Showing metabocard for Dehydroepiandrosterone (BMDB0000077)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Show more...Show more...
Record Information
Version1.0
Creation Date2016-09-30 22:19:22 UTC
Update Date2020-06-04 23:02:28 UTC
BMDB IDBMDB0000077
Secondary Accession Numbers
  • BMDB00077
Metabolite Identification
Common NameDehydroepiandrosterone
DescriptionDehydroepiandrosterone, 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
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 Number53-43-0
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 KeyFMGSKLZLMKYGDP-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.53ALOGPS
logP3.36ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m³·mol⁻¹ChemAxon
Polarizability34.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004i-4920000000-9dc14963a290268534b8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-2bbc760dbeb7f9f1ebfcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0abi-1790000000-52f5e67bc4d1fab73561View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-022a-1229000000-5fc1bd40299ad859ad1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fk9-0190000000-66ac82624767dc6821e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0w90-1690000000-b3a231fc509b7a34e09cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-08gj-1930000000-309dc082cc36ec9dcd8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-06sj-2910000000-378638f2a861c948f79dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0536-3900000000-72e80e1a07c4d3a40a7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0036-4900000000-26c8272483a80d1b5eabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0290000000-1a3588ca5d5bacb9ad30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bta-3920000000-2df257db43df6cc86570View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0036-4900000000-a5988c20b9c2dcaaa0b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0536-3900000000-9a88dec56cfcb5147a12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-08gj-1930000000-7cae68c709391babec19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-06sj-2910000000-370c122c31de467a2a1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-05d1-0930000000-890b3cea5a94fdd69458View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0w90-0690000000-cd7d0ebd514f0a8966d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0fk9-0190000000-8d6dc67ca77600c3affaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-89da8cb383a0718d9033View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-e6efd70cef2520255bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udm-4690000000-e304b251e97b02f672adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-89da8cb383a0718d9033View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-e6efd70cef2520255bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udm-4690000000-e304b251e97b02f672adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7498c93972acc3c16404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-d3ddffc56e91bed39fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2190000000-15aba54ba135047ffe9aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-6940000000-948ad487c238d48aa9beView in MoNA
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView 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
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000884 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone		 details
BloodDetected and Quantified0.00118 uMNot SpecifiedNot Specified
Treated with estradiol benzoate		 details
HMDB IDHMDB0000077
DrugBank IDDB01708
Phenol Explorer Compound IDNot Available
FooDB IDFDB021808
KNApSAcK IDNot Available
Chemspider ID8036443
KEGG Compound IDC01227
BioCyc ID3-BETA-HYDROXYANDROST-5-EN-17-ONE
BiGG ID37131
Wikipedia LinkDehydroepiandrosterone
METLIN ID5133
PubChem Compound5881
PDB IDNot Available
ChEBI ID28689
References
Synthesis ReferenceNguyen 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
  1. 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 ]
  2. 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 ]
  3. 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 → Dehydroepiandrosteronedetails
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 + Sulfatedetails
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 sulfatedetails