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Carnosic acid
- Family: Plantae - Lamiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Benzenediol Abietane Diterpene
| Canonical Smiles | OC(=O)[C@@]12CCCC([C@@H]2CCc2c1c(O)c(c(c2)C(C)C)O)(C)C |
|---|---|
| InChI | InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1 |
| InChIKey | QRYRORQUOLYVBU-VBKZILBWSA-N |
| Formula | C20H28O4 |
| HBA | 3 |
| HBD | 3 |
| MW | 332.44 |
| Rotatable Bonds | 2 |
| TPSA | 77.76 |
| LogP | 4.32 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 332.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rosmarinuseriocalyx | Lamiaceae | Plantae | — |
Showing of synonyms
Carnosic acid
3650-09-7
Salvin
LI791SXT24
CHEBI:65585
UNII-LI791SXT24
11,12-dihydroxyabieta-8,11,13-trien-20-oic acid
11,12-dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-oic acid
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid
4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-trans)-
CARNOSIC ACID (USP-RS)
CARNOSIC ACID [USP-RS]
Podocarpa-8,11,13-trien-17-oic acid, 11,12-dihydroxy-13-isopropyl-
(4AR,10AS)-1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-4A(2H)-PHENANTHRENECARBOXYLIC ACID
CARNOSIC ACID (CONSTITUENT OF ROSEMARY)
139236-75-2
MFCD02259459
NSC694080
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-rel-
(4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic Acid
RoseOx
Rosamox
Carnosic-acid
Carsonic acid
Carnosic acid (Standard)
UPCMLD-DP056
CARNOSIC ACID [MI]
CHEMBL484853
SCHEMBL9923661
UPCMLD-DP056:001
HY-N0644R
DTXSID20904450
BCPP000299
Carnosic acid, analytical standard
HY-N0644
MSK40209
BDBM50371232
S3838
AKOS015901362
AC-6030
BCP9000491
CCG-207954
FC32525
NSC-694080
SMP2_000204
NCGC00161623-01
1ST40209
AS-31052
NCI60_033653
BCP0726000155
C2488
C3477
CS-0009671
NS00124779
C21818
A918580
Q412827
SR-05000002202
SR-05000002202-2
CARNOSIC ACID (CONSTITUENT OF ROSEMARY) [DSC]
Carnosic acid, primary pharmaceutical reference standard
Carnosic acid from Rosmarinus officinalis, >=91%, powder
Carnosic acid, United States Pharmacopeia (USP) Reference Standard
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylicacid
Pubchem:
65126
Cas:
3650-09-7
Gnps:
CCMSLIB00006581498
Zinc:
ZINC000003984016
Chebi:
65585
Nmrshiftdb2:
60022507
Metabolights:
MTBLC65585
Chembl:
CHEMBL484853
Bindingdb:
50371232
CPRiL:
56520
SMILES: c1cccc(c12)CCC3C2CCCC3
Level: 0
Mol. Weight: 332.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.23
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.01
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.08
- Plasma Protein Binding
- 102.9
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.34
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.25
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.17
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.5
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.57
- Rat (Acute)
- 2.3
- Rat (Chronic Oral)
- 3.28
- Fathead Minnow
- 3.94
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 390.22
- Hydration Free Energy
- -6.19
- Log(D) at pH=7.4
- 1.69
- Log(P)
- 3.87
- Log S
- -3.87
- Log(Vapor Pressure)
- -9.09
- Melting Point
- 196.69
- pKa Acid
- 5.61
- pKa Basic
- 7.61