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Record Information
Version2.0
Created at2022-09-03 01:27:37 UTC
Updated at2022-09-03 01:27:37 UTC
NP-MRD IDNP0166145
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r,4r,5r,6r)-5-(acetyloxy)-4,6-dihydroxy-2-methyloxan-3-yl (2e)-3-(4-methoxyphenyl)prop-2-enoate
Description2-O-Acetyl-4-O-(4-methoxy-trans-cinnamoyl)-alpha-L-rhamnopyranose belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. (2s,3r,4r,5r,6r)-5-(acetyloxy)-4,6-dihydroxy-2-methyloxan-3-yl (2e)-3-(4-methoxyphenyl)prop-2-enoate is found in Buddleja asiatica. Based on a literature review very few articles have been published on 2-O-Acetyl-4-O-(4-methoxy-trans-cinnamoyl)-alpha-L-rhamnopyranose.
Structure
Thumb
Synonyms
ValueSource
2-O-Acetyl-4-O-(4-methoxy-trans-cinnamoyl)-a-L-rhamnopyranoseGenerator
2-O-Acetyl-4-O-(4-methoxy-trans-cinnamoyl)-α-L-rhamnopyranoseGenerator
Chemical FormulaC18H22O8
Average Mass366.3660 Da
Monoisotopic Mass366.13147 Da
IUPAC Name(2S,3R,4R,5R,6R)-5-(acetyloxy)-4,6-dihydroxy-2-methyloxan-3-yl (2E)-3-(4-methoxyphenyl)prop-2-enoate
Traditional Name(2S,3R,4R,5R,6R)-5-(acetyloxy)-4,6-dihydroxy-2-methyloxan-3-yl (2E)-3-(4-methoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=CC=C(\C=C\C(=O)O[C@H]2[C@H](C)O[C@@H](O)[C@H](OC(C)=O)[C@@H]2O)C=C1
InChI Identifier
InChI=1S/C18H22O8/c1-10-16(15(21)17(18(22)24-10)25-11(2)19)26-14(20)9-6-12-4-7-13(23-3)8-5-12/h4-10,15-18,21-22H,1-3H3/b9-6+/t10-,15+,16-,17+,18+/m0/s1
InChI KeyGWYPCEPXZGWZNI-ZQFUGIFUSA-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
Buddleja asiaticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Cinnamic acid or derivatives
  • Hexose monosaccharide
  • Cinnamic acid ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Hemiacetal
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • 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
logP1.49ALOGPS
logP1.43ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.56 m³·mol⁻¹ChemAxon
Polarizability37.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 Compound102394756
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]