Pimelic acid (CED0006729)

Record Information
Version1.0
Creation Date2016-05-19 03:03:12 UTC
Update Date2026-05-14 17:18:35 UTC
Accession NumberCHEM009343
Identification
Common NamePimelic acid
ClassSmall Molecule
Description
Pimelic acid is an organic compound with the chemical formula C7H12O4 and an average molecular weight of 160.17 g/mol. Pimelic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This compound is found in or released from 27 recorded sources. These include electrical and electronic equipment such as antennas, communication cables or conductors, discharge lamps, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials. In the category of household cleaning and consumer products, it is associated with soap detergents, bleaching agents, perfumes within detergents and soaps, cigar cigarettes, and tobacco smoke filters. Within food, food processing, and cookware, it is found in food contact materials, food preservation, and the processing of meats and fish. Additionally, it is present in building and construction materials, specifically ladders, ceilings, and tents or canopies. Recorded exposure routes for this substance include touch, oral, and inhalation. Regarding its biological activity, one protein target has been recorded for pimelic acid: 2,3,4,5-tetrahydropyridine-2,6-dicarboxylate N-succinyltransferase (dapD).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1,5-Pentanedicarboxylic acidChEBI
6-Carboxyhexanoic acidChEBI
Heptanedioic acidChEBI
PimelateChEBI
6-CarboxyhexanoateKegg
1,5-PentanedicarboxylateGenerator
HeptanedioateGenerator
Acid, pimelicHMDB
Acids, pimelicHMDB
Pimelic acidsHMDB
1,7-HeptanedioateHMDB
1,7-Heptanedioic acidHMDB
HeptandioateHMDB
Heptandioic acidHMDB
Heptane-1,7-dioateHMDB
Heptane-1,7-dioic acidHMDB
PilerateHMDB
Pileric acidHMDB
Chemical FormulaC7H12O4
Average Molecular Mass160.168 g/mol
Monoisotopic Mass160.074 g/mol
CAS Registry Number111-16-0
IUPAC Nameheptanedioic acid
Traditional Namepimelic acid
SMILESOC(=O)CCCCCC(O)=O
InChI IdentifierInChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)
InChI KeyWLJVNTCWHIRURA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.3 g/LALOGPS
logP0.51ALOGPS
logP0.94ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity37.34 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-056s-1910000000-58bf29a41b2e4b405df9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0r7l-9100000000-aeff5d9828ac92b33028Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-054k-1910000000-fc6cb63b081b4f5f7fd3Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-056s-1910000000-58bf29a41b2e4b405df9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-054k-1900000000-403538c5b4091abf0a3dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9400000000-3bc5f898da696375482fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00y0-9720000000-f599c8c7e2d374dc1d0cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9300000000-a3d2b3924fcede41e331Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-7050dc1518d598ad5051Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052e-9200000000-84550d0cfeb05e8d79bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0r7l-9100000000-b698134a5d1e523a961eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-a3b877a40a98e4d07993Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9500000000-6f90176eaadac29eae28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-859f1028218d04c20dc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-ef436118494b323530f4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-15fa4059d8c10e1e3a03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-a3b877a40a98e4d07993Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9500000000-6f90176eaadac29eae28Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-0ece97699a3ecbbd29c5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-aa9d7a3b0b034eb999acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-15fa4059d8c10e1e3a03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9100000000-bbaaf04acf7504d9af12Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-2467588398a0cc1a7173Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ufr-9000000000-2c0303cc46347643edeeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9200000000-62e7353cf7ec99f7b257Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9700000000-51105e097da7cfc85c56Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9000000000-5f81718aec628d62d56eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-9400000000-8de819a33deb2f72275dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-ae8da8f0d1188118fcecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-75f0e6c423b0aaa98dd1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9600000000-a115161016301c7856d1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9700000000-c8d2c2d74442fa20c8efNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-9700000000-54440cce2ab94f030f6fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-7900000000-9e4f71a0886b488276d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-1900000000-f72d396c48eae140d2eaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02tc-6900000000-148d1369a6cc8216a4d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aou-9000000000-8148e8a28ecc0a5f1819Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-97c3b22812cb1495f92eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2900000000-ec8e65ccb8032a2fffa0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9100000000-c8c106238d3a22f75dbcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052e-4900000000-4ce307beebb72fed19b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-8900000000-cc2f54c02062e38b9c6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0005-9100000000-0482c16016c2f68f8e4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9600000000-1b7d1b06eddf2917a016Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9100000000-25abffb238db4943db22Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9000000000-826ae64136b0e88d08abNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6680.0Log mg/kg[3800:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
495CeilingsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)1.63483
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)1.32344
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)0.155698
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)2.10193
Peroxisome proliferator-activated receptor gamma structureClick to view 3D structurePeroxisome proliferator-activated receptor gammaP37231HumansPredicted (SEA)3.42537
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)2.17978
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)2.17978
G-protein coupled receptor 84 structureClick to view 3D structureG-protein coupled receptor 84Q9NQS5HumansPredicted (SEA)1.08989
Free fatty acid receptor 1 structureClick to view 3D structureFree fatty acid receptor 1O14842HumansPredicted (SEA)5.0602
Click to view 3D structureCytochrome P450 4A4P10611Oryctolagus cuniculusPredicted (SEA)0.0778492
Fatty acid-binding protein, adipocyte structureClick to view 3D structureFatty acid-binding protein, adipocyteP15090HumansPredicted (SEA)1.08989
Free fatty acid receptor 4 structureClick to view 3D structureFree fatty acid receptor 4Q5NUL3HumansPredicted (SEA)4.67095
Betaine--homocysteine S-methyltransferase 1 structureClick to view 3D structureBetaine--homocysteine S-methyltransferase 1Q93088HumansPredicted (SEA)0.544945
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)2.17978
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)0.155698
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)0.155698
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)7.62922
Toll-like receptor 2 structureClick to view 3D structureToll-like receptor 2O60603HumansPredicted (SEA)1.08989
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)0.233548
Fatty acid-binding protein, heart structureClick to view 3D structureFatty acid-binding protein, heartP05413HumansPredicted (SEA)0.544945
Click to view 3D structureOxoeicosanoid receptor 1Q8TDS5HumansPredicted (SEA)2.33548
Fatty acid-binding protein 5 structureClick to view 3D structureFatty acid-binding protein 5Q01469HumansPredicted (SEA)0.467095
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)66.2497
Click to view 3D structureN-acetylaspartylglutamate synthase AQ8IXN7HumansPredicted (SEA)3.97031
Click to view 3D structureCAI-1 autoinducer sensor kinase/phosphatase CqsSQ9KM66Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)Predicted (SEA)3.42537
Concentrations
Not Available
External Links
DrugBank IDDB01856
HMDB IDHMDB0000857
FooDB IDFDB022283
Phenol Explorer IDNot Available
KNApSAcK IDC00001199
BiGG IDNot Available
BioCyc IDCPD-205
METLIN ID3280
PDB IDNot Available
Wikipedia LinkPimelic_acid
Chemspider ID376
ChEBI ID30531
PubChem Compound ID385
Kegg Compound IDC02656
YMDB IDNot Available
ECMDB IDECMDB00857
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20693992
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21437340
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24486440
5. Murib, Jawad H.; Kahn, John H. Production of pimelic acid by carbonylation of e-caprolactone using excess water. U.S. (1989), 3 pp.
6. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.
7. Passi S, Picardo M, Mingrone G, Breathnach AS, Nazzaro-Porro M: Azelaic acid--biochemistry and metabolism. Acta Derm Venereol Suppl (Stockh). 1989;143:8-13.
8. Pettit BR: The analysis of thiodiglycollic acid by selected ion monitoring. Clin Chim Acta. 1986 Apr 15;156(1):85-90.
9. Niwa T, Ohki T, Maeda K, Saito A, Kobayashi K: Pattern of aliphatic dicarboxylic acids in uremic serum including a new organic acid, 2,4-dimethyladipic acid. Clin Chim Acta. 1979 Nov 15;99(1):71-83.
10. Mahadevappa VG, Holub BJ: The molecular species composition of individual diacyl phospholipids in human platelets. Biochim Biophys Acta. 1982 Oct 14;713(1):73-9.
11. Cronan JE, Lin S: Synthesis of the alpha,omega-dicarboxylic acid precursor of biotin by the canonical fatty acid biosynthetic pathway. Curr Opin Chem Biol. 2011 Jun;15(3):407-13. doi: 10.1016/j.cbpa.2011.03.001. Epub 2011 Mar 23.
12. Manandhar M, Cronan JE: Pimelic acid, the first precursor of the Bacillus subtilis biotin synthesis pathway, exists as the free acid and is assembled by fatty acid synthesis. Mol Microbiol. 2017 May;104(4):595-607. doi: 10.1111/mmi.13648. Epub 2017 Mar 3.
13. Ohsugi M, Miyauchi K, Tachibana K, Nakao S: Formation of a biotin precursor, pimelic acid, in yeasts from C18 fatty acids. J Nutr Sci Vitaminol (Tokyo). 1988 Aug;34(4):343-52. doi: 10.3177/jnsv.34.343.
14. Bennett MJ, Ragni MC, Hood I, Hale DE: Azelaic and pimelic acids: metabolic intermediates or artefacts? J Inherit Metab Dis. 1992;15(2):220-3. doi: 10.1007/BF01799635.