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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:30:12 UTC
HMDB IDHMDB0000672
Secondary Accession Numbers
  • HMDB00672
Metabolite Identification
Common NameHexadecanedioic acid
DescriptionHexadecanedioic acid, also known as thapsic acid, 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. Hexadecanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hexadecanedioic acid is activated by mitochondrial and microsomal fractions in the liver (PMID: 4372285 ). It has antitumor activity (PMID: 14987827 ).
Structure
Data?1583428709
Synonyms
ValueSource
1,14-Tetradecanedicarboxylic acidChEBI
1,16-Hexadecanedioic acidChEBI
Thapsic acidChEBI
1,14-TetradecanedicarboxylateGenerator
1,16-HexadecanedioateGenerator
ThapsateGenerator
HexadecanedioateGenerator
Α,ω-tetrαdecαnedicαrboxylαteHMDB
N-Tetradecane-ω,ω'-dicarboxylateHMDB
N-Tetradecane-ω,ω'-dicarboxylic acidHMDB
alpha,Omega-tetradecanedicarboxylic acidHMDB
N-Tetradecane-omega,omega'-dicarboxylic acidHMDB
N-Tetradecane-ω,ω’-dicarboxylic acidHMDB
Α,ω-tetradecanedicarboxylic acidHMDB
Hexadecanedioic acidMeSH
Chemical FormulaC16H30O4
Average Molecular Weight286.407
Monoisotopic Molecular Weight286.214409448
IUPAC Namehexadecanedioic acid
Traditional Namehexadecanedioic acid
CAS Registry Number505-54-4
SMILES
OC(=O)CCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)
InChI KeyQQHJDPROMQRDLA-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

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point120 - 123 °CNot Available
Boiling Point457.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.49 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.050 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP10(4.68) g/LALOGPS
logP10(4.94) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity78.75 m³·mol⁻¹ChemAxon
Polarizability35.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.84831661259
DarkChem[M-H]-171.23231661259
AllCCS[M+H]+173.38732859911
AllCCS[M-H]-174.832859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hexadecanedioic acid,1TMS,#1C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCC(=O)O2423.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Hexadecanedioic acid,2TMS,#1C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2508.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Hexadecanedioic acid,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCC(=O)O2679.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Hexadecanedioic acid,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3052.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-07do-2940000000-8c28631b1022d33189362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0109-7691100000-587f0a395c2991f760962017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hexadecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ow-9210000000-ae9c39d4b07c3e8cb7422015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000i-0090000000-2311edb5a21bc7c118542012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-01b9-0090000000-29b1e4612ce1b89fe1322012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0a4i-9000000000-cb4b2bb791cf66c26ad12012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid n/a 20V, positive-QTOFsplash10-014r-0490000000-dacc672eeb75f850682b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 2V, positive-QTOFsplash10-014i-0090000000-9e4148fba4082bf62e1e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 4V, positive-QTOFsplash10-014i-2590000000-8bc2ce9bfb76d9bb26b72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 5V, positive-QTOFsplash10-066s-4950000000-47159163bf80115de8b22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 7V, positive-QTOFsplash10-053b-6920000000-8a0094cbb6f9d16505662020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 9V, positive-QTOFsplash10-0012-8910000000-2a109bc90ccab90ea68b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 10V, positive-QTOFsplash10-00l2-9700000000-d514011d0869df067d522020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 12V, positive-QTOFsplash10-05o1-9500000000-983b1d8b6bb3f3f63b352020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 13V, positive-QTOFsplash10-015a-9300000000-69f141c415f5b32f34032020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 14V, positive-QTOFsplash10-067j-9200000000-7b8fa454eb425f3e106e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 18V, positive-QTOFsplash10-067i-9100000000-a8b8484850ff331b59c42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 22V, positive-QTOFsplash10-067i-9000000000-2d72212014cb905b53ba2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 27V, positive-QTOFsplash10-066r-9000000000-5f4d3971357b080285ef2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 33V, positive-QTOFsplash10-0aor-9000000000-1f5e11f8710cbd1da2c22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 39V, positive-QTOFsplash10-0ar0-9100000000-203172aa59c73e5881232020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hexadecanedioic acid Orbitrap 49V, positive-QTOFsplash10-0ar0-9200000000-2f3b6e1eff5a4c95e99b2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 10V, Positive-QTOFsplash10-014r-0090000000-21fd3982c0181bc066702017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 20V, Positive-QTOFsplash10-014u-0390000000-67df6952912c86a0cd982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 40V, Positive-QTOFsplash10-001j-5900000000-ff60e3a81da2e330db672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 10V, Negative-QTOFsplash10-000i-0090000000-6c700a9c0357a7d235a82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 20V, Negative-QTOFsplash10-00kr-0090000000-fb79a4abfe50390ddb882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hexadecanedioic acid 40V, Negative-QTOFsplash10-0a4l-9140000000-7aba6aa5bd7692dcc5322017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. 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 ]
  3. 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 IDFDB003049
KNApSAcK IDC00007429
Chemspider ID10027
KEGG Compound IDC19615
BioCyc IDCPD-10511
BiGG IDNot Available
Wikipedia LinkThapsic acid
METLIN ID5642
PubChem Compound10459
PDB IDNot Available
ChEBI ID73722
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1249661
References
Synthesis ReferenceKreuchunas, Algird. The synthesis of higher aliphatic a,w-dicarboxylic acids. Journal of the American Chemical Society (1953), 75 3339-44.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pettersen JE, Aas M: Subcellular localization of hexadecanedioic acid activation in human liver. J Lipid Res. 1974 Nov;15(6):551-6. [PubMed:4372285 ]
  2. You YJ, Kim Y, Nam NH, Bang SC, Ahn BZ: Alkyl and carboxylalkyl esters of 4'-demethyl-4-deoxypodophyllotoxin: synthesis, cytotoxic, and antitumor activity. Eur J Med Chem. 2004 Feb;39(2):189-93. [PubMed:14987827 ]