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Showing NP-Card for 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (NP0334603)

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Record Information
Version2.0
Created at2024-09-10 19:06:22 UTC
Updated at2024-09-10 19:06:22 UTC
NP-MRD IDNP0334603
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one
Description1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one, also known as fongoren or pyroquilone, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one was first documented in 2014 (PMID: 24646830). A pyrroloquinoline that is 1,2,5,6-tetrahydro-4H-pyrroloquinoline in which the hydrogens at position 4 are replaced by an oxo group.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)


  Mrv0541 02231216262D          

 13 15  0  0  0  0            999 V2000
   -1.5558    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
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3D MOL for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

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3D SDF for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

  Mrv0541 02231216262D          

 13 15  0  0  0  0            999 V2000
   -1.5558    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334603

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC2=CC=CC3=C2N1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO/c13-10-5-4-8-2-1-3-9-6-7-12(10)11(8)9/h1-3H,4-7H2

> <INCHI_KEY>
XRJLAOUDSILTFT-UHFFFAOYSA-N

> <FORMULA>
C11H11NO

> <MOLECULAR_WEIGHT>
173.2111

> <EXACT_MASS>
173.084063979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.78977771088972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-azatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-11-one

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.4205734269999997

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4964955335292154

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
50.61140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyroquilon

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)
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PDB for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.904   0.479   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.240   0.480   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.860   2.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

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3D PDB for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)
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SMILES for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)
O=C1CCC2=CC=CC3=C2N1CC3
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INCHI for NP0334603 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)
InChI=1S/C11H11NO/c13-10-5-4-8-2-1-3-9-6-7-12(10)11(8)9/h1-3H,4-7H2
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View in JSmol
Synonyms
ValueSource
1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-oneChEBI
CoratopChEBI
FongorenChEBI
FongoreneChEBI
LilolidoneChEBI
PyroquiloneChEBI
1,2,5,6-Tetrahydro-4H-pyrrolo(3,2,1-ij)quinolin-4-oneHMDB
1,2,5,6-Tetrahydro-4H-pyrrolo(3,2,1-ij)quinolin-4-one (9ci)HMDB
1,2,5,6-Tetrahydropyrrolo(3,2,1-ij)quinolin-4-oneHMDB
4-OxolilidineHMDB
PYQHMDB
PyroquilonHMDB
Pyroquilon, bsi, isoHMDB
Chemical FormulaC11H11NO
Average Mass173.2111 Da
Monoisotopic Mass173.08406 Da
IUPAC Name1-azatricyclo[6.3.1.0⁴,¹²]dodeca-4(12),5,7-trien-11-one
Traditional Namepyroquilon
CAS Registry NumberNot Available
SMILES
O=C1CCC2=CC=CC3=C2N1CC3
InChI Identifier
InChI=1S/C11H11NO/c13-10-5-4-8-2-1-3-9-6-7-12(10)11(8)9/h1-3H,4-7H2
InChI KeyXRJLAOUDSILTFT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassQuinolones and derivatives  
Direct ParentHydroquinolones  
Alternative Parents
Substituents
  • Tetrahydroquinolone
    • 

  • Tetrahydroquinoline
    • 

  • Indole or derivatives
    • 

  • Benzenoid
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen 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
logP1.1ALOGPS
logP1.42ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.61 m³·mol⁻¹ChemAxon
Polarizability18.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037113  
DrugBank IDDB02756  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016106  
KNApSAcK IDNot Available
Chemspider ID82768  
KEGG Compound IDC18487  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91665  
PDB IDPYQ  
ChEBI ID45141  
Good Scents IDNot Available
References
General References
  1. Beltran-Garcia MJ, Prado FM, Oliveira MS, Ortiz-Mendoza D, Scalfo AC, Pessoa A Jr, Medeiros MH, White JF, Di Mascio P: Singlet molecular oxygen generation by light-activated DHN-melanin of the fungal pathogen Mycosphaerella fijiensis in black Sigatoka disease of bananas. PLoS One. 2014 Mar 19;9(3):e91616. doi: 10.1371/journal.pone.0091616. eCollection  2014. [PubMed:24646830  ]