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Record Information
Version2.0
Created at2022-04-29 03:24:02 UTC
Updated at2022-04-29 03:24:02 UTC
NP-MRD IDNP0082363
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Maejaposide C
Description(2S,3S,4S,5R,6R)-6-{[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21,22-bis({[(2Z)-2-methylbut-2-enoyl]oxy})-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracosan-10-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (-)-Maejaposide C is found in Maesa japonica . Based on a literature review very few articles have been published on (2S,3S,4S,5R,6R)-6-{[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21,22-bis({[(2Z)-2-methylbut-2-enoyl]oxy})-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracosan-10-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
(2S,3S,4S,5R,6R)-6-{[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21,22-bis({[(2Z)-2-methylbut-2-enoyl]oxy})-24-oxahexacyclo[15.5.2.0,.0,.0,.0,]tetracosan-10-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylateGenerator
Chemical FormulaC69H108O32
Average Mass1449.5910 Da
Monoisotopic Mass1448.68237 Da
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21,22-bis({[(2Z)-2-methylbut-2-enoyl]oxy})-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,21R,22R,23S)-2,23-dihydroxy-4,5,9,9,13,20,20-heptamethyl-21,22-bis({[(2Z)-2-methylbut-2-enoyl]oxy})-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl]oxy}-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C\C=C(\C)C(=O)O[C@H]1[C@H](OC(=O)C(\C)=C/C)C(C)(C)C[C@H]2[C@@]34CC[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7O[C@@H]([C@@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@H](O)[C@H](O)[C@H]8O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)C(O)=O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]3(C)C[C@@H](O)[C@]12[C@@H](O)O4
InChI Identifier
InChI=1S/C69H108O32/c1-13-26(3)55(86)99-52-53(100-56(87)27(4)14-2)69-34(21-63(52,6)7)68(101-62(69)88)20-16-33-65(10)18-17-36(64(8,9)32(65)15-19-66(33,11)67(68,12)22-35(69)73)93-61-51(98-58-45(82)41(78)39(76)30(23-70)91-58)47(46(83)48(95-61)54(84)85)94-60-50(43(80)40(77)31(24-71)92-60)97-59-49(42(79)37(74)28(5)90-59)96-57-44(81)38(75)29(72)25-89-57/h13-14,28-53,57-62,70-83,88H,15-25H2,1-12H3,(H,84,85)/b26-13-,27-14-/t28-,29+,30+,31+,32-,33+,34-,35+,36-,37-,38-,39-,40-,41-,42+,43-,44+,45+,46-,47-,48-,49+,50+,51+,52-,53-,57-,58-,59-,60-,61+,62-,65-,66+,67-,68-,69-/m0/s1
InChI KeyGMWFLRBBLJCJDG-ZJUMRMRQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Maesa japonicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • Oligosaccharide
  • Fatty acyl glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Tricarboxylic acid or derivatives
  • Oxepane
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • 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
logP1.12ALOGPS
logP0.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count30ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area494.88 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity338.13 m³·mol⁻¹ChemAxon
Polarizability142.08 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 Compound162991912
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available