NP-MRD: Showing NP-Card for 3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol (NP0158313)

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Record Information

Version

2.0

Created at

2022-09-02 15:52:46 UTC

Updated at

2022-09-02 15:52:46 UTC

NP-MRD ID

NP0158313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol

Description

MEGxm0_000340 belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. 3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol is found in Penicillium janczewskii. MEGxm0_000340 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    5.1471   -1.3161    1.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4778   -1.2913   -0.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1423   -0.9741   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5844   -0.9803   -1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2504   -0.6657   -1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -0.3477   -0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -0.0107   -0.7839 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2669   -0.1274   -2.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778    1.3492   -0.3041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850    2.3239   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    3.6063    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523    3.9495    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    3.0013    0.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    1.7299    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5809    0.7353    0.0329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2548   -0.5756   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1198   -1.2564   -0.9959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8661   -1.0088   -0.1052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6030   -2.2836   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757   -3.2150    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -0.3323    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354   -0.6492    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2630   -0.3090    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5580   -1.9433    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1539   -1.7879    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -1.2229   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -0.6769   -2.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4090    0.7733   -2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    2.0455   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2108    4.3626    0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    4.9408    0.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8696    3.2046    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5643    1.0119    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7456   -0.9688    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702   -3.3763    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625   -4.1497   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3930   -2.8500    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -0.0767    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504   -0.6381    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 22  1  0
 22 21  2  0
  7 18  1  0
 21  6  1  0
  9 14  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 18 34  1  1
 15 33  1  0
 13 32  1  0
 12 31  1  0
 11 30  1  0
 10 29  1  0
  8 28  1  0
  5 27  1  0
  4 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 39  1  0
 21 38  1  0
M  END


  Mrv1533004161507002D          

 22 24  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.0000    0.0000    0.0000 O   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
    1.8163   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -3.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203   -4.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -5.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 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
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(=O)NC2=CC=CC=C2C1(O)C1=CC=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO4/c1-21-12-9-7-11(8-10-12)17(20)13-5-3-4-6-14(13)18-16(19)15(17)22-2/h3-10,15,20H,1-2H3,(H,18,19)

> <INCHI_KEY>
VCKUOSKDXLTBDG-UHFFFAOYSA-N

> <FORMULA>
C17H17NO4

> <MOLECULAR_WEIGHT>
299.326

> <EXACT_MASS>
299.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.70117396848058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-methoxy-4-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-2-one

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.7215342479999998

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.917891072879433

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.776405150799658

> <JCHEM_PKA_STRONGEST_BASIC>
-4.051728304615316

> <JCHEM_POLAR_SURFACE_AREA>
67.79

> <JCHEM_REFRACTIVITY>
82.8032

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-methoxy-4-(4-methoxyphenyl)-1,3-dihydroquinolin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+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       3.390  -4.440   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.498  -7.159   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.225  -8.519   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.591  -9.825   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.318  -5.853   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.405  -4.493   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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    3   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇NO₄

Average Mass

299.3260 Da

Monoisotopic Mass

299.11576 Da

IUPAC Name

4-hydroxy-3-methoxy-4-(4-methoxyphenyl)-1,2,3,4-tetrahydroquinolin-2-one

Traditional Name

4-hydroxy-3-methoxy-4-(4-methoxyphenyl)-1,3-dihydroquinolin-2-one

CAS Registry Number

Not Available

SMILES

COC1C(=O)NC2=CC=CC=C2C1(O)C1=CC=C(OC)C=C1

InChI Identifier

InChI=1S/C17H17NO4/c1-21-12-9-7-11(8-10-12)17(20)13-5-3-4-6-14(13)18-16(19)15(17)22-2/h3-10,15,20H,1-2H3,(H,18,19)

InChI Key

VCKUOSKDXLTBDG-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 janczewskii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Phenylquinolines

Alternative Parents

Substituents

Phenylquinoline
Quinolone
Tetrahydroquinolone
Tetrahydroquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	2.13	ALOGPS
logP	1.72	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.8 m³·mol⁻¹	ChemAxon
Polarizability	30.7 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

23843957

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol (NP0158313)

MOL for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

3D MOL for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

3D SDF for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

3D-SDF for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

PDB for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

3D PDB for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

SMILES for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

INCHI for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

Structure for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)

3D Structure for NP0158313 (3-methoxy-4-(4-methoxyphenyl)-3h-quinoline-2,4-diol)