NP-MRD: Showing NP-Card for {3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate (NP0157829)

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Record Information

Version

2.0

Created at

2022-09-02 15:18:52 UTC

Updated at

2022-09-02 15:18:52 UTC

NP-MRD ID

NP0157829

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate

Description

2-(Acetoxyamino)-3-methylimidazo[4,5-f]quinoline, also known as N-acetoxy-iq, belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. 2-(Acetoxyamino)-3-methylimidazo[4,5-f]quinoline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. {3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate is found in Apis cerana. {3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate was first documented in 1994 (PMID: 7696529). Based on a literature review very few articles have been published on 2-(acetoxyamino)-3-methylimidazo[4,5-f]quinoline.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.4036    0.4964   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3116    0.1329    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932   -0.9297    0.8204 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1958    0.9220    0.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2287    0.4873    1.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    0.1654    0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1673    0.8920    0.9737 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995    0.3083    0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5309    0.6785    0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0152    1.7932    0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3463    2.0660    0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1697    1.2638    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6681    0.1962   -0.5999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535   -0.1205   -0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -1.2318   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -1.5607   -1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793   -0.7843   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -0.8844   -0.0818 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799   -1.8954   -0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0557    1.2278   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452   -0.4430   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9360    0.8657   -1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785    0.4127    2.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542    2.4077    1.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203    2.9212    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2394    1.5079   -0.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5229   -1.8538   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -2.4102   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9989   -2.7394   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -2.3783    0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518   -1.5135   -1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  7  2  0
  7  8  1  0
  8 17  2  0
 17 16  1  0
 16 15  2  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
 17 18  1  0
  9 14  1  0
  9  8  1  0
 19 29  1  0
 19 30  1  0
 19 31  1  0
  5 23  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 28  1  0
 15 27  1  0
 12 26  1  0
 11 25  1  0
 10 24  1  0
M  END


  Mrv1652309022217182D          

 19 21  0  0  0  0            999 V2000
   -2.6652   -1.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9382   -1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124   -0.2619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -1.5211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099   -1.1311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913   -1.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9551   -1.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4877   -1.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7469   -1.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5715   -1.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -1.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5269   -2.6624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023   -2.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2677   -3.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431   -3.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531   -2.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2519   -2.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781   -2.9211    0.0000 C   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  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  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  8 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157829

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(NOC(C)=O)=NC2=C1C=CC1=NC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N4O2/c1-8(18)19-16-13-15-12-9-4-3-7-14-10(9)5-6-11(12)17(13)2/h3-7H,1-2H3,(H,15,16)

> <INCHI_KEY>
ZNLLBBZONQYLII-UHFFFAOYSA-N

> <FORMULA>
C13H12N4O2

> <MOLECULAR_WEIGHT>
256.265

> <EXACT_MASS>
256.096025642

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.69977036720674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-methyl-3H-imidazo[4,5-f]quinolin-2-yl}amino acetate

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.9762475963333332

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.134228952891343

> <JCHEM_PKA_STRONGEST_BASIC>
4.83205292244104

> <JCHEM_POLAR_SURFACE_AREA>
69.03999999999999

> <JCHEM_REFRACTIVITY>
69.39850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.975  -2.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.618  -2.028   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.570  -0.489   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.309  -2.839   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -0.952  -2.111   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.357  -2.923   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.783  -2.341   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.777  -3.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.316  -3.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.128  -2.256   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.667  -2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.395  -3.661   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.584  -4.970   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.044  -4.922   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.233  -6.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.694  -6.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.966  -4.826   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.470  -4.459   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.706  -5.453   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
N-Acetoxy-iq	ChEBI

Chemical Formula

C₁₃H₁₂N₄O₂

Average Mass

256.2650 Da

Monoisotopic Mass

256.09603 Da

IUPAC Name

{3-methyl-3H-imidazo[4,5-f]quinolin-2-yl}amino acetate

Traditional Name

{3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate

CAS Registry Number

Not Available

SMILES

CN1C(NOC(C)=O)=NC2=C1C=CC1=NC=CC=C21

InChI Identifier

InChI=1S/C13H12N4O2/c1-8(18)19-16-13-15-12-9-4-3-7-14-10(9)5-6-11(12)17(13)2/h3-7H,1-2H3,(H,15,16)

InChI Key

ZNLLBBZONQYLII-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Not Available

Direct Parent

Quinolines and derivatives

Alternative Parents

Substituents

Quinoline
N-acetoxyarylamine
Benzimidazole
N-substituted imidazole
Pyridine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Acetate salt
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic salt
Organic nitrogen compound
Carbonyl group
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	1.87	ALOGPS
logP	1.98	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.13	ChemAxon
pKa (Strongest Basic)	4.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.4 m³·mol⁻¹	ChemAxon
Polarizability	26.7 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

129282

KEGG Compound ID

C20290

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146575

PDB ID

Not Available

ChEBI ID

133918

Good Scents ID

Not Available

References

General References

Turesky RJ, Markovic J: DNA adduct formation of the food carcinogen 2-amino-3-methylimidazo[4,5- f]quinoline at the C-8 and N2 atoms of guanine. Chem Res Toxicol. 1994 Nov-Dec;7(6):752-61. doi: 10.1021/tx00042a007. [PubMed:7696529 ]
LOTUS database [Link]

Showing NP-Card for {3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate (NP0157829)

MOL for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

3D MOL for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

3D SDF for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

3D-SDF for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

PDB for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

3D PDB for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

SMILES for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

INCHI for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

Structure for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)

3D Structure for NP0157829 ({3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate)