NP-MRD: Showing NP-Card for Penicinoline (NP0140102)

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Record Information

Version

2.0

Created at

2022-06-29 20:46:05 UTC

Updated at

2022-06-29 20:46:05 UTC

NP-MRD ID

NP0140102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penicinoline

Description

Penicinoline belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Penicinoline is found in Penicillium citrinum. Penicinoline is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.2130   -3.2358   -0.7276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8041   -2.5703    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038   -3.0816    1.5457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590   -1.3429    0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142   -0.1114   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    0.1611    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -0.7005    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -0.0108    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9943    1.2893    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6520    1.3735   -0.0475 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2016    0.9750   -0.2056 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334    0.8849   -0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    2.0263   -0.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6678    1.9353   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2761    0.7014   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080   -0.4438   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.3544   -0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -1.4464   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -2.5837    0.0859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7288   -2.6019    2.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527   -1.7695    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3178   -0.4646    0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6761    2.1447    0.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086    2.2526   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2504    1.9232   -0.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.9874   -0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041    2.8597   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3533    0.6263   -0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9486   -1.4234   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 18  4  1  0
 10  6  1  0
 17 12  1  0
  3 20  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
M  END


  Mrv1533004231517412D          

 19 21  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537   -0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8932    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862    0.8205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(NC2=CC=CC=C2C1=O)C1=CC=CN1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N2O3/c17-13-8-4-1-2-5-9(8)16-12(11(13)14(18)19)10-6-3-7-15-10/h1-7,15H,(H,16,17)(H,18,19)

> <INCHI_KEY>
DWKAQISLZUQZNU-UHFFFAOYSA-N

> <FORMULA>
C14H10N2O3

> <MOLECULAR_WEIGHT>
254.245

> <EXACT_MASS>
254.06914219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.415860617874785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-oxo-2-(1H-pyrrol-2-yl)-1,4-dihydroquinoline-3-carboxylic acid

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.8349628163333334

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.041897252077135

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.3951411702474035

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8125844893267091

> <JCHEM_POLAR_SURFACE_AREA>
82.19

> <JCHEM_REFRACTIVITY>
71.41240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxo-2-(1H-pyrrol-2-yl)-1H-quinoline-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.407  -0.626   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.437   0.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.667   1.852   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.161   1.532   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₀N₂O₃

Average Mass

254.2450 Da

Monoisotopic Mass

254.06914 Da

IUPAC Name

4-oxo-2-(1H-pyrrol-2-yl)-1,4-dihydroquinoline-3-carboxylic acid

Traditional Name

4-oxo-2-(1H-pyrrol-2-yl)-1H-quinoline-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(NC2=CC=CC=C2C1=O)C1=CC=CN1

InChI Identifier

InChI=1S/C14H10N2O3/c17-13-8-4-1-2-5-9(8)16-12(11(13)14(18)19)10-6-3-7-15-10/h1-7,15H,(H,16,17)(H,18,19)

InChI Key

DWKAQISLZUQZNU-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline carboxylic acids

Alternative Parents

Substituents

Quinoline-3-carboxylic acid
Dihydroquinolone
Dihydroquinoline
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Vinylogous amide
Pyrrole
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
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	1.82	ALOGPS
logP	1.83	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.19 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.41 m³·mol⁻¹	ChemAxon
Polarizability	25.42 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46890175

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Penicinoline (NP0140102)

MOL for NP0140102 (Penicinoline)

3D MOL for NP0140102 (Penicinoline)

3D SDF for NP0140102 (Penicinoline)

3D-SDF for NP0140102 (Penicinoline)

PDB for NP0140102 (Penicinoline)

3D PDB for NP0140102 (Penicinoline)

SMILES for NP0140102 (Penicinoline)

INCHI for NP0140102 (Penicinoline)

Structure for NP0140102 (Penicinoline)

3D Structure for NP0140102 (Penicinoline)