Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:31:55 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
Data?1582752165
Synonyms
ValueSource
(2E)-Dodecenedioic acidChEBI
2E-Dodecenedioic acidChEBI
Dodec-2-enedioic acidChEBI
trans-2-Dodecenedioic acidChEBI
(2E)-DodecenedioateGenerator
2E-DodecenedioateGenerator
Dodec-2-enedioateGenerator
trans-2-DodecenedioateGenerator
TraumatateGenerator
(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 acidHMDB
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
Description 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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point165.5 °CNot Available
Boiling Point376.00 to 377.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility229.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.686 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg149.85230932474
[M-H]-Not Available149.852http://allccs.zhulab.cn/database/detail?ID=AllCCS00000228
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP10(2.96) g/LALOGPS
logP10(3.16) g/LChemAxon
logS10(-3.1) g/LALOGPS
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
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]+157.21231661259
DarkChem[M-H]-155.04731661259
AllCCS[M+H]+153.58632859911
AllCCS[M-H]-156.79932859911
DeepCCS[M+H]+153.74630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Traumatic acidOC(=O)CCCCCCCC\C=C\C(O)=O3295.1Standard polar33892256
Traumatic acidOC(=O)CCCCCCCC\C=C\C(O)=O1742.2Standard non polar33892256
Traumatic acidOC(=O)CCCCCCCC\C=C\C(O)=O1955.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Traumatic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC/C=C/C(=O)O2080.4Semi standard non polar33892256
Traumatic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O2066.5Semi standard non polar33892256
Traumatic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O[Si](C)(C)C2130.2Semi standard non polar33892256
Traumatic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC/C=C/C(=O)O2313.6Semi standard non polar33892256
Traumatic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O2294.5Semi standard non polar33892256
Traumatic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2604.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-5900000000-68484d0dfe58678792f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00ei-5690000000-d4e9dc447f5e9cb326272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Traumatic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Traumatic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-0390000000-fbdef4f440546733d6ff2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Traumatic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0ars-8940000000-030825564cd79acdb5d12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Traumatic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-8900000000-f51c2f9058d1c10dd1432012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 10V, Positive-QTOFsplash10-03fr-0390000000-2a8c785591aec8fbb5a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 20V, Positive-QTOFsplash10-040r-1940000000-63519f2dee20f2bb486e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 40V, Positive-QTOFsplash10-059l-9400000000-efca9114ed7b26dac71c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 10V, Negative-QTOFsplash10-004i-0190000000-07c0b0dbe35c52bd096a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 20V, Negative-QTOFsplash10-056r-0390000000-4887cde057ee3c2d60ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 40V, Negative-QTOFsplash10-0a4l-9410000000-5f7fb26b05524072cccb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 10V, Positive-QTOFsplash10-03fr-2790000000-6a9dfdfdc43b0043ae3c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 20V, Positive-QTOFsplash10-0aba-9200000000-bee5de3ec350f5d430972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 40V, Positive-QTOFsplash10-0a4l-9200000000-6ae6163d2fc55c7e84852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 10V, Negative-QTOFsplash10-004i-0190000000-1996bc83b0b3636819362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 20V, Negative-QTOFsplash10-0a4i-0690000000-a5211c275855968693522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Traumatic acid 40V, Negative-QTOFsplash10-052g-9500000000-a09d1e00399ea05253702021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableLCHAD/Trifunctional Protein Deficiency details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableMyoadenylate deaminase deficiency details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableKetosis details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
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 ]
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 ]
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
FooDB IDFDB006541
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1291501
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