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Record Information
Version1.0
Created at2022-04-28 18:52:31 UTC
Updated at2022-04-28 18:52:31 UTC
NP-MRD IDNP0073647
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Periperoxide B
Description(2R,3R,4S,6S)-6-{[(2R,3R,4S,6S)-6-{[(2R,3S,4R,6S)-6-{[(2R,3R,4S,6S)-6-[(2S,4R,5R,5'aR,6R,7'S,9'R,9'aR)-7'-[(1S)-1-[(1S,2R,5S,10R,11S,14R,15S)-14-hydroxy-5-{[(2S,6R)-4-methoxy-6-methyl-3-oxo-3,6-dihydro-2H-pyran-2-yl]oxy}-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-hydroxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-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. (-)-Periperoxide B is found in Periploca forrestii, Periploca forrestii Schltr. and Periploca sepium Bge. . Based on a literature review very few articles have been published on (2R,3R,4S,6S)-6-{[(2R,3R,4S,6S)-6-{[(2R,3S,4R,6S)-6-{[(2R,3R,4S,6S)-6-[(2S,4R,5R,5'aR,6R,7'S,9'R,9'aR)-7'-[(1S)-1-[(1S,2R,5S,10R,11S,14R,15S)-14-hydroxy-5-{[(2S,6R)-4-methoxy-6-methyl-3-oxo-3,6-dihydro-2H-pyran-2-yl]oxy}-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-hydroxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S,6S)-6-{[(2R,3R,4S,6S)-6-{[(2R,3S,4R,6S)-6-{[(2R,3R,4S,6S)-6-[(2S,4R,5R,5'ar,6R,7's,9'r,9'ar)-7'-[(1S)-1-[(1S,2R,5S,10R,11S,14R,15S)-14-hydroxy-5-{[(2S,6R)-4-methoxy-6-methyl-3-oxo-3,6-dihydro-2H-pyran-2-yl]oxy}-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-hydroxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl acetic acidGenerator
Chemical FormulaC71H112O26
Average Mass1381.6510 Da
Monoisotopic Mass1380.74418 Da
IUPAC Name(2R,3R,4S,6S)-6-{[(2R,3R,4S,6S)-6-{[(2R,3S,4R,6S)-6-{[(2R,3R,4S,6S)-6-[(2S,4R,5R,5'aR,6R,7'S,9'R,9'aR)-7'-[(1S)-1-[(1S,2R,5S,10R,11S,14R,15S)-14-hydroxy-5-{[(2S,6R)-4-methoxy-6-methyl-3-oxo-3,6-dihydro-2H-pyran-2-yl]oxy}-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-hydroxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl acetate
Traditional Name(2R,3R,4S,6S)-6-{[(2R,3R,4S,6S)-6-{[(2R,3S,4R,6S)-6-{[(2R,3R,4S,6S)-6-[(2S,4R,5R,5'aR,6R,7'S,9'R,9'aR)-7'-[(1S)-1-[(1S,2R,5S,10R,11S,14R,15S)-14-hydroxy-5-{[(2S,6R)-4-methoxy-6-methyl-3-oxo-2,6-dihydropyran-2-yl]oxy}-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-hydroxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl acetate
CAS Registry NumberNot Available
SMILES
CO[C@H]1C[C@H](O[C@H]2[C@H](O)C[C@H](O[C@@H]3[C@@H](C)O[C@H](C[C@@H]3OC)O[C@@H]3[C@@H](C)O[C@]4(C[C@H]3OC)CO[C@@H]3C[C@H](O[C@@H](C)[C@@]5(O)CC[C@H]6[C@@H]7CC=C8C[C@H](CC[C@]8(C)[C@H]7CC[C@]56C)O[C@H]5O[C@H](C)C=C(OC)C5=O)O[C@H](C)[C@H]3OO4)O[C@@H]2C)O[C@H](C)[C@H]1O[C@H]1C[C@H](OC)[C@H](OC(C)=O)[C@@H](C)O1
InChI Identifier
InChI=1S/C71H112O26/c1-34-25-49(76-12)60(74)67(82-34)90-44-19-22-68(10)43(26-44)17-18-45-46(68)20-23-69(11)47(45)21-24-71(69,75)41(8)88-56-31-53-66(39(6)87-56)96-97-70(33-81-53)32-54(80-16)65(40(7)95-70)94-59-30-52(79-15)63(37(4)86-59)92-55-27-48(73)61(35(2)83-55)91-57-29-51(78-14)64(38(5)85-57)93-58-28-50(77-13)62(36(3)84-58)89-42(9)72/h17,25,34-41,44-48,50-59,61-67,73,75H,18-24,26-33H2,1-16H3/t34-,35-,36-,37-,38-,39-,40-,41+,44+,45-,46+,47+,48-,50+,51+,52+,53-,54-,55+,56+,57+,58+,59+,61-,62-,63-,64-,65-,66-,67-,68+,69+,70+,71+/m1/s1
InChI KeyXMRMWAHPQIKBRO-OLKTWSSMSA-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 forrestiiLOTUS Database
Periploca forrestii Schltr.Plant
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
  • Pregnane-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • O-glycosyl compound
  • Glycosyl compound
  • Dihydropyranone
  • Pyran
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Dialkyl peroxide
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • 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
logP3.37ALOGPS
logP8.61ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.35ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area277.66 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity339.67 m³·mol⁻¹ChemAxon
Polarizability152.26 ųChemAxon
Number of Rings12ChemAxon
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 Compound154497180
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available