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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:34:14 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
Thumb
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
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
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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 ]