Record Information
Version1.0
Creation date2010-04-08 22:09:25 UTC
Update date2019-11-26 03:04:28 UTC
Primary IDFDB011017
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHeterophylliin G
DescriptionHeterophylliin G 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. Heterophylliin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Heterophylliin G has been detected, but not quantified in, nuts. This could make heterophylliin g a potential biomarker for the consumption of these foods.
CAS Number211190-41-9
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility5.51 g/LALOGPS
logP4.37ALOGPS
logP9.42ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)6.31ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count58ChemAxon
Hydrogen Donor Count41ChemAxon
Polar Surface Area1243.78 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity600.27 m³·mol⁻¹ChemAxon
Polarizability235.59 ųChemAxon
Number of Rings22ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC116H78O74
IUPAC name(10R,11S,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2,4,6,19,21-hexaen-13-yl 2-{[(1S,2S,19R,20S,22R)-20-(2-{[(1R,2S,19R,22R)-7,8,9,12,13,14,20,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-28-yl]oxy}-3,4,5-trihydroxybenzoyloxy)-7,8,9,12,13,14,29,30,33,34,35-undecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0^{2,19}.0^{5,10}.0^{11,16}.0^{26,31}.0^{32,37}]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-28-yl]oxy}-3,4,5-trihydroxybenzoate
InChI IdentifierInChI=1S/C116H78O74/c117-34-1-20(2-35(118)63(34)131)100(157)183-95-92-51(18-173-102(159)22-5-38(121)65(133)77(145)53(22)54-23(106(163)181-92)6-39(122)66(134)78(54)146)178-115(98(95)187-101(158)21-3-36(119)64(132)37(120)4-21)189-112(169)32-13-46(129)73(141)87(155)89(32)176-49-16-31-62(86(154)76(49)144)60-25(8-41(124)72(140)84(60)152)107(164)182-93-52(19-174-104(31)161)179-116(99-96(93)185-109(166)27-10-43(126)68(136)80(148)56(27)58-29(111(168)188-99)12-45(128)70(138)82(58)150)190-113(170)33-14-47(130)74(142)88(156)90(33)175-48-15-30-61(85(153)75(48)143)59-24(7-40(123)71(139)83(59)151)105(162)180-91-50(17-172-103(30)160)177-114(171)97-94(91)184-108(165)26-9-42(125)67(135)79(147)55(26)57-28(110(167)186-97)11-44(127)69(137)81(57)149/h1-16,50-52,91-99,114-156,171H,17-19H2/t50-,51-,52-,91-,92-,93+,94+,95+,96+,97-,98-,99-,114?,115+,116+/m1/s1
InChI KeyDPOQQDMKYYPGKM-FKIBXKAQSA-N
Isomeric SMILESOC1O[C@@H]2COC(=O)C3=C(C(O)=C(O)C(OC4=C(C=C(O)C(O)=C4O)C(=O)O[C@@H]4O[C@@H]5COC(=O)C6=C(C(O)=C(O)C(OC7=C(C=C(O)C(O)=C7O)C(=O)O[C@@H]7O[C@@H]8COC(=O)C9=C(C(O)=C(O)C(O)=C9)C9=C(O)C(O)=C(O)C=C9C(=O)O[C@H]8[C@H](OC(=O)C8=CC(O)=C(O)C(O)=C8)[C@H]7OC(=O)C7=CC(O)=C(O)C(O)=C7)=C6)C6=C(O)C(O)=C(O)C=C6C(=O)O[C@@H]5[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)O[C@@H]45)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]2[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)O[C@@H]12
Average Molecular Weight2655.8161
Monoisotopic Molecular Weight2654.234034524
Classification
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
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Diaryl ether
  • Benzoate ester
  • Pyrogallol derivative
  • Benzoic acid or derivatives
  • Benzenetriol
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.46%; H 2.96%; O 44.58%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +91.7 (c, 1 in MeOH)DFC
Spectroscopic UV Data285 (log e 5.24) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33025
CRC / DFC (Dictionary of Food Compounds) IDFYF42-Z:FYF42-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference