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Record Information
Version2.0
Created at2022-04-28 10:33:27 UTC
Updated at2022-04-28 10:33:27 UTC
NP-MRD IDNP0066283
Secondary Accession NumbersNone
Natural Product Identification
Common NameAllofusicoccin
Description(2R)-2-[(3R,4S,8R,9R,10R,11S,14S)-8-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-{[(2-methylbut-3-en-2-yl)oxy]methyl}oxan-2-yl]oxy}-4,9-dihydroxy-14-(methoxymethyl)-2,10-dimethyltricyclo[9.3.0.0³,⁷]Tetradeca-1,6-dien-6-yl]propyl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Allofusicoccin is found in Fusicoccum amygdali. Based on a literature review very few articles have been published on (2R)-2-[(3R,4S,8R,9R,10R,11S,14S)-8-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-{[(2-methylbut-3-en-2-yl)oxy]methyl}oxan-2-yl]oxy}-4,9-dihydroxy-14-(methoxymethyl)-2,10-dimethyltricyclo[9.3.0.0³,⁷]Tetradeca-1,6-dien-6-yl]propyl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-[(3R,4S,8R,9R,10R,11S,14S)-8-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-{[(2-methylbut-3-en-2-yl)oxy]methyl}oxan-2-yl]oxy}-4,9-dihydroxy-14-(methoxymethyl)-2,10-dimethyltricyclo[9.3.0.0,]tetradeca-1,6-dien-6-yl]propyl acetic acidGenerator
Chemical FormulaC36H56O12
Average Mass680.8320 Da
Monoisotopic Mass680.37718 Da
IUPAC Name(2R)-2-[(3R,4S,8R,9R,10R,11S,14S)-8-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-{[(2-methylbut-3-en-2-yl)oxy]methyl}oxan-2-yl]oxy}-4,9-dihydroxy-14-(methoxymethyl)-2,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-6-yl]propyl acetate
Traditional Name(2R)-2-[(3R,4S,8R,9R,10R,11S,14S)-8-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-{[(2-methylbut-3-en-2-yl)oxy]methyl}oxan-2-yl]oxy}-4,9-dihydroxy-14-(methoxymethyl)-2,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-6-yl]propyl acetate
CAS Registry NumberNot Available
SMILES
COC[C@H]1CC[C@H]2[C@@H](C)[C@@H](O)[C@H](O[C@H]3O[C@H](COC(C)(C)C=C)[C@@H](O)[C@H](O)[C@H]3OC(C)=O)C3=C(C[C@H](O)[C@@H]3C(C)=C12)[C@@H](C)COC(C)=O
InChI Identifier
InChI=1S/C36H56O12/c1-10-36(7,8)45-16-26-31(41)32(42)34(46-21(6)38)35(47-26)48-33-29-24(17(2)14-44-20(5)37)13-25(39)28(29)19(4)27-22(15-43-9)11-12-23(27)18(3)30(33)40/h10,17-18,22-23,25-26,28,30-35,39-42H,1,11-16H2,2-9H3/t17-,18+,22+,23-,25-,26+,28-,30+,31+,32-,33+,34+,35+/m0/s1
InChI KeyVIDHLMDVVXUKKF-DABSYBQPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fusicoccum amygdaliFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Fusicoccane diterpenoid
  • Diterpenoid
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP2.06ALOGPS
logP1.22ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.67ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.44 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity175.65 m³·mol⁻¹ChemAxon
Polarizability72.92 ųChemAxon
Number of Rings4ChemAxon
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 Compound163106296
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available