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Record Information
Version2.0
Created at2022-09-06 18:52:48 UTC
Updated at2022-09-06 18:52:48 UTC
NP-MRD IDNP0236072
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,3as,3bs,9ar,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-2-yl acetate
Description(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-13-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (1r,2r,3as,3bs,9ar,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-8-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthren-2-yl acetate is found in Gratiola officinalis. Based on a literature review very few articles have been published on (1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-13-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-13-yl acetic acidGenerator
Chemical FormulaC38H54O13
Average Mass718.8370 Da
Monoisotopic Mass718.35644 Da
IUPAC Name(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-13-yl acetate
Traditional Name(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H]1C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]2(C)[C@H]1[C@@](C)(O)C(=O)\C=C\C(C)(C)O
InChI Identifier
InChI=1S/C38H54O13/c1-18(40)49-22-15-35(6)24-11-10-19-20(14-21(31(46)34(19,4)5)50-32-29(45)28(44)27(43)23(17-39)51-32)37(24,8)26(42)16-36(35,7)30(22)38(9,48)25(41)12-13-33(2,3)47/h10,12-14,20,22-24,27-30,32,39,43-45,47-48H,11,15-17H2,1-9H3/b13-12+/t20-,22-,23-,24+,27-,28+,29-,30+,32-,35+,36-,37+,38+/m1/s1
InChI KeyWVVGJLXJXQDKGS-KSWGJDELSA-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
Gratiola officinalisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative Parents
Substituents
  • Cucurbitacin glycoside skeleton
  • Cucurbitacin skeleton
  • Triterpenoid
  • 25-hydroxysteroid
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • Steroid ester
  • 3-oxosteroid
  • 3-oxo-delta-1-steroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • 14-alpha-methylsteroid
  • Delta-1-steroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Cyclohexenone
  • Oxane
  • Monosaccharide
  • Acyloin
  • Alpha,beta-unsaturated ketone
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Enone
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • 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
logP1.18ChemAxon
pKa (Strongest Acidic)12.13ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area217.35 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity185.03 m³·mol⁻¹ChemAxon
Polarizability75.82 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 ID10185190
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21575884
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]