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Showing NP-Card for Gentianine (NP0047117)

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Record Information
Version2.0
Created at2022-03-17 20:34:55 UTC
Updated at2022-03-17 20:34:55 UTC
NP-MRD IDNP0047117
Secondary Accession NumbersNone
Natural Product Identification
Common NameGentianine
Description Gentianine is found in Anthocleista procera, Dipsacus azureus Schrenk., Fagraea fragrans, Gentiana caucasica, Gentiana kaufmanniana Rgl.et Schamlh., Gentiana kirilowii, Gentiana kiriowi, Gentiana lutea, Gentiana olivieri Griseb.Rgl.et Schamlh., Gentiana pedicellata, Gentiana punctata, Gentiana rigescens, Gentiana spp., Gentiana turkestanorum Gand., Gentianella caucasea, Gentianella turkestanorum, Hunteria zeylanica, Schenkia spicata, Schultesia guianensis, Strychnos lucida, Strychnos pungens, Strychnos xantha, Swertia angustifolia, Swertia ciliata, Swertia macrosperma, Swertia marginata, Swertia marginata Schrenk., Swertia randaiensis and Swertia spp..
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047117 (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
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3D MOL for NP0047117 (Gentianine)

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3D SDF for NP0047117 (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>
NP0047117

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0047117 (Gentianine)
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PDB for NP0047117 (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 NP0047117 (Gentianine)
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SMILES for NP0047117 (Gentianine)
C=CC1=C2CCOC(=O)C2=CN=C1
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INCHI for NP0047117 (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 JSmol
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 Mass175.1840 Da
Monoisotopic Mass175.06333 Da
IUPAC Name5-ethenyl-1H,3H,4H-pyrano[3,4-c]pyridin-1-one
Traditional Namegentianine
CAS Registry Number439-89-4
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anthocleista proceraPlant
Dipsacus azureus Schrenk.Plant
Fagraea fragransLOTUS Database
Gentiana caucasicaPlant
Gentiana kaufmanniana Rgl.et Schamlh.Plant
Gentiana kirilowiiPlant
Gentiana kiriowiPlant
Gentiana luteaLOTUS Database
Gentiana olivieri Griseb.Rgl.et Schamlh.Plant
Gentiana pedicellataLOTUS Database
Gentiana punctataLOTUS Database
Gentiana rigescensLOTUS Database
Gentiana spp.Plant
Gentiana turkestanorum Gand.Plant
Gentianella caucaseaLOTUS Database
Gentianella turkestanorumLOTUS Database
Hunteria zeylanicaLOTUS Database
Schenkia spicataLOTUS Database
Schultesia guianensisLOTUS Database
Strychnos lucidaLOTUS Database
Strychnos pungensLOTUS Database
Strychnos xanthaLOTUS Database
Swertia angustifoliaLOTUS Database
Swertia ciliataLOTUS Database
Swertia macrospermaLOTUS Database
Swertia marginataLOTUS Database
Swertia marginata Schrenk.Plant
Swertia randaiensisPlant
Swertia spp.Plant
Trigonella foenum-graecumFooDB
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
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
logP1.01ALOGPS
logP1.34ChemAxon
logS-0.96ALOGPS
pKa (Strongest Basic)3.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.92 m³·mol⁻¹ChemAxon
Polarizability17.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007359  
KNApSAcK IDC00001977  
Chemspider IDNot Available
KEGG Compound IDC06525  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound354616  
PDB IDNot Available
ChEBI ID28981  
Good Scents IDNot Available
References
General ReferencesNot Available