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Record Information
Version2.0
Created at2022-09-08 08:37:20 UTC
Updated at2022-09-08 08:37:20 UTC
NP-MRD IDNP0264851
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-[(2s)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one
DescriptionMeranzin 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).
Structure
Thumb
Synonyms
ValueSource
Meranzin hydric acidGenerator
Chemical FormulaC15H18O5
Average Mass278.3040 Da
Monoisotopic Mass278.11542 Da
IUPAC Name8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-methoxy-2H-chromen-2-one
Traditional Name8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-methoxychromen-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C=CC(=O)OC2=C1C[C@H](O)C(C)(C)O
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
InChI KeyKGGUASRIGLRPAX-LBPRGKRZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cnidium monnieriLOTUS Database
Murraya exoticaLOTUS Database
Murraya paniculataLOTUS Database
Phebalium canaliculatumLOTUS Database
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.21ChemAxon
pKa (Strongest Acidic)13.67ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.6 m³·mol⁻¹ChemAxon
Polarizability28.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00029304
Chemspider ID24744504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound821434
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. LOTUS database [Link]