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Record Information
Version2.0
Created at2022-09-11 23:01:22 UTC
Updated at2022-09-11 23:01:22 UTC
NP-MRD IDNP0321034
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl (1s,4as,7r,7as)-4'-[(s)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Description(1S,7R)-1alpha-(beta-D-Glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphaH),2'(5'H)-furan]-4-carboxylic acid methyl ester belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4as,7r,7as)-4'-[(s)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate is found in Morinda morindoides. Based on a literature review very few articles have been published on (1S,7R)-1alpha-(beta-D-Glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphaH),2'(5'H)-furan]-4-carboxylic acid methyl ester.
Structure
Thumb
Synonyms
ValueSource
(1S,7R)-1a-(b-D-Glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1a-(b-D-Glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl esterGenerator
(1S,7R)-1alpha-(beta-D-Glucopyranosyloxy)-4'-[(alphas)-alpha,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1Α-(β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1Α-(β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl esterGenerator
Chemical FormulaC26H28O13
Average Mass548.4970 Da
Monoisotopic Mass548.15299 Da
IUPAC Namemethyl (1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Traditional Namemethyl (1S,4aS,7R,7aS)-4'-[(S)-hydroxy(4-hydroxyphenyl)methyl]-5'-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C=C[C@]21OC(=O)C(=C1)[C@@H](O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C26H28O13/c1-35-22(33)15-10-36-24(38-25-21(32)20(31)19(30)16(9-27)37-25)17-13(15)6-7-26(17)8-14(23(34)39-26)18(29)11-2-4-12(28)5-3-11/h2-8,10,13,16-21,24-25,27-32H,9H2,1H3/t13-,16-,17-,18+,19-,20+,21-,24+,25+,26-/m1/s1
InChI KeyHGHZVZYRYYMUTI-SLLMLHAYSA-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
Morinda morindoidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentIridoid O-glycosides
Alternative Parents
Substituents
  • Iridoid o-glycoside
  • Terpene lactone
  • Hexose monosaccharide
  • O-glycosyl compound
  • Iridoid-skeleton
  • Glycosyl compound
  • Aromatic monoterpenoid
  • Monoterpenoid
  • Bicyclic monoterpenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Monocyclic benzene moiety
  • 2-furanone
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Dihydrofuran
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Alcohol
  • Aromatic alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • 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
logP-0.57ChemAxon
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.67 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity128.88 m³·mol⁻¹ChemAxon
Polarizability53.05 ųChemAxon
Number of Rings5ChemAxon
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 Compound101365211
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]