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Record Information
Version1.0
Created at2022-09-05 23:17:37 UTC
Updated at2022-09-05 23:17:37 UTC
NP-MRD IDNP0221659
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3s)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-{[(2e)-3-(3-methoxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}butanedioic acid
DescriptionShomaside B 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. (2r,3s)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-{[(2e)-3-(3-methoxy-4-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}butanedioic acid is found in Actaea dahurica. It was first documented in 2019 (PMID: 30914330). Based on a literature review very few articles have been published on Shomaside B.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H30O15
Average Mass594.5220 Da
Monoisotopic Mass594.15847 Da
IUPAC Name(2R,3S)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-{[(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}butanedioic acid
Traditional Name(2R,3S)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]-3-{[(2E)-3-(3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoyl]oxy}butanedioic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)O[C@H](C(O)=O)[C@](O)(CC2=CC=C(O)C=C2)C(O)=O)=CC=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C27H30O15/c1-39-17-10-13(4-8-16(17)40-25-22(33)21(32)20(31)18(12-28)41-25)5-9-19(30)42-23(24(34)35)27(38,26(36)37)11-14-2-6-15(29)7-3-14/h2-10,18,20-23,25,28-29,31-33,38H,11-12H2,1H3,(H,34,35)(H,36,37)/b9-5+/t18-,20+,21+,22-,23-,25-,27-/m1/s1
InChI KeyUEFRIVIHMWFPPY-SAZVBQAKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actaea dahuricaLOTUS 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 ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • 3-phenylpropanoic-acid
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Phenol ether
  • Phenoxy compound
  • Styrene
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Fatty acid ester
  • Sugar acid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Acetal
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary alcohol
  • 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
logP0.26ChemAxon
pKa (Strongest Acidic)3.1ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area249.97 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity137.68 m³·mol⁻¹ChemAxon
Polarizability56.81 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 ID24671906
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46209784
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lu Q, Zhang WY, Pan DB, Shi DF, Pang QQ, Li HB, Yao XJ, Yao ZH, Yu Y, Yao XS: Phenolic acids and their glycosides from the rhizomes of Cimicifuga dahurica. Fitoterapia. 2019 Apr;134:485-492. doi: 10.1016/j.fitote.2019.03.023. Epub 2019 Mar 23. [PubMed:30914330 ]
  2. LOTUS database [Link]