NP-MRD: Showing NP-Card for 2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one (NP0219164)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 20:04:31 UTC

Updated at

2022-09-05 20:04:32 UTC

NP-MRD ID

NP0219164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one

Description

Peroxysimulenoline belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. Peroxysimulenoline is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Peroxysimulenoline has been detected, but not quantified in, fruits and herbs and spices. 2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one is found in Zanthoxylum simulans. This could make peroxysimulenoline a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306172D          

 25 27  0  0  0  0            999 V2000
    1.1423   -2.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -0.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -0.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317   -1.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1998   -1.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 23  1  0  0  0  0
M  END


  Mrv0541 05061306172D          

 25 27  0  0  0  0            999 V2000
    1.1423   -2.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5060   -0.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493   -0.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8317   -1.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1998   -1.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 18  2  0  0  0  0
 24 17  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)C2=C(OC(C)(C\C=C\C(C)(C)OO)C=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO4/c1-19(2,25-23)11-7-12-20(3)13-10-15-17(24-20)14-8-5-6-9-16(14)21(4)18(15)22/h5-11,13,23H,12H2,1-4H3/b11-7+

> <INCHI_KEY>
SAIWHEDPKCDURN-YRNVUSSQSA-N

> <FORMULA>
C20H23NO4

> <MOLECULAR_WEIGHT>
341.4009

> <EXACT_MASS>
341.162708229

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.200648537881854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
2.5936666503333323

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.700085305368768

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9439693995341875

> <JCHEM_POLAR_SURFACE_AREA>
59.000000000000014

> <JCHEM_REFRACTIVITY>
99.30919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.132  -3.787   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.186  -0.893   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.217   1.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   7.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.945  -0.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.212  -1.814   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.503   0.230   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.659  -2.340   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.080   5.747   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       0.770   7.081   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.286  -1.877   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.770   1.746   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.106  -2.867   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7   11   12                                                       
CONECT    8    5   14                                                       
CONECT    9    6   16                                                       
CONECT   10   13   15                                                       
CONECT   11    7   19                                                       
CONECT   12    7   20                                                       
CONECT   13   10   20                                                       
CONECT   14    8   16   17                                                  
CONECT   15   10   17   18                                                  
CONECT   16    9   14   21                                                  
CONECT   17   14   15   24                                                  
CONECT   18   15   21   22                                                  
CONECT   19    1    2   11   25                                             
CONECT   20    3   12   13   24                                             
CONECT   21    4   16   18                                                  
CONECT   22   18                                                            
CONECT   23   25                                                            
CONECT   24   17   20                                                       
CONECT   25   19   23                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₄

Average Mass

341.4009 Da

Monoisotopic Mass

341.16271 Da

IUPAC Name

2-[(2E)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethyl-2H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

2-[(2E)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one

CAS Registry Number

Not Available

SMILES

CN1C(=O)C2=C(OC(C)(C\C=C\C(C)(C)OO)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C20H23NO4/c1-19(2,25-23)11-7-12-20(3)13-10-15-17(24-20)14-8-5-6-9-16(14)21(4)18(15)22/h5-11,13,23H,12H2,1-4H3/b11-7+

InChI Key

SAIWHEDPKCDURN-YRNVUSSQSA-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
Zanthoxylum simulans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoquinolines. These are polycyclic compounds containing a pyran ring fused to a quinoline moiety. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Pyranoquinolines

Alternative Parents

Substituents

Pyranoquinoline
Dihydroquinolone
Dihydroquinoline
Pyranopyridine
Alkyl aryl ether
Pyridinone
Pyran
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Hydroperoxide
Lactam
Oxacycle
Peroxol
Alkyl hydroperoxide
Ether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
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	3.45	ALOGPS
logP	2.59	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.31 m³·mol⁻¹	ChemAxon
Polarizability	37.2 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

HMDB0031998

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008693

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

101936038

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one (NP0219164)

MOL for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

3D MOL for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

3D SDF for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

3D-SDF for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

PDB for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

3D PDB for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

SMILES for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

INCHI for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

Structure for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)

3D Structure for NP0219164 (2-[(2e)-4-hydroperoxy-4-methylpent-2-en-1-yl]-2,6-dimethylpyrano[3,2-c]quinolin-5-one)