Livestock Metabolome Database: Showing metabocard for Dehydroepiandrosterone sulfate (LMDB00773)

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

Record Information

Version

1.0

Creation Date

2016-07-30 18:17:46 UTC

Update Date

2016-08-06 20:10:56 UTC

Lmdb

LMDB00773

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydroepiandrosterone sulfate

Description

Dehydroepiandrosterone sulfate, also known as 17-ketoandrost-5-en-3b-yl sulfate or 3-O-sulfodehydroepiandrosterone, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Dehydroepiandrosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dehydroepiandrosterone sulfate is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-beta)-3-(Sulfooxy)androst-5-en-17-one	ChEBI
17-Ketoandrost-5-en-3beta-yl sulfate	ChEBI
17-Oxoandrost-5-en-3beta-yl hydrogen sulphate	ChEBI
3-O-Sulfodehydroepiandrosterone	ChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfate	ChEBI
Androst-5-en-17-on-3beta-yl sulfuric acid	ChEBI
Dehydroepiandrosterone 3-sulfate	ChEBI
Dehydroepiandrosterone monosulfate	ChEBI
Dehydroepiandrosterone sulphate	ChEBI
Dehydroisoandrosterone sulfate	ChEBI
Dehydroisoandrosterone-3-sulfate	ChEBI
DHEA sulfate	ChEBI
DHEA-S	ChEBI
DHEAS	ChEBI
Prasterone sulfate	ChEBI
(3-b)-3-(Sulfooxy)androst-5-en-17-one	Generator
(3-b)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-beta)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulfooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulphooxy)androst-5-en-17-one	Generator
17-Ketoandrost-5-en-3b-yl sulfate	Generator
17-Ketoandrost-5-en-3b-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3b-yl sulphate	Generator
17-Ketoandrost-5-en-3b-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulphate	Generator
17-Ketoandrost-5-en-3beta-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulfate	Generator
17-Ketoandrost-5-en-3β-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulphate	Generator
17-Ketoandrost-5-en-3β-yl sulphuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acid	Generator
3-O-Sulphodehydroepiandrosterone	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
Androst-5-en-17-on-3b-yl sulfate	Generator
Androst-5-en-17-on-3b-yl sulfuric acid	Generator
Androst-5-en-17-on-3b-yl sulphate	Generator
Androst-5-en-17-on-3b-yl sulphuric acid	Generator
Androst-5-en-17-on-3beta-yl sulfate	Generator
Androst-5-en-17-on-3beta-yl sulphate	Generator
Androst-5-en-17-on-3beta-yl sulphuric acid	Generator
Androst-5-en-17-on-3β-yl sulfate	Generator
Androst-5-en-17-on-3β-yl sulfuric acid	Generator
Androst-5-en-17-on-3β-yl sulphate	Generator
Androst-5-en-17-on-3β-yl sulphuric acid	Generator
Dehydroepiandrosterone 3-sulfuric acid	Generator
Dehydroepiandrosterone 3-sulphate	Generator
Dehydroepiandrosterone 3-sulphuric acid	Generator
Dehydroepiandrosterone monosulfuric acid	Generator
Dehydroepiandrosterone monosulphate	Generator
Dehydroepiandrosterone monosulphuric acid	Generator
Dehydroepiandrosterone sulfuric acid	Generator
Dehydroepiandrosterone sulphuric acid	Generator
Dehydroisoandrosterone sulfuric acid	Generator
Dehydroisoandrosterone sulphate	Generator
Dehydroisoandrosterone sulphuric acid	Generator
Dehydroisoandrosterone-3-sulfuric acid	Generator
Dehydroisoandrosterone-3-sulphate	Generator
Dehydroisoandrosterone-3-sulphuric acid	Generator
DHEA sulfuric acid	Generator
DHEA sulphate	Generator
DHEA sulphuric acid	Generator
Prasterone sulfuric acid	Generator
Prasterone sulphate	Generator
Prasterone sulphuric acid	Generator
(3beta)-3-(Sulfooxy)-androst-5-en-17-one	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfate	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
Dehydroepiandrosterone-3-sulfate	HMDB
Dehydroepiandrosterone-3-sulphate	HMDB
Formylisoglutamic acid	HMDB
Prasterone-3-sulfate	HMDB
Prasterone-3-sulphate	HMDB
DHA sulfate	HMDB
Sulfate, dehydroisoandrosterone	HMDB
Sulfate, prasterone	HMDB
Sulfate, dhea	HMDB
Sulfate, dehydroepiandrosterone	HMDB
Sulfate, dha	HMDB

Chemical Formula

C₁₉H₂₈O₅S

Average Molecular Weight

368.488

Monoisotopic Molecular Weight

368.165744696

IUPAC Name

[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

CZWCKYRVOZZJNM-USOAJAOKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Androstane-skeleton
17-oxosteroid
Oxosteroid
Delta-5-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:16814 )
17-oxo steroid (CHEBI:16814 )
sulfates (C04555 )
C19 steroids (androgens) and derivatives (C04555 )
Androgens (C04555 )
Sulfates (LMST05020010 )

Ontology

Status

Detected but not 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	0.49	ALOGPS
logP	3.42	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.65 m³·mol⁻¹	ChemAxon
Polarizability	39.85 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0097000000-e6d4f60e9803940d2f55	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-d49a8b7164a230745f20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3009000000-bd7e895ed74eba8a0f23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-8d7ea5bd8a8a0d5219c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-9001000000-5d89a4081c0f6b0c3324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0049000000-f9a938b029283c157bdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0091000000-c2b83d86ae8174524e1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5792000000-20638b1484fe342eb3c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0029000000-79344bc1ba3ea2c26db7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1092000000-3b129a6c30b2629e1661	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-008i-6090000000-35cc2726715438281170	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-c58c9c29bacda1fca240	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1009000000-d5f9b663138c7975150b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9105000000-a5c4a9d21c991c730dab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-e7315ac14210f0dc3930	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0292000000-06a461930592bd575f19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-4920000000-e6055497e2f92515f76a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	13C NMR Spectrum	Not Available	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
1D NMR	13C NMR Spectrum	Not Available	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