NP-MRD: Showing NP-Card for Quinolactacide (NP0005895)

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Record Information

Version

2.0

Created at

2020-12-09 03:01:16 UTC

Updated at

2021-07-15 16:53:16 UTC

NP-MRD ID

NP0005895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinolactacide

Provided By

NPAtlas

Description

Quinolactacide is found in Penicillium citrinum. Quinolactacide was first documented in 2005 (PMID: 15973055). Based on a literature review very few articles have been published on 4H,9H,10H-pyrrolizino[1,2-b]quinoline-9,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118233D          

 26 29  0  0  0  0            999 V2000
   -2.0151   -2.7975   -1.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504   -1.6544   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -1.0678   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    0.1852    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    0.9818    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807    0.6097    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6169    1.4720    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9262    1.0930    0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642   -0.1456   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1351   -1.0020   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -0.6292   -0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739   -1.4543   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -2.5787   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1837    0.3767    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.2568    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4187    0.7149    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -0.5307   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7164   -0.2381 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    1.9231    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    2.4327    1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    1.7521    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -0.4165   -0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440   -1.9640   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238    2.2242    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3837    1.1783    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.2434   -0.4245 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18  2  1  0  0  0  0
 12  3  1  0  0  0  0
 18 14  1  0  0  0  0
 11  6  1  0  0  0  0
  5 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 15 24  1  0  0  0  0
 16 25  1  0  0  0  0
 17 26  1  0  0  0  0
M  END


  Mrv1652306242118233D          

 26 29  0  0  0  0            999 V2000
   -2.0151   -2.7975   -1.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8504   -1.6544   -0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419   -1.0678   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349    0.1852    0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3205    0.9818    0.4427 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807    0.6097    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6169    1.4720    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9262    1.0930    0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642   -0.1456   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1351   -1.0020   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8267   -0.6292   -0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739   -1.4543   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -2.5787   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1837    0.3767    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.2568    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4187    0.7149    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -0.5307   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8296   -0.7164   -0.2381 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472    1.9231    0.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625    2.4327    1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    1.7521    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -0.4165   -0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440   -1.9640   -0.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238    2.2242    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3837    1.1783    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9252   -1.2434   -0.4245 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18  2  1  0  0  0  0
 12  3  1  0  0  0  0
 18 14  1  0  0  0  0
 11  6  1  0  0  0  0
  5 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
 10 23  1  0  0  0  0
 15 24  1  0  0  0  0
 16 25  1  0  0  0  0
 17 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C(C(=O)N3C([H])=C([H])C([H])=C23)C(=O)C2=C([H])C([H])=C([H])C([H])=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O2/c17-13-8-4-1-2-5-9(8)15-12-10-6-3-7-16(10)14(18)11(12)13/h1-7H,(H,15,17)

> <INCHI_KEY>
QFTHRUCJNWMSRD-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O2

> <MOLECULAR_WEIGHT>
236.23

> <EXACT_MASS>
236.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
24.259711231265815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4H,9H,10H-pyrrolizino[1,2-b]quinoline-9,10-dione

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.3781176400000001

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.041631910789752

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4093267439960413

> <JCHEM_POLAR_SURFACE_AREA>
51.1

> <JCHEM_REFRACTIVITY>
68.03900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4H-pyrrolizino[1,2-b]quinoline-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.015  -2.797  -1.177  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.850  -1.654  -0.675  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.542  -1.068  -0.445  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.735   0.185   0.114  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.321   0.982   0.443  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.581   0.610   0.250  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.617   1.472   0.608  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.926   1.093   0.412  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.164  -0.146  -0.142  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.135  -1.002  -0.497  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.827  -0.629  -0.303  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.774  -1.454  -0.645  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.000  -2.579  -1.147  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.184   0.377   0.231  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.166   1.257   0.642  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.419   0.715   0.430  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.173  -0.531  -0.126  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.830  -0.716  -0.238  0.00  0.00           N+0
HETATM   19  H   UNK     0       0.147   1.923   0.863  0.00  0.00           H+0
HETATM   20  H   UNK     0       2.362   2.433   1.039  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.736   1.752   0.685  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.212  -0.417  -0.285  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.344  -1.964  -0.928  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.924   2.224   1.065  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.384   1.178   0.657  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.925  -1.243  -0.425  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12                                                            
CONECT   14    4   15   18                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17    2   14                                                  
CONECT   19    5                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₈N₂O₂

Average Mass

236.2300 Da

Monoisotopic Mass

236.05858 Da

IUPAC Name

4H,9H,10H-pyrrolizino[1,2-b]quinoline-9,10-dione

Traditional Name

4H-pyrrolizino[1,2-b]quinoline-9,10-dione

CAS Registry Number

Not Available

SMILES

O=C1N2C=CC=C2C2=C1C(=O)C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C14H8N2O2/c17-13-8-4-1-2-5-9(8)15-12-10-6-3-7-16(10)14(18)11(12)13/h1-7H,(H,15,17)

InChI Key

QFTHRUCJNWMSRD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium citrinum	NPAtlas	15973055

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroquinolones. These 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

Dihydroquinolone
Dihydroquinoline
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Pyrrole
Lactam
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.46	ALOGPS
logP	1.38	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.04	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.1 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.04 m³·mol⁻¹	ChemAxon
Polarizability	24.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016789

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052399

Chemspider ID

9656580

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11481760

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abe M, Imai T, Ishii N, Usui M, Okuda T, Oki T: Quinolactacide, a new quinolone insecticide from Penicillium citrinum Thom F 1539. Biosci Biotechnol Biochem. 2005 Jun;69(6):1202-5. doi: 10.1271/bbb.69.1202. [PubMed:15973055 ]

Showing NP-Card for Quinolactacide (NP0005895)

MOL for NP0005895 (Quinolactacide)

3D MOL for NP0005895 (Quinolactacide)

3D SDF for NP0005895 (Quinolactacide)

3D-SDF for NP0005895 (Quinolactacide)

PDB for NP0005895 (Quinolactacide)

3D PDB for NP0005895 (Quinolactacide)

SMILES for NP0005895 (Quinolactacide)

INCHI for NP0005895 (Quinolactacide)

Structure for NP0005895 (Quinolactacide)

3D Structure for NP0005895 (Quinolactacide)