Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2021-10-13 04:39:01 UTC
HMDB IDHMDB0002358
Secondary Accession Numbers
  • HMDB02358
Metabolite Identification
Common NameCarnosic acid
DescriptionCarnosic acid is the major rosemary polyphenol. Carnosic acid appears to enhance the anti-cancer activity of vitamin D(3) and its analogs. Carnosic acid enhances monocytic differentiation of HL60 cells when combined not only with 1alpha,25-dihydroxyvitamin D3 (1,25D3) or 12-O-tetradecanoyl phorbol 13-acetate (TPA) but also with the 'classic' granulocytic inducer all-trans retinoic acid (ATRA). Carnosic acid alone increases the expression of vitamin D receptor (VDR) and retinoid X receptor (RXR) alpha, which was greatly enhanced in the presence of 1alpha,25-dihydroxyvitamin D3 and all-trans retinoic acid. (PMID: 15265684 ).
Structure
Data?1582752245
Synonyms
ValueSource
CarnosateGenerator
4a(2H)-Phenanthrenecarboxylic acidHMDB
RoseOxHMDB
SalvinHMDB
(4AR)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylateHMDB
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name(4aR)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
Traditional Name(4aR)-5,6-dihydroxy-7-isopropyl-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
CAS Registry Number3650-09-7
SMILES
CC(C)C1=CC2=C(C(O)=C1O)[C@]1(CCCC(C)(C)C1CC2)C(O)=O
InChI Identifier
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-/m1/s1
InChI KeyQRYRORQUOLYVBU-YBMSBYLISA-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point499.00 to 503.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.73 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.405 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP10(4.16) g/LALOGPS
logP10(5.14) g/LChemAxon
logS10(-3.6) g/LALOGPS
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
Polarizability37.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.21631661259
DarkChem[M-H]-174.76131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carnosic acidCC(C)C1=CC2=C(C(O)=C1O)[C@]1(CCCC(C)(C)C1CC2)C(O)=O3612.8Standard polar33892256
Carnosic acidCC(C)C1=CC2=C(C(O)=C1O)[C@]1(CCCC(C)(C)C1CC2)C(O)=O2574.2Standard non polar33892256
Carnosic acidCC(C)C1=CC2=C(C(O)=C1O)[C@]1(CCCC(C)(C)C1CC2)C(O)=O2784.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carnosic acid,1TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)[C@@]1(C(=O)O)CCCC(C)(C)C1CC22663.5Semi standard non polar33892256
Carnosic acid,1TMS,isomer #2CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)[C@@]1(C(=O)O)CCCC(C)(C)C1CC22641.9Semi standard non polar33892256
Carnosic acid,1TMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O)[C@@]1(C(=O)O[Si](C)(C)C)CCCC(C)(C)C1CC22555.1Semi standard non polar33892256
Carnosic acid,2TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]1(C(=O)O)CCCC(C)(C)C1CC22632.1Semi standard non polar33892256
Carnosic acid,2TMS,isomer #2CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O)[C@@]1(C(=O)O[Si](C)(C)C)CCCC(C)(C)C1CC22528.3Semi standard non polar33892256
Carnosic acid,2TMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C)[C@@]1(C(=O)O[Si](C)(C)C)CCCC(C)(C)C1CC22512.2Semi standard non polar33892256
Carnosic acid,3TMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C)=C1O[Si](C)(C)C)[C@@]1(C(=O)O[Si](C)(C)C)CCCC(C)(C)C1CC22549.7Semi standard non polar33892256
Carnosic acid,1TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)[C@@]1(C(=O)O)CCCC(C)(C)C1CC22916.4Semi standard non polar33892256
Carnosic acid,1TBDMS,isomer #2CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]1(C(=O)O)CCCC(C)(C)C1CC22916.5Semi standard non polar33892256
Carnosic acid,1TBDMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O)[C@@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC(C)(C)C1CC22821.3Semi standard non polar33892256
Carnosic acid,2TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]1(C(=O)O)CCCC(C)(C)C1CC23083.2Semi standard non polar33892256
Carnosic acid,2TBDMS,isomer #2CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O)[C@@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC(C)(C)C1CC22985.5Semi standard non polar33892256
Carnosic acid,2TBDMS,isomer #3CC(C)C1=CC2=C(C(O)=C1O[Si](C)(C)C(C)(C)C)[C@@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC(C)(C)C1CC23031.5Semi standard non polar33892256
Carnosic acid,3TBDMS,isomer #1CC(C)C1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C)[C@@]1(C(=O)O[Si](C)(C)C(C)(C)C)CCCC(C)(C)C1CC23157.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carnosic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-5095000000-44e26f30355230a536dd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carnosic acid GC-MS (3 TMS) - 70eV, Positivesplash10-001i-2000690000-96a4336cd84ad1b219c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carnosic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 10V, Positive-QTOFsplash10-00lr-0029000000-e821b75be9717da6d0fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 20V, Positive-QTOFsplash10-014u-1394000000-57d59ef310187aab716d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 40V, Positive-QTOFsplash10-0a4i-6091000000-88ac05dfb8953a29e1f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 10V, Negative-QTOFsplash10-001i-0039000000-972f7cd92d10a793b20a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 20V, Negative-QTOFsplash10-0019-0096000000-369ae0ecc5d29eb5d42d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 40V, Negative-QTOFsplash10-060d-0191000000-d082f039be91d413111d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 10V, Positive-QTOFsplash10-001r-0079000000-bad105879d4f91261b642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 20V, Positive-QTOFsplash10-000i-0292000000-37f8d04b9c0413eaf7ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 40V, Positive-QTOFsplash10-0kor-5953000000-8230bf6f6378187b30a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 10V, Negative-QTOFsplash10-001i-0029000000-5af13dd36351bcc03c7f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 20V, Negative-QTOFsplash10-000i-0090000000-7f862075621f5ede20b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carnosic acid 40V, Negative-QTOFsplash10-00y0-0290000000-eaf40225b10a387ebefc2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014905
KNApSAcK IDC00036880
Chemspider ID400886
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarnosic acid
METLIN IDNot Available
PubChem Compound455260
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588221
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Danilenko M, Studzinski GP: Enhancement by other compounds of the anti-cancer activity of vitamin D(3) and its analogs. Exp Cell Res. 2004 Aug 15;298(2):339-58. [PubMed:15265684 ]