Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:53:06 UTC |
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Updated at | 2021-11-26 17:46:01 UTC |
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NP-MRD ID | NP0044153 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | cis-Melilotoside |
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Description | Cis-beta-D-Glucosyl-2-hydroxycinnamate, also known as beta-D-glucosyl-2-coumarinic acid or cis-coumarinic acid-beta-D-glucoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Cis-beta-D-Glucosyl-2-hydroxycinnamate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cis-beta-D-Glucosyl-2-hydroxycinnamate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, cis-beta-D-Glucosyl-2-hydroxycinnamate has been detected, but not quantified in, several different foods, such as chinese broccoli, european cranberries, black chokeberries, grapefruit/pummelo hybrids, and cardoons. This could make cis-beta-D-glucosyl-2-hydroxycinnamate a potential biomarker for the consumption of these foods. cis-Melilotoside is found in Ephedra nebrodensis. It was first documented in 2007 (PMID: 17421059). These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond (PMID: 23455439) (PMID: 17497625). |
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Structure | OC[C@H]1O[C@@H](OC2=CC=CC=C2\C=C/C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5-/t10-,12-,13+,14-,15-/m1/s1 |
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Synonyms | Value | Source |
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(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid | ChEBI | beta-D-Glucosyl-2-coumarinate | ChEBI | beta-D-Glucosyl-2-coumarinic acid | ChEBI | cis-beta-D-Glucosyl-2-hydroxycinnamic acid | ChEBI | cis-Coumarinic acid-beta-D-glucoside | ChEBI | cis-Melilotoside | ChEBI | (2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylate | Generator | (2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acid | Generator | (2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylate | Generator | (2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylate | Generator | (2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylic acid | Generator | cis-Coumarinate-β-D-glucoside | Generator | b-D-Glucosyl-2-coumarinate | Generator | b-D-Glucosyl-2-coumarinic acid | Generator | β-D-Glucosyl-2-coumarinate | Generator | β-D-Glucosyl-2-coumarinic acid | Generator | cis-b-D-Glucosyl-2-hydroxycinnamate | Generator | cis-b-D-Glucosyl-2-hydroxycinnamic acid | Generator | cis-beta-D-Glucosyl-2-hydroxycinnamate | Generator | cis-β-D-Glucosyl-2-hydroxycinnamate | Generator | cis-β-D-Glucosyl-2-hydroxycinnamic acid | Generator | cis-Coumarinate-b-D-glucoside | Generator | cis-Coumarinate-beta-D-glucoside | Generator | cis-Coumarinic acid-b-D-glucoside | Generator | cis-Coumarinic acid-β-D-glucoside | Generator | (2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid | HMDB | (2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid | HMDB | 2'-(beta-D-Glucopyranosyloxy)cinnamic acid | HMDB | 2'-(β-D-Glucopyranosyloxy)cinnamic acid | HMDB | 2’-(β-D-Glucopyranosyloxy)cinnamic acid | HMDB | 3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid | HMDB | 3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid | HMDB | Coumarin glucoside | HMDB | Coumarinate glucoside | HMDB | Coumarinic acid glucoside | HMDB | beta-D-Glucosyl-2-coumarate | HMDB | beta-D-Glucosyl-2-coumaric acid | HMDB | cis-o-Hydroxycinnamic acid glucoside | HMDB | o-(Glucosyloxy)cinnamic acid | HMDB | o-Coumaroyl beta-D-glucopyranoside | HMDB | o-Coumaroyl β-D-glucopyranoside | HMDB | β-D-Glucosyl-2-coumarate | HMDB | β-D-Glucosyl-2-coumaric acid | HMDB |
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Chemical Formula | C15H18O8 |
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Average Mass | 326.2986 Da |
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Monoisotopic Mass | 326.10017 Da |
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IUPAC Name | (2Z)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid |
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Traditional Name | cis-melilotoside |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC2=CC=CC=C2\C=C/C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5-/t10-,12-,13+,14-,15-/m1/s1 |
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InChI Key | GVRIYIMNJGULCZ-QLFWQTQQSA-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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1D NMR | 13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Phenolic glycosides |
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Alternative Parents | |
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Substituents | - Phenolic glycoside
- Cinnamic acid
- Cinnamic acid or derivatives
- Coumaric acid
- Coumaric acid or derivatives
- Hexose monosaccharide
- O-glycosyl compound
- Styrene
- Phenol ether
- Phenoxy compound
- Benzenoid
- Monocyclic benzene moiety
- Oxane
- Monosaccharide
- Secondary alcohol
- Polyol
- Carboxylic acid derivative
- Carboxylic acid
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Primary alcohol
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | - Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Yang L, Han H, Nakamura N, Hattori M, Wang Z, Xu L: Bio-guided isolation of antioxidants from the stems of Dendrobium aurantiacum var. denneanum. Phytother Res. 2007 Jul;21(7):696-8. doi: 10.1002/ptr.2133. [PubMed:17421059 ]
- Yang L, Nakamura N, Hattori M, Wang Z, Bligh SW, Xu L: High-performance liquid chromatography-diode array detection/electrospray ionization mass spectrometry for the simultaneous analysis of cis-, trans- and dihydro-2-glucosyloxycinnamic acid derivatives from Dendrobium medicinal plants. Rapid Commun Mass Spectrom. 2007;21(12):1833-40. doi: 10.1002/rcm.3025. [PubMed:17497625 ]
- Livia Macedo Dutra et al. (2020). 1H HR-MAS NMR and chemometric methods for discrimination and classification of Baccharis (Asteraceae): A proposal for quality control of Baccharis trimera. Journal of Pharmaceutical and Biomedical Analysis, Volume 184, 30 May 2020, 113200. DOI: 10.1016/j.jpba.2020.113200. Journal of Pharmaceutical and Biomedical Analysis.
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