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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:06:35 UTC
Update Date2022-03-07 02:54:23 UTC
HMDB IDHMDB0035163
Secondary Accession Numbers
  • HMDB35163
Metabolite Identification
Common NameChestanin
DescriptionChestanin belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Chestanin has been detected, but not quantified in, nuts. This could make chestanin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chestanin.
Structure
Data?1563862676
Synonyms
ValueSource
Chestanin aHMDB
MP3HMDB
(3,5-Dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(5-{[(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC40H42O26
Average Molecular Weight938.7459
Monoisotopic Molecular Weight938.196431516
IUPAC Name(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(5-{[(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoate
Traditional Name(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(5-{[(3,5-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methoxy]carbonyl}-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoate
CAS Registry Number68325-50-8
SMILES
OCC1OC(OC2=C(O)C=C(COC(=O)C3=CC(O)=C(O)C(OC4=C(O)C(O)=C(O)C=C4C(=O)OCC4=CC(O)=C(OC5OC(CO)C(O)C(O)C5O)C(O)=C4)=C3)C=C2O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C40H42O26/c41-8-23-27(51)29(53)32(56)39(63-23)65-35-18(45)1-12(2-19(35)46)10-60-37(58)14-5-16(43)25(49)22(6-14)62-34-15(7-17(44)26(50)31(34)55)38(59)61-11-13-3-20(47)36(21(48)4-13)66-40-33(57)30(54)28(52)24(9-42)64-40/h1-7,23-24,27-30,32-33,39-57H,8-11H2
InChI KeyNSFIWSANZNJXLP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Phenolic glycoside
  • Diphenylether
  • Galloyl ester
  • Gallic acid or derivatives
  • O-glycosyl compound
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Glycosyl compound
  • Diaryl ether
  • Benzoate ester
  • Benzyloxycarbonyl
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Benzoyl
  • Phenoxy compound
  • Resorcinol
  • Phenol ether
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.19ALOGPS
logP-0.95ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area442.66 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity211.65 m³·mol⁻¹ChemAxon
Polarizability87.84 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+282.16630932474
DeepCCS[M-H]-280.43130932474
DeepCCS[M-2H]-314.46330932474
DeepCCS[M+Na]+288.53730932474
AllCCS[M+H]+266.532859911
AllCCS[M+H-H2O]+267.232859911
AllCCS[M+NH4]+265.932859911
AllCCS[M+Na]+265.732859911
AllCCS[M-H]-269.932859911
AllCCS[M+Na-2H]-274.532859911
AllCCS[M+HCOO]-279.532859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 10V, Positive-QTOFsplash10-05i9-0202214905-d3a08f55fd3408e4786c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 20V, Positive-QTOFsplash10-08fr-0403309701-bb9cc78a4165622df8372016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 40V, Positive-QTOFsplash10-08g0-1614729421-19c09ebaed8f7024b8492016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 10V, Negative-QTOFsplash10-00p0-0200225729-5ffe24d63edd7003a9a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 20V, Negative-QTOFsplash10-00or-0500433913-5588439ad253d5024ad22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 40V, Negative-QTOFsplash10-08i0-4905507220-306d06c812afc5a32ee22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 10V, Positive-QTOFsplash10-054t-0911102702-55d0a84f50bc1c1bb8502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 20V, Positive-QTOFsplash10-07vi-0300109400-a7ae41f0e163d14344c12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 40V, Positive-QTOFsplash10-06ri-9603122488-c9a7c9d9e083eddb37362021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 10V, Negative-QTOFsplash10-000i-0109008005-fbb0102959b483f49a952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 20V, Negative-QTOFsplash10-00ks-2352029165-5e8c41e9cf4f581c2e4f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chestanin 40V, Negative-QTOFsplash10-08or-1002957322-87076d829334b868bd402021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB013801
KNApSAcK IDC00042384
Chemspider ID382600
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound432620
PDB IDNot Available
ChEBI IDNot Available
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.. .