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Showing NP-Card for 3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid (NP0200763)

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Record Information
Version2.0
Created at2022-09-04 19:40:31 UTC
Updated at2022-09-04 19:40:32 UTC
NP-MRD IDNP0200763
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid
DescriptionPhomanone B belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Based on a literature review very few articles have been published on Phomanone B.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)


  Mrv1652309042221402D          

 14 14  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
    4.1339   -1.1469    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838   -0.1514    0.6815 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    0.2734    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1448    0.9323   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822    1.3873   -1.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8512    2.0188   -2.6018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2710    1.0841   -0.7902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -0.1056    0.0201 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5284   -0.1106    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7181   -0.0840   -0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0026   -0.0860    0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1074   -0.1072    1.9633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1673   -0.0627   -0.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9212   -0.0333    0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3721   -0.8055   -0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -2.0645    0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0437   -1.3201    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.1441   -1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540   -1.0053   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -1.0426    1.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5540    0.7414    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691    0.8770   -0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.8925   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344    0.7640   -0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.9960    1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.7917    1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  8 14  1  0
 14  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  8 19  1  6
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
 13 24  1  0
 14 25  1  0
 14 26  1  0
M  END
Download

3D SDF for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)


  Mrv1652309042221402D          

 14 14  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)O[C@H](CCC(O)=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O5/c1-13-7-4-6(2-3-8(10)11)14-9(12)5-7/h5-6H,2-4H2,1H3,(H,10,11)/t6-/m1/s1

> <INCHI_KEY>
RFSJIFOJAVZVDT-ZCFIWIBFSA-N

> <FORMULA>
C9H12O5

> <MOLECULAR_WEIGHT>
200.19

> <EXACT_MASS>
200.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.9967004360387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2R)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]propanoic acid

> <JCHEM_LOGP>
0.10198013766666687

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.48885128897545

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.128950428931789

> <JCHEM_PKA_STRONGEST_BASIC>
-4.787811526469697

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
47.96550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)

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PDB for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)
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SMILES for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)
COC1=CC(=O)O[C@H](CCC(O)=O)C1
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INCHI for NP0200763 (3-[(2r)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid)
InChI=1S/C9H12O5/c1-13-7-4-6(2-3-8(10)11)14-9(12)5-7/h5-6H,2-4H2,1H3,(H,10,11)/t6-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H12O5
Average Mass200.1900 Da
Monoisotopic Mass200.06847 Da
IUPAC Name3-[(2R)-4-methoxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]propanoic acid
Traditional Name3-[(2R)-4-methoxy-6-oxo-2,3-dihydropyran-2-yl]propanoic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)O[C@H](CCC(O)=O)C1
InChI Identifier
InChI=1S/C9H12O5/c1-13-7-4-6(2-3-8(10)11)14-9(12)5-7/h5-6H,2-4H2,1H3,(H,10,11)/t6-/m1/s1
InChI KeyRFSJIFOJAVZVDT-ZCFIWIBFSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Vinylogous ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.1ChemAxon
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.97 m³·mol⁻¹ChemAxon
Polarizability19 ųChemAxon
Number of Rings1ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146683519  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]