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Record Information
Version2.0
Created at2022-09-12 01:05:47 UTC
Updated at2022-09-12 01:05:48 UTC
NP-MRD IDNP0322364
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one
Description110187-24-1, Also known as maquiroside a, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. 4-{3a-hydroxy-7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9a-(hydroxymethyl)-11a-methyl-tetradecahydrocyclopenta[a]phenanthren-1-yl}-5h-furan-2-one is found in Maquira calophylla and Maquira sclerophylla. Based on a literature review very few articles have been published on 110187-24-1.
Structure
Thumb
Synonyms
ValueSource
Maquiroside aMeSH
Chemical FormulaC30H46O8
Average Mass534.6900 Da
Monoisotopic Mass534.31927 Da
IUPAC Name4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-2,5-dihydrofuran-2-one
Traditional Name4-{11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
COC1CC(OC2CCC3(CO)C(CCC4C3CCC3(C)C(CCC43O)C3=CC(=O)OC3)C2)OC(C)C1O
InChI Identifier
InChI=1S/C30H46O8/c1-17-27(33)24(35-3)14-26(37-17)38-20-6-10-29(16-31)19(13-20)4-5-23-22(29)7-9-28(2)21(8-11-30(23,28)34)18-12-25(32)36-15-18/h12,17,19-24,26-27,31,33-34H,4-11,13-16H2,1-3H3
InChI KeyFXZKDRVSINFUOY-UHFFFAOYSA-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
Maquira calophyllaLOTUS Database
Maquira sclerophyllaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolide glycosides and derivatives
Alternative Parents
Substituents
  • Cardanolide-glycoside
  • Steroidal glycoside
  • 19-hydroxysteroid
  • 14-hydroxysteroid
  • Hydroxysteroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 2-furanone
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Acetal
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP2.61ChemAxon
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)0.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.53 m³·mol⁻¹ChemAxon
Polarizability60.56 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID143670
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163813
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]