| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 23:03:13 UTC |
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| Update Date | 2020-06-04 22:56:32 UTC |
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| BMDB ID | BMDB0003229 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Palmitoleic acid |
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| Description | Palmitoleic acid, also known as (Z)-9-hexadecenoate or palmitoleate, 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. Palmitoleic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Palmitoleic acid exists in all living species, ranging from bacteria to humans. In cattle, palmitoleic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Palmitoleic acid has been found to be associated with several diseases known as colorectal cancer and cirrhosis; also palmitoleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (9Z)-Hexadecenoic acid | ChEBI | | (Z)-9-Hexadecenoic acid | ChEBI | | (Z)-Hexadec-9-enoic acid | ChEBI | | 16:1DElta9 | ChEBI | | 9-cis-Hexadecenoic acid | ChEBI | | cis-9-Hexadecenoic acid | ChEBI | | cis-9-Palmitoleic acid | ChEBI | | cis-delta-9-Hexadecenoic acid | ChEBI | | cis-Delta(9)-Hexadecenoic acid | ChEBI | | cis-Palmitoleic acid | ChEBI | | Oleopalmitic acid | ChEBI | | Palmitolinoleic acid | ChEBI | | Zoomaric acid | ChEBI | | Zoomeric acid | ChEBI | | (9Z)-Hexadec-9-enoate | Kegg | | (9Z)-Hexadecenoate | Generator | | (Z)-9-Hexadecenoate | Generator | | (Z)-Hexadec-9-enoate | Generator | | 9-cis-Hexadecenoate | Generator | | cis-9-Hexadecenoate | Generator | | cis-9-Palmitoleate | Generator | | cis-delta-9-Hexadecenoate | Generator | | cis-Δ-9-hexadecenoate | Generator | | cis-Δ-9-hexadecenoic acid | Generator | | cis-delta(9)-Hexadecenoate | Generator | | cis-Δ(9)-hexadecenoate | Generator | | cis-Δ(9)-hexadecenoic acid | Generator | | cis-Palmitoleate | Generator | | Oleopalmitate | Generator | | Palmitolinoleate | Generator | | Zoomarate | Generator | | Zoomerate | Generator | | (9Z)-Hexadec-9-enoic acid | Generator | | Palmitoleate | Generator | | 9-Hexadecenoate | HMDB | | 9-Hexadecenoic acid | HMDB | | Hexadecenoate | HMDB | | Hexadecenoate (N-C16:1) | HMDB | | Hexadecenoic acid | HMDB | | Palmitoleic acid, (Z)-isomer | HMDB | | Palmitoleic acid, (e)-isomer | HMDB | | C16:1 trans-9 | HMDB | | Palmitelaidic acid | HMDB | | (9Z)-9-Hexadecenoic acid | HMDB | | 9Z-Hexadecenoic acid | HMDB | | C16:1 | HMDB | | FA(16:1(9Z)) | HMDB | | FA(16:1n7) | HMDB | | cis-delta9-Hexadecenoic acid | HMDB | | cis-Δ9-hexadecenoic acid | HMDB | | Palmitoleic acid | HMDB |
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| Chemical Formula | C16H30O2 |
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| Average Molecular Weight | 254.4082 |
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| Monoisotopic Molecular Weight | 254.224580204 |
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| IUPAC Name | (9Z)-hexadec-9-enoic acid |
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| Traditional Name | palmitoleic acid |
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| CAS Registry Number | 373-49-9 |
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| SMILES | CCCCCC\C=C/CCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7- |
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| InChI Key | SECPZKHBENQXJG-FPLPWBNLSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Fatty Acyls |
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| Sub Class | Fatty acids and conjugates |
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| Direct Parent | Long-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Long-chain fatty acid
- Unsaturated 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -0.1 °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 | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Adiposome
- Cell membrane
- Cytoplasm
- Membrane
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| Biospecimen Locations | - Adipose Tissue
- Blood
- Liver
- Milk
- Oocyte
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Skeletal Muscle
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 6812.56 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 7043.64 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 40560.92 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 54913.44 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 158404.29 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 194465.59 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 185371.38 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 169805.85 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 186597.76 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 172176.05 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 275.148 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 235.841 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 275.148 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2987.325 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4166.532 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 18081.178 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4166.532 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 18474.247 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 23191.0764 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2358.416 +/- 1179.208 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Oocyte | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.6 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.6 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details |
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| External Links |
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| HMDB ID | HMDB0003229 |
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| DrugBank ID | DB04257 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031085 |
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| KNApSAcK ID | C00001234 |
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| Chemspider ID | 393216 |
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| KEGG Compound ID | C08362 |
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| BioCyc ID | CPD-9245 |
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| BiGG ID | 246167 |
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| Wikipedia Link | Palmitoleic acid |
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| METLIN ID | 188 |
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| PubChem Compound | 445638 |
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| PDB ID | Not Available |
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| ChEBI ID | 28716 |
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| References |
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| Synthesis Reference | Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
- Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
- Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
- GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
- Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
- van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
- Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
- M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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