| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:38:57 UTC |
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| Update Date | 2020-06-04 21:07:38 UTC |
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| BMDB ID | BMDB0000944 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Behenic acid |
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| Description | Behenic acid, also known as docosanoate or 1-docosanoic acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Behenic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Behenic acid is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Docosanoic acid | ChEBI | | Behensaeure | ChEBI | | CH3-[CH2]20-COOH | ChEBI | | Docosanic acid | ChEBI | | Docosanoate | ChEBI | | Docosansaeure | ChEBI | | Docosoic acid | ChEBI | | Dokosansaeure | ChEBI | | N-Docosanoic acid | ChEBI | | 1-Docosanoate | Generator | | Docosanate | Generator | | Docosanoic acid | Generator | | Docosoate | Generator | | N-Docosanoate | Generator | | Behenate | Generator | | FA(22:0) | HMDB | | Behenic acid | HMDB |
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| Chemical Formula | C22H44O2 |
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| Average Molecular Weight | 340.5836 |
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| Monoisotopic Molecular Weight | 340.334130652 |
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| IUPAC Name | docosanoic acid |
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| Traditional Name | behenic acid |
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| CAS Registry Number | 112-85-6 |
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| SMILES | CCCCCCCCCCCCCCCCCCCCCC(O)=O |
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| InChI Identifier | InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24) |
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| InChI Key | UKMSUNONTOPOIO-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 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 | Very long-chain fatty acids |
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| Alternative Parents | |
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| Substituents | - Very 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
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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 | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 81 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1.6e-05 mg/mL | 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
- Liver
- Milk
- Muscle
- Oocyte
- Placenta
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Detected and Quantified | 77.4 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 80.45 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1111.86 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 1340.49 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 520.11 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Adipose Tissue | Detected and Quantified | 481 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 | | Liver | 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 | 293.614 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | 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 |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000944 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB005830 |
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| KNApSAcK ID | C00001211 |
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| Chemspider ID | 7923 |
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| KEGG Compound ID | C08281 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Behenic acid |
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| METLIN ID | 260 |
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| PubChem Compound | 8215 |
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| PDB ID | Not Available |
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| ChEBI ID | 28941 |
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| References |
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| Synthesis Reference | Lu, Jianmin; Li, He; Yang, Yiping; Du, Baoshan. Preparation of behenic acid from erucic acid by hydrogenation at ordinary pressure. Zhongguo Youzhi (1997), 22(5), 57-58. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]
- Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
- 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.
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