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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-25 14:42:57 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005099
Secondary Accession Numbers
  • HMDB05099
Metabolite Identification
Common NameThromboxane B3
DescriptionThromboxane B3 (TXB3) is a prostanoid that is formed by the hydrolysis of TXA3, a product of dietary eicosapentaenoic acid transformed in humans. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 , 2996649 )Thromboxanes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Data?1582752345
Synonyms
ValueSource
(5Z,9a,13E,15S,17Z)-9,11,15-Trihydroxy-thromboxa-5,13,17-trien-1-OateHMDB
(5Z,9a,13E,15S,17Z)-9,11,15-Trihydroxy-thromboxa-5,13,17-trien-1-Oic acidHMDB
9S,11,15S-Trihydroxy-thromboxa-5Z,13E,17Z-trien-1-OateHMDB
9S,11,15S-Trihydroxy-thromboxa-5Z,13E,17Z-trien-1-Oic acidHMDB
TXB3HMDB, MeSH
[2R(1E,3S,5Z),3S(Z),4S]-[Partial]-7-[tetrahydro-4,6-dihydroxy-2-(3-hydroxy-1,5-octadienyl)-2H-pyran-3-yl]-5-heptenoateHMDB
[2R(1E,3S,5Z),3S(Z),4S]-[Partial]-7-[tetrahydro-4,6-dihydroxy-2-(3-hydroxy-1,5-octadienyl)-2H-pyran-3-yl]-5-heptenoic acidHMDB
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name(5E)-7-{4,6-dihydroxy-2-[(1E,5E)-3-hydroxyocta-1,5-dien-1-yl]oxan-3-yl}hept-5-enoic acid
Traditional Namethromboxane B3
CAS Registry Number71953-80-5
SMILES
CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h3-4,6-7,12-13,15-18,20-22,25H,2,5,8-11,14H2,1H3,(H,23,24)/b6-3+,7-4+,13-12+
InChI KeyOYPPJMLKAYYWHH-OHVJZDGFSA-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
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.23Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP3.11ALOGPS
logP2.56ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity102.3 m³·mol⁻¹ChemAxon
Polarizability41.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.131661259
DarkChem[M-H]-190.21431661259
DeepCCS[M+H]+188.45830932474
DeepCCS[M-H]-186.130932474
DeepCCS[M-2H]-219.40130932474
DeepCCS[M+Na]+194.62830932474
AllCCS[M+H]+196.432859911
AllCCS[M+H-H2O]+193.732859911
AllCCS[M+NH4]+198.832859911
AllCCS[M+Na]+199.532859911
AllCCS[M-H]-192.932859911
AllCCS[M+Na-2H]-194.332859911
AllCCS[M+HCOO]-196.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Thromboxane B3CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O4374.5Standard polar33892256
Thromboxane B3CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O2467.2Standard non polar33892256
Thromboxane B3CC\C=C\CC(O)\C=C\C1OC(O)CC(O)C1C\C=C\CCCC(O)=O2903.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thromboxane B3,1TMS,isomer #1CC/C=C/CC(/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C3170.9Semi standard non polar33892256
Thromboxane B3,1TMS,isomer #2CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C)CC(O)C1C/C=C/CCCC(=O)O3069.4Semi standard non polar33892256
Thromboxane B3,1TMS,isomer #3CC/C=C/CC(O)/C=C/C1OC(O)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O3122.6Semi standard non polar33892256
Thromboxane B3,1TMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C3058.8Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C)CC(O)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C3069.9Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #2CC/C=C/CC(/C=C/C1OC(O)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C3079.1Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #3CC/C=C/CC(/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3029.7Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O3036.4Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #5CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C2957.8Semi standard non polar33892256
Thromboxane B3,2TMS,isomer #6CC/C=C/CC(O)/C=C/C1OC(O)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C2971.3Semi standard non polar33892256
Thromboxane B3,3TMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C2981.3Semi standard non polar33892256
Thromboxane B3,3TMS,isomer #2CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2929.6Semi standard non polar33892256
Thromboxane B3,3TMS,isomer #3CC/C=C/CC(/C=C/C1OC(O)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2926.3Semi standard non polar33892256
Thromboxane B3,3TMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C2916.0Semi standard non polar33892256
Thromboxane B3,4TMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C)CC(O[Si](C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2835.1Semi standard non polar33892256
Thromboxane B3,1TBDMS,isomer #1CC/C=C/CC(/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3413.8Semi standard non polar33892256
Thromboxane B3,1TBDMS,isomer #2CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O)C1C/C=C/CCCC(=O)O3290.6Semi standard non polar33892256
Thromboxane B3,1TBDMS,isomer #3CC/C=C/CC(O)/C=C/C1OC(O)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O3348.0Semi standard non polar33892256
Thromboxane B3,1TBDMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3311.3Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3487.3Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #2CC/C=C/CC(/C=C/C1OC(O)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3523.6Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #3CC/C=C/CC(/C=C/C1OC(O)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3525.8Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O3461.1Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #5CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3421.3Semi standard non polar33892256
Thromboxane B3,2TBDMS,isomer #6CC/C=C/CC(O)/C=C/C1OC(O)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3450.4Semi standard non polar33892256
Thromboxane B3,3TBDMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O)O[Si](C)(C)C(C)(C)C3621.5Semi standard non polar33892256
Thromboxane B3,3TBDMS,isomer #2CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3620.1Semi standard non polar33892256
Thromboxane B3,3TBDMS,isomer #3CC/C=C/CC(/C=C/C1OC(O)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3626.4Semi standard non polar33892256
Thromboxane B3,3TBDMS,isomer #4CC/C=C/CC(O)/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C3596.5Semi standard non polar33892256
Thromboxane B3,4TBDMS,isomer #1CC/C=C/CC(/C=C/C1OC(O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C1C/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3753.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thromboxane B3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9667000000-f4ce2aa3c5ab9901d9ba2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thromboxane B3 GC-MS (4 TMS) - 70eV, Positivesplash10-0006-4300089000-51bd4164d954c93c28e42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thromboxane B3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thromboxane B3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 10V, Positive-QTOFsplash10-0uei-0239000000-d3055e5b46f3ead5d5ea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 20V, Positive-QTOFsplash10-0pc0-2149000000-3a365f4768659805dca52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 40V, Positive-QTOFsplash10-014r-9210000000-6b4c19a67971e21744af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 10V, Negative-QTOFsplash10-016v-0059000000-f381f931b44061fd55152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 20V, Negative-QTOFsplash10-0002-2579000000-1c860ae580e6e8ed53492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 40V, Negative-QTOFsplash10-0a4m-9551000000-d08a5187728b44f9f9282017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 10V, Negative-QTOFsplash10-014i-0009000000-5a2cdf7255286b655e612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 20V, Negative-QTOFsplash10-066s-1069000000-69f11b87e1bf34bbe8242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 40V, Negative-QTOFsplash10-0007-7390000000-b258f7d4798fa158b5192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 10V, Positive-QTOFsplash10-0ue9-0019000000-9a935972b1a88c20ecaa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 20V, Positive-QTOFsplash10-053u-9313000000-663c96f23d66b2d8a26d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thromboxane B3 40V, Positive-QTOFsplash10-0api-9410000000-464dcb232bc3855b48262021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000017 +/- 0.000003 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023630
KNApSAcK IDNot Available
Chemspider ID4943166
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438711
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fischer S, Weber PC: Thromboxane (TX)A3 and prostaglandin (PG)I3 are formed in man after dietary eicosapentaenoic acid: identification and quantification by capillary gas chromatography-electron impact mass spectrometry. Biomed Mass Spectrom. 1985 Sep;12(9):470-6. [PubMed:2996649 ]
  2. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]
  3. Lipid Maps (LMFA03030006) [Link]