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Showing NP-Card for Ethyl maltol (NP0333371)

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Record Information
Version1.0
Created at2024-06-05 17:45:13 UTC
Updated at2024-06-07 00:01:38 UTC
NP-MRD IDNP0333371
Secondary Accession NumbersNone
Natural Product Identification
Common NameEthyl maltol
DescriptionEthyl maltol, also known as E637 or fema 3487, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Ethyl maltol is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl maltol is a sweet, bitter, and candy tasting compound. Outside of the human body,. It is a white solid with a sweet smell that can be described as caramelized sugar and cooked fruit. In such compounds, the heterocycle is a bidentate ligand. Ethyl maltol is an organic compound that is a common flavourant in some confectioneries. It is related to the more common flavorant maltol by replacement of the methyl group by an ethyl group. The conjugate base derived from ethylmaltol, again like maltol, has a high affinity for iron, forming a red coordination complex.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333371 (Ethyl maltol)


  Mrv0541 05061306062D          

 10 10  0  0  0  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 C   0  0  0  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.0000    0.8250    0.0000 C   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
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3D MOL for NP0333371 (Ethyl maltol)

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3D SDF for NP0333371 (Ethyl maltol)

  Mrv0541 05061306062D          

 10 10  0  0  0  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 C   0  0  0  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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.0000    0.8250    0.0000 C   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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C(O)C(=O)C=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3

> <INCHI_KEY>
YIKYNHJUKRTCJL-UHFFFAOYSA-N

> <FORMULA>
C7H8O3

> <MOLECULAR_WEIGHT>
140.1366

> <EXACT_MASS>
140.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
13.496368777975961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-3-hydroxy-4H-pyran-4-one

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
1.0689503143333332

> <ALOGPS_LOGS>
-0.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.531116194751377

> <JCHEM_PKA_STRONGEST_BASIC>
-3.559349776453973

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
38.246

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl maltol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333371 (Ethyl maltol)
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PDB for NP0333371 (Ethyl maltol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3    7    8                                                  
CONECT    6    2    7   10                                                  
CONECT    7    5    6    9                                                  
CONECT    8    5                                                            
CONECT    9    7                                                            
CONECT   10    4    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0333371 (Ethyl maltol)
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SMILES for NP0333371 (Ethyl maltol)
CCC1=C(O)C(=O)C=CO1
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INCHI for NP0333371 (Ethyl maltol)
InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
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Synonyms
ValueSource
2-Ethyl-3-hydroxy-4-pyroneHMDB
2-Ethylpyromeconic acidHMDB
3-Hydroxy-2-ethyl-1,4-pyroneHMDB
3-Hydroxy-2-ethyl-4-pyroneHMDB
3-Hydroxy-2-ethyl-4H-pyran-4-oneHMDB
3-Hydroxy-2-ethyl-laquo gammaraquo -pyroneHMDB
e637HMDB
FEMA 3487HMDB
Ilekudinoside aHMDB
Veltol plusHMDB
EthylmaltolHMDB
Indium ethylmaltolHMDB
Chemical FormulaC7H8O3
Average Mass140.1366 Da
Monoisotopic Mass140.04734 Da
IUPAC Name2-ethyl-3-hydroxy-4H-pyran-4-one
Traditional Nameethyl maltol
CAS Registry NumberNot Available
SMILES
CCC1=C(O)C(=O)C=CO1
InChI Identifier
InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
InChI KeyYIKYNHJUKRTCJL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-05View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Cyclic ketone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP0.34ALOGPS
logP1.07ChemAxon
logS-0.38ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.25 m³·mol⁻¹ChemAxon
Polarizability13.5 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031735  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008403  
KNApSAcK IDNot Available
Chemspider ID19804  
KEGG Compound IDC20362  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl maltol  
METLIN IDNot Available
PubChem Compound21059  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available