Cyclolariciresinol (CHEM023011)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:55 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM023011
Identification
Common NameCyclolariciresinol
ClassSmall Molecule
DescriptionA lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,3-naphthalenedimethanolChEBI
(+)-CyclolariciresinolPhytoBank
(+)-IsolariciresinolPhytoBank
CyclolariciresinolPhytoBank
alpha-Conidendryl alcoholPhytoBank
α-Conidendryl alcoholPhytoBank
Chemical FormulaC20H24O6
Average Molecular Mass360.401 g/mol
Monoisotopic Mass360.157 g/mol
CAS Registry NumberNot Available
IUPAC Name(6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol
Traditional Name(6R,7R,8S)-8-(4-hydroxy-3-methoxyphenyl)-6,7-bis(hydroxymethyl)-3-methoxy-5,6,7,8-tetrahydronaphthalen-2-ol
SMILESCOC1=CC2=C(C=C1O)[C@@H]([C@@H](CO)[C@H](CO)C2)C1=CC=C(O)C(OC)=C1
InChI IdentifierInChI=1S/C20H24O6/c1-25-18-6-11(3-4-16(18)23)20-14-8-17(24)19(26-2)7-12(14)5-13(9-21)15(20)10-22/h3-4,6-8,13,15,20-24H,5,9-10H2,1-2H3/t13-,15-,20-/m0/s1
InChI KeyOGFXBIXJCWAUCH-KPHUOKFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassAryltetralin lignans
Sub Class9,9p-dihydroxyaryltetralin lignans
Direct Parent9,9p-dihydroxyaryltetralin lignans
Alternative Parents
Substituents
  • 9,9p-dihydroxyaryltetralin lignan
  • Methoxyphenol
  • Tetralin
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • 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 Solubility0.027 g/LALOGPS
logP1.79ALOGPS
logP1.78ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.84ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.87 m³·mol⁻¹ChemAxon
Polarizability38.1 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0009000000-c62347f7d23f139500b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-0029000000-2e701260ff02204a6db4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-046r-1296000000-2462184e5f2381cc8003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-f73a7a954d179ba82441Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i3-0019000000-549e39425b6f669403a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0049000000-a00f15bc0e90788a9ef8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-f2b72c239d8ad9f0868eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08i1-0029000000-1fd70a6bd2e6aaef22c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-0039000000-fb105fedab647c96f590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0009000000-90ecf9cf4ec9788affbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0019000000-9e373060a35df37cf5f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01r6-0149000000-0f7bca44b9b554426eb0Spectrum
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 IDHMDB0301739
FooDB IDFDB000328
Phenol Explorer IDNot Available
KNApSAcK IDC00007204
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID141054
ChEBI ID69542
PubChem Compound IDNot Available
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=21138310
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21973054