Human Metabolome Database Version 3.5

Showing metabocard for Heptadecanoic acid (HMDB02259)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:44 -0600
Update Date 2013-05-29 13:35:09 -0600
HMDB ID HMDB02259
Secondary Accession Numbers None
Metabolite Identification
Common Name Heptadecanoic acid
Description Heptadecanoic 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Heptadecanoate
  2. Heptadecanoic acid
  3. Margarate
  4. Margaric acid
  5. Margarinate
  6. Margarinic acid
  7. Margaroate
  8. Margaroic acid
  9. N-Heptadecanoate
  10. N-Heptadecanoic acid
  11. N-Heptadecoate
  12. N-Heptadecoic acid
  13. N-Heptadecylate
  14. N-Heptadecylic acid
  15. Normal-heptadecanoate
  16. Normal-heptadecanoic acid
Chemical Formula C17H34O2
Average Molecular Weight 270.4507
Monoisotopic Molecular Weight 270.255880332
IUPAC Name heptadecanoic acid
Traditional IUPAC Name heptadecanoic acid
CAS Registry Number 506-12-7
SMILES CCCCCCCCCCCCCCCCC(O)=O
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 Key KEMQGTRYUADPNZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Straight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight chain fatty acids(Lipidmaps)
  • long-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Straight Chain Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 61.3 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.510E-04 g/L ALOGPS
LogP 7.66 ALOGPS
LogP 6.7 ChemAxon
LogS -6.25 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 81.68 ChemAxon
Polarizability 36.49 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Sorry, spectra are temporarily unavailable.
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Skeletal Muscle
  • Prostate
  • Adipose Tissue
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.89 +/- 0.92 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
1.2 +/- 0.003 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB004676
KNApSAcK ID C00007426 Link_out
Chemspider ID 10033 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID 215873 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB02259 Link_out
Metagene Link HMDB02259 Link_out
METLIN ID 6578 Link_out
PubChem Compound 10465 Link_out
PDB ID Not Available
ChEBI ID 32365 Link_out
References
Synthesis Reference Heiduschka, A.; Ripper, J. Heptadecylic acid. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1923), 56B 1736-9.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  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 Link_out

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 64 enzymes in total.

Name: Fatty acid synthase
Reactions: Not Available
Gene Name: FASN
Uniprot ID: P49327 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside-binding soluble lectin 13
Reactions: Not Available
Gene Name: LGALS13
Uniprot ID: Q9UHV8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIA secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G12A
Uniprot ID: Q9BZM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions: Not Available
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2, membrane associated
Reactions: Not Available
Gene Name: PLA2G2A
Uniprot ID: P14555 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic triacylglycerol lipase
Reactions: Not Available
Gene Name: PNLIP
Uniprot ID: P16233 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inactive pancreatic lipase-related protein 1
Reactions: Not Available
Gene Name: PNLIPRP1
Uniprot ID: P54315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 3
Reactions: Not Available
Gene Name: PNPLA3
Uniprot ID: Q9NST1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastric triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPF
Uniprot ID: P07098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Endothelial lipase
Reactions: Not Available
Gene Name: LIPG
Uniprot ID: Q9Y5X9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 2
Reactions: Not Available
Gene Name: PNLIPRP2
Uniprot ID: P54317 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoprotein lipase
Reactions: Not Available
Gene Name: LPL
Uniprot ID: P06858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions: Not Available
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cocaine esterase
Reactions: Not Available
Gene Name: CES2
Uniprot ID: O00748 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 gamma
Reactions: Not Available
Gene Name: PLA2G4C
Uniprot ID: Q9UP65 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-2
Reactions: Not Available
Gene Name: ACYP2
Uniprot ID: P14621 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-1
Reactions: Not Available
Gene Name: ACYP1
Uniprot ID: P07311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aminoacylase-1
Reactions: Not Available
Gene Name: ACY1
Uniprot ID: Q03154 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aspartoacylase
Reactions: Not Available
Gene Name: ASPA
Uniprot ID: P45381 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aspartoacylase-2
Reactions: Not Available
Gene Name: ACY3
Uniprot ID: Q96HD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acid ceramidase
Reactions: Not Available
Gene Name: ASAH1
Uniprot ID: Q13510 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Homeodomain-interacting protein kinase 1
Reactions: Not Available
Gene Name: HIPK1
Uniprot ID: Q86Z02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor gamma
Reactions: Not Available
Gene Name: PPARG
Uniprot ID: P37231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 6
Reactions: Not Available
Gene Name: SLC27A6
Uniprot ID: Q9Y2P4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 3
Reactions: Not Available
Gene Name: SLC27A3
Uniprot ID: Q5K4L6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 4
Reactions: Not Available
Gene Name: PNPLA4
Uniprot ID: P41247 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 4
Reactions: Not Available
Gene Name: SLC27A4
Uniprot ID: Q6P1M0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60 kDa lysophospholipase
Reactions: Not Available
Gene Name: ASPG
Uniprot ID: Q86U10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated
Reactions: Not Available
Gene Name: PLB1
Uniprot ID: Q6P1J6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 2
Reactions: Not Available
Gene Name: PNPLA2
Uniprot ID: Q96AD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 delta
Reactions: Not Available
Gene Name: PLA2G4D
Uniprot ID: Q86XP0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 epsilon
Reactions: Not Available
Gene Name: PLA2G4E
Uniprot ID: Q3MJ16 Link_out
Protein Sequence: FASTA
Name: Cytosolic phospholipase A2 zeta
Reactions: Not Available
Gene Name: PLA2G4F
Uniprot ID: Q68DD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-independent phospholipase A2-gamma
Reactions: Not Available
Gene Name: PNPLA8
Uniprot ID: Q9NP80 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 beta
Reactions: Not Available
Gene Name: PLA2G4B
Uniprot ID: P0C869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative neutral ceramidase C
Reactions: Not Available
Gene Name: ASAH2C
Uniprot ID: P0C7U2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alkaline ceramidase 2
Reactions: Not Available
Gene Name: ACER2
Uniprot ID: Q5QJU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Long-chain fatty acid transport protein 1
Reactions: Not Available
Gene Name: SLC27A1
Uniprot ID: Q6PCB7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA