Bovine Metabolome Database: Showing metabocard for Dehydroepiandrosterone (BMDB0000077)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:22 UTC

Update Date

2020-06-04 23:02:28 UTC

BMDB ID

BMDB0000077

Secondary Accession Numbers

BMDB00077

Metabolite Identification

Common Name

Dehydroepiandrosterone

Description

Dehydroepiandrosterone, also known as 5-androsten-3b-ol-17-one or diandron, 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, dehydroepiandrosterone is considered to be a steroid lipid molecule. Dehydroepiandrosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dehydroepiandrosterone participates in a number of enzymatic reactions, within cattle. In particular, Dehydroepiandrosterone can be biosynthesized from 17a-hydroxypregnenolone through its interaction with the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In addition, Dehydroepiandrosterone can be converted into androstenedione through the action of the enzyme 3-beta-HSD 1. In cattle, dehydroepiandrosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Dehydroepiandrosterone is a potentially toxic compound. Dehydroepiandrosterone has been found to be associated with several diseases known as rheumatoid arthritis, antley-bixler syndrome with genital anomalies and disordered steroidogenesis, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and adrenal insufficiency, congenital, with 46,xy sex reversal, partial or complete; also dehydroepiandrosterone has been linked to the inborn metabolic disorders including 21-hydroxylase deficiency.

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

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

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-USOAJAOKSA-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

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Physical Properties

State

Solid

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
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-004i-4920000000-9dc14963a290268534b8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3910000000-2bbc760dbeb7f9f1ebfc	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0abi-1790000000-52f5e67bc4d1fab73561	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-022a-1229000000-5fc1bd40299ad859ad1c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fk9-0190000000-66ac82624767dc6821e5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0w90-1690000000-b3a231fc509b7a34e09c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-08gj-1930000000-309dc082cc36ec9dcd8c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-06sj-2910000000-378638f2a861c948f79d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0536-3900000000-72e80e1a07c4d3a40a7a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0036-4900000000-26c8272483a80d1b5eab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0290000000-1a3588ca5d5bacb9ad30	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0bta-3920000000-2df257db43df6cc86570	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0036-4900000000-a5988c20b9c2dcaaa0b0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0536-3900000000-9a88dec56cfcb5147a12	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-08gj-1930000000-7cae68c709391babec19	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-06sj-2910000000-370c122c31de467a2a1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-05d1-0930000000-890b3cea5a94fdd69458	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0w90-0690000000-cd7d0ebd514f0a8966d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0fk9-0190000000-8d6dc67ca77600c3affa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0090000000-89da8cb383a0718d9033	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-e6efd70cef2520255bf5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udm-4690000000-e304b251e97b02f672ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0090000000-89da8cb383a0718d9033	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0390000000-e6efd70cef2520255bf5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udm-4690000000-e304b251e97b02f672ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-7498c93972acc3c16404	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-d3ddffc56e91bed39fc4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-2190000000-15aba54ba135047ffe9a	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-6940000000-948ad487c238d48aa9be	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 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

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Brain
Epidermis
Fibroblasts
Kidney
Liver
Milk
Neuron
Ovary
Placenta
Platelet
Prostate Tissue
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

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	<0.000884 uM	Not Specified	Not Specified	Normal	PMID: 21172370	details
Blood	Detected and Quantified	0.00052 uM	Not Specified	Not Specified	Normal	PMID: 21172370	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	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	0.000183 +/- 0.00006241 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.000118 +/- 0.00004299 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.000227 +/- 0.00007766 uM	Not Specified	Not Specified	Normal	PMID: 17852390	details
Milk	Detected and Quantified	0.000199 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.000142 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected and Quantified	0.000415 uM	Not Specified	Not Specified	Normal	PMID: 18412364	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	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
Platelet	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	<0.000884 uM	Not Specified	Not Specified	Treated with estradiol benzoate and progesterone	PMID: 21172370	details
Blood	Detected and Quantified	0.00118 uM	Not Specified	Not Specified	Treated with estradiol benzoate	PMID: 21172370	details

External Links

HMDB ID

HMDB0000077

DrugBank ID

DB01708

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021808

KNApSAcK ID

Not Available

Chemspider ID

8036443

KEGG Compound ID

C01227

BioCyc ID

3-BETA-HYDROXYANDROST-5-EN-17-ONE

BiGG ID

37131

Wikipedia Link

Dehydroepiandrosterone

METLIN ID

5133

PubChem Compound

5881

PDB ID

Not Available

ChEBI ID

28689

References

Synthesis Reference

Nguyen Xuan Cuong; Nguyen Van Dan. Synthesis of dehydroepiandrosterone (DHA) from 16-dehydropregnenolone acetate (DPA). Tap Chi Duoc Hoc (1983), (4), 12-14.

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 ]
Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

Enzyme Details

1. 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

17a-Hydroxypregnenolone → Dehydroepiandrosterone	details

Enzyme Details

2. Arylsulfatase A

General function:: Inorganic ion transport and metabolism
Specific function:: Hydrolyzes cerebroside sulfate.
Gene Name:: ARSA
Uniprot ID:: Q08DD1
Molecular weight:: 53807.0

Reactions

DHEA sulfate + Water → Dehydroepiandrosterone + Sulfate	details

Enzyme Details

3. Sulfotransferase 1A1

General function:: Involved in aryl sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk (By similarity).
Gene Name:: SULT1A1
Uniprot ID:: P50227
Molecular weight:: 34184.0

Reactions

Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + DHEA sulfate	details

Showing metabocard for Dehydroepiandrosterone (BMDB0000077)

Structure for BMDB0000077 (Dehydroepiandrosterone)

Enzymes

Reactions

Reactions

Reactions