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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:21:25 UTC

Update Date

2023-02-21 17:25:34 UTC

HMDB ID

HMDB0037113

Secondary Accession Numbers

HMDB37113

Metabolite Identification

Common Name

1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Description

1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one, also known as fongoren or coratop, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Based on a literature review very few articles have been published on 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2,5,6-Tetrahydropyrrolo[3,2,1-ij]quinolin-4-one	ChEBI
Coratop	ChEBI
Fongoren	ChEBI
Fongorene	ChEBI
Lilolidone	ChEBI
Pyroquilone	ChEBI
1,2,5,6-tetrahydro-4H-pyrrolo(3,2,1-Ij)quinolin-4-one	HMDB
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-one	HMDB
4-Oxolilidine	HMDB
PYQ	HMDB
Pyroquilon	HMDB
Pyroquilon, bsi, iso	HMDB

Chemical Formula

C₁₁H₁₁NO

Average Molecular Weight

173.2111

Monoisotopic Molecular Weight

173.084063979

IUPAC Name

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

Traditional Name

pyroquilon

CAS Registry Number

57369-32-1

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyrroloquinoline (CHEBI:45141 )
delta-lactam (CHEBI:45141 )
Pesticides (C18487 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037113)
Cytoplasm (HMDB: HMDB0037113)

Source

Exogenous

Food

Food (HMDB: HMDB0037113)

Process

Not Available

Role

Environmental role

Environmental contaminant (HMDB: HMDB0037113)

Biological role

Nutrient (HMDB: HMDB0037113)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0037113)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	112 - 113 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4 mg/mL at 20 °C	Not Available
LogP	1.57	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	1.1	ALOGPS
logP	1.42	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.61 m³·mol⁻¹	ChemAxon
Polarizability	18.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.085	31661259
DarkChem	[M-H]-	135.493	31661259
DeepCCS	[M+H]+	140.08	30932474
DeepCCS	[M-H]-	137.684	30932474
DeepCCS	[M-2H]-	173.275	30932474
DeepCCS	[M+Na]+	148.261	30932474
AllCCS	[M+H]+	137.5	32859911
AllCCS	[M+H-H2O]+	133.0	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	141.4	32859911
AllCCS	[M+Na-2H]-	141.5	32859911
AllCCS	[M+HCOO]-	141.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one	O=C1CCC2=CC=CC3=C2N1CC3	2963.9	Standard polar	33892256
1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one	O=C1CCC2=CC=CC3=C2N1CC3	1691.0	Standard non polar	33892256
1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one	O=C1CCC2=CC=CC3=C2N1CC3	1924.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-008a-0900000000-ffe4f8f6416b7f66037b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 10V, Positive-QTOF	splash10-00di-0900000000-d97975a5b1dd3dc54b00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 20V, Positive-QTOF	splash10-00di-0900000000-dc8b09bb91da65b7dbe6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 40V, Positive-QTOF	splash10-066r-0900000000-9e49a756e944af4820c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 10V, Negative-QTOF	splash10-00di-0900000000-d009fa59ccfee463f488	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 20V, Negative-QTOF	splash10-00di-0900000000-07e9b055551e5f2fdfc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 40V, Negative-QTOF	splash10-0006-2900000000-94c145da43ec5d6eff51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 10V, Positive-QTOF	splash10-00di-0900000000-3473e1d34af1c83c8904	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 20V, Positive-QTOF	splash10-00di-0900000000-bd044b74560d63d23b23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 40V, Positive-QTOF	splash10-06dj-0900000000-fff91be4fd40fa7f2f82	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 10V, Negative-QTOF	splash10-00di-0900000000-4c1ad417189eea157a87	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 20V, Negative-QTOF	splash10-00di-0900000000-4c1ad417189eea157a87	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one 40V, Negative-QTOF	splash10-006x-0900000000-481b117a0ebc4aa207b7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02756

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016106

KNApSAcK ID

Not Available

Chemspider ID

82768

KEGG Compound ID

C18487

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91665

PDB ID

PYQ

ChEBI ID

45141

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (HMDB0037113)

MOL for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

3D MOL for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

3D SDF for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

3D-SDF for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

PDB for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

3D PDB for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

SMILES for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

INCHI for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

Structure for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

3D Structure for HMDB0037113 (1,2,5,6-Tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra