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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:53:44 UTC

Update Date

2022-03-07 02:56:34 UTC

HMDB ID

HMDB0040367

Secondary Accession Numbers

HMDB40367

Metabolite Identification

Common Name

Azacridone A

Description

Azacridone A belongs to the class of organic compounds known as chromenopyridines. These are aromatic heterocyclic compounds structurally characterized by a pyridine ring fused to a chromene moiety. Azacridone A has been detected, but not quantified in, citrus. This could make azacridone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Azacridone A.

Structure

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

HMDB0040367
     RDKit          3D
Azacridone A
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.0118    1.8639   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417    0.8119   -0.4795 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162    0.7275   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.7680   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778    1.6599   -0.6814 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5516    0.5689   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586   -0.4701    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670   -0.4052    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6046   -1.4352    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -2.4701    1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -1.3375    0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394   -2.3652    0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -3.4722    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.2853    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -1.1664    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -0.0901   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -0.1844   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    1.1417   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    1.2242   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.1424    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -0.1513   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1327    0.5519    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572   -1.0550    0.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    2.0908   -2.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.8859   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2714    1.5371   -2.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873    2.6563   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6453    0.4997   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2140   -1.3436    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -4.2404    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284   -3.0879    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    2.0299   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1374    2.1495   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3135   -0.9267   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4634   -0.6691   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    0.7545   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    1.3282    1.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021   -0.3088    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3284    1.0723    1.9440 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
M  END


  Mrv0541 05061311472D          

 23 26  0  0  0  0            999 V2000
    1.5274    2.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269    1.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    2.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685    2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    1.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786    2.2736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182    1.9618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -0.8446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -0.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    1.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
 10  5  2  0  0  0  0
 11  4  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  2  0  0  0  0
 19  9  1  0  0  0  0
 20  3  1  0  0  0  0
 20 12  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 22 17  2  0  0  0  0
 23 14  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040367

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=CN=CC=C2C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16N2O3/c1-18(2)6-4-11-14(23-18)8-13(21)15-16(11)20(3)12-9-19-7-5-10(12)17(15)22/h4-9,21H,1-3H3

> <INCHI_KEY>
GSYTWFSUSXURDO-UHFFFAOYSA-N

> <FORMULA>
C18H16N2O3

> <MOLECULAR_WEIGHT>
308.3312

> <EXACT_MASS>
308.116092388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.470337263103715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5,7-diazatetraphen-10-one

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.152340531666666

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.142094108937165

> <JCHEM_PKA_STRONGEST_BASIC>
3.3262682218395154

> <JCHEM_POLAR_SURFACE_AREA>
62.66

> <JCHEM_REFRACTIVITY>
88.17579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-2,2,5-trimethyl-1-oxa-5,7-diazatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040367
     RDKit          3D
Azacridone A
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.0118    1.8639   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417    0.8119   -0.4795 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162    0.7275   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.7680   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778    1.6599   -0.6814 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5516    0.5689   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586   -0.4701    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670   -0.4052    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6046   -1.4352    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -2.4701    1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -1.3375    0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394   -2.3652    0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -3.4722    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.2853    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -1.1664    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -0.0901   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -0.1844   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    1.1417   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    1.2242   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.1424    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -0.1513   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1327    0.5519    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572   -1.0550    0.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    2.0908   -2.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.8859   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2714    1.5371   -2.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873    2.6563   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6453    0.4997   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2140   -1.3436    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -4.2404    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284   -3.0879    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    2.0299   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1374    2.1495   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3135   -0.9267   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4634   -0.6691   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    0.7545   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    1.3282    1.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021   -0.3088    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3284    1.0723    1.9440 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
 22 37  1  0
 22 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       2.851   4.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.477   2.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.863   5.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.343   4.244   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.896   1.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.831   4.535   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.904   2.789   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.343   0.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.888   4.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.384   1.916   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.847   2.789   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.880   3.371   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.855  -0.121   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.839   1.625   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.863   1.043   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.359   2.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.375   0.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.822   3.371   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      13.400   4.244   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       9.367   3.662   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       8.359  -1.577   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.880  -0.703   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.327   1.916   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   20                                                            
CONECT    4    6   11                                                       
CONECT    5    7   10                                                       
CONECT    6    4   18                                                       
CONECT    7    5   19                                                       
CONECT    8   13   14                                                       
CONECT    9   12   19                                                       
CONECT   10    5   12   17                                                  
CONECT   11    4   14   16                                                  
CONECT   12    9   10   20                                                  
CONECT   13    8   15   21                                                  
CONECT   14    8   11   23                                                  
CONECT   15   13   16   17                                                  
CONECT   16   11   15   20                                                  
CONECT   17   10   15   22                                                  
CONECT   18    1    2    6   23                                             
CONECT   19    7    9                                                       
CONECT   20    3   12   16                                                  
CONECT   21   13                                                            
CONECT   22   17                                                            
CONECT   23   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0040367
HETATM    1  C1  UNL     1       1.012   1.864  -1.339  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.442   0.812  -0.479  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.816   0.728  -0.381  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.632   1.768  -0.816  1.00  0.00           C  
HETATM    5  N2  UNL     1       4.978   1.660  -0.681  1.00  0.00           N  
HETATM    6  C4  UNL     1       5.552   0.569  -0.135  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.759  -0.470   0.304  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.367  -0.405   0.188  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.605  -1.435   0.654  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.110  -2.470   1.168  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.247  -1.338   0.559  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.439  -2.365   1.000  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.087  -3.472   1.548  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.910  -2.285   0.897  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.491  -1.166   0.354  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.710  -0.090  -0.107  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.687  -0.184  -0.014  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.327   1.142  -0.495  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.684   1.224  -0.418  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.531   0.142   0.032  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.680  -0.151  -0.941  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.133   0.552   1.384  1.00  0.00           C  
HETATM   23  O3  UNL     1      -2.857  -1.055   0.236  1.00  0.00           O  
HETATM   24  H1  UNL     1       1.833   2.091  -2.150  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.007   2.886  -0.999  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.271   1.537  -2.145  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.187   2.656  -1.221  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.645   0.500  -0.036  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.214  -1.344   0.742  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.516  -4.240   1.880  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.528  -3.088   1.236  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.857   2.030  -0.746  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.137   2.149  -0.710  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.313  -0.927  -1.676  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.463  -0.669  -0.344  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.034   0.755  -1.445  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.919   1.328   1.206  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.502  -0.309   1.946  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.328   1.072   1.944  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   17
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
CONECT   15   16   23
CONECT   16   17   17   18
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   22   23
CONECT   21   34   35   36
CONECT   22   37   38   39
END

HMDB0040367
     RDKit          3D
Azacridone A
 39 42  0  0  0  0  0  0  0  0999 V2000
    1.0118    1.8639   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417    0.8119   -0.4795 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162    0.7275   -0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.7680   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778    1.6599   -0.6814 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5516    0.5689   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586   -0.4701    0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670   -0.4052    0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6046   -1.4352    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099   -2.4701    1.1679 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -1.3375    0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394   -2.3652    0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -3.4722    1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -2.2853    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4911   -1.1664    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -0.0901   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -0.1844   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268    1.1417   -0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    1.2242   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    0.1424    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6804   -0.1513   -0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1327    0.5519    1.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572   -1.0550    0.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    2.0908   -2.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0068    2.8859   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2714    1.5371   -2.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1873    2.6563   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6453    0.4997   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2140   -1.3436    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5163   -4.2404    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284   -3.0879    1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    2.0299   -0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1374    2.1495   -0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3135   -0.9267   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4634   -0.6691   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0336    0.7545   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193    1.3282    1.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5021   -0.3088    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3284    1.0723    1.9440 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 17  2  1  0
  8  3  1  0
 17 11  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 13 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
 21 35  1  0
 21 36  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Azacridone a	MeSH

Chemical Formula

C₁₈H₁₆N₂O₃

Average Molecular Weight

308.3312

Monoisotopic Molecular Weight

308.116092388

IUPAC Name

11-hydroxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5,7-diazatetraphen-10-one

Traditional Name

11-hydroxy-2,2,5-trimethyl-1-oxa-5,7-diazatetraphen-10-one

CAS Registry Number

150050-14-9

SMILES

CN1C2=CN=CC=C2C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O

InChI Identifier

InChI=1S/C18H16N2O3/c1-18(2)6-4-11-14(23-18)8-13(21)15-16(11)20(3)12-9-19-7-5-10(12)17(15)22/h4-9,21H,1-3H3

InChI Key

GSYTWFSUSXURDO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromenopyridines. These are aromatic heterocyclic compounds structurally characterized by a pyridine ring fused to a chromene moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromenopyridines

Alternative Parents

Substituents

Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
Diazanaphthalene
Dihydroquinoline
Naphthyridine
Quinoline
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Vinylogous acid
Heteroaromatic compound
Vinylogous amide
Oxacycle
Ether
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen 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: HMDB0040367)

Membrane (HMDB: HMDB0040367)
Cell membrane (HMDB: HMDB0040367)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040367)

Source

Exogenous

Food

Food (HMDB: HMDB0040367)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0040367)

Not Available

Nutrient (HMDB: HMDB0040367)

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	4.62 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	0.51 g/L	ALOGPS
logP	2.82	ALOGPS
logP	3.15	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	3.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	32.47 Å³	ChemAxon
Number of Rings	4	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]+	170.422	31661259
DarkChem	[M-H]-	167.176	31661259
DeepCCS	[M+H]+	167.688	30932474
DeepCCS	[M-H]-	165.33	30932474
DeepCCS	[M-2H]-	198.297	30932474
DeepCCS	[M+Na]+	173.782	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	178.9	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azacridone A	CN1C2=CN=CC=C2C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O	3391.6	Standard polar	33892256
Azacridone A	CN1C2=CN=CC=C2C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O	2706.4	Standard non polar	33892256
Azacridone A	CN1C2=CN=CC=C2C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O	3020.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Azacridone A,1TMS,isomer #1	CN1C2=CN=CC=C2C(=O)C2=C(O[Si](C)(C)C)C=C3OC(C)(C)C=CC3=C21	3011.7	Semi standard non polar	33892256
Azacridone A,1TBDMS,isomer #1	CN1C2=CN=CC=C2C(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C3OC(C)(C)C=CC3=C21	3158.8	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 - Azacridone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0191000000-c4ce72b8400043a6ddd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacridone A GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-2219000000-22c8e5d7479e26edf4e5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azacridone A 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 - Azacridone A 10V, Positive-QTOF	splash10-0a4i-0039000000-c0bc18e36bda24ffbcab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 20V, Positive-QTOF	splash10-0a4l-0095000000-781648d5f8b6bf0ad87e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 40V, Positive-QTOF	splash10-0fb9-2190000000-75dc651883367707fe5b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 10V, Negative-QTOF	splash10-0a4i-0009000000-ef2027dc5d52bb564c73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 20V, Negative-QTOF	splash10-0a4i-0019000000-4eb105ff59f3592d30e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 40V, Negative-QTOF	splash10-0006-1190000000-22a9258ba6954e6f9749	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 10V, Positive-QTOF	splash10-0a4i-0009000000-d1457b0390f71ec75696	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 20V, Positive-QTOF	splash10-0a4i-0009000000-81c2407fcbcf16753fb3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 40V, Positive-QTOF	splash10-001i-0290000000-26c676bafa56973ee6c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 10V, Negative-QTOF	splash10-0a4i-0009000000-2e386d675ad15bb583f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 20V, Negative-QTOF	splash10-0a4i-0009000000-2e386d675ad15bb583f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azacridone A 40V, Negative-QTOF	splash10-0fr6-0090000000-522d81a124a575d4a322	2021-09-22	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

FDB020097

KNApSAcK ID

C00055348

Chemspider ID

8533361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10357912

PDB ID

Not Available

ChEBI ID

174947

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1882861

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 Azacridone A (HMDB0040367)

MOL for HMDB0040367 (Azacridone A)

3D MOL for HMDB0040367 (Azacridone A)

3D SDF for HMDB0040367 (Azacridone A)

3D-SDF for HMDB0040367 (Azacridone A)

PDB for HMDB0040367 (Azacridone A)

3D PDB for HMDB0040367 (Azacridone A)

SMILES for HMDB0040367 (Azacridone A)

INCHI for HMDB0040367 (Azacridone A)

Structure for HMDB0040367 (Azacridone A)

3D Structure for HMDB0040367 (Azacridone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra