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Record Information
Version1.0
Created at2006-05-22 14:17:44 UTC
Updated at2021-08-19 23:58:25 UTC
NP-MRD IDNP0000741
Secondary Accession NumbersNone
Natural Product Identification
Common NameHeptadecanoic acid
DescriptionHeptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61% Of milk fat and 0.83% Of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185 ).
Structure
Data?1628564081
Synonyms
ValueSource
17:0ChEBI
C17:0ChEBI
CH3-[CH2]15-COOHChEBI
Heptadecoic acidChEBI
Heptadecylic acidChEBI
Margaric acidChEBI
Margarinic acidChEBI
MargarinsaeureChEBI
N-Heptadecanoic acidChEBI
N-Heptadecoic acidChEBI
N-Heptadecylic acidChEBI
HeptadecoateGenerator
HeptadecylateGenerator
MargarateGenerator
MargarinateGenerator
N-HeptadecanoateGenerator
N-HeptadecoateGenerator
N-HeptadecylateGenerator
HeptadecanoateGenerator
MargaroateHMDB
Margaroic acidHMDB
Normal-heptadecanoateHMDB
Normal-heptadecanoic acidHMDB
Margaric acid, 1-(11)C-labeledHMDB
Margaric acid, nickel (2+) saltHMDB
Omega I-123 heptadecanoic acidHMDB
Margaric acid, potassium saltHMDB
Margaric acid, sodium saltHMDB
FA(17:0)HMDB
Heptadecanoic acidMeSH
Chemical FormulaC17H34O2
Average Mass270.4507 Da
Monoisotopic Mass270.25588 Da
IUPAC Nameheptadecanoic acid
Traditional Nameheptadecanoic acid
CAS Registry Number506-12-7
SMILES
[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
InChI Identifier
InChI=1S/C17H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
InChI KeyKEMQGTRYUADPNZ-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
Allium cepa L.FooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Armoracia rusticanaFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Belone beloneFooDB
Bertholletia excelsaFooDB
Beta vulgaris ssp. ciclaFooDB
Bos taurusFooDB
BrachyuraFooDB
Brassica hirtaKNApSAcK Database
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
CarideaFooDB
Carthamus tinctoriusFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
ColumbidaeFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Cucumis meloFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cynara scolymusFooDB
Daucus carota ssp. sativusFooDB
DioscoreaFooDB
DiospyrosFooDB
ElaeisFooDB
EngraulidaeFooDB
Eriobotrya japonicaFooDB
Esox luciusFooDB
EucheumaFooDB
Fagopyrum esculentumFooDB
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
GastropodaFooDB
Glycine maxFooDB
GossypiumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hippoglossus hippoglossusFooDB
Hordeum vulgareFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans nigra L.FooDB
Lactuca sativaFooDB
Lagopus mutaFooDB
Lens culinarisFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
MalusFooDB
Malus pumilaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Musa x paradisiacaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Octopus vulgarisFooDB
Olea europaeaFooDB
Oncorhynchus mykissFooDB
OpuntiaFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PerciformesFooDB
Persea americanaFooDB
Petroselinum crispumFooDB
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
PinusFooDB
Pinus sibiricaKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Psidium guajavaFooDB
Punica granatumFooDB
Pyrus communisFooDB
RanidaeFooDB
Raphanus sativus var. longipinnatusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rumex acetosaFooDB
Saccharina japonicaFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
SiluriformesFooDB
Sinapis albaFooDB
Solanum lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumKNApSAcK Database
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Sus scrofa domesticaFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
ThunnusFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum durumFooDB
VacciniumFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
Vigna angularisFooDB
Vigna radiataFooDB
VitisFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
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
  • Straight chain fatty acid
  • Monocarboxylic 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61.3 °CNot Available
Boiling Point363.00 to 364.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.2 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP7.320 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00015 g/LALOGPS
logP10(7.66) g/LALOGPS
logP10(6.7) g/LChemAxon
logS10(-6.2) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.68 m³·mol⁻¹ChemAxon
Polarizability36.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002259
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004676
KNApSAcK IDC00007426
Chemspider ID10033
KEGG Compound IDNot Available
BioCyc IDCPD-7830
BiGG ID215873
Wikipedia LinkHeptadecanoic_acid
METLIN ID6578
PubChem Compound10465
PDB IDNot Available
ChEBI ID32365
Good Scents IDrw1249291
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Takala TO, Nuutila P, Pulkki K, Oikonen V, Gronroos T, Savunen T, Vahasilta T, Luotolahti M, Kallajoki M, Bergman J, Forsback S, Knuuti J: 14(R,S)-[18F]Fluoro-6-thia-heptadecanoic acid as a tracer of free fatty acid uptake and oxidation in myocardium and skeletal muscle. Eur J Nucl Med Mol Imaging. 2002 Dec;29(12):1617-22. Epub 2002 Oct 3. [PubMed:12458396 ]
  3. Hvid-Jacobsen K, Nielsen SL, Jensen VJ, Thomsen HS: Demonstration of the thoracic duct by 123I heptadecanoic acid. Report of a case. Acta Radiol. 1987 Nov-Dec;28(6):783-4. [PubMed:2962620 ]
  4. Steer P, Basu S, Lithell H, Vessby B, Berne C, Lind L: Acute elevations of medium- and long-chain fatty acid have different impacts on endothelium-dependent vasodilation in humans. Lipids. 2003 Jan;38(1):15-9. [PubMed:12669814 ]
  5. Van Roosmalen PB, Drummond I: Simultaneous determination by gas chromatography of the major metabolites in urine of toluene, xylenes and styrene. Br J Ind Med. 1978 Feb;35(1):56-60. [PubMed:629890 ]
  6. Mertens J, Vanryckeghem W, Bossuyt A: Fast, low-temperature preparation of carrier-free 17-123I-heptadecanoic acid applied for liver and heart scintigraphy. Eur J Nucl Med. 1986;11(9):361-2. [PubMed:3956529 ]
  7. Wolk A, Vessby B, Ljung H, Barrefors P: Evaluation of a biological marker of dairy fat intake. Am J Clin Nutr. 1998 Aug;68(2):291-5. [PubMed:9701185 ]