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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:31:55 UTC
HMDB IDHMDB0000782
Secondary Accession Numbers
  • HMDB00782
Metabolite Identification
Common NameOctadecanedioic acid
DescriptionOctadecanedioic acid, also known as 1,18-octadecanedioate or octadecane-1,18-dioate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. In the case of octadecanedioic acid, it has carboxyl groups at both ends of the chain, not just one. Octadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water). Octadecanedioic acid is a long-chain dicarboxylic acid normally not found in humans that has been identified in the blood serum in Reye's syndrome patients (PMID: 3746531). There may also be an association with colorectal cancer (PMID: 25037050 ).
Structure
Data?1582752156
Synonyms
ValueSource
1,16-Hexadecanedicarboxylic acidChEBI
1,18-Octadecadioic acidChEBI
1,18-Octadecanedioic acidChEBI
Octadecane-1,18-dioic acidChEBI
1,16-HexadecanedicarboxylateGenerator
1,18-OctadecadioateGenerator
1,18-OctadecanedioateGenerator
Octadecane-1,18-dioateGenerator
OctadecanedioateGenerator
Chemical FormulaC18H34O4
Average Molecular Weight314.4602
Monoisotopic Molecular Weight314.245709576
IUPAC Nameoctadecanedioic acid
Traditional Nameoctadecanedioic acid
CAS Registry Number871-70-5
SMILES
OC(=O)CCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H34O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-16H2,(H,19,20)(H,21,22)
InChI KeyBNJOQKFENDDGSC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain 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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00099 g/LALOGPS
logP5.86ALOGPS
logP5.83ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity87.95 m³·mol⁻¹ChemAxon
Polarizability39.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.46631661259
DarkChem[M-H]-178.1131661259
AllCCS[M+H]+183.34832859911
AllCCS[M-H]-182.46932859911
DeepCCS[M+H]+171.44530932474
DeepCCS[M-H]-168.4230932474
DeepCCS[M-2H]-204.93930932474
DeepCCS[M+Na]+180.60330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Octadecanedioic acidOC(=O)CCCCCCCCCCCCCCCCC(O)=O3731.8Standard polar33892256
Octadecanedioic acidOC(=O)CCCCCCCCCCCCCCCCC(O)=O2329.5Standard non polar33892256
Octadecanedioic acidOC(=O)CCCCCCCCCCCCCCCCC(O)=O2532.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octadecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)O2631.0Semi standard non polar33892256
Octadecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2706.3Semi standard non polar33892256
Octadecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)O2881.5Semi standard non polar33892256
Octadecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3270.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-1960000000-1a1de4df85b64456c6092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00g3-8793100000-e57ed61ea61cf59b7cd22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-03di-0009000000-a2515d8c7963934e2a462012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0udi-0090000000-34f70f1f293855bd09742012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-053r-9031000000-710cc2000cff7ec1da492012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid Linear Ion Trap , negative-QTOFsplash10-0udi-0090000000-a9905162398a1b115ae82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid Linear Ion Trap , positive-QTOFsplash10-000i-0009000000-1e898a1ef2a3530c7abd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octadecanedioic acid 35V, Negative-QTOFsplash10-0w2a-0094000000-b1bcc3b35a58553701972021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 10V, Positive-QTOFsplash10-00kb-0093000000-4dba2641eb93c9c6dfd92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 20V, Positive-QTOFsplash10-014j-0191000000-914c9498be171f4aebe92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 40V, Positive-QTOFsplash10-0aba-7960000000-4a5dccb025f8c03f9bd72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 10V, Negative-QTOFsplash10-03di-0039000000-26c22cea9b6a162e1de02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 20V, Negative-QTOFsplash10-03dj-1096000000-bb4eb78e2e5823b3cb4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9040000000-7c45927a58a212304a892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 10V, Negative-QTOFsplash10-03di-0039000000-79913cd1df5af5e896af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 20V, Negative-QTOFsplash10-0002-1091000000-62cc3aa0ccaba7d4e40b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 40V, Negative-QTOFsplash10-0a4m-9260000000-51d4d9a456a5dd9d5ed82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 10V, Positive-QTOFsplash10-00kb-1392000000-47fef5bfae93858d2b832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 20V, Positive-QTOFsplash10-00kb-5691000000-68cbbc4b111106e935a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanedioic acid 40V, Positive-QTOFsplash10-05o1-9100000000-fe2ac604378eb9e11a262021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022239
KNApSAcK IDNot Available
Chemspider ID63283
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5748
PubChem Compound70095
PDB IDNot Available
ChEBI ID133086
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDrake, Nathan L.; Melamed, Sidney. Tetratriacontanoic acid and related compounds. Journal of the American Chemical Society (1948), 70 364-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tonsgard JH: Serum dicarboxylic acids in patients with Reye syndrome. J Pediatr. 1986 Sep;109(3):440-5. [PubMed:3746531 ]
  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 ]