(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
PubChem CID: 2579
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| Compound Synonyms | (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one, 3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one, MEGxp0_001119, SCHEMBL18290355, DTXSID30863665, HMS3649B03, BCP20030, NSC39143, SMP2_000248, SR-01000946633, SR-01000946633-1, 11,12-Dihydroxy-7,20-epoxyabieta-8(14),9(11),12-trien-20-one, (1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.0^{1,10.0^{2,7]hexadeca-2,4,6-trien-15-one, 3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0(1),(1)?.0(2),?]hexadeca-2,4,6-trien-15-one |
|---|---|
| Topological Polar Surface Area | 66.8 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | XUSYGBPHQBWGAD-UHFFFAOYSA-N |
| Rotatable Bond Count | 1.0 |
| State | Solid |
| Synonyms | 1,3,4,9,10,10AS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4ar-(epoxymethano)phenanthren-12-one, 11,12-Dihydroxy-8,11,13-abietatrien-20,7-olide, Picrosalvin |
| Heavy Atom Count | 24.0 |
| Compound Name | (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one |
| 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) |
| Exact Mass | 330.183 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 330.183 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 542.0 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 330.4 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one |
| Total Atom Stereocenter Count | 3.0 |
| Total Bond Stereocenter Count | 0.0 |
| Inchi | 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 |
| Smiles | CC(C)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)O)O |
| Xlogp | 4.4 |
| Defined Bond Stereocenter Count | 0.0 |
| Molecular Formula | C20H26O4 |
- 1. Outgoing r'ship
FOUND_INto/from Rosmarinus Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all - 2. Outgoing r'ship
FOUND_INto/from Salvia Officinalis (Plant) Rel Props:Source_db:fooddb_chem_all