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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 20:39:28 UTC
HMDB IDHMDB0000933
Secondary Accession Numbers
  • HMDB00933
Metabolite Identification
Common NameTraumatic acid
DescriptionTraumatic acid is a monounsaturated dicarboxylic acid naturally ocurring in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Aire Jan Haagen-Smit in 1939. Traumatic acid is a potent wound healing agent in plants ("wound hormone") that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzimatic oxidation of traumatin (12-oxo-trans-10-dodecanoic acid), another wound hormone. At normal conditions, traumatic acid is a solid, crystalized, water insoluble substance.
Structure
Thumb
Synonyms
ValueSource
(2E)-Dodecenedioic acidChEBI
2E-Dodecenedioic acidChEBI
Dodec-2-enedioic acidChEBI
trans-2-Dodecenedioic acidChEBI
(2E)-DodecenedioateGenerator
TraumatateGenerator
2E-DodecenedioateGenerator
Dodec-2-enedioateGenerator
trans-2-DodecenedioateGenerator
(Z)-2-DodecenedioateHMDB
(Z)-2-Dodecenedioic acidHMDB
1-Decene-1,10-dicarboxylic acidHMDB
2-DodecendioateHMDB
2-Dodecendioic acidHMDB
2-DodecenedioateHMDB
2-Dodecenedioic acidHMDB
Dodec-2C-enedioateHMDB
Dodec-2C-enedioic acidHMDB
Dodec-2t-enedioateHMDB
Dodec-2t-enedioic acidHMDB
DodecanedioateHMDB
Dodecanedioic acidHMDB
Dodecanedioic acid-2-eneHMDB
trans-TraumatateHMDB
trans-Traumatic acidHMDB
2-Dodecene-1,12-dicarboxylic acidMeSH
Chemical FormulaC12H20O4
Average Molecular Weight228.2848
Monoisotopic Molecular Weight228.136159128
IUPAC Name(2E)-dodec-2-enedioic acid
Traditional Nametraumatic acid
CAS Registry Number6402-36-4
SMILES
OC(=O)CCCCCCCC\C=C\C(O)=O
InChI Identifier
InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+
InChI KeyMAZWDMBCPDUFDJ-VQHVLOKHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.96ALOGPS
logP3.16ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity61.44 m³·mol⁻¹ChemAxon
Polarizability26.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0159-5900000000-68484d0dfe58678792f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-5690000000-d4e9dc447f5e9cb32627View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0390000000-fbdef4f440546733d6ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0ars-8940000000-030825564cd79acdb5d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-8900000000-f51c2f9058d1c10dd143View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0390000000-2a8c785591aec8fbb5a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-040r-1940000000-63519f2dee20f2bb486eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059l-9400000000-efca9114ed7b26dac71cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-07c0b0dbe35c52bd096aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0390000000-4887cde057ee3c2d60aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9410000000-5f7fb26b05524072cccbView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    UrineDetected but not Quantified Not AvailableNot AvailableVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
    UrineDetected but not Quantified Not AvailableNot AvailableLCHAD/Trifunctional Protein Deficiency details
    UrineDetected but not Quantified Not AvailableNot AvailableMyoadenylate deaminase deficiency details
    UrineDetected but not Quantified Not AvailableNot AvailableKetosis details
    Associated Disorders and Diseases
    Disease References
    Very Long Chain Acyl-CoA Dehydrogenase Deficiency
    1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
    Colorectal cancer
    1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
    2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
    Ketosis
    1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
    Myoadenylate deaminase deficiency
    1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
    Mitochondrial trifunctional protein deficiency
    1. Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
    Associated OMIM IDs
    • 114500 (Colorectal cancer)
    • 201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
    • 609015 (Mitochondrial trifunctional protein deficiency)
    • 102770 (Myoadenylate deaminase deficiency)
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022323
    KNApSAcK IDNot Available
    Chemspider ID4446155
    KEGG Compound IDC16308
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkTraumatic acid
    METLIN ID5882
    PubChem Compound5283028
    PDB IDNot Available
    ChEBI ID545687
    References
    Synthesis ReferenceDupont, G.; Dulou, R.; Quantin, P. Polycarboxylic acids and their derivatives. (1952), FR 1018186 19521229 CAN 52:6571 AN 1958:6571
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available