Record Information |
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Version | 2.0 |
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Created at | 2021-06-22 17:26:50 UTC |
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Updated at | 2021-08-20 00:00:46 UTC |
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NP-MRD ID | NP0043872 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Farnesol |
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Description | Farnesol, also known as (2E,6E)-farnesol or trans-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, farnesol is considered to be an isoprenoid. Farnesol exists in all eukaryotes, ranging from yeast to plants to humans. In humans, farnesol is involved in the bile acid indirect signalling pathway. Farnesol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Farnesol is found in Abies firma, Acokanthera oblongifolia, Ageratum conyzoides, Alpinia conchigera, Artemisia monosperma, Boletinus cavipes, Bombus hortorum, Bothriochloa bladhii, Centella asiatica, Chaerophyllum macrospermum, Cinnamomum sieboldii, Citrus aurantiifolia, Citrus aurantium, Citrus maxima, Citrus paradise x Poncirus trifoliata, Poncirus trifoliata , Cleistopholis patens, Coluria geoides, Cymbopogon distans, Cymbopogon martinii, Cymbopogon schoenanthus, Daphne odora, Eucalyptus globulus , Eucommia ulmoides, Humulus lupulus, Juniperus communis, Laggera alata, Lantana camara, Larix kaempferi, Lentinellus cochleatus, Lonicera japonica, Loxodonta africana, Matricaria chamomilla, Melaleuca leucadendra, Monodora myristica , Murraya paniculata , Nicotiana alata, Origanum majorana, Origanum sipyleum, Paeonia lactiflora, Perilla frutescens, Pinus thunbergii, Pittosporum tobira, Poncirus trifoliate x Citrus sinensis, Pulicaria arabica, Rosa centifolia, Rudbeckia mollis, Sideritis tragoriganum, Suillus cavipes, Tagetes lucida, Tanacetum millefolium, Torreya nucifera, Uvaria pandensis, Zanthoxylum simulans, Zanthoxylum zanthoxyloides and Zieria minutiflora. Farnesol was first documented in 2000 (PMID: 10753967). Based on a literature review a small amount of articles have been published on Farnesol (PMID: 15840382) (PMID: 11254751) (PMID: 15158752) (PMID: 16845684). |
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Structure | CC(C)=CCC\C(C)=C\CC\C(C)=C\CO InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+ |
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Synonyms | Value | Source |
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(2-trans,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol | ChEBI | (2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol | ChEBI | (2E,6E)-Farnesol | ChEBI | (e)-Farnesol | ChEBI | (e,e)-Farnesol | ChEBI | 2-trans,6-trans-Farnesol | ChEBI | all-trans-Farnesol | ChEBI | trans,trans-alpha-Farnesol | ChEBI | trans,trans-Farnesol | ChEBI | trans-Farnesol | ChEBI | Ditrans,polycis-polyprenol | Kegg | trans,trans-a-Farnesol | Generator | trans,trans-Α-farnesol | Generator | 2-cis,6-trans-Farnesol | HMDB | 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol | HMDB | Farnesyl alcohol | HMDB | FCI 119a | HMDB | Nikkosome | HMDB | Farnesol | MeSH | (E)-beta-Farnesol | PhytoBank | (E)-β-Farnesol | PhytoBank | (E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol | PhytoBank | (E,E)-Farnesyl alcohol | PhytoBank | (t,t)-Farnesol | PhytoBank | 2,6-Di-trans-farnesol | PhytoBank | 2,6-trans,trans-Farnesol | PhytoBank | 3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol | PhytoBank | all-E-Farnesol | PhytoBank | trans-1-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatriene | PhytoBank | trans-2,trans-6-Farnesol | PhytoBank | 3,7,11-Trimethyl-2,6,10-dodecen-1-ol | PhytoBank |
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Chemical Formula | C15H26O |
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Average Mass | 222.3663 Da |
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Monoisotopic Mass | 222.19837 Da |
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IUPAC Name | (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol |
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Traditional Name | (E)-farnesol |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CCC\C(C)=C\CC\C(C)=C\CO |
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InChI Identifier | InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+ |
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InChI Key | CRDAMVZIKSXKFV-YFVJMOTDSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 62.9 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 250.1 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Farsesane sesquiterpenoid
- Sesquiterpenoid
- Fatty alcohol
- Fatty acyl
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Horn TL, Long L, Cwik MJ, Morrissey RL, Kapetanovic IM, McCormick DL: Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol. Chem Biol Interact. 2005 Apr 15;152(2-3):79-99. doi: 10.1016/j.cbi.2005.02.006. [PubMed:15840382 ]
- Hanley K, Wood L, Ng DC, He SS, Lau P, Moser A, Elias PM, Bikle DD, Williams ML, Feingold KR: Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D. J Lipid Res. 2001 Mar;42(3):390-8. [PubMed:11254751 ]
- DeBarber AE, Bleyle LA, Roullet JB, Koop DR: Omega-hydroxylation of farnesol by mammalian cytochromes p450. Biochim Biophys Acta. 2004 Jun 1;1682(1-3):18-27. doi: 10.1016/j.bbalip.2004.01.003. [PubMed:15158752 ]
- Saidi S, Luitaud C, Rouabhia M: In vitro synergistic effect of farnesol and human gingival cells against Candida albicans. Yeast. 2006 Jul 15;23(9):673-87. doi: 10.1002/yea.1389. [PubMed:16845684 ]
- Hanley K, Komuves LG, Ng DC, Schoonjans K, He SS, Lau P, Bikle DD, Williams ML, Elias PM, Auwerx J, Feingold KR: Farnesol stimulates differentiation in epidermal keratinocytes via PPARalpha. J Biol Chem. 2000 Apr 14;275(15):11484-91. doi: 10.1074/jbc.275.15.11484. [PubMed:10753967 ]
- Tomonari Wada, Kenji Kobata, Yasuo Hayashi & Hisao Shibata (1995). Tomonari Wada, Kenji Kobata, Yasuo Hayashi & Hisao Shibata (1995) Two Chemotypes of Boletinus cavipes, Bioscience, Biotechnology, and Biochemistry, 59:6, 1036-1039, DOI: 10.1271/bbb.59.1036. Bioscience, Biotechnology, and Biochemistry.
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