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Showing NP-Card for 6-Methylcoumarin (NP0136987)

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Record Information
Version2.0
Created at2022-05-30 16:38:12 UTC
Updated at2024-09-03 04:19:09 UTC
NP-MRD IDNP0136987
Natural Product DOIhttps://doi.org/10.57994/1650
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Methylcoumarin
Description6-Methylcoumarin, also known as 6-methylbenzopyrone or cocodescol, 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). 6-Methylcoumarin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Methylcoumarin is a sweet, anise, and balsam tasting compound. 6-Methylcoumarin was first documented in 1978 (PMID: 718225). Outside of the human body, (PMID: 16242086) (PMID: 16867823) (PMID: 4060155).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136987 (6-Methylcoumarin)


  Mrv0541 05061306292D          

 12 13  0  0  0  0            999 V2000
   -1.4289    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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    1.2375    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
Download

3D MOL for NP0136987 (6-Methylcoumarin)

     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.1549   -0.6018    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557   -0.1058    0.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378    1.2364    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    1.7478    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8535    0.9394    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0812    1.4011    0.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415    0.6493   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3153    1.1194   -0.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233   -0.7084   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -1.2207   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6404   -0.4057   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -0.9163   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -1.7004   -0.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6489   -0.4349    1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -0.1274   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    1.9053    0.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0669    2.7913    0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8886   -1.3373   -0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -2.2715   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.9597   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 12  2  0
 12 11  1  0
 11  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
 10 11  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
 12 20  1  0
  9 18  1  0
 10 19  1  0
  4 17  1  0
  3 16  1  0
M  END
Download

3D SDF for NP0136987 (6-Methylcoumarin)


  Mrv0541 05061306292D          

 12 13  0  0  0  0            999 V2000
   -1.4289    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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    1.2375    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=C(OC(=O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3

> <INCHI_KEY>
FXFYOPQLGGEACP-UHFFFAOYSA-N

> <FORMULA>
C10H8O2

> <MOLECULAR_WEIGHT>
160.1693

> <EXACT_MASS>
160.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.576503764497946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.296781004666667

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.940032990292916

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
46.58980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methylchromen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0136987 (6-Methylcoumarin)

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PDB for NP0136987 (6-Methylcoumarin)
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   1.540   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    4    7                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    7    8                                                       
CONECT    7    1    2    6                                                  
CONECT    8    3    6    9                                                  
CONECT    9    4    8   12                                                  
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0136987 (6-Methylcoumarin)
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SMILES for NP0136987 (6-Methylcoumarin)
CC1=CC2=C(OC(=O)C=C2)C=C1
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INCHI for NP0136987 (6-Methylcoumarin)
InChI=1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3
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View in JSmol
Synonyms
ValueSource
5-Methyl-2-hydroxyphenylpropenoic acid lactoneChEBI
6-Methyl-1,2-benzopyroneChEBI
6-Methyl-2H-1-benzopyran-2-oneChEBI
6-Methyl-cis-O-coumarinic lactoneChEBI
6-MethylbenzopyroneChEBI
6-Methylcoumarinic anhydrideChEBI
Methyl coumarinChEBI
5-Methyl-2-hydroxyphenylpropenoate lactoneGenerator
6-Methyl coumarinHMDB
6-Methyl-1, 2-benzopyroneHMDB
6-Methyl-2H-chromen-2-oneHMDB
6-Methyl-coumarinHMDB
6-MethylcumarinHMDB
CocodescolHMDB
PralinaHMDB
ToncairHMDB
ToncarineHMDB
Chemical FormulaC10H8O2
Average Mass160.1693 Da
Monoisotopic Mass160.05243 Da
IUPAC Name6-methyl-2H-chromen-2-one
Traditional Name6-methylchromen-2-one
CAS Registry NumberNot Available
SMILES
CC1=CC2=C(OC(=O)C=C2)C=C1
InChI Identifier
InChI=1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3
InChI KeyFXFYOPQLGGEACP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-23View Spectrum
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 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
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.94ALOGPS
logP2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.59 m³·mol⁻¹ChemAxon
Polarizability16.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032394  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009822  
KNApSAcK IDNot Available
Chemspider ID6825  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylcoumarin  
METLIN IDNot Available
PubChem Compound7092  
PDB IDNot Available
ChEBI ID563586  
Good Scents IDNot Available
References
General References
  1. Vachiramon V, Wattanakrai P: Photoallergic contact sensitization to 6-methylcoumarin in poikiloderma of Civatte. Dermatitis. 2005 Sep;16(3):136-8. [PubMed:16242086  ] 
  2. Bettero A, Benassi CA: Determination of coumarin and 6-methylcoumarin in cosmetics by high-performance liquid chromatography. J Pharm Biomed Anal. 1983;1(2):229-33. doi: 10.1016/0731-7085(83)80032-6. [PubMed:16867823  ] 
  3. Kato S, Seki T, Katsumura Y, Kobayashi T, Komatsu K, Fukushima S: Mechanism for 6-methylcoumarin photoallergenicity. Toxicol Appl Pharmacol. 1985 Nov;81(2):295-301. doi:  10.1016/0041-008x(85)90166-8. [PubMed:4060155  ] 
  4. Kaidbey KH, Kligman AM: Contact photoallergy to 6-methylcoumarin in proprietary sunscreens. Arch Dermatol. 1978 Nov;114(11):1709-10. [PubMed:718225  ]