| Record Information |
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:44 -0600 |
| Update Date |
2013-02-08 17:11:39 -0700 |
| 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Heptadecanoate
- Heptadecanoic acid
- Margarate
- Margaric acid
- Margarinate
- Margarinic acid
- 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 |
| 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)
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| Substituents |
|
| Direct Parent |
Straight Chain Fatty Acids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| 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 |
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| Predicted Properties |
|
| Spectra |
|
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
|
| Tissue Location |
- Skeletal Muscle
- Prostate
- Adipose Tissue
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| Pathways |
Not Available
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
1.89 +/- 0.92 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
1.2 +/- 0.003 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB004676 |
| KNApSAcK ID |
C00007426  |
| Chemspider ID |
10033  |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
215873  |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB02259  |
| Metagene Link |
HMDB02259  |
| METLIN ID |
6578  |
| PubChem Compound |
10465  |
| PDB ID |
Not Available |
| ChEBI ID |
32365  |
| 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 |
- 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
- 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
- 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
- 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
- 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
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| Enzymes |
| Name: |
Fatty acid synthase
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| Reactions: |
- a (3R)-3-hydroxypalmitoyl-[acyl-carrier protein] = a hexadec-2-enoyl-[acyl-carrier protein] + H2O [RN:R04462]
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| Gene Name: |
FASN |
| Uniprot ID: |
P49327  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytosolic phospholipase A2
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| Reactions: |
- 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
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| Gene Name: |
PLA2G4A |
| Uniprot ID: |
P47712  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Phospholipase A2
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| Reactions: |
- phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
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| Gene Name: |
PLA2G1B |
| Uniprot ID: |
P04054  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Endothelial lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LIPG |
| Uniprot ID: |
Q9Y5X9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lipoprotein lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LPL |
| Uniprot ID: |
P06858  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 2
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES2 |
| Uniprot ID: |
O00748  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cholinesterase
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| Reactions: |
- an acylcholine + H2O = choline + a carboxylate [RN:R01029]
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| Gene Name: |
BCHE |
| Uniprot ID: |
P06276  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hormone-sensitive lipase
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| Reactions: |
- (1) diacylglycerol + H2O = monoacylglycerol + a carboxylate [RN:R05209]
- (2) triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
- (3) monoacylglycerol + H2O = glycerol + a carboxylate [RN:R07293]
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| Gene Name: |
LIPE |
| Uniprot ID: |
Q05469  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acylphosphatase-2
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| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
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| Gene Name: |
ACYP2 |
| Uniprot ID: |
P14621  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acylphosphatase-1
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| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
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| Gene Name: |
ACYP1 |
| Uniprot ID: |
P07311  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Aminoacylase-1
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| Reactions: |
- an N-acyl-L-amino acid + H2O = a carboxylate + an L-amino acid [RN:R01263]
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| Gene Name: |
ACY1 |
| Uniprot ID: |
Q03154  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Aspartoacylase
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| Reactions: |
- N-acyl-L-aspartate + H2O = a carboxylate + L-aspartate [RN:R00546]
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| Gene Name: |
ASPA |
| Uniprot ID: |
P45381  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acid ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH1 |
| Uniprot ID: |
Q13510  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 2
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER2 |
| Uniprot ID: |
Q5QJU3  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Neutral ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH2 |
| Uniprot ID: |
Q9NR71  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 7
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES7 |
| Uniprot ID: |
Q6NT32  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 1
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER1 |
| Uniprot ID: |
Q8TDN7  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 3
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES3 |
| Uniprot ID: |
Q6UWW8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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