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Showing Compound Carnosolic acid (FDB006923)

Record Information
Version1.0
Creation date2010-04-08 22:07:22 UTC
Update date2025-11-18 23:03:05 UTC
Primary IDFDB006923
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCarnosolic acid
DescriptionCarnosolic acid, also known as carnosolate, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Carnosolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Carnosolic acid can be found in common sage and rosemary, which makes carnosolic acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5,6,9-Trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylateGenerator
CarnosolateGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP2.96ALOGPS
logP3.91ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.92 m³·mol⁻¹ChemAxon
Polarizability37.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O5
IUPAC name5,6,9-trihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
InChI IdentifierInChI=1S/C20H28O5/c1-10(2)11-8-12-13(21)9-14-19(3,4)6-5-7-20(14,18(24)25)15(12)17(23)16(11)22/h8,10,13-14,21-23H,5-7,9H2,1-4H3,(H,24,25)
InChI KeyXMKKZBYHMFTMOJ-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2O)C(O)=O
Average Molecular Weight348.4333
Monoisotopic Molecular Weight348.193674006
Classification
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
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0029000000-28f733fa6fe524fa23242016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-2379000000-427ae0dde798041032bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-4191000000-0b4e25f339b4099e3fe72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-66cb4210fadd62bacc7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-0059000000-ea2e0022679ea0912d4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-1493000000-8c82c23e91e1873a6acb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f72-0029000000-2edfd512cb334a1720d42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uds-0749000000-6c5a9d152fc41ad1d4242021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-3911000000-7cfc03591df2eadcd6342021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-283500a6f5515a0b930c2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0093000000-38395c3361a15a508ada2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-0391000000-0ba3b5ff68afed68c9a12021-10-21View Spectrum
NMRNot Available
ChemSpider ID9741216
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID11566445
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJWJ41-W:OYG11-P
EAFUS IDNot Available
Dr. Duke IDCARNOSOLIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti hepatotoxic62868 An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti lipoperoxidantAn agent that prevents peroxidation of lipids, reducing oxidative stress and cell damage. Its biological role involves protecting cell membranes from degradation. Therapeutically, it has applications in managing conditions related to oxidative stress, with key medical uses including neuroprotection, anti-inflammation, and antioxidant therapy.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Protease inhibitor37670 An agent that blocks the activity of proteases, enzymes that break down proteins. It has therapeutic applications in treating viral infections, cancer, and genetic disorders, with key medical uses including HIV/AIDS management and hepatitis C treatment.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).