Margaric acid (PAMDB001901)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001901
Identification
Name: Margaric acid
Description:Margaric acid, also known as heptadecanoic acid, is a saturated fatty acid with a 17-carbon chain. Exogenous propionate can be incorporated by Pseudomonas aeruginosa as a primer to produce lipids with fatty acids of odd chain lengths.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 17:0
  • CH31[CH2]151COOH
  • Heptadecanoate
  • Heptadecanoate (ACD/Name 4.0)
  • Heptadecanoic acid
  • Heptadecanoic acid (ACD/Name 4.0)
  • Heptadecoate
  • Heptadecoic acid
  • Heptadecylate
  • Heptadecylic acid
  • Margarate
  • Margaric acid
  • Margarinate
  • Margarinic acid
  • Margarinsaure
  • Margaroate
  • Margaroic acid
  • N-Heptadecanoate
  • N-Heptadecanoic acid
  • N-Heptadecoate
  • N-Heptadecoic acid
  • N-Heptadecylate
  • N-Heptadecylic acid
  • Normal-heptadecanoate
  • Normal-heptadecanoic acid
Chemical Formula: C17H34O2
Average Molecular Weight: 270.4507
Monoisotopic Molecular Weight: 270.255880332
InChI Key: KEMQGTRYUADPNZ-UHFFFAOYSA-N
InChI: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)
CAS number: 506-12-7
IUPAC Name:heptadecanoic acid
Traditional IUPAC Name: heptadecanoic acid
SMILES:CCCCCCCCCCCCCCCCC(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Long-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 61.3 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000151 mg/mLALOGPS
logP7.66ALOGPS
logP6.7ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity81.68 m3·mol-1ChemAxon
Polarizability36.49 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-017i-0900000000-ebd7708ca40db1f69377View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-1900000000-140a09beb5b6859644fdView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-3452bef1d9fd1091e354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi0-4590000000-727243a3559dd7ed991fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9710000000-f50bf2fb7778841f9f16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-98c6dcf5eaea4132deb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gdi-1090000000-e7ed55db02f1210fe7e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-24fa7a34c1095502e707View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05fu-9210000000-099bddb00b5e5f57a591View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • 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
  • 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. Pubmed: 19212411
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID32365
HMDB IDHMDB02259
Pubchem Compound ID10465
Kegg IDNot Available
ChemSpider ID10033
WikipediaMargaric_acid
BioCyc IDNot Available

Enzymes

Protein Details
• 3-oxoacyl-[acyl-carrier-protein] synthase 2
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Has a preference for short chain acid substrates and may function to supply the octanoic substrates for lipoic acid biosynthesis
Gene Name:
fabF
Locus Tag:
PA2965
Molecular weight:
43.5 kDa
Reactions
(Z)-hexadec-11-enoyl-[acyl-carrier-protein] + malonyl-[acyl-carrier-protein] = (Z)-3-oxooctadec-13-enoyl-[acyl-carrier-protein] + CO(2) + [acyl-carrier-protein].
Protein Details
• 3-oxoacyl-[acyl-carrier-protein] reductase
General function:
Involved in 3-oxoacyl-[acyl-carrier-protein] reductase (NADPH) activity
Specific function:
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH
Gene Name:
fabG
Locus Tag:
PA2967
Molecular weight:
25.6 kDa
Reactions
(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH.
Protein Details
• Acyl carrier protein
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa

Transporters