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Record Information
Version2.0
Created at2022-09-04 09:36:25 UTC
Updated at2022-09-04 09:36:25 UTC
NP-MRD IDNP0192395
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-[(1s,2r)-2-hydroxy-1-methoxy-3-methylbut-3-en-1-yl]-7-methoxychromen-2-one
DescriptionMurracarpin 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-[(1s,2r)-2-hydroxy-1-methoxy-3-methylbut-3-en-1-yl]-7-methoxychromen-2-one is found in Murraya paniculata. 8-[(1s,2r)-2-hydroxy-1-methoxy-3-methylbut-3-en-1-yl]-7-methoxychromen-2-one was first documented in 2010 (PMID: 20738224). Based on a literature review very few articles have been published on Murracarpin (PMID: 24694618).
Structure
Thumb
Synonyms
ValueSource
2H-8-(2-Hydroxy-1-methoxy-3-methyl-3-buten-1-yl)-7-methoxy-1-benzopyran-2-oneMeSH
Chemical FormulaC16H18O5
Average Mass290.3150 Da
Monoisotopic Mass290.11542 Da
IUPAC Name8-[(1S,2R)-2-hydroxy-1-methoxy-3-methylbut-3-en-1-yl]-7-methoxy-2H-chromen-2-one
Traditional Name8-[(1S,2R)-2-hydroxy-1-methoxy-3-methylbut-3-en-1-yl]-7-methoxychromen-2-one
CAS Registry NumberNot Available
SMILES
CO[C@H]([C@H](O)C(C)=C)C1=C2OC(=O)C=CC2=CC=C1OC
InChI Identifier
InChI=1S/C16H18O5/c1-9(2)14(18)16(20-4)13-11(19-3)7-5-10-6-8-12(17)21-15(10)13/h5-8,14,16,18H,1H2,2-4H3/t14-,16+/m1/s1
InChI KeyDBPWCIPDCMVUFT-ZBFHGGJFSA-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
Murraya paniculataLOTUS 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
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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
logP1.91ChemAxon
pKa (Strongest Acidic)13.42ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.66 m³·mol⁻¹ChemAxon
Polarizability29.41 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 IDC00019966
Chemspider ID107562737
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14102500
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Cuong NM, Khanh PN, Duc HV, Huong TT, Tai BH, Binh NQ, Durante M, Fusi F: Vasorelaxing activity of two coumarins from Murraya paniculata leaves. Biol Pharm Bull. 2014;37(4):694-7. doi: 10.1248/bpb.b13-00905. [PubMed:24694618 ]
  2. Wu L, Li P, Wang X, Zhuang Z, Farzaneh F, Xu R: Evaluation of anti-inflammatory and antinociceptive activities of Murraya exotica. Pharm Biol. 2010 Dec;48(12):1344-53. doi: 10.3109/13880201003793723. Epub 2010 Aug 26. [PubMed:20738224 ]
  3. LOTUS database [Link]