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Record Information
Version2.0
Created at2022-09-12 14:39:05 UTC
Updated at2022-09-12 14:39:05 UTC
NP-MRD IDNP0329852
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid
Description5-Carboxymellein belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton. (3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid is found in Cytospora ceratosperma, Halorosellinia oceanica and Taxus mairei. (3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid was first documented in 2009 (PMID: 20034211). Based on a literature review very few articles have been published on 5-Carboxymellein (PMID: 21922657).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H10O5
Average Mass222.1960 Da
Monoisotopic Mass222.05282 Da
IUPAC Name(3S)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-5-carboxylic acid
Traditional Name(3S)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-5-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H]1CC2=C(C=CC(O)=C2C(=O)O1)C(O)=O
InChI Identifier
InChI=1S/C11H10O5/c1-5-4-7-6(10(13)14)2-3-8(12)9(7)11(15)16-5/h2-3,5,12H,4H2,1H3,(H,13,14)/t5-/m0/s1
InChI KeyQRLBIKRXEQOMSF-YFKPBYRVSA-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
Cytospora ceratospermaLOTUS Database
Halorosellinia oceanicaLOTUS Database
Taxus maireiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-phthalate esters. These are ester derivatives of m-phthalic acids, which are based on a benzene 1,3-dicarboxylic acid skeleton.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parentm-Phthalate esters
Alternative Parents
Substituents
  • Meta-phthalic acid ester
  • Meta_phthalic_acid
  • Benzopyran
  • Isochromane
  • Hydroxybenzoic acid
  • 2-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen 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
logP2.24ChemAxon
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.92 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 IDNot Available
Chemspider ID426324
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound486250
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yan S, Li S, Wu W, Zhao F, Bao L, Ding R, Gao H, Wen HA, Song F, Liu HW: Terpenoid and phenolic metabolites from the fungus xylaria sp. associated with termite nests. Chem Biodivers. 2011 Sep;8(9):1689-700. doi: 10.1002/cbdv.201100026. [PubMed:21922657 ]
  2. Xia XK, Liu CH, Yuan WP, Wang XJ, Meng XM, Zhang MS, She ZG, Lin YC: [The secondary metabolites of the mangrove endophytic fungi ZZF13 and Guignardia sp. 4382 from the South China Sea]. Zhong Yao Cai. 2009 Sep;32(9):1385-7. [PubMed:20034211 ]
  3. LOTUS database [Link]