| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 08:37:20 UTC |
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| Updated at | 2022-09-08 08:37:20 UTC |
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| NP-MRD ID | NP0264851 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 8-[(2s)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one |
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| Description | Meranzin hydrate belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 8-[(2s)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one is found in Cnidium monnieri, Murraya exotica, Murraya paniculata and Phebalium canaliculatum. 8-[(2s)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one was first documented in 2020 (PMID: 32636752). Based on a literature review a small amount of articles have been published on Meranzin hydrate (PMID: 35881212) (PMID: 35099722) (PMID: 34770967) (PMID: 32905810). |
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| Structure | COC1=CC=C2C=CC(=O)OC2=C1C[C@H](O)C(C)(C)O InChI=1S/C15H18O5/c1-15(2,18)12(16)8-10-11(19-3)6-4-9-5-7-13(17)20-14(9)10/h4-7,12,16,18H,8H2,1-3H3/t12-/m0/s1 |
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| Synonyms | | Value | Source |
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| Meranzin hydric acid | Generator |
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| Chemical Formula | C15H18O5 |
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| Average Mass | 278.3040 Da |
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| Monoisotopic Mass | 278.11542 Da |
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| IUPAC Name | 8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-methoxy-2H-chromen-2-one |
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| Traditional Name | 8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | COC1=CC=C2C=CC(=O)OC2=C1C[C@H](O)C(C)(C)O |
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| InChI Identifier | InChI=1S/C15H18O5/c1-15(2,18)12(16)8-10-11(19-3)6-4-9-5-7-13(17)20-14(9)10/h4-7,12,16,18H,8H2,1-3H3/t12-/m0/s1 |
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| InChI Key | KGGUASRIGLRPAX-LBPRGKRZSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | 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 coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Coumarins and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Coumarins and derivatives |
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| Alternative Parents | |
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| Substituents | - Coumarin
- Benzopyran
- 1-benzopyran
- Anisole
- Alkyl aryl ether
- Pyranone
- Pyran
- Benzenoid
- Tertiary alcohol
- Heteroaromatic compound
- Secondary alcohol
- 1,2-diol
- Lactone
- Oxacycle
- Ether
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- 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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| General References | - Liu YL, Xu JJ, Han LR, Liu XF, Lin MH, Wang Y, Xiao Z, Huang YK, Ren P, Huang X: Meranzin Hydrate Improves Depression-Like Behaviors and Hypomotility via Ghrelin and Neurocircuitry. Chin J Integr Med. 2023 Jun;29(6):490-499. doi: 10.1007/s11655-022-3308-2. Epub 2022 Jul 26. [PubMed:35881212 ]
- Nie K, Liu L, Peng L, Zhang M, Zhang C, Xiao B, Xia Z, Huang W: Effects of Meranzin Hydrate On the LncRNA-miRNA-mRNA Regulatory Network in the Hippocampus of a Rat Model of Depression. J Mol Neurosci. 2022 Apr;72(4):910-922. doi: 10.1007/s12031-022-01971-6. Epub 2022 Jan 31. [PubMed:35099722 ]
- Cheng Y, Ma X, Zhao Q, Wang C, Yan D, Li F: Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics. Molecules. 2021 Oct 29;26(21):6558. doi: 10.3390/molecules26216558. [PubMed:34770967 ]
- Liu X, Zhou J, Zhang T, Chen K, Xu M, Wu L, Liu J, Huang Y, Nie B, Shen X, Ren P, Huang X: Meranzin hydrate elicits antidepressant effects and restores reward circuitry. Behav Brain Res. 2021 Feb 1;398:112898. doi: 10.1016/j.bbr.2020.112898. Epub 2020 Sep 6. [PubMed:32905810 ]
- Yuan J, Wei F, Luo X, Zhang M, Qiao R, Zhong M, Chen H, Yang W: Multi-Component Comparative Pharmacokinetics in Rats After Oral Administration of Fructus aurantii Extract, Naringin, Neohesperidin, and Naringin-Neohesperidin. Front Pharmacol. 2020 Jun 19;11:933. doi: 10.3389/fphar.2020.00933. eCollection 2020. [PubMed:32636752 ]
- LOTUS database [Link]
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