| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-29 03:24:02 UTC |
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| Updated at | 2022-04-29 03:24:02 UTC |
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| NP-MRD ID | NP0082363 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (-)-Maejaposide C |
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| 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. |
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| Structure | 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=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 |
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| Synonyms | | Value | Source |
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| (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-carboxylate | Generator |
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| Chemical Formula | C69H108O32 |
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| Average Mass | 1449.5910 Da |
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| Monoisotopic Mass | 1448.68237 Da |
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| 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 |
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| 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 |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | GMWFLRBBLJCJDG-ZJUMRMRQSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene glycosides |
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| Direct Parent | Triterpene saponins |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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