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-2190000000-264074b1eefeed0e3103	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-059m-3940000000-9cb32ac21e46afb2829a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	0.000716 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000545 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000545 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.000320&0.000545 uM	Not Available	Bovine	21172370	details