You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:10 UTC
Update Date2019-07-23 06:09:24 UTC
HMDB IDHMDB0031746
Secondary Accession Numbers
  • HMDB31746
Metabolite Identification
Common NameVescalin
DescriptionCastalin is found in nuts. Castalin is isolated from wood of Castanea sativa (sweet chestnut).
Structure
Data?1563862164
Synonyms
ValueSource
Vescalagin, (33beta)-isomerMeSH
CastalaginMeSH
VescalaginMeSH
VescaleneMeSH
Chemical FormulaC27H20O18
Average Molecular Weight632.4369
Monoisotopic Molecular Weight632.064963836
IUPAC Name7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-24-(hydroxymethyl)-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11(28),12,14,16(21),17,19-nonaene-4,22,27-trione
Traditional Namecastalin
CAS Registry Number34112-28-2
SMILES
OCC1OC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(O)C(O)=C(O)C3=C2C(=O)OC(C2OC(=O)C4=C(C2O)C(O)=C(O)C(O)=C34)C1O
InChI Identifier
InChI=1S/C27H20O18/c28-2-5-14(31)23-24-20(37)12-11(27(42)45-24)9(18(35)22(39)19(12)36)8-10(26(41)44-23)7(16(33)21(38)17(8)34)6-3(25(40)43-5)1-4(29)13(30)15(6)32/h1,5,14,20,23-24,28-39H,2H2
InChI KeyPPUHUWSVCUJGTD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Gallic acid or derivatives
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Tricarboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.8 g/LALOGPS
logP1.14ALOGPS
logP-0.42ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area321.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity142.08 m³·mol⁻¹ChemAxon
Polarizability54.84 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-1000029000-a1d913cc63d1d351f1aeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-05363fd6437f11a14f36JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-2000049000-929818df4948fdd4bf01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0597-9002421000-776146555e43b040777eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000019000-32d329a8dcdb4edf8596JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1000059000-e8e82efa161d2cacd0c0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dl-9100030000-31de2b03ce8e9cd6aea6JSpectraViewer | MoNA
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
FoodDB IDFDB008415
KNApSAcK IDNot Available
Chemspider ID90329
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound99973
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Vescalin → ({7,8,9,12,13,14,17,18,19,25,29-undecahydroxy-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-24-yl}methoxy)sulfonic aciddetails
Vescalin → [7,8,9,12,13,14,17,18,19,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-25-yl]oxidanesulfonic aciddetails
Vescalin → [7,8,9,12,13,14,17,18,19,25-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-29-yl]oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Vescalin → 6-{[7,8,9,12,13,14,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-17-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,9,12,13,14,17,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-18-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,9,12,13,14,17,18,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-19-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,9,13,14,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-12-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,9,12,14,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-13-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,9,12,13,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11(28),12,14,16,18,20-nonaen-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[8,9,12,13,14,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,9,12,13,14,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5(10),6,8,11,13,15(28),16,18,20-nonaen-8-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vescalin → 6-{[7,8,12,13,14,17,18,19,25,29-decahydroxy-24-(hydroxymethyl)-4,22,27-trioxo-3,23,26-trioxahexacyclo[13.10.3.1²,⁶.0⁵,¹⁰.0¹¹,²⁸.0¹⁶,²¹]nonacosa-5,7,9,11,13,15(28),16,18,20-nonaen-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails