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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:56:08 UTC
Update Date2022-03-07 02:55:27 UTC
HMDB IDHMDB0037673
Secondary Accession Numbers
  • HMDB37673
Metabolite Identification
Common NameCinnamtannin D1
DescriptionCinnamtannin D1 belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Cinnamtannin D1 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cinnamtannin D1 has been detected, but not quantified in, fruits and lingonberries. This could make cinnamtannin D1 a potential biomarker for the consumption of these foods. A proanthocyanidin found in Cinnamomum cassia.
Structure
Data?1563863071
Synonyms
ValueSource
Epicatechin(2b->7,4b->8)epicatechin(4b->8)catechinHMDB
Cinnamtannin b-1HMDB
Cinnamtannin D-1HMDB
Chemical FormulaC45H36O18
Average Molecular Weight864.765
Monoisotopic Molecular Weight864.190164319
IUPAC Name(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-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,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-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
CAS Registry Number97233-06-2
SMILES
[H][C@@]12[C@@H](O)[C@@](OC3=CC(O)=CC(O)=C13)(OC1=C2C2=C([C@@H]([C@@H](O)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@@H](O)C3)C2=CC=C(O)C(O)=C2)C(O)=C1)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37-,38+,39+,40+,41+,44+,45-/m0/s1
InChI KeyBYSRPHRKESMCPO-HMQYECKYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassBiflavonoids and polyflavonoids
Direct ParentBiflavonoids and polyflavonoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.54ALOGPS
logP4.91ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.6ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area320.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity216.7 m³·mol⁻¹ChemAxon
Polarizability85.34 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-304.70130932474
DeepCCS[M+Na]+278.21130932474
AllCCS[M+H]+282.232859911
AllCCS[M+H-H2O]+282.032859911
AllCCS[M+NH4]+282.232859911
AllCCS[M+Na]+282.232859911
AllCCS[M-H]-277.532859911
AllCCS[M+Na-2H]-282.132859911
AllCCS[M+HCOO]-287.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cinnamtannin D1[H][C@@]12[C@@H](O)[C@@](OC3=CC(O)=CC(O)=C13)(OC1=C2C2=C([C@@H]([C@@H](O)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@@H](O)C3)C2=CC=C(O)C(O)=C2)C(O)=C1)C1=CC=C(O)C(O)=C19970.6Standard polar33892256
Cinnamtannin D1[H][C@@]12[C@@H](O)[C@@](OC3=CC(O)=CC(O)=C13)(OC1=C2C2=C([C@@H]([C@@H](O)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@@H](O)C3)C2=CC=C(O)C(O)=C2)C(O)=C1)C1=CC=C(O)C(O)=C17044.2Standard non polar33892256
Cinnamtannin D1[H][C@@]12[C@@H](O)[C@@](OC3=CC(O)=CC(O)=C13)(OC1=C2C2=C([C@@H]([C@@H](O)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C=C(O)C3=C2O[C@@H]([C@@H](O)C3)C2=CC=C(O)C(O)=C2)C(O)=C1)C1=CC=C(O)C(O)=C18377.5Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 10V, Positive-QTOFsplash10-0292-0300013490-ec26e82ac3cbfe2e2b342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 20V, Positive-QTOFsplash10-06r7-0601093740-7b261c7017bedecadbca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 40V, Positive-QTOFsplash10-0a4i-0903020120-941235b046ebe1534e232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 10V, Negative-QTOFsplash10-03di-0100010290-e775ab4962207ca269ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 20V, Negative-QTOFsplash10-0gw1-0940220440-743d2b7bb64c3c3212792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 40V, Negative-QTOFsplash10-06vr-0962322000-e8fd77cb8ef30e20331b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 10V, Positive-QTOFsplash10-014i-0000000190-9b689094479cf9a1a18d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 20V, Positive-QTOFsplash10-014i-0210100590-170e2f269eed5e69760a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 40V, Positive-QTOFsplash10-00xr-1710101960-7cfe213402c5bcdff38b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 10V, Negative-QTOFsplash10-03di-0000000090-8dd342560dbe7ef6a1522021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 20V, Negative-QTOFsplash10-03di-0000000390-134540ced36417c6563e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinnamtannin D1 40V, Negative-QTOFsplash10-0bt9-1730000790-99e7da205ab13d512b512021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB016800
KNApSAcK IDC00009289
Chemspider ID25053959
KEGG Compound IDC17632
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46173958
PDB IDNot Available
ChEBI ID69305
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .