Record Information |
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Version | 1.0 |
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Created at | 2020-09-21 21:51:00 UTC |
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Updated at | 2021-08-10 02:55:15 UTC |
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NP-MRD ID | NP0001561 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Ophioglonol 4'-O-beta-D-glucopyranoside |
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Description | Ophioglonol 4'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Ophioglonol 4'-O-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1975 (PMID: 1234567). Based on a literature review a small amount of articles have been published on ophioglonol 4'-O-beta-D-glucopyranoside (PMID: 21401115) (PMID: 15787440) (PMID: 30132647). |
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Structure | [H]OC1=C([H])C(O[H])=C2C(=O)C(=C(OC2=C1[H])C1=C([H])C(O[H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C1[H])C([H])([H])O[H] InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1 |
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Synonyms | Value | Source |
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Ophioglonol 4'-O-b-D-glucopyranoside | Generator | Ophioglonol 4'-O-β-D-glucopyranoside | Generator |
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Chemical Formula | C22H22O12 |
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Average Mass | 478.4060 Da |
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Monoisotopic Mass | 478.11113 Da |
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IUPAC Name | 5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)-4H-chromen-4-one |
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Traditional Name | 5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)chromen-4-one |
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CAS Registry Number | Not Available |
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SMILES | [H]OC1=C([H])C(O[H])=C2C(=O)C(=C(OC2=C1[H])C1=C([H])C(O[H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C1[H])C([H])([H])O[H] |
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InChI Identifier | InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1 |
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InChI Key | XTPXAOSAGWJNDB-VQIXPAPJSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500MHz, H2O, simulated) | Mb1 | | | 2021-03-23 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500Mz, DMSO, simulated) | Rgf8b | | | 2020-09-21 | View Spectrum |
| 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 o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. |
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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 O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-4p-o-glycoside
- Flavonoid o-glycoside
- 3'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Phenolic glycoside
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- Phenoxy compound
- Phenol ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Pyran
- Oxane
- Monocyclic benzene moiety
- Monosaccharide
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Acetal
- Polyol
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Aromatic alcohol
- Primary alcohol
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | - Rauramo L, Lagerspetz K, Engblom P, Punnonen R: The effect of castration and peroral estrogen therapy on some psychological functions. Front Horm Res. 1975;3:94-104. doi: 10.1159/000398269. [PubMed:1234567 ]
- Wan CX, Zhang PH, Luo JG, Kong LY: Homoflavonoid glucosides from Ophioglossum pedunculosum and their anti-HBV activity. J Nat Prod. 2011 Apr 25;74(4):683-9. doi: 10.1021/np100745z. Epub 2011 Mar 14. [PubMed:21401115 ]
- Lin YL, Shen CC, Huang YJ, Chang YY: Homoflavonoids from Ophioglossum petiolatum. J Nat Prod. 2005 Mar;68(3):381-4. doi: 10.1021/np0401819. [PubMed:15787440 ]
- Hu WC, Zhou ZB, Wan CX: [Study on Flavonoids of Ophioglossum thermal]. Zhong Yao Cai. 2016 May;39(5):1035-7. [PubMed:30132647 ]
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