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Record Information
Version1.0
Created at2020-08-27 00:32:45 UTC
Updated at2021-08-10 02:55:05 UTC
NP-MRD IDNP0001537
Secondary Accession NumbersNone
Natural Product Identification
Common NameKHAINAOSIDE C
Description[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. KHAINAOSIDE C is found in Balanophora laxiflora and Vitex glabrata. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.
Structure
Data?1628564105
Synonyms
ValueSource
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC25H28O11
Average Mass504.4880 Da
Monoisotopic Mass504.16316 Da
IUPAC Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxan-2-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
[H]OC1=C(O[H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(OC3=C(OC([H])([H])[H])C([H])=C(\C([H])=C(/[H])C([H])([H])O[H])C([H])=C3[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]
InChI Identifier
InChI=1S/C25H28O11/c1-33-19-12-14(3-2-10-26)5-8-18(19)35-25-24(32)23(31)22(30)20(36-25)13-34-21(29)9-6-15-4-7-16(27)17(28)11-15/h2-9,11-12,20,22-28,30-32H,10,13H2,1H3/b3-2+,9-6+/t20-,22-,23+,24-,25-/m1/s1
InChI KeyOVXNLDIJUODSJZ-WNTHUPNMSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400Mz MHz, Methanol, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400Mz, Methanol, simulated)Rgf8b2020-08-27View Spectrum
Species
Species of Origin
Species NameSourceReference
Balanophora laxifloraLOTUS Database
Vitex glabrataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • O-glycosyl compound
  • Cinnamyl alcohol
  • Anisole
  • Catechol
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP1.6ALOGPS
logP1.51ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.31 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings3ChemAxon
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 ID24664593
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44606239
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available