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Showing metabocard for Herniarin (HMDB0029758)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:26 UTC
Update Date2023-02-21 17:19:14 UTC
HMDB IDHMDB0029758
Secondary Accession Numbers
  • HMDB29758
Metabolite Identification
Common NameHerniarin
DescriptionHerniarin, also known as 7-methoxycoumarin or ayapanin, 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). Herniarin is a sweet, balsamic, and tonka tasting compound. Herniarin has been detected, but not quantified, in several different foods, such as barley, tarragons, roman camomiles, fruits, and wild celeries. This could make herniarin a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029758 (Herniarin)

Herniarin
  Mrv1652303202019002D          

 13 14  0  0  0  0            999 V2000
    0.0000   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9999    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.0000    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  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0029758 (Herniarin)

HMDB0029758
     RDKit          3D
Herniarin
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.5864    0.2124   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735    0.1272    0.5080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778    0.0557    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9232   -0.0299    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -0.1011    1.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410   -0.0900    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231   -0.1616    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3367   -0.1450   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300   -0.0581   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948   -0.0442   -2.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    0.0080   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -0.0041   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003    0.0672   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687    0.4548   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.7900   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560    1.0000   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5244   -0.0397    2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726   -0.1686    2.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1339   -0.2289    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4072   -0.1985   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1344   -1.5357 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
 12  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 13 21  1  0
M  END
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3D SDF for HMDB0029758 (Herniarin)

Herniarin
  Mrv1652303202019002D          

 13 14  0  0  0  0            999 V2000
    0.0000   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -1.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9999    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549   -0.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    0.0000    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  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029758

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3

> <INCHI_KEY>
LIIALPBMIOVAHH-UHFFFAOYSA-N

> <FORMULA>
C10H8O3

> <MOLECULAR_WEIGHT>
176.171

> <EXACT_MASS>
176.047344118

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.425221380753513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
1.6256883496666668

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.830651313921493

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
48.01180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylumbelliferone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0029758 (Herniarin)

HMDB0029758
     RDKit          3D
Herniarin
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.5864    0.2124   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735    0.1272    0.5080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778    0.0557    0.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9232   -0.0299    1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567   -0.1011    1.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2410   -0.0900    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231   -0.1616    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3367   -0.1450   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300   -0.0581   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948   -0.0442   -2.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086    0.0080   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -0.0041   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003    0.0672   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687    0.4548   -0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4707   -0.7900   -1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1560    1.0000   -1.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5244   -0.0397    2.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726   -0.1686    2.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1339   -0.2289    1.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4072   -0.1985   -0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3065    0.1344   -1.5357 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
 12  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 13 21  1  0
M  END
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PDB for HMDB0029758 (Herniarin)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Herniarin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.000  -0.775   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.669  -0.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.669  -2.315   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.004  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.329  -2.315   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.664  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.998  -2.315   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.998  -0.775   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.333   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.664   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.329  -0.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.004   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12    6   11   13                                                  
CONECT   13    3   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0029758 (Herniarin)

COMPND    HMDB0029758
HETATM    1  C1  UNL     1       3.586   0.212  -0.742  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.974   0.127   0.508  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.578   0.056   0.560  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.923  -0.030   1.770  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.457  -0.101   1.836  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.241  -0.090   0.700  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.623  -0.162   0.769  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.337  -0.145  -0.411  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.630  -0.058  -1.592  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.295  -0.044  -2.659  1.00  0.00           O  
HETATM   11  O3  UNL     1      -1.309   0.008  -1.606  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.583  -0.004  -0.514  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.800   0.067  -0.577  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.669   0.455  -0.653  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.471  -0.790  -1.237  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.156   1.000  -1.402  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.524  -0.040   2.672  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.973  -0.169   2.789  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.134  -0.229   1.725  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.407  -0.199  -0.400  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.306   0.134  -1.536  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   12
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13
CONECT   13   21
END
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SMILES for HMDB0029758 (Herniarin)

COC1=CC2=C(C=CC(=O)O2)C=C1
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INCHI for HMDB0029758 (Herniarin)

InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
7-Methoxy-2H-1-benzopyran-2-oneChEBI
7-MethoxycoumarinChEBI
AyapaninChEBI
HerniarineChEBI
MethylumbelliferoneChEBI
7-(Methyloxy)-2H-chromen-2-oneHMDB
7-Methoxy-2H-1-benzopyran-2-one, 9ciHMDB
7-Methoxy-2H-chromen-2-oneHMDB
7-Methoxy-coumarinHMDB
7-METHOXYCOURMARINHMDB
7-Methyl ether derivative OF umbelliferoneHMDB
Coumarin, 7-methoxy- (8ci)HMDB
Herniarin (6ci)HMDB
Methyl umbelliferyl etherHMDB
Umbelliferone methyl etherHMDB
Chemical FormulaC10H8O3
Average Molecular Weight176.171
Monoisotopic Molecular Weight176.047344118
IUPAC Name7-methoxy-2H-chromen-2-one
Traditional Namemethylumbelliferone
CAS Registry Number531-59-9
SMILES
COC1=CC2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3
InChI KeyLIIALPBMIOVAHH-UHFFFAOYSA-N
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
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling Point334.00 to 335.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.13 mg/mLNot Available
LogP1.821 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000963
KNApSAcK IDC00002476
Chemspider ID10295
KEGG Compound IDC09268
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHerniarin
METLIN IDNot Available
PubChem Compound10748
PDB IDNot Available
ChEBI ID5679
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031831
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .