Showing metabocard for Thromboxane A2 (BMDB0001452)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:10 UTC
Update Date2020-05-21 16:27:00 UTC
BMDB IDBMDB0001452
Secondary Accession Numbers
  • BMDB01452
Metabolite Identification
Common NameThromboxane A2
DescriptionThromboxane A2, also known as TXA2, belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring. Thus, thromboxane A2 is considered to be an eicosanoid. Based on a literature review very few articles have been published on Thromboxane A2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoateChEBI
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidChEBI
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oic acidChEBI
TXA-2ChEBI
TXA2ChEBI
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoateGenerator
(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoateGenerator
(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoic acidGenerator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-OateGenerator
(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acidGenerator
9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-OateGenerator
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoateHMDB
(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoic acidHMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoateHMDB
(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoic acidHMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoateHMDB
(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoic acidHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoateHMDB
(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acidHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-OateHMDB
(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oic acidHMDB
7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoateHMDB
7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoic acidHMDB
CidHMDB
Rabbit aorta contracting substanceHMDB, MeSH
RCSHMDB
a2, ThromboxaneMeSH, HMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid
Traditional Namethromboxane
CAS Registry Number57576-52-0
SMILES
CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1
InChI KeyDSNBHJFQCNUKMA-SCKDECHMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentThromboxanes
Alternative Parents
Substituents
  • Thromboxane
  • Long-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Meta-dioxane
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Secondary alcohol
  • Oxetane
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not 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
logP4.31ALOGPS
logP4.08ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity97.67 m³·mol⁻¹ChemAxon
Polarizability39.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5c-8092000000-447fd05a27e321c2cde4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05d0-9412500000-8ee6a6da7d17d4a312adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0019000000-0d4465c059cecdc63423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9377000000-bbdaa5d2f847ef4ce9edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9230000000-95f4e70640a0a301ed86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-c75e176e0b60712ef7c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-2149000000-030f294fbd453ce195d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9231000000-e7bad0956de1ed773d0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-380bcdac41775c30cac2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-99b3f8cff0edf57c5c84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ki2-4490000000-4417bbfe96ca092158b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-69a34801f1522c7965b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3229000000-1ee59a8ff7e44516dba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rr-9500000000-fc766f27d3958eb30b52View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Smooth MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001452
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444137
KEGG Compound IDC02198
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThromboxane A2
METLIN IDNot Available
PubChem Compound5280497
PDB IDNot Available
ChEBI ID15627
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Thromboxane-A synthase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
TBXAS1
Uniprot ID:
Q2KIG5
Molecular weight:
60539.0
Reactions
Prostaglandin H2 → Thromboxane A2details
Enzyme Details
2. Thromboxane A2 receptor
General function:
Involved in thromboxane receptor activity
Specific function:
Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C and adenylyl cyclase.
Gene Name:
TBXA2R
Uniprot ID:
Q95125
Molecular weight:
37841.0