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Record Information
Version2.0
Created at2022-09-12 08:14:35 UTC
Updated at2022-09-12 08:14:35 UTC
NP-MRD IDNP0326568
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,3r,4s,5r,6r)-2-{[(1r,2e,3s,4r,5s)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
DescriptionSimmondsin 3'-cis-ferulate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2r,3r,4s,5r,6r)-2-{[(1r,2e,3s,4r,5s)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Simmondsia chinensis. Based on a literature review very few articles have been published on Simmondsin 3'-cis-ferulate.
Structure
Thumb
Synonyms
ValueSource
Simmondsin 3'-cis-ferulic acidGenerator
Chemical FormulaC26H33NO12
Average Mass551.5450 Da
Monoisotopic Mass551.20028 Da
IUPAC Name(2R,3R,4S,5R,6R)-2-{[(1R,2E,3S,4R,5S)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(2R,3R,4S,5R,6R)-2-{[(1R,2E,3S,4R,5S)-2-(cyanomethylidene)-3-hydroxy-4,5-dimethoxycyclohexyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
CO[C@H]1C[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](OC(=O)\C=C\C3=CC=C(O)C(OC)=C3)[C@H]2O)\C(=C\C#N)[C@H](O)[C@H]1OC
InChI Identifier
InChI=1S/C26H33NO12/c1-34-17-10-13(4-6-15(17)29)5-7-20(30)39-25-22(32)19(12-28)38-26(23(25)33)37-16-11-18(35-2)24(36-3)21(31)14(16)8-9-27/h4-8,10,16,18-19,21-26,28-29,31-33H,11-12H2,1-3H3/b7-5+,14-8-/t16-,18+,19-,21+,22-,23-,24+,25+,26-/m1/s1
InChI KeyFEUUHPJKQACSKU-YIJSCCIGSA-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
Simmondsia chinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Hexose monosaccharide
  • Coumaric acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Cyclitol or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP-0.34ChemAxon
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area197.39 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.86 m³·mol⁻¹ChemAxon
Polarizability55.27 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101993517
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]