Hexadecanedioic acid (CHEM025054)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:06:30 UTC
Update Date2016-11-09 01:18:00 UTC
Accession NumberCHEM025054
Identification
Common NameHexadecanedioic acid
ClassSmall Molecule
DescriptionAn alpha,omega-dicarboxylic acid that is the 1,14-dicarboxy derivative of tetradecane.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass286.407 g/mol
Monoisotopic Mass286.214 g/mol
CAS Registry Number505-54-4
IUPAC Namehexadecanedioic acid
Traditional Namehexadecanedioic acid
SMILESOC(=O)CCCCCCCCCCCCCCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07do-2940000000-8c28631b1022d3318936Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0109-7691100000-587f0a395c2991f76096Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0090000000-2311edb5a21bc7c11854Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-01b9-0090000000-29b1e4612ce1b89fe132Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-cb4b2bb791cf66c26ad1Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-014r-0490000000-dacc672eeb75f850682bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-014i-0090000000-9e4148fba4082bf62e1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-2590000000-8bc2ce9bfb76d9bb26b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-066s-4950000000-47159163bf80115de8b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-053b-6920000000-8a0094cbb6f9d1650566Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0012-8910000000-2a109bc90ccab90ea68bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00l2-9700000000-d514011d0869df067d52Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-05o1-9500000000-983b1d8b6bb3f3f63b35Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-015a-9300000000-69f141c415f5b32f3403Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-067j-9200000000-7b8fa454eb425f3e106eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-067i-9100000000-a8b8484850ff331b59c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-067i-9000000000-2d72212014cb905b53baSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-066r-9000000000-5f4d3971357b080285efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-0aor-9000000000-1f5e11f8710cbd1da2c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 39V, positivesplash10-0ar0-9100000000-203172aa59c73e588123Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 49V, positivesplash10-0ar0-9200000000-2f3b6e1eff5a4c95e99bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-21fd3982c0181bc06670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-0390000000-67df6952912c86a0cd98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-5900000000-ff60e3a81da2e330db67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-6c700a9c0357a7d235a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0090000000-fb79a4abfe50390ddb88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9140000000-7aba6aa5bd7692dcc532Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ow-9210000000-ae9c39d4b07c3e8cb742Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000672
FooDB IDFDB003049
Phenol Explorer IDNot Available
KNApSAcK IDC00007429
BiGG IDNot Available
BioCyc IDCPD-10511
METLIN ID5642
PDB IDNot Available
Wikipedia LinkThapsic acid
Chemspider ID10027
ChEBI ID73722
PubChem Compound ID10459
Kegg Compound IDC19615
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23239314
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=4372285
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=4703570
4. Kreuchunas, Algird. The synthesis of higher aliphatic a,w-dicarboxylic acids. Journal of the American Chemical Society (1953), 75 3339-44.
5. Pettersen JE, Aas M: Subcellular localization of hexadecanedioic acid activation in human liver. J Lipid Res. 1974 Nov;15(6):551-6.
6. 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.