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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:06 UTC

Update Date

2022-03-07 02:53:12 UTC

HMDB ID

HMDB0031998

Secondary Accession Numbers

HMDB31998

Metabolite Identification

Common Name

Peroxysimulenoline

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. Based on a literature review very few articles have been published on Peroxysimulenoline.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0031998
     RDKit          3D
Peroxysimulenoline
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.9512    0.5734    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.4778    0.0155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8313    1.5172   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775    2.6135   -0.7806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    1.4442   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    0.2454   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -0.8329    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394   -2.0271    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392   -3.1036    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995   -2.9486    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.7637    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -0.6821    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    0.1581   -0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157    1.1790   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    0.6120   -2.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152    1.5619   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961    0.4254    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    0.5035   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.6118    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9322   -0.1134    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073   -1.1837    1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3503   -1.5735   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -0.9762   -1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    2.4341   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    2.5591   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    0.3419    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4810   -0.0705   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    1.6093    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692   -2.0736    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -4.0390    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121   -3.7677    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7016   -1.6212    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793    1.3742   -2.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    0.1684   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.2553   -2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.9942    0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    2.3800   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.5026    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    1.4214   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5582   -0.7996    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174    0.8974    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3741   -0.1287   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -1.5971    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346   -1.9813    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.3802    2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -0.2533   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    3.2977   -1.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    3.4974   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  2  0
 12  2  1  0
 25  5  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  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>
HMDB0031998

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0031998
     RDKit          3D
Peroxysimulenoline
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.9512    0.5734    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.4778    0.0155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8313    1.5172   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775    2.6135   -0.7806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    1.4442   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    0.2454   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -0.8329    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394   -2.0271    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392   -3.1036    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995   -2.9486    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.7637    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -0.6821    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    0.1581   -0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157    1.1790   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    0.6120   -2.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152    1.5619   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961    0.4254    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    0.5035   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.6118    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9322   -0.1134    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073   -1.1837    1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3503   -1.5735   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -0.9762   -1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    2.4341   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    2.5591   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    0.3419    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4810   -0.0705   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    1.6093    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692   -2.0736    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -4.0390    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121   -3.7677    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7016   -1.6212    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793    1.3742   -2.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    0.1684   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.2553   -2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.9942    0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    2.3800   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.5026    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    1.4214   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5582   -0.7996    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174    0.8974    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3741   -0.1287   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -1.5971    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346   -1.9813    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.3802    2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -0.2533   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    3.2977   -1.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    3.4974   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  2  0
 12  2  1  0
 25  5  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

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

COMPND    HMDB0031998
HETATM    1  C1  UNL     1       5.951   0.573   0.218  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.531   0.478   0.016  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.831   1.517  -0.476  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.378   2.613  -0.781  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.453   1.444  -0.680  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.855   0.245  -0.347  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.559  -0.833   0.159  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.939  -2.027   0.487  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.639  -3.104   0.992  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.000  -2.949   1.163  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.628  -1.764   0.840  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.923  -0.682   0.333  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.501   0.158  -0.542  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.316   1.179  -1.047  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.944   0.612  -2.329  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.415   1.562  -0.070  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.296   0.425   0.241  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.587   0.504  -0.033  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.513  -0.612   0.262  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.932  -0.113   0.260  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.207  -1.184   1.619  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.350  -1.574  -0.733  1.00  0.00           O  
HETATM   23  O4  UNL     1      -4.647  -0.976  -1.882  1.00  0.00           O  
HETATM   24  C19 UNL     1       0.395   2.434  -1.381  1.00  0.00           C  
HETATM   25  C20 UNL     1       1.693   2.559  -1.209  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.261   0.342   1.257  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.481  -0.071  -0.527  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.316   1.609   0.015  1.00  0.00           H  
HETATM   29  H4  UNL     1       0.869  -2.074   0.325  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.150  -4.039   1.248  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.612  -3.768   1.561  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.702  -1.621   0.968  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.479   1.374  -2.892  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.106   0.168  -2.906  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.592  -0.255  -2.038  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.927   1.994   0.837  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.029   2.380  -0.492  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.951  -0.503   0.695  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.994   1.421  -0.493  1.00  0.00           H  
HETATM   40  H15 UNL     1      -6.558  -0.800   0.878  1.00  0.00           H  
HETATM   41  H16 UNL     1      -6.017   0.897   0.712  1.00  0.00           H  
HETATM   42  H17 UNL     1      -6.374  -0.129  -0.774  1.00  0.00           H  
HETATM   43  H18 UNL     1      -5.166  -1.597   2.017  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.435  -1.981   1.580  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.876  -0.380   2.286  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.998  -0.253  -2.083  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.175   3.298  -1.788  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.217   3.497  -1.460  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6    6   25
CONECT    6    7   13
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   13   14
CONECT   14   15   16   24
CONECT   15   33   34   35
CONECT   16   17   36   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   21   22
CONECT   20   40   41   42
CONECT   21   43   44   45
CONECT   22   23
CONECT   23   46
CONECT   24   25   25   47
CONECT   25   48
END

HMDB0031998
     RDKit          3D
Peroxysimulenoline
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.9512    0.5734    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5306    0.4778    0.0155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8313    1.5172   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775    2.6135   -0.7806 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    1.4442   -0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    0.2454   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5593   -0.8329    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394   -2.0271    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6392   -3.1036    0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995   -2.9486    1.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6276   -1.7637    0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9234   -0.6821    0.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    0.1581   -0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157    1.1790   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    0.6120   -2.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4152    1.5619   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961    0.4254    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    0.5035   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.6118    0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9322   -0.1134    0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073   -1.1837    1.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3503   -1.5735   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6466   -0.9762   -1.8819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    2.4341   -1.3809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932    2.5591   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    0.3419    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4810   -0.0705   -0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    1.6093    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692   -2.0736    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -4.0390    1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121   -3.7677    1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7016   -1.6212    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793    1.3742   -2.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    0.1684   -2.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -0.2553   -2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    1.9942    0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    2.3800   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.5026    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    1.4214   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5582   -0.7996    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174    0.8974    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3741   -0.1287   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -1.5971    2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346   -1.9813    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.3802    2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9982   -0.2533   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    3.2977   -1.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    3.4974   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 14 24  1  0
 24 25  2  0
 12  2  1  0
 25  5  1  0
 12  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 23 46  1  0
 24 47  1  0
 25 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₃NO₄

Average Molecular Weight

341.4009

Monoisotopic Molecular Weight

341.162708229

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

198336-57-1

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

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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031998)
Cell membrane (HMDB: HMDB0031998)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031998)

Source

Endogenous

Endogenous (HMDB: HMDB0031998)

Plant

Plant (HMDB: HMDB0031998)

Exogenous

Food

Food (HMDB: HMDB0031998)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031998)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.725	31661259
DarkChem	[M-H]-	180.519	31661259
DeepCCS	[M-2H]-	211.246	30932474
DeepCCS	[M+Na]+	186.598	30932474
AllCCS	[M+H]+	182.4	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	185.4	32859911
AllCCS	[M+Na]+	186.3	32859911
AllCCS	[M-H]-	187.7	32859911
AllCCS	[M+Na-2H]-	187.8	32859911
AllCCS	[M+HCOO]-	187.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Peroxysimulenoline	CN1C(=O)C2=C(OC(C)(C\C=C\C(C)(C)OO)C=C2)C2=CC=CC=C12	3588.6	Standard polar	33892256
Peroxysimulenoline	CN1C(=O)C2=C(OC(C)(C\C=C\C(C)(C)OO)C=C2)C2=CC=CC=C12	2447.6	Standard non polar	33892256
Peroxysimulenoline	CN1C(=O)C2=C(OC(C)(C\C=C\C(C)(C)OO)C=C2)C2=CC=CC=C12	2814.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Peroxysimulenoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9524000000-df5f7201e30418968dec	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Peroxysimulenoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 10V, Positive-QTOF	splash10-052f-0119000000-5d3284dc0afc0406e962	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 20V, Positive-QTOF	splash10-0k9i-3965000000-c02227fae50f71beb410	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 40V, Positive-QTOF	splash10-0uxr-7970000000-e524da2016c88b8ebe8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 10V, Negative-QTOF	splash10-0006-1009000000-83afa0e49aa6d00a0e5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 20V, Negative-QTOF	splash10-006x-1039000000-3861c794dfc8668adcb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 40V, Negative-QTOF	splash10-052f-2932000000-bbb6d478dea64a78177d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 10V, Positive-QTOF	splash10-0a4i-0079000000-5da6a0a213a1c7a4a518	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 20V, Positive-QTOF	splash10-0zi0-0093000000-d3e69500152bd01111d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 40V, Positive-QTOF	splash10-0fb9-2290000000-1f3ea7f7e5d2e7fb3a9e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 10V, Negative-QTOF	splash10-0006-0009000000-2b6bb353672bd8e4916a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 20V, Negative-QTOF	splash10-0006-0039000000-928edfda4838bf176ec2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Peroxysimulenoline 40V, Negative-QTOF	splash10-0h3v-0391000000-452bfb1557d373688bd6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008693

KNApSAcK ID

C00057213

Chemspider ID

35013426

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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Peroxysimulenoline (HMDB0031998)

MOL for HMDB0031998 (Peroxysimulenoline)

3D MOL for HMDB0031998 (Peroxysimulenoline)

3D SDF for HMDB0031998 (Peroxysimulenoline)

3D-SDF for HMDB0031998 (Peroxysimulenoline)

PDB for HMDB0031998 (Peroxysimulenoline)

3D PDB for HMDB0031998 (Peroxysimulenoline)

SMILES for HMDB0031998 (Peroxysimulenoline)

INCHI for HMDB0031998 (Peroxysimulenoline)

Structure for HMDB0031998 (Peroxysimulenoline)

3D Structure for HMDB0031998 (Peroxysimulenoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra