Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 07:35:06 UTC |
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Updated at | 2022-09-12 07:35:06 UTC |
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NP-MRD ID | NP0326218 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one |
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Description | Narcissin belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, narcissin is considered to be a flavonoid. 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one is found in Cardiocrinum cordatum, Sparganium eurycarpum, Styphnolobium japonicum and Tetraena coccinea. It was first documented in 2021 (PMID: 34946755). Based on a literature review a significant number of articles have been published on Narcissin (PMID: 35631468) (PMID: 35358623) (PMID: 35056848) (PMID: 34885771). |
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Structure | COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@H](CO[C@H]3O[C@H](C)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16-,18-,19-,21+,22+,23+,24-,27+,28+/m1/s1 |
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Synonyms | Value | Source |
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Narcissin flavonol | MeSH |
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Chemical Formula | C28H32O16 |
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Average Mass | 624.5480 Da |
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Monoisotopic Mass | 624.16903 Da |
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IUPAC Name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one |
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Traditional Name | 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC=C1O)C1=C(O[C@@H]2O[C@H](CO[C@H]3O[C@H](C)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C=C2O1 |
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InChI Identifier | InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16-,18-,19-,21+,22+,23+,24-,27+,28+/m1/s1 |
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InChI Key | UIDGLYUNOUKLBM-OPUWVCDQSA-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 flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavonoid glycosides |
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Direct Parent | Flavonoid-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- 3p-methoxyflavonoid-skeleton
- Hydroxyflavonoid
- Flavone
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Chromone
- 1-benzopyran
- Methoxyphenol
- Benzopyran
- Phenol ether
- Phenoxy compound
- Anisole
- Methoxybenzene
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Pyranone
- Phenol
- Alkyl aryl ether
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Oxane
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Ether
- Organoheterocyclic compound
- Oxacycle
- Acetal
- Polyol
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- 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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General References | - Wahid M, Saqib F, Akhtar S, Ali A, Wilairatana P, Mubarak MS: Possible Mechanisms Underlying the Antispasmodic, Bronchodilator, and Antidiarrheal Activities of Polarity-Based Extracts of Cucumis sativus L. Seeds in In Silico, In Vitro, and In Vivo Studies. Pharmaceuticals (Basel). 2022 May 23;15(5):641. doi: 10.3390/ph15050641. [PubMed:35631468 ]
- Zavala-Ocampo LM, Aguirre-Hernandez E, Lopez-Camacho PY, Cardenas-Vazquez R, Dorazco-Gonzalez A, Basurto-Islas G: Acetylcholinesterase inhibition and antioxidant activity properties of Petiveria alliacea L. J Ethnopharmacol. 2022 Jun 28;292:115239. doi: 10.1016/j.jep.2022.115239. Epub 2022 Mar 28. [PubMed:35358623 ]
- Kozachok S, Kolodziejczyk-Czepas J, Marchyshyn S, Wojtanowski KK, Zgorka G, Oleszek W: Comparison of Phenolic Metabolites in Purified Extracts of Three Wild-Growing Herniaria L. Species and Their Antioxidant and Anti-Inflammatory Activities In Vitro. Molecules. 2022 Jan 14;27(2):530. doi: 10.3390/molecules27020530. [PubMed:35056848 ]
- Merlin-Lucas V, Ordonez-Razo RM, Calzada F, Solis A, Garcia-Hernandez N, Barbosa E, Valdes M: Antitumor Potential of Annona muricata Linn. An Edible and Medicinal Plant in Mexico: In Vitro, In Vivo, and Toxicological Studies. Molecules. 2021 Dec 18;26(24):7675. doi: 10.3390/molecules26247675. [PubMed:34946755 ]
- Li Y, Li P, Yang K, He Q, Wang Y, Sun Y, He C, Xiao P: Impact of Drying Methods on Phenolic Components and Antioxidant Activity of Sea Buckthorn (Hippophae rhamnoides L.) Berries from Different Varieties in China. Molecules. 2021 Nov 26;26(23):7189. doi: 10.3390/molecules26237189. [PubMed:34885771 ]
- LOTUS database [Link]
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