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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:22 UTC
HMDB IDHMDB0000672
Secondary Accession Numbers
  • HMDB00672
Metabolite Identification
Common NameHexadecanedioic acid
DescriptionHexadecanedioic acid is activated by mitochondrial and microsomal fractions in liver (PMID 4372285 ). It has an antitumor activity (PMID 14987827 ).
Structure
Data?1563860662
Synonyms
ValueSource
1,14-Tetradecanedicarboxylic acidChEBI
1,16-Hexadecanedioic acidChEBI
Thapsic acidChEBI
1,14-TetradecanedicarboxylateGenerator
1,16-HexadecanedioateGenerator
ThapsateGenerator
HexadecanedioateGenerator
a,W-TetradecanedicarboxylateHMDB
a,W-Tetradecanedicarboxylic acidHMDB
N-Tetradecane-W,w'-dicarboxylateHMDB
N-Tetradecane-W,w'-dicarboxylic 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 123 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP4.68ALOGPS
logP4.94ChemAxon
logS-4.7ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07do-2940000000-8c28631b1022d3318936JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0109-7691100000-587f0a395c2991f76096JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0090000000-2311edb5a21bc7c11854JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-01b9-0090000000-29b1e4612ce1b89fe132JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-cb4b2bb791cf66c26ad1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-21fd3982c0181bc06670JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-0390000000-67df6952912c86a0cd98JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-5900000000-ff60e3a81da2e330db67JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-6c700a9c0357a7d235a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0090000000-fb79a4abfe50390ddb88JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-7aba6aa5bd7692dcc532JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-01ow-9210000000-ae9c39d4b07c3e8cb742JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11(0.078-0.19) uMInfant (0-1 year old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
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
BloodDetected and Quantified0.088-3.4 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
3-Hydroxydicarboxylic aciduria
  1. Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
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
FoodDB IDFDB003049
KNApSAcK IDC00007429
Chemspider ID10027
KEGG Compound IDC19615
BioCyc IDCPD-10511
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5642
PubChem Compound10459
PDB IDNot Available
ChEBI ID73722
Food Biomarker OntologyNot Available
VMH IDNot Available
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 ]