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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:25:02 UTC

Update Date

2022-03-07 02:56:23 UTC

HMDB ID

HMDB0039879

Secondary Accession Numbers

HMDB39879

Metabolite Identification

Common Name

N-Acetoxymethylflindersine

Description

N-Acetoxymethylflindersine 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. N-Acetoxymethylflindersine has been detected, but not quantified in, fruits and herbs and spices. This could make N-acetoxymethylflindersine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Acetoxymethylflindersine.

Structure

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

HMDB0039879
     RDKit          3D
N-Acetoxymethylflindersine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.1512    0.7329   -1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070    1.0685   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9369   -1.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    0.4936    0.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    0.6508    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880    0.3835    0.9142 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.3582    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    2.5551    0.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6911    1.0737    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -0.2174    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2728   -1.2140    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.5048    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269   -3.5205    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -3.2608    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8808   -1.9425    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -0.9043    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713   -0.5004   -0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.5037   -0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    0.4676    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.2737   -2.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    1.8822   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    2.1628   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760    0.5325   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9095   -0.1052   -2.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.6331   -2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    0.0444    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    1.7114    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -2.7561    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171   -4.5480    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -4.0486    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -1.7845    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1929    0.7947    1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    1.2048    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9472   -0.5599    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3832   -0.6585   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020    1.1470   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.0670   -2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    2.6852   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    3.1621   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  6  1  0
 22  9  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
M  END


  Mrv0541 05061311272D          

 22 24  0  0  0  0            999 V2000
    4.1250    4.5079    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
   -0.2692    0.1231    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
    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
   -0.8250    1.6500    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
    3.3000    4.5079    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
   -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
    2.8875    5.2224    0.0000 O   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
    2.8875    3.7934    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
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  2  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 20 16  2  0  0  0  0
 21 10  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039879

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCN1C(=O)C2=C(OC(C)(C)C=C2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO4/c1-11(19)21-10-18-14-7-5-4-6-12(14)15-13(16(18)20)8-9-17(2,3)22-15/h4-9H,10H2,1-3H3

> <INCHI_KEY>
JXPDGNCKRXEJET-UHFFFAOYSA-N

> <FORMULA>
C17H17NO4

> <MOLECULAR_WEIGHT>
299.3212

> <EXACT_MASS>
299.115758037

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.540777036229343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2,2-dimethyl-5-oxo-2H,5H,6H-pyrano[3,2-c]quinolin-6-yl}methyl acetate

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.5393370090000005

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2245941692447997

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
82.538

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2,2-dimethyl-5-oxopyrano[3,2-c]quinolin-6-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039879
     RDKit          3D
N-Acetoxymethylflindersine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.1512    0.7329   -1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070    1.0685   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9369   -1.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    0.4936    0.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    0.6508    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880    0.3835    0.9142 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.3582    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    2.5551    0.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6911    1.0737    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -0.2174    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2728   -1.2140    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.5048    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269   -3.5205    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -3.2608    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8808   -1.9425    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -0.9043    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713   -0.5004   -0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.5037   -0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    0.4676    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.2737   -2.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    1.8822   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    2.1628   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760    0.5325   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9095   -0.1052   -2.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.6331   -2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    0.0444    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    1.7114    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -2.7561    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171   -4.5480    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -4.0486    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -1.7845    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1929    0.7947    1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    1.2048    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9472   -0.5599    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3832   -0.6585   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020    1.1470   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.0670   -2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    2.6852   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    3.1621   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  6  1  0
 22  9  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  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       7.700   8.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.217   1.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.503   0.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   7.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.160   8.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.080   5.747   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.390   9.748   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.770   7.081   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.390   7.081   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.770   1.746   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   17                                                       
CONECT   10   18   21                                                       
CONECT   11    1   19   21                                                  
CONECT   12    6   14   15                                                  
CONECT   13    8   15   16                                                  
CONECT   14    7   12   18                                                  
CONECT   15   12   13   22                                                  
CONECT   16   13   18   20                                                  
CONECT   17    2    3    9   22                                             
CONECT   18   10   14   16                                                  
CONECT   19   11                                                            
CONECT   20   16                                                            
CONECT   21   10   11                                                       
CONECT   22   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0039879
HETATM    1  C1  UNL     1       5.151   0.733  -1.805  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.007   1.069  -0.888  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.190   1.937  -1.273  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.816   0.494   0.309  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.866   0.651   1.272  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.488   0.383   0.914  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.629   1.358   0.584  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.016   2.555   0.622  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.691   1.074   0.201  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.163  -0.217   0.149  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.273  -1.214   0.492  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.740  -2.505   0.438  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.127  -3.521   0.771  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.428  -3.261   1.148  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.881  -1.942   1.196  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.033  -0.904   0.868  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.471  -0.500  -0.230  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.362   0.504  -0.574  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.562   0.468   0.357  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.786   0.274  -2.012  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.822   1.882  -0.508  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.591   2.163  -0.152  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.076   0.533  -1.198  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.910  -0.105  -2.462  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.379   1.633  -2.411  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.197   0.044   2.171  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.899   1.711   1.731  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.740  -2.756   0.152  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.217  -4.548   0.737  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.109  -4.049   1.409  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.901  -1.784   1.490  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.193   0.795   1.358  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.318   1.205   0.033  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.947  -0.560   0.402  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.383  -0.659  -2.053  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.302   1.147  -2.442  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.853   0.067  -2.580  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.483   2.685  -0.767  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.205   3.162  -0.105  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   26   27
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    9   10   10   22
CONECT   10   11   17
CONECT   11   12   12   16
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   17   18
CONECT   18   19   20   21
CONECT   19   32   33   34
CONECT   20   35   36   37
CONECT   21   22   22   38
CONECT   22   39
END

HMDB0039879
     RDKit          3D
N-Acetoxymethylflindersine
 39 41  0  0  0  0  0  0  0  0999 V2000
    5.1512    0.7329   -1.8051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070    1.0685   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903    1.9369   -1.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    0.4936    0.3094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    0.6508    1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880    0.3835    0.9142 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289    1.3582    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0161    2.5551    0.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6911    1.0737    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626   -0.2174    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2728   -1.2140    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -2.5048    0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269   -3.5205    0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -3.2608    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8808   -1.9425    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -0.9043    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713   -0.5004   -0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.5037   -0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    0.4676    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    0.2737   -2.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221    1.8822   -0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    2.1628   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760    0.5325   -1.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9095   -0.1052   -2.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3793    1.6331   -2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    0.0444    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8993    1.7114    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7399   -2.7561    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171   -4.5480    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1088   -4.0486    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011   -1.7845    1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1929    0.7947    1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182    1.2048    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9472   -0.5599    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3832   -0.6585   -2.0528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020    1.1470   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    0.0670   -2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829    2.6852   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2048    3.1621   -0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  6  1  0
 22  9  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
{2,2-dimethyl-5-oxo-2H,5H,6H-pyrano[3,2-c]quinolin-6-yl}methyl acetic acid	HMDB

Chemical Formula

C₁₇H₁₇NO₄

Average Molecular Weight

299.3212

Monoisotopic Molecular Weight

299.115758037

IUPAC Name

{2,2-dimethyl-5-oxo-2H,5H,6H-pyrano[3,2-c]quinolin-6-yl}methyl acetate

Traditional Name

{2,2-dimethyl-5-oxopyrano[3,2-c]quinolin-6-yl}methyl acetate

CAS Registry Number

149998-45-8

SMILES

CC(=O)OCN1C(=O)C2=C(OC(C)(C)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C17H17NO4/c1-11(19)21-10-18-14-7-5-4-6-12(14)15-13(16(18)20)8-9-17(2,3)22-15/h4-9H,10H2,1-3H3

InChI Key

JXPDGNCKRXEJET-UHFFFAOYSA-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
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Vinylogous ester
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen 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

Extracellular (HMDB: HMDB0039879)
Cytoplasm (HMDB: HMDB0039879)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039879)

Source

Exogenous

Food

Food (HMDB: HMDB0039879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039879)

Not Available

Nutrient (HMDB: HMDB0039879)

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	195.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.15	ALOGPS
logP	1.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.54 m³·mol⁻¹	ChemAxon
Polarizability	31.54 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]+	170.03	31661259
DarkChem	[M-H]-	169.442	31661259
DeepCCS	[M-2H]-	197.127	30932474
DeepCCS	[M+Na]+	172.596	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.3	32859911
AllCCS	[M+Na]+	172.3	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetoxymethylflindersine	CC(=O)OCN1C(=O)C2=C(OC(C)(C)C=C2)C2=CC=CC=C12	3377.9	Standard polar	33892256
N-Acetoxymethylflindersine	CC(=O)OCN1C(=O)C2=C(OC(C)(C)C=C2)C2=CC=CC=C12	2321.7	Standard non polar	33892256
N-Acetoxymethylflindersine	CC(=O)OCN1C(=O)C2=C(OC(C)(C)C=C2)C2=CC=CC=C12	2474.7	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 - N-Acetoxymethylflindersine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-5190000000-aef43592fef09517a6fa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetoxymethylflindersine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetoxymethylflindersine 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 - N-Acetoxymethylflindersine 10V, Positive-QTOF	splash10-0udi-0029000000-5981920ec32d19a731e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 20V, Positive-QTOF	splash10-0pb9-1091000000-7e52fa6bd7986cc4cbef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 40V, Positive-QTOF	splash10-014l-6390000000-db0467654c8ae788c899	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 10V, Negative-QTOF	splash10-0002-1090000000-eaa56d22f876ac0ae0fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 20V, Negative-QTOF	splash10-0002-1090000000-191520557a26e9711ae0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 40V, Negative-QTOF	splash10-0006-4290000000-73ed0c968075507856d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 10V, Negative-QTOF	splash10-002b-0090000000-d7edff1046bc6010e163	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 20V, Negative-QTOF	splash10-004i-0090000000-174ffcbc6ecf8ec62d3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 40V, Negative-QTOF	splash10-03gi-0390000000-ea91d9faada7152a26d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 10V, Positive-QTOF	splash10-0006-0090000000-fbc2d0a30ba98f88c3ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 20V, Positive-QTOF	splash10-0006-0090000000-3e52fabcb0d03e969750	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetoxymethylflindersine 40V, Positive-QTOF	splash10-0075-0980000000-b54dfc1ae845f5c49703	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB019538

KNApSAcK ID

C00054250

Chemspider ID

9464539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11289552

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1880701

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 N-Acetoxymethylflindersine (HMDB0039879)

MOL for HMDB0039879 (N-Acetoxymethylflindersine)

3D MOL for HMDB0039879 (N-Acetoxymethylflindersine)

3D SDF for HMDB0039879 (N-Acetoxymethylflindersine)

3D-SDF for HMDB0039879 (N-Acetoxymethylflindersine)

PDB for HMDB0039879 (N-Acetoxymethylflindersine)

3D PDB for HMDB0039879 (N-Acetoxymethylflindersine)

SMILES for HMDB0039879 (N-Acetoxymethylflindersine)

INCHI for HMDB0039879 (N-Acetoxymethylflindersine)

Structure for HMDB0039879 (N-Acetoxymethylflindersine)

3D Structure for HMDB0039879 (N-Acetoxymethylflindersine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra