Bovine Metabolome Database: Showing metabocard for 17beta-Estradiol 3-sulfate (BMDB0004448)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:09:29 UTC

Update Date

2020-05-11 20:23:48 UTC

BMDB ID

BMDB0004448

Secondary Accession Numbers

BMDB0063708
BMDB04448
BMDB63708

Metabolite Identification

Common Name

17beta-Estradiol 3-sulfate

Description

17beta-Estradiol 3-sulfate, also known as estradiol 3-sulfuric acid or estradiol-17beta 3-sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Based on a literature review a significant number of articles have been published on 17beta-Estradiol 3-sulfate.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	ChEBI
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	ChEBI
Estradiol 3-sulphate	ChEBI
Estradiol-17beta 3-sulfate	ChEBI
Estradiol-3-sulfate	ChEBI
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
Estradiol 3-sulfate	Generator
Estradiol 3-sulfuric acid	Generator
Estradiol 3-sulphuric acid	Generator
Estradiol-17b 3-sulfate	Generator
Estradiol-17b 3-sulfuric acid	Generator
Estradiol-17b 3-sulphate	Generator
Estradiol-17b 3-sulphuric acid	Generator
Estradiol-17beta 3-sulfuric acid	Generator
Estradiol-17beta 3-sulphate	Generator
Estradiol-17beta 3-sulphuric acid	Generator
Estradiol-17β 3-sulfate	Generator
Estradiol-17β 3-sulfuric acid	Generator
Estradiol-17β 3-sulphate	Generator
Estradiol-17β 3-sulphuric acid	Generator
Estradiol-3-sulfuric acid	Generator
Estradiol-3-sulphate	Generator
Estradiol-3-sulphuric acid	Generator
17b-Estradiol 3-sulfate	Generator
17b-Estradiol 3-sulfuric acid	Generator
17b-Estradiol 3-sulphate	Generator
17b-Estradiol 3-sulphuric acid	Generator
17beta-Estradiol 3-sulfuric acid	Generator
17beta-Estradiol 3-sulphate	Generator
17beta-Estradiol 3-sulphuric acid	Generator
17Β-estradiol 3-sulfate	Generator
17Β-estradiol 3-sulfuric acid	Generator
17Β-estradiol 3-sulphate	Generator
17Β-estradiol 3-sulphuric acid	Generator
17beta-Estradiol sulfate	HMDB
17beta-Estradiol sulphate	HMDB
17Β-estradiol sulfate	HMDB
17Β-estradiol sulphate	HMDB
17beta-Estradiol 3-sulfate	HMDB

Chemical Formula

C₁₈H₂₄O₅S

Average Molecular Weight

352.45

Monoisotopic Molecular Weight

352.134445047

IUPAC Name

[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid

CAS Registry Number

481-96-9

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C18H24O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,17+,18+/m1/s1

InChI Key

QZIGLSSUDXBTLJ-ZBRFXRBCSA-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
Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Phenanthrene
Arylsulfate
Tetralin
Benzenoid
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:4866 )
17beta-hydroxy steroid (CHEBI:4866 )
sulfates (C08357 )
C18 steroids (estrogens) and derivatives (C08357 )
Sulfates (LMST05020005 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	178.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.6 mg/L at 27 °C	Not Available
LogP	2.936	Not Available

Predicted Properties

Property	Value	Source
logP	0.16	ALOGPS
logP	1.57	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.9 m³·mol⁻¹	ChemAxon
Polarizability	37.68 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0019000000-ca9cb18127c021c08b1b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0297000000-01f46b2a5b35f2cc509d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002u-3961000000-490f7ea3a427ec2aeee8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-0b04c74e16882ade2cae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-0093000000-0df31e427e4f5bdca884	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0knc-4090000000-1547f1a5a0346810c829	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-94abf727a93858289286	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1009000000-0d419d0dc3e14754ecc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9015000000-33c33a97f8108eb6169f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-f5481d1faa140b88ef32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0269000000-d5fe5f3755fc2f0a06a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-1930000000-99a045d39fd4ca0d3b5e	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Kidney
Liver
Urine

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Treated with steroids	PMID: 21742123	details

External Links

HMDB ID

HMDB0004448

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112363

KNApSAcK ID

Not Available

Chemspider ID

59790

KEGG Compound ID

C08357

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66416

PDB ID

Not Available

ChEBI ID

4866

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 17-beta-hydroxysteroid dehydrogenase type 6

General function:: Lipid transport and metabolism
Specific function:: NAD-dependent oxidoreductase with broad substrate specificity that shows both oxidative and reductive activity (in vitro). Has 17-beta-hydroxysteroid dehydrogenase activity towards various steroids (in vitro). Converts 5-alpha-androstan-3-alpha,17-beta-diol to androsterone and estradiol to estrone (in vitro). Has 3-alpha-hydroxysteroid dehydrogenase activity towards androsterone (in vitro). Has retinol dehydrogenase activity towards all-trans-retinol (in vitro). Can convert androsterone to epi-androsterone. Androsterone is first oxidized to 5-alpha-androstane-3,17-dione and then reduced to epi-andosterone. Can act on both C-19 and C-21 3-alpha-hydroxysteroids (By similarity).
Gene Name:: HSD17B6
Uniprot ID:: Q3T001
Molecular weight:: 36198.0

Enzyme Details

2. Very-long-chain 3-oxoacyl-CoA reductase

General function:: Involved in binding
Specific function:: Catalyzes the second of the four reactions of the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process, allows the addition of two carbons to the chain of long- and very long-chain fatty acids/VLCFAs per cycle. This enzyme has a 3-ketoacyl-CoA reductase activity, reducing 3-ketoacyl-CoA to 3-hydroxyacyl-CoA, within each cycle of fatty acid elongation. Thereby, it may participate in the production of VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators. May also catalyze the transformation of estrone (E1) into estradiol (E2) and play a role in estrogen formation.
Gene Name:: HSD17B12
Uniprot ID:: Q5E9H7
Molecular weight:: 34495.0

Enzyme Details

3. Estrogen receptor

General function:: Involved in protein binding
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (By similarity).
Gene Name:: ESR1
Uniprot ID:: P49884
Molecular weight:: 66489.0

Enzyme Details

4. Calcium-activated potassium channel subunit beta-1

General function:: Involved in potassium ion transport
Specific function:: Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Increases the apparent Ca(2+)/voltage sensitivity of the KCNMA1 channel. It also modifies KCNMA1 channel kinetics and alters its pharmacological properties. It slows down the activation and the deactivation kinetics of the channel. Acts as a negative regulator of smooth muscle contraction by enhancing the calcium sensitivity to KCNMA1. Its presence is also a requirement for internal binding of the KCNMA1 channel opener dehydrosoyasaponin I (DHS-1) triterpene glycoside and for external binding of the agonist hormone 17-beta-estradiol (E2). Increases the binding activity of charybdotoxin (CTX) toxin to KCNMA1 peptide blocker by increasing the CTX association rate and decreasing the dissociation rate (By similarity).
Gene Name:: KCNMB1
Uniprot ID:: Q28067
Molecular weight:: 21957.0

Showing metabocard for 17beta-Estradiol 3-sulfate (BMDB0004448)

Structure for BMDB0004448 (17beta-Estradiol 3-sulfate)

Enzymes