| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:29 UTC |
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| Update date | 2019-11-26 03:10:48 UTC |
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| Primary ID | FDB014814 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Carnosol |
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| Description | Bitter principle in Salvia carnosa, Salvia officinalis (sage), Salvia triloba (Greek sage) and Rosmarinus officinalis (rosemary). Nutriceutical with anticancer props.
Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462); Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665) |
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| CAS Number | 5957-80-2 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C20H26O4 |
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| IUPAC name | 3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one |
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| InChI Identifier | InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3 |
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| InChI Key | XUSYGBPHQBWGAD-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=O |
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| Average Molecular Weight | 330.418 |
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| Monoisotopic Molecular Weight | 330.18310932 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. |
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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 | Terpene lactones |
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| Direct Parent | Diterpene lactones |
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| Alternative Parents | |
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| Substituents | - Diterpene lactone
- Diterpenoid
- Phenanthrene
- Benzopyran
- Isochromane
- 2-benzopyran
- Tetralin
- 1-hydroxy-4-unsubstituted benzenoid
- Delta valerolactone
- Delta_valerolactone
- Benzenoid
- Oxane
- Carboxylic acid ester
- Lactone
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0009000000-a5b241b8344c36c2f0bf | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0019000000-e7accf1a4d2c8280c2f4 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03y0-1093000000-a5175230ca7dfd038446 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0019000000-08dcb84c59b0d280b13f | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001r-6097000000-b2894527af41d8c29ad8 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-067l-9041000000-63e8a7af26ccd9f942f7 | 2016-08-03 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 390568 |
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| ChEMBL ID | CHEMBL218693 |
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| KEGG Compound ID | C09069 |
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| Pubchem Compound ID | 442009 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 668 |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02121 |
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| CRC / DFC (Dictionary of Food Compounds) ID | JWJ41-W:JWJ41-W |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | PICROSALVIN|CARNOSOL |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003410 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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