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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:35 UTC

Update Date

2022-03-07 02:53:10 UTC

HMDB ID

HMDB0031929

Secondary Accession Numbers

HMDB31929

Metabolite Identification

Common Name

Zanthodioline

Description

Zanthodioline 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 Zanthodioline.

Structure

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

HMDB0031929
     RDKit          3D
Zanthodioline
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.4032   -0.1222   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1012    0.4251   -0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480   -0.3718   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530   -1.7065    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -2.5525    0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -2.0338    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -0.7016    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422   -0.2321    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    1.0630    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502    1.8762   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    3.1061   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.4571   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    2.3409   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644    0.1615   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.6483    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    2.2730   -1.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    0.6994    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.8978   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.7429    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884   -1.3872   -0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8089   -1.4920    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.0526    0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.6017    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391    0.6914   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.9227   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -2.1469    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -3.6071    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -2.6498    0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    2.5492    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697    2.0790   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    3.3531   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060    2.4975    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    2.0488   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7117    0.9555    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.8812   -0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.3571   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.7222   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -1.4896   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8538   -1.1572    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962   -1.3807    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -2.5739    1.1573 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 14  3  1  0
 14  7  2  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END


  Mrv0541 05061306142D          

 22 24  0  0  0  0            999 V2000
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 14  1  0  0  0  0
 17  3  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  2  0  0  0  0
 21  4  1  0  0  0  0
 21  9  1  0  0  0  0
 22 13  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031929

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO5/c1-16(2)14(19)12(18)10-13(22-16)8-6-5-7-9(21-4)11(8)17(3)15(10)20/h5-7,12,14,18-19H,1-4H3

> <INCHI_KEY>
GQGXEILPTLCMFO-UHFFFAOYSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.3258

> <EXACT_MASS>
305.126322723

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.385600104234143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
-0.26734415466666617

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.201001232984375

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.756903202673954

> <JCHEM_PKA_STRONGEST_BASIC>
-1.330338727156589

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
80.3543

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3H,4H-pyrano[3,2-c]quinolin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031929
     RDKit          3D
Zanthodioline
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.4032   -0.1222   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1012    0.4251   -0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480   -0.3718   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530   -1.7065    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -2.5525    0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -2.0338    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -0.7016    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422   -0.2321    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    1.0630    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502    1.8762   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    3.1061   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.4571   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    2.3409   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644    0.1615   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.6483    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    2.2730   -1.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    0.6994    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.8978   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.7429    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884   -1.3872   -0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8089   -1.4920    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.0526    0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.6017    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391    0.6914   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.9227   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -2.1469    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -3.6071    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -2.6498    0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    2.5492    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697    2.0790   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    3.3531   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060    2.4975    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    2.0488   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7117    0.9555    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.8812   -0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.3571   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.7222   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -1.4896   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8538   -1.1572    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962   -1.3807    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -2.5739    1.1573 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 14  3  1  0
 14  7  2  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  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      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.414   3.437   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   21                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   11   13                                                  
CONECT    9    7   11   21                                                  
CONECT   10   12   13   15                                                  
CONECT   11    8    9   17                                                  
CONECT   12   10   14   18                                                  
CONECT   13    8   10   22                                                  
CONECT   14   12   16   19                                                  
CONECT   15   10   17   20                                                  
CONECT   16    1    2   14   22                                             
CONECT   17    3   11   15                                                  
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21    4    9                                                       
CONECT   22   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0031929
HETATM    1  C1  UNL     1       5.403  -0.122  -0.464  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.101   0.425  -0.421  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.048  -0.372  -0.064  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.253  -1.706   0.254  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.231  -2.552   0.619  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.956  -2.034   0.666  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.753  -0.702   0.349  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.542  -0.232   0.412  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.797   1.063   0.113  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.250   1.876  -0.248  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.061   3.106  -0.540  1.00  0.00           O  
HETATM   12  N1  UNL     1       1.530   1.457  -0.322  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.613   2.341  -0.706  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.764   0.162  -0.019  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.153   1.648   0.155  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.348   2.273  -1.095  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.244   0.699   0.405  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.302   0.898  -0.515  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.915  -0.743   0.431  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.188  -1.387  -0.922  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.809  -1.492   1.430  1.00  0.00           C  
HETATM   22  O5  UNL     1      -1.594  -1.053   0.775  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.577  -0.602   0.535  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.139   0.691  -0.639  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.502  -0.923  -1.225  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.256  -2.147   0.225  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.415  -3.607   0.867  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.111  -2.650   0.947  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.327   2.549   0.106  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.070   2.079  -1.681  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.144   3.353  -0.909  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.106   2.498   0.893  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.657   2.049  -1.741  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.712   0.955   1.404  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.490   1.881  -0.596  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.690  -2.357  -0.952  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.741  -0.722  -1.715  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.274  -1.490  -1.119  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.854  -1.157   1.338  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.396  -1.381   2.450  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.692  -2.574   1.157  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   28
CONECT    7    8   14   14
CONECT    8    9    9   22
CONECT    9   10   15
CONECT   10   11   11   12
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   15   16   17   32
CONECT   16   33
CONECT   17   18   19   34
CONECT   18   35
CONECT   19   20   21   22
CONECT   20   36   37   38
CONECT   21   39   40   41
END

HMDB0031929
     RDKit          3D
Zanthodioline
 41 43  0  0  0  0  0  0  0  0999 V2000
    5.4032   -0.1222   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1012    0.4251   -0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480   -0.3718   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2530   -1.7065    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2312   -2.5525    0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -2.0338    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528   -0.7016    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5422   -0.2321    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    1.0630    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502    1.8762   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    3.1061   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    1.4571   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6135    2.3409   -0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644    0.1615   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1534    1.6483    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3483    2.2730   -1.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2445    0.6994    0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021    0.8978   -0.5147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -0.7429    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1884   -1.3872   -0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8089   -1.4920    1.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.0526    0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.6017    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1391    0.6914   -0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.9227   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2555   -2.1469    0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -3.6071    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -2.6498    0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    2.5492    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697    2.0790   -1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    3.3531   -0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060    2.4975    0.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    2.0488   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7117    0.9555    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.8812   -0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.3571   -0.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.7222   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2741   -1.4896   -1.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8538   -1.1572    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962   -1.3807    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917   -2.5739    1.1573 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  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 14  3  1  0
 14  7  2  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉NO₅

Average Molecular Weight

305.3258

Monoisotopic Molecular Weight

305.126322723

IUPAC Name

3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-2H,3H,4H,5H,6H-pyrano[3,2-c]quinolin-5-one

Traditional Name

3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3H,4H-pyrano[3,2-c]quinolin-5-one

CAS Registry Number

198336-59-3

SMILES

COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O

InChI Identifier

InChI=1S/C16H19NO5/c1-16(2)14(19)12(18)10-13(22-16)8-6-5-7-9(21-4)11(8)17(3)15(10)20/h5-7,12,14,18-19H,1-4H3

InChI Key

GQGXEILPTLCMFO-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
Anisole
Alkyl aryl ether
Pyridinone
Pyran
Pyridine
Benzenoid
Vinylogous ester
Heteroaromatic compound
Secondary alcohol
Lactam
1,2-diol
Azacycle
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031929)
Cytoplasm (HMDB: HMDB0031929)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031929)

Source

Endogenous

Endogenous (HMDB: HMDB0031929)

Plant

Plant (HMDB: HMDB0031929)

Exogenous

Food

Food (HMDB: HMDB0031929)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

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	8.68 g/L	ALOGPS
logP	0.82	ALOGPS
logP	-0.27	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.35 m³·mol⁻¹	ChemAxon
Polarizability	31.39 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]+	169.872	31661259
DarkChem	[M-H]-	173.089	31661259
DeepCCS	[M+H]+	169.355	30932474
DeepCCS	[M-H]-	166.997	30932474
DeepCCS	[M-2H]-	200.747	30932474
DeepCCS	[M+Na]+	175.974	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.2	32859911
AllCCS	[M+NH4]+	173.8	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zanthodioline	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O	3384.2	Standard polar	33892256
Zanthodioline	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O	2450.7	Standard non polar	33892256
Zanthodioline	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O	2666.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zanthodioline,1TMS,isomer #1	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O[Si](C)(C)C)C1O	2566.0	Semi standard non polar	33892256
Zanthodioline,1TMS,isomer #2	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O[Si](C)(C)C	2569.3	Semi standard non polar	33892256
Zanthodioline,2TMS,isomer #1	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2516.9	Semi standard non polar	33892256
Zanthodioline,1TBDMS,isomer #1	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O[Si](C)(C)C(C)(C)C)C1O	2829.8	Semi standard non polar	33892256
Zanthodioline,1TBDMS,isomer #2	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O)C1O[Si](C)(C)C(C)(C)C	2812.5	Semi standard non polar	33892256
Zanthodioline,2TBDMS,isomer #1	COC1=CC=CC2=C1N(C)C(=O)C1=C2OC(C)(C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3000.8	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 - Zanthodioline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00n0-0290000000-3578c8b544ef37e15e7a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zanthodioline GC-MS (2 TMS) - 70eV, Positive	splash10-0019-8926800000-5e56c0961c2be1c1d779	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zanthodioline 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 - Zanthodioline 10V, Positive-QTOF	splash10-0a4i-1039000000-94951294b4c45e6573f9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 20V, Positive-QTOF	splash10-0a5i-2092000000-21327a5aea35b1321c8f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 40V, Positive-QTOF	splash10-00bi-9770000000-b0217d997f84c554983d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 10V, Negative-QTOF	splash10-0udi-1029000000-e5fc9369001c7e17b9b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 20V, Negative-QTOF	splash10-0uki-7095000000-b5e649633701dfa2e028	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 40V, Negative-QTOF	splash10-05g0-5930000000-a5751e5acd328082a4b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 10V, Negative-QTOF	splash10-0udi-0009000000-2a97fc4fd7c1579620dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 20V, Negative-QTOF	splash10-0udi-0097000000-f070b1413a175710aea0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 40V, Negative-QTOF	splash10-0pi0-0192000000-744dabf7895fbc0b1f64	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 10V, Positive-QTOF	splash10-0a4i-0009000000-97ce49a427ba396eab80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 20V, Positive-QTOF	splash10-0a4i-0039000000-914b9e6ddba55e2273d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zanthodioline 40V, Positive-QTOF	splash10-0f76-1390000000-d6ca5bb0d43f1b443b56	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008617

KNApSAcK ID

C00026497

Chemspider ID

35013415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78384601

PDB ID

Not Available

ChEBI ID

168670

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 Zanthodioline (HMDB0031929)

MOL for HMDB0031929 (Zanthodioline)

3D MOL for HMDB0031929 (Zanthodioline)

3D SDF for HMDB0031929 (Zanthodioline)

3D-SDF for HMDB0031929 (Zanthodioline)

PDB for HMDB0031929 (Zanthodioline)

3D PDB for HMDB0031929 (Zanthodioline)

SMILES for HMDB0031929 (Zanthodioline)

INCHI for HMDB0031929 (Zanthodioline)

Structure for HMDB0031929 (Zanthodioline)

3D Structure for HMDB0031929 (Zanthodioline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra