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Showing metabocard for Gentianine (HMDB0303030)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 22:45:01 UTC
Update Date2021-09-23 22:45:02 UTC
HMDB IDHMDB0303030
Secondary Accession NumbersNone
Metabolite Identification
Common NameGentianine
DescriptionGentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate g-lactone, is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring. Gentianine is soluble (in water) and a strong basic compound (based on its pKa). Gentianine is a bitter tasting compound found in fenugreek, which makes gentianine a potential biomarker for the consumption of this food product.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0303030 (Gentianine)

  Mrv0541 02241221182D          

 13 14  0  0  0  0            999 V2000
   16.3029  -15.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5868  -15.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0122  -15.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3098  -14.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8741  -15.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5868  -16.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0122  -16.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7249  -15.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5971  -13.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8810  -14.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1579  -15.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3029  -16.6970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4410  -15.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  1  0  0  0  0
  8 13  2  0  0  0  0
  7 12  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for HMDB0303030 (Gentianine)

HMDB0303030
     RDKit          3D
Gentianine
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.2746   -0.9631   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010   -0.9833   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    0.1819   -0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    1.4308   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735    2.5435   -0.4788 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4505    2.4263   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015    1.1804   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    0.0414    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -1.2770    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -1.3364   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -0.1400    0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    1.1056    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    2.1463    0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569   -0.1043   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -1.8980   -0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556   -1.9459    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    1.5130   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890    3.2965   -0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8023   -1.5204    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3354   -2.0729   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -2.1564    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.4682   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  8  3  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  4 17  1  0
  6 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
M  END
Download

3D SDF for HMDB0303030 (Gentianine)

  Mrv0541 02241221182D          

 13 14  0  0  0  0            999 V2000
   16.3029  -15.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5868  -15.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0122  -15.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3098  -14.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8741  -15.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5868  -16.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0122  -16.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7249  -15.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5971  -13.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8810  -14.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1579  -15.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3029  -16.6970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4410  -15.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  1  0  0  0  0
  8 13  2  0  0  0  0
  7 12  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303030

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CC1=C2CCOC(=O)C2=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2

> <INCHI_KEY>
DFNZYFAJQPLJFI-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.184

> <EXACT_MASS>
175.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.609614526809725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.3356409273333334

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.0113062502608607

> <JCHEM_POLAR_SURFACE_AREA>
39.19

> <JCHEM_REFRACTIVITY>
48.92230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gentianine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0303030 (Gentianine)

HMDB0303030
     RDKit          3D
Gentianine
 22 23  0  0  0  0  0  0  0  0999 V2000
    3.2746   -0.9631   -0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010   -0.9833   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    0.1819   -0.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    1.4308   -0.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8735    2.5435   -0.4788 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4505    2.4263   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0015    1.1804   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2498    0.0414    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8600   -1.2770    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -1.3364   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -0.1400    0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    1.1056    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1782    2.1463    0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569   -0.1043   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -1.8980   -0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5556   -1.9459    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    1.5130   -0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0890    3.2965   -0.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8023   -1.5204    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3354   -2.0729   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8191   -2.1564    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849   -1.4682   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  8  3  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  4 17  1  0
  6 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
 10 22  1  0
M  END
Download

PDB for HMDB0303030 (Gentianine)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      30.432 -28.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.095 -28.861   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.756 -28.861   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.445 -26.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.765 -28.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.095 -30.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.756 -30.396   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.086 -28.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.115 -25.775   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.778 -26.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      26.428 -28.841   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      30.432 -31.168   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      34.423 -28.854   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13                                                       
CONECT    9    4   10                                                       
CONECT   10    5    9                                                       
CONECT   11    5                                                            
CONECT   12    6    7                                                       
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for HMDB0303030 (Gentianine)

COMPND    HMDB0303030
HETATM    1  C1  UNL     1       3.275  -0.963  -0.221  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.001  -0.983  -0.002  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.136   0.182  -0.113  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.653   1.431  -0.373  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.873   2.544  -0.479  1.00  0.00           N  
HETATM    6  C5  UNL     1      -0.450   2.426  -0.324  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.002   1.180  -0.061  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.250   0.041   0.051  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.860  -1.277   0.324  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.328  -1.336  -0.033  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.995  -0.140   0.378  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.445   1.106   0.108  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.178   2.146   0.010  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.857  -0.104  -0.509  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.852  -1.898  -0.112  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.556  -1.946   0.293  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.737   1.513  -0.496  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.089   3.297  -0.403  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.802  -1.520   1.420  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.335  -2.073  -0.251  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.819  -2.156   0.525  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.385  -1.468  -1.138  1.00  0.00           H  
CONECT    1    2    2   14   15
CONECT    2    3   16
CONECT    3    4    4    8
CONECT    4    5   17
CONECT    5    6    6
CONECT    6    7   18
CONECT    7    8    8   12
CONECT    8    9
CONECT    9   10   19   20
CONECT   10   11   21   22
CONECT   11   12
CONECT   12   13   13
END
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SMILES for HMDB0303030 (Gentianine)

C=CC1=C2CCOC(=O)C2=CN=C1
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INCHI for HMDB0303030 (Gentianine)

InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-(2-Hydroxyethyl)-5-vinylnicotinic acid gamma-lactoneChEBI
4-(2-Hydroxyethyl)-5-vinylnicotinate g-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinate gamma-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinate γ-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid g-lactoneGenerator
4-(2-Hydroxyethyl)-5-vinylnicotinic acid γ-lactoneGenerator
5-Ethenyl-3,4-dihydro-1H-pyrano(3,4-c)pyridin-1-oneMeSH
Chemical FormulaC10H9NO2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
IUPAC Name5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one
Traditional Namegentianine
CAS Registry NumberNot Available
SMILES
C=CC1=C2CCOC(=O)C2=CN=C1
InChI Identifier
InChI=1S/C10H9NO2/c1-2-7-5-11-6-9-8(7)3-4-13-10(9)12/h2,5-6H,1,3-4H2
InChI KeyDFNZYFAJQPLJFI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranopyridines. These are polycyclic aromatic compounds containing a pyran ring fused to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyranopyridines
Sub ClassNot Available
Direct ParentPyranopyridines
Alternative Parents
Substituents
  • Pyranopyridine
  • Pyridine carboxylic acid
  • Pyridine
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
Role
Industrial applicationBiological roleIndirect biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB007359
KNApSAcK IDC00001977
Chemspider ID314782
KEGG Compound IDC06525
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound354616
PDB IDNot Available
ChEBI ID28981
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available