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Carnosol
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Diterpenoid Phenol
| Canonical Smiles | O=C1O[C@H]2C[C@@H]3[C@]1(CCCC3(C)C)c1c2cc(c(c1O)O)C(C)C |
|---|---|
| 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/t13-,14-,20+/m0/s1 |
| InChIKey | XUSYGBPHQBWGAD-PJSUUKDQSA-N |
| Formula | C20H26O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 330.42 |
| Rotatable Bonds | 1 |
| TPSA | 66.76 |
| LogP | 4.29 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 330.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Salvia officinalis | Lamiaceae | Plantae | 38868 |
| 2 | Rosmarinuseriocalyx | Lamiaceae | Plantae | — |
Showing of synonyms
Carnosol
5957-80-2
Picrosalvin
UNII-483O455CKD
CCRIS 7122
HSDB 7680
483O455CKD
CARNOSOL [HSDB]
CARNOSOL [MI]
DTXSID80904451
NSC 39143
NSC-39143
CARNOSOL (CONSTITUENT OF ROSEMARY) [DSC]
(1R,8S,10S)-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
1,3,4,9,10,10aS-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-one
2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-(4aalpha,9alpha,10abeta))-
(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
2H-9,4A-(EPOXYMETHANO)PHENANTHREN-12-ONE, 1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-, (4AR,9S,10AS)-
2H-9,4A-(EPOXYMETHANO)PHENANTHREN-12-ONE, 1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-, (4AR-(4A.ALPHA.,9.ALPHA.,10A.BETA.))-
PODOCARPA-8,11,13-TRIEN-17-OIC ACID, 7.BETA.,11,12-TRIHYDROXY-13-ISOPROPYL-, 17,7-LACTONE
(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
(1R,8S,10S)-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
DTXCID301333605
CARNOSOL (CONSTITUENT OF ROSEMARY)
PODOCARPA-8,11,13-TRIEN-17-OIC ACID, 7BETA,11,12-TRIHYDROXY-13-ISOPROPYL-, 17,7-LACTONE
Xusygbphqbwgad-uhfffaoysa-n
MFCD02752467
CHEBI:3429
CHEMBL218693
(4aR,9S,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydro-1H-9,4a-(epoxymethano)phenanthren-12-one
Carnosol (Standard)
SCHEMBL42365
Carnosol, analytical standard
HY-N0643R
XUSYGBPHQBWGAD-PJSUUKDQSA-N
HY-N0643
MSK40210
BDBM50213683
S9127
AKOS015897159
CCG-208130
FC41666
1ST40210
AC-34727
DA-51592
CS-0009670
NS00126746
C09069
BRD-K67265981-001-01-5
Q16634054
- Sallam A, Mira A, et al. (2016). Acetylcholine esterase inhibitors and melanin synthesis inhibitors from Salvia officinalis.. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2016, 23(10), 1005-11. [View] [PubMed]
- Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
Pubchem:
442009
Cas:
5957-80-2
Zinc:
ZINC000003871891
Kegg Ligand:
C09069
Chebi:
3429
Nmrshiftdb2:
60025085
Chembl:
CHEMBL218693
Bindingdb:
50213683
CPRiL:
55870
SMILES: c1cccc(c1C234)C(OC2=O)CC3CCCC4
Level: 0
Mol. Weight: 330.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.73
- Plasma Protein Binding
- 75.86
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.5
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.81
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.65
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.41
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 1.99
- Rat (Acute)
- 2.34
- Rat (Chronic Oral)
- 2.62
- Fathead Minnow
- 3.96
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 386.5
- Hydration Free Energy
- -6.37
- Log(D) at pH=7.4
- 3.56
- Log(P)
- 3.97
- Log S
- -4.71
- Log(Vapor Pressure)
- -7.57
- Melting Point
- 189.53
- pKa Acid
- 7.8
- pKa Basic
- 5.63