| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 23:42:29 UTC |
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| Updated at | 2022-09-08 23:42:30 UTC |
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| NP-MRD ID | NP0275832 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | methyl (1s,4as,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(s)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate |
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| Description | (1S,7R)-1alpha-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphaH),2'(5'H)-furan]-4-carboxylic acid methyl ester belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4as,7r,7as)-1-{[(2s,3r,4s,5s,6r)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(s)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate is found in Morinda morindoides. Based on a literature review very few articles have been published on (1S,7R)-1alpha-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphaS)-alpha,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphaH),2'(5'H)-furan]-4-carboxylic acid methyl ester. |
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| Structure | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C=C[C@]21OC(=O)C(=C1)[C@@H](O)C1=CC=C(O)C(OC)=C1 InChI=1S/C29H32O15/c1-12(30)40-11-19-22(33)23(34)24(35)28(42-19)43-27-20-14(16(10-41-27)25(36)39-3)6-7-29(20)9-15(26(37)44-29)21(32)13-4-5-17(31)18(8-13)38-2/h4-10,14,19-24,27-28,31-35H,11H2,1-3H3/t14-,19-,20-,21+,22-,23+,24-,27+,28+,29-/m1/s1 |
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| Synonyms | | Value | Source |
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| (1S,7R)-1a-(6-O-Acetyl-b-D-glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl ester | Generator | | (1S,7R)-1a-(6-O-Acetyl-b-D-glucopyranosyloxy)-4'-[(alphas)-a,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl ester | Generator | | (1S,7R)-1alpha-(6-O-Acetyl-beta-D-glucopyranosyloxy)-4'-[(alphas)-alpha,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl ester | Generator | | (1S,7R)-1Α-(6-O-acetyl-β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylate methyl ester | Generator | | (1S,7R)-1Α-(6-O-acetyl-β-D-glucopyranosyloxy)-4'-[(alphas)-α,4-dihydroxy-3-methoxybenzyl]-5'-oxo-1,4aalpha-dihydrospiro[cyclopenta[c]pyran-7(7aalphah),2'(5'H)-furan]-4-carboxylic acid methyl ester | Generator |
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| Chemical Formula | C29H32O15 |
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| Average Mass | 620.5600 Da |
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| Monoisotopic Mass | 620.17412 Da |
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| IUPAC Name | methyl (1S,4aS,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate |
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| Traditional Name | methyl (1S,4aS,7R,7aS)-1-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4'-[(S)-hydroxy(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxo-4a,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-furan]-4-carboxylate |
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| CAS Registry Number | Not Available |
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| SMILES | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C=C[C@]21OC(=O)C(=C1)[C@@H](O)C1=CC=C(O)C(OC)=C1 |
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| InChI Identifier | InChI=1S/C29H32O15/c1-12(30)40-11-19-22(33)23(34)24(35)28(42-19)43-27-20-14(16(10-41-27)25(36)39-3)6-7-29(20)9-15(26(37)44-29)21(32)13-4-5-17(31)18(8-13)38-2/h4-10,14,19-24,27-28,31-35H,11H2,1-3H3/t14-,19-,20-,21+,22-,23+,24-,27+,28+,29-/m1/s1 |
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| InChI Key | UJGUSKGCTXMCER-JFPLEXQZSA-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 iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid 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 | Iridoid O-glycosides |
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| Alternative Parents | |
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| Substituents | - Iridoid o-glycoside
- Terpene lactone
- O-glycosyl compound
- Iridoid-skeleton
- Glycosyl compound
- Bicyclic monoterpenoid
- Methoxyphenol
- Monoterpenoid
- Aromatic monoterpenoid
- Tricarboxylic acid or derivatives
- Methoxybenzene
- Phenoxy compound
- Phenol ether
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- 2-furanone
- Benzenoid
- Monosaccharide
- Oxane
- Methyl ester
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Dihydrofuran
- Vinylogous ester
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Ether
- Polyol
- Carboxylic acid derivative
- Oxacycle
- Acetal
- Organoheterocyclic compound
- Organic oxide
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Aromatic alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic 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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