Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 22:52:20 UTC |
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Updated at | 2022-09-05 22:52:20 UTC |
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NP-MRD ID | NP0221325 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r,3r,4r,5r,6r)-6-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Description | Ligurobustoside B belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (2r,3r,4r,5r,6r)-6-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Ligustrum robustum. It was first documented in 2003 (PMID: 12828473). Based on a literature review very few articles have been published on Ligurobustoside B (PMID: 33316854). |
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Structure | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OC\C=C(/C)CCC=C(C)C)O[C@H](CO)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C31H44O13/c1-16(2)6-5-7-17(3)12-13-40-30-27(39)29(44-31-26(38)25(37)24(36)18(4)41-31)28(22(15-32)42-30)43-23(35)11-9-19-8-10-20(33)21(34)14-19/h6,8-12,14,18,22,24-34,36-39H,5,7,13,15H2,1-4H3/b11-9+,17-12+/t18-,22+,24-,25+,26+,27+,28+,29+,30+,31-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C31H44O13 |
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Average Mass | 624.6800 Da |
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Monoisotopic Mass | 624.27819 Da |
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IUPAC Name | (2R,3R,4R,5R,6R)-6-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Traditional Name | (2R,3R,4R,5R,6R)-6-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-5-hydroxy-2-(hydroxymethyl)-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OC\C=C(/C)CCC=C(C)C)O[C@H](CO)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C31H44O13/c1-16(2)6-5-7-17(3)12-13-40-30-27(39)29(44-31-26(38)25(37)24(36)18(4)41-31)28(22(15-32)42-30)43-23(35)11-9-19-8-10-20(33)21(34)14-19/h6,8-12,14,18,22,24-34,36-39H,5,7,13,15H2,1-4H3/b11-9+,17-12+/t18-,22+,24-,25+,26+,27+,28+,29+,30+,31-/m0/s1 |
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InChI Key | TYRGLPMBSNUUEL-IGJBFUINSA-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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. |
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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 | Terpene glycosides |
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Alternative Parents | |
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Substituents | - Terpene glycoside
- Fatty acyl glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Alkyl glycoside
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid or derivatives
- Cinnamic acid ester
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Aromatic monoterpenoid
- Monocyclic monoterpenoid
- Monoterpenoid
- Catechol
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Benzenoid
- Fatty acyl
- Monocyclic benzene moiety
- Oxane
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Carboxylic acid derivative
- Polyol
- Primary alcohol
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Organooxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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General References | - He ZD, Lau KM, But PP, Jiang RW, Dong H, Ma SC, Fung KP, Ye WC, Sun HD: Antioxidative glycosides from the leaves of Ligustrum robustum. J Nat Prod. 2003 Jun;66(6):851-4. doi: 10.1021/np020568g. [PubMed:12828473 ]
- Zhang Z, Zeng J, Zhou X, Xu Q, Li C, Liu Y, Zhang C, Wang L, Zeng W, Li Y: Activity of Ligustrum robustum (Roxb.) Blume extract against the biofilm formation and exopolysaccharide synthesis of Streptococcus mutans. Mol Oral Microbiol. 2021 Feb;36(1):67-79. doi: 10.1111/omi.12328. Epub 2020 Dec 31. [PubMed:33316854 ]
- LOTUS database [Link]
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