Livestock Metabolome Database: Showing metabocard for Dehydroepiandrosterone (LMDB00034)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:55 UTC

Update Date

2016-09-23 18:44:30 UTC

Lmdb

LMDB00034

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydroepiandrosterone

Description

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the animal body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-BETA-HYDROXY-5-androsten-17-one	ChEBI
3beta-Hydroxyandrost-5-en-17-one	ChEBI
Dehydroisoandrosterone	ChEBI
DHA	ChEBI
DHEA	ChEBI
Intrarosa	ChEBI
Prasterone	ChEBI
Biolaif	Kegg
3-b-HYDROXY-5-androsten-17-one	Generator
3-Β-hydroxy-5-androsten-17-one	Generator
3b-Hydroxyandrost-5-en-17-one	Generator
3Β-hydroxyandrost-5-en-17-one	Generator
(+)-Dehydroisoandrosterone	HMDB
(3-beta)-3-Hydroxyandrost-5-en-17-one	HMDB
(3beta)-3-Hydroxy-androst-5-en-17-one	HMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one	HMDB
17-Chetovis	HMDB
17-Hormoforin	HMDB
3-beta-Hydroxyandrost-5-en-17-one	HMDB
3b-Hydroxy-D5-androsten-17-one	HMDB
3beta-Hydroxy-5-androsten-17-one	HMDB
3beta-Hydroxy-androst-5-en-17-one	HMDB
3beta-Hydroxy-D5-androsten-17-one	HMDB
5,6-Dehydroisoandrosterone	HMDB
5,6-Didehydroisoandrosterone	HMDB
5-Androsten-3-beta-ol-17-one	HMDB
5-Androsten-3b-ol-17-one	HMDB
5-Androsten-3beta-ol-17-one	HMDB
5-Dehydro-epiandrosterone	HMDB
5-Dehydroepiandrosterone	HMDB
Andrestenol	HMDB
Androst-5-ene-3b-ol-17-one	HMDB
Androst-5-ene-3beta-ol-17-one	HMDB
Androsten-3beta-ol-17-one	HMDB
Androstenolone	HMDB
Astenile	HMDB
D5-Androsten-3b-ol-17-one	HMDB
D5-Androsten-3beta-ol-17-one	HMDB
Deandros	HMDB
Dehydro-epi-androsterone	HMDB
Diandron	HMDB
Diandrone	HMDB
Hydroxyandrostenone	HMDB
Prasterona	HMDB
Prasteronum	HMDB
Prestara	HMDB
Psicosterone	HMDB
trans-Dehydroandrosterone	HMDB
Prasterone, 3 alpha-isomer	HMDB
5 Androsten 3 beta hydroxy 17 one	HMDB
5-Androsten-3-beta-hydroxy-17-one	HMDB
5 Androsten 3 ol 17 one	HMDB
Prasterone, 3 alpha isomer	HMDB
5-Androsten-3-ol-17-one	HMDB
EM-760Dehydroandrosterone	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

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

Traditional Name

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

CAS Registry Number

53-43-0

SMILES

C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CCC2=O

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/h3,13-16,20H,4-11H2,1-2H3/t13-,14?,15?,16?,18-,19-/m0/s1

InChI Key

FMGSKLZLMKYGDP-INNQQZFDSA-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-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28689 )
17-oxo steroid (CHEBI:28689 )
androstanoid (CHEBI:28689 )
C19 steroids (androgens) and derivatives (C01227 )
Androstane and derivatives (C01227 )
Androgens (C01227 )
C19 steroids (androgens) and derivatives (LMST02020021 )

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	3.53	ALOGPS
logP	3.36	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	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	84.66 m³·mol⁻¹	ChemAxon
Polarizability	34.1 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 (1 MEOX; 1 TMS)	splash10-004i-4920000000-9dc14963a290268534b8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3910000000-2bbc760dbeb7f9f1ebfc	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0abi-1790000000-52f5e67bc4d1fab73561	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-022a-1229000000-5fc1bd40299ad859ad1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fk9-0190000000-66ac82624767dc6821e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0w90-1690000000-b3a231fc509b7a34e09c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-08gj-1930000000-309dc082cc36ec9dcd8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-06sj-2910000000-378638f2a861c948f79d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0536-3900000000-72e80e1a07c4d3a40a7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0036-4900000000-26c8272483a80d1b5eab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0290000000-1a3588ca5d5bacb9ad30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0bta-3920000000-2df257db43df6cc86570	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0036-4900000000-a5988c20b9c2dcaaa0b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0536-3900000000-9a88dec56cfcb5147a12	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-08gj-1930000000-7cae68c709391babec19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-06sj-2910000000-370c122c31de467a2a1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-05d1-0930000000-890b3cea5a94fdd69458	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0w90-0690000000-cd7d0ebd514f0a8966d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0fk9-0190000000-8d6dc67ca77600c3affa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0090000000-89da8cb383a0718d9033	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-e6efd70cef2520255bf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udm-4690000000-e304b251e97b02f672ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0090000000-89da8cb383a0718d9033	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-e6efd70cef2520255bf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udm-4690000000-e304b251e97b02f672ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7498c93972acc3c16404	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-d3ddffc56e91bed39fc4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-2190000000-15aba54ba135047ffe9a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-6940000000-948ad487c238d48aa9be	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C 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

Milk
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Serum	Detected and Quantified	0.00052 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.00118 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000884 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000884 uM	Not Available	Bovine	21172370	details