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Showing Compound Carnosic acid (FDB014905)

Record Information
Version1.0
Creation date2010-04-08 22:11:32 UTC
Update date2019-11-26 03:10:54 UTC
Primary IDFDB014905
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCarnosic acid
DescriptionCarnosic acid, also known as carnosate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Carnosic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number3650-09-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
CarnosateGenerator
11,12-Dihydroxy-8,11,13-abietatrien-20-oic aciddb_source
2,4(1H,3H)-Pyrimidinedione, 5-fluorodihydro-6-hydroxy-biospider
4a(2H)-Phenanthrenecarboxylic acidHMDB
Carnosic aciddb_source
Deoxypicrosalvinic aciddb_source
RoseOxHMDB
SalvinHMDB
Salvin?db_source
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
Polarizability37.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O4
IUPAC name5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
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)
InChI KeyQRYRORQUOLYVBU-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2)C(O)=O
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
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
  • 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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 72.26%; H 8.49%; O 19.25%DFC
Melting PointMp 185-190° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D +191 (c, 1.07 in MeOH)DFC
Spectroscopic UV Data284 (e 1690) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID400886
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID455260
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID666
DrugBank IDNot Available
HMDB IDHMDB02358
CRC / DFC (Dictionary of Food Compounds) IDKWD08-Y:JXH93-K
EAFUS IDNot Available
Dr. Duke IDSALVIN|CARNOSIC-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 bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti mutagenicDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).