Carnosic acid (CHEM020998)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 02:50:39 UTC
Update Date2016-10-28 10:02:00 UTC
Accession NumberCHEM020998
Identification
Common NameCarnosic acid
ClassSmall Molecule
DescriptionAn abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis) and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4AR,10as)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acidChEBI
11,12-Dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-Oic acidChEBI
SalvinChEBI
(4AR,10as)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylateGenerator
11,12-Dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-OateGenerator
CarnosateGenerator
Chemical FormulaC20H28O4
Average Molecular Mass332.434 g/mol
Monoisotopic Mass332.199 g/mol
CAS Registry NumberNot Available
IUPAC Name(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
Traditional Namesalvin
SMILES[H][C@@]12CCC3=CC(C(C)C)=C(O)C(O)=C3[C@]1(CCCC2(C)C)C(O)=O
InChI IdentifierInChI=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
InChI KeyQRYRORQUOLYVBU-VBKZILBWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Abietane diterpenoid
  • Diterpenoid
  • Hydrophenanthrene
  • Phenanthrene
  • 1-naphthalenecarboxylic acid
  • 1-naphthalenecarboxylic acid or derivatives
  • Tetralin
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP4.16ALOGPS
logP5.14ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.29ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.41 m³·mol⁻¹ChemAxon
Polarizability37.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0049000000-43d0b97be08dba4a4834Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lf-2593000000-a81c2079ae36eb908bf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-6291000000-25c353457ea06ed837ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0039000000-bff7afde01ef5a0e34e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0094000000-03d58e3ec8693ee52d99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rm-0191000000-d75a037304fd9570e2f9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-18103
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarnosic_acid
Chemspider IDNot Available
ChEBI ID65585
PubChem Compound ID65126
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11504768
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17177234
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22232247
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22246562
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22687582
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22828666
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26976595
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27694001
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27703160
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27716981
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27957651
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28008719
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28159594
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28282784
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28288941
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=28343998
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=28440400
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=28674855
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28877257
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=28887507
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28916593
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28918123
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=29100552
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=8229021