Cinnamtannin B2 (CHEM031175)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:26:56 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031175
Identification
Common NameCinnamtannin B2
ClassSmall Molecule
DescriptionAlkaloid from the fruits of Limonia acidissima (wood apple). Acidissiminin is found in beverages and fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epicatechin(4b->8)epicatechin(2b->7,4b->8)epicatechin(4b->8)epicatechinHMDB
Chemical FormulaC60H48O24
Average Molecular Mass1153.009 g/mol
Monoisotopic Mass1152.254 g/mol
CAS Registry Number88038-12-4
IUPAC Name(1R,5R,6R,7S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
Traditional Name(1R,5R,6R,7S,13R,21R)-5,13-bis(3,4-dihydroxyphenyl)-16-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-7-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol
SMILESO[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=C5[C@@H]6[C@@H](O)[C@](OC5=CC(O)=C34)(OC3=C([C@@H]4[C@@H](O)[C@H](OC5=CC(O)=CC(O)=C45)C4=CC=C(O)C(O)=C4)C(O)=CC(O)=C63)C3=CC=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1
InChI IdentifierInChI=1S/C60H48O24/c61-23-13-34(71)42-40(14-23)80-54(20-2-6-26(63)31(68)10-20)51(77)48(42)45-36(73)17-37(74)46-50-47-41(83-60(59(50)79,84-58(45)46)22-4-8-28(65)33(70)12-22)18-38(75)44-49(52(78)55(82-57(44)47)21-3-7-27(64)32(69)11-21)43-35(72)16-29(66)24-15-39(76)53(81-56(24)43)19-1-5-25(62)30(67)9-19/h1-14,16-18,39,48-55,59,61-79H,15H2/t39-,48-,49+,50-,51-,52-,53-,54-,55-,59-,60-/m1/s1
InChI KeyQRQAODSINXAOBF-UKTWWWBFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Benzamide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Carboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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 Solubility0.41 g/LALOGPS
logP4.18ALOGPS
logP6.23ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.6ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area430.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity289.21 m³·mol⁻¹ChemAxon
Polarizability114.88 ųChemAxon
Number of Rings13ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2900000015-c4ee94ec97f7c6743f80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0560-6500000096-379d26826180ca51adb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000022-3a79a420dc697bcc54f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900010001-f54ecc8779f7542d0b8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f80-3930100020-f8c168b2764eb0350793Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2891301003-3103092846542baeab7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000010-2c28163d4e8c963bf12cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5930000010-effabc07debc13537794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9800010202-020a184d1bfb96ead98eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-2205b63bf992254f6c30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5900000000-1b97c49bacefa7ce4434Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9600010010-46f62210df6e360b66ddSpectrum
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 IDHMDB0038619
FooDB IDFDB018013
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4946792
ChEBI IDNot Available
PubChem Compound ID6442730
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM