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Record Information
Version1.0
Created at2022-04-28 18:52:52 UTC
Updated at2022-04-28 18:52:52 UTC
NP-MRD IDNP0073653
Secondary Accession NumbersNone
Natural Product Identification
Common NamePeriplocoside E
Description(2R,3S,4R,5S,6S)-2-{[(2S,3R,4S,6R)-6-{[(2S,3R,4S,6R)-6-{[(2R,3S,4S,6R)-6-[(2S,4R,5R,5'aS,6R,7'R,9'S,9'aR)-7'-[(1S)-1-[(1S,2R,5R,10S,11S,14S,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl]ethoxy]-4-methoxy-6,9'-dimethyl-hexahydrospiro[oxane-2,3'-pyrano[3,4-c][1,2,5]trioxepine]oxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Periplocoside E is found in Periploca forrestii Schltr., Periploca sepium and Periploca sepium Bge. . Based on a literature review very few articles have been published on (2R,3S,4R,5S,6S)-2-{[(2S,3R,4S,6R)-6-{[(2S,3R,4S,6R)-6-{[(2R,3S,4S,6R)-6-[(2S,4R,5R,5'aS,6R,7'R,9'S,9'aR)-7'-[(1S)-1-[(1S,2R,5R,10S,11S,14S,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl]ethoxy]-4-methoxy-6,9'-dimethyl-hexahydrospiro[oxane-2,3'-pyrano[3,4-c][1,2,5]trioxepine]oxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R,3S,4R,5S,6S)-2-{[(2S,3R,4S,6R)-6-{[(2S,3R,4S,6R)-6-{[(2R,3S,4S,6R)-6-[(2S,4R,5R,5'as,6R,7'r,9's,9'ar)-7'-[(1S)-1-[(1S,2R,5R,10S,11S,14S,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-14-yl]ethoxy]-4-methoxy-6,9'-dimethyl-hexahydrospiro[oxane-2,3'-pyrano[3,4-c][1,2,5]trioxepine]oxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetic acidGenerator
Chemical FormulaC65H106O24
Average Mass1271.5390 Da
Monoisotopic Mass1270.70740 Da
IUPAC Name(2R,3S,4R,5S,6S)-2-{[(2S,3R,4S,6R)-6-{[(2S,3R,4S,6R)-6-{[(2R,3S,4S,6R)-6-[(2S,4R,5R,5'aS,6R,7'R,9'S,9'aR)-7'-[(1S)-1-[(1S,2R,5R,10S,11S,14S,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethoxy]-4-methoxy-6,9'-dimethyl-hexahydrospiro[oxane-2,3'-pyrano[3,4-c][1,2,5]trioxepine]oxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetate
Traditional Name(2R,3S,4R,5S,6S)-2-{[(2S,3R,4S,6R)-6-{[(2S,3R,4S,6R)-6-{[(2R,3S,4S,6R)-6-[(2S,4R,5R,5'aS,6R,7'R,9'S,9'aR)-7'-[(1S)-1-[(1S,2R,5R,10S,11S,14S,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethoxy]-4-methoxy-6,9'-dimethyl-hexahydrospiro[oxane-2,3'-pyrano[3,4-c][1,2,5]trioxepine]oxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetate
CAS Registry NumberNot Available
SMILES
CO[C@H]1C[C@@H](O[C@H]2[C@@H](C)O[C@@H](C[C@@H]2OC)O[C@@H]2[C@@H](C)O[C@]3(C[C@H]2OC)CO[C@H]2C[C@@H](O[C@@H](C)[C@]4(O)CC[C@H]5[C@H]6CC=C7C[C@H](O)CC[C@]7(C)[C@H]6CC[C@]45C)O[C@@H](C)[C@H]2OO3)O[C@@H](C)[C@H]1O[C@@H]1C[C@H](OC)[C@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](OC)[C@@H]2OC(C)=O)[C@H](C)O1
InChI Identifier
InChI=1S/C65H106O24/c1-31-53(68)59(74-15)60(82-38(8)66)61(80-31)86-56-34(4)78-51(27-46(56)72-13)84-54-32(2)76-50(25-44(54)70-11)83-55-33(3)77-52(26-45(55)71-12)85-57-36(6)87-64(29-48(57)73-14)30-75-47-28-49(79-35(5)58(47)88-89-64)81-37(7)65(69)23-20-43-41-17-16-39-24-40(67)18-21-62(39,9)42(41)19-22-63(43,65)10/h16,31-37,40-61,67-69H,17-30H2,1-15H3/t31-,32-,33+,34-,35-,36+,37-,40+,41-,42-,43-,44-,45-,46-,47-,48+,49+,50+,51+,52+,53-,54+,55-,56+,57+,58+,59+,60-,61+,62-,63-,64-,65+/m0/s1
InChI KeyJRBMXUSQGKDVNO-POMNYOPYSA-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
Periploca forrestii Schltr.Plant
Periploca sepiumLOTUS Database
Periploca sepium BGE.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Oligosaccharide
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Dialkyl peroxide
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • 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
logP3.28ALOGPS
logP7.15ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)12.97ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area262.36 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity310.62 m³·mol⁻¹ChemAxon
Polarizability139.14 ųChemAxon
Number of Rings11ChemAxon
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 Compound154497185
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available