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Record Information
Version2.0
Created at2022-09-08 23:42:29 UTC
Updated at2022-09-08 23:42:30 UTC
NP-MRD IDNP0275832
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl (1s,4as,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(s)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Description(1S,7R)-1alpha-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxy-3-methoxybenzyl]-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)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(s)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-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-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxy-3-methoxybenzyl]-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-(6-O-Acetyl-b-D-glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1a-(6-O-Acetyl-b-D-glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl esterGenerator
(1S,7R)-1alpha-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphas)-alpha,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1Α-(6-O-acetyl-β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl esterGenerator
(1S,7R)-1Α-(6-O-acetyl-β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl esterGenerator
Chemical FormulaC29H32O15
Average Mass620.5600 Da
Monoisotopic Mass620.17412 Da
IUPAC Namemethyl (1S,4aS,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Traditional Namemethyl (1S,4aS,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-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](COC(C)=O)[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(OC)=C1
InChI Identifier
InChI=1S/C29H32O15/c1-12(30)40-11-19-22(33)23(34)24(35)28(42-19)43-27-20-14(16(10-41-27)25(36)39-3)6-7-29(20)9-15(26(37)44-29)21(32)13-4-5-17(31)18(8-13)38-2/h4-10,14,19-24,27-28,31-35H,11H2,1-3H3/t14-,19-,20-,21+,22-,23+,24-,27+,28+,29-/m1/s1
InChI KeyUJGUSKGCTXMCER-JFPLEXQZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
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
  • O-glycosyl compound
  • Iridoid-skeleton
  • Glycosyl compound
  • Bicyclic monoterpenoid
  • Methoxyphenol
  • Monoterpenoid
  • Aromatic monoterpenoid
  • Tricarboxylic acid or derivatives
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • 2-furanone
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Dihydrofuran
  • Vinylogous ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Ether
  • Polyol
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic alcohol
  • 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-0.29ChemAxon
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area216.97 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity144.49 m³·mol⁻¹ChemAxon
Polarizability60.28 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 Compound46864995
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]