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Record Information
Version2.0
Created at2022-04-28 17:53:28 UTC
Updated at2022-04-28 17:53:28 UTC
NP-MRD IDNP0072550
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Vaticaside D
Description(1R,2R,3S,4R,10R,11R)-4-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]Tetracosa-5(24),6,8,12(17),13,15,18(23),19,21-nonaene-6,8,14,19,21-pentol belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. (+)-Vaticaside D is found in Cotylelobium lanceolatum. Based on a literature review very few articles have been published on (1R,2R,3S,4R,10R,11R)-4-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1²,⁵.0¹²,¹⁷.0¹⁸,²³.0⁹,²⁴]Tetracosa-5(24),6,8,12(17),13,15,18(23),19,21-nonaene-6,8,14,19,21-pentol.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC48H42O14
Average Mass842.8500 Da
Monoisotopic Mass842.25746 Da
IUPAC Name(1R,2R,3S,4R,10R,11R)-4-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1^{2,5}.0^{12,17}.0^{18,23}.0^{9,24}]tetracosa-5,7,9(24),12(17),13,15,18(23),19,21-nonaene-6,8,14,19,21-pentol
Traditional Name(1R,2R,3S,4R,10R,11R)-4-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,11-bis(4-hydroxyphenyl)hexacyclo[8.7.6.1^{2,5}.0^{12,17}.0^{18,23}.0^{9,24}]tetracosa-5,7,9(24),12(17),13,15,18(23),19,21-nonaene-6,8,14,19,21-pentol
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=CC(=C2)[C@H]2[C@H]([C@@H]3[C@@H]4C5=C(C=C(O)C=C5)[C@H]([C@H](C5=C4C(O)=CC(O)=C5)C4=C3C2=C(O)C=C4O)C2=CC=C(O)C=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C48H42O14/c49-18-34-45(58)46(59)47(60)48(62-34)61-27-12-21(11-25(53)13-27)37-36(20-3-7-23(51)8-4-20)43-39-28-10-9-24(52)14-29(28)35(19-1-5-22(50)6-2-19)40(30-15-26(54)16-31(55)38(30)39)42-33(57)17-32(56)41(37)44(42)43/h1-17,34-37,39-40,43,45-60H,18H2/t34-,35-,36-,37+,39-,40+,43-,45-,46+,47-,48-/m1/s1
InChI KeyVJNCSOQWERNPTK-PPZBUIQTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cotylelobium lanceolatumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassStilbene glycosides
Direct ParentStilbene glycosides
Alternative Parents
Substituents
  • Stilbene glycoside
  • Lignan glycoside
  • Linear 1,7-diphenylheptane skeleton
  • Neolignan skeleton
  • Phenolic glycoside
  • Dibenzocycloheptene
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Indane
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP4.07ALOGPS
logP5.54ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.9ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area261.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity223.6 m³·mol⁻¹ChemAxon
Polarizability109.19 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound154497657
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References