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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:44 UTC

Update Date

2022-03-07 02:53:35 UTC

HMDB ID

HMDB0033100

Secondary Accession Numbers

HMDB33100

Metabolite Identification

Common Name

Atroviridin

Description

Atroviridin belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. Atroviridin has been detected, but not quantified in, fruits. This could make atroviridin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Atroviridin.

Structure

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

HMDB0033100
     RDKit          3D
Atroviridin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -4.9029    0.7022    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615    0.0632   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.0305   -1.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093   -1.2940    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -1.7544    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -0.9217    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.3737   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    1.2145   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    2.5013   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    0.8026   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    1.6130   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    1.2558   -0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    2.1540   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    1.7483    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853    0.4679    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9841    0.0706    0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6154   -0.4011    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.0263    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -0.9026    0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.0756    1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798   -0.4832    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778   -1.3756    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6530    0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8123    0.8204   -0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0250    1.7831    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5207    0.4893    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025    0.2377    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0111   -1.0960   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6780    0.5316   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    0.3041   -2.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5694   -2.0010    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -2.7830    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682    3.1776   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778    3.1576   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2791    2.4407   -0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4967   -0.3515    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -1.4180    1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -3.3096    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  1  0
M  END


  Mrv0541 05061306552D          

 24 27  0  0  0  0            999 V2000
    0.6165    3.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1468    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 12  2  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  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033100

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=C(O)C3=C(C(O)=C2C=C1)C(=O)C1=C(O3)C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/c1-18(2)6-5-9-13(20)12-14(21)10-7-8(19)3-4-11(10)23-17(12)15(22)16(9)24-18/h3-7,19-20,22H,1-2H3

> <INCHI_KEY>
LPOCFPIHJNBUIN-UHFFFAOYSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.3002

> <EXACT_MASS>
326.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.02631238892038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8,12-trihydroxy-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.599567657333333

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.34027116263621

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.703645705162836

> <JCHEM_PKA_STRONGEST_BASIC>
-4.222364451213871

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
87.1524

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8,12-trihydroxy-2,2-dimethyl-1,11-dioxatetracen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033100
     RDKit          3D
Atroviridin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -4.9029    0.7022    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615    0.0632   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.0305   -1.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093   -1.2940    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -1.7544    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -0.9217    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.3737   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    1.2145   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    2.5013   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    0.8026   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    1.6130   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    1.2558   -0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    2.1540   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    1.7483    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853    0.4679    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9841    0.0706    0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6154   -0.4011    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.0263    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -0.9026    0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.0756    1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798   -0.4832    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778   -1.3756    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6530    0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8123    0.8204   -0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0250    1.7831    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5207    0.4893    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025    0.2377    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0111   -1.0960   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6780    0.5316   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    0.3041   -2.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5694   -2.0010    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -2.7830    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682    3.1776   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778    3.1576   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2791    2.4407   -0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4967   -0.3515    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -1.4180    1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -3.3096    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  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       1.151   5.893   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.141   7.607   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.671   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3    4    8                                                       
CONECT    4    3   11                                                       
CONECT    5    6    9                                                       
CONECT    6    5   18                                                       
CONECT    7    8   10                                                       
CONECT    8    3    7   19                                                  
CONECT    9    5   13   16                                                  
CONECT   10    7   11   14                                                  
CONECT   11    4   10   23                                                  
CONECT   12   13   14   17                                                  
CONECT   13    9   12   20                                                  
CONECT   14   10   12   21                                                  
CONECT   15   16   17   22                                                  
CONECT   16    9   15   24                                                  
CONECT   17   12   15   23                                                  
CONECT   18    1    2    6   24                                             
CONECT   19    8                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23   11   17                                                       
CONECT   24   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033100
HETATM    1  C1  UNL     1      -4.903   0.702   0.604  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.962   0.063  -0.451  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.726  -0.031  -1.773  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.709  -1.294   0.040  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.525  -1.754   0.337  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.346  -0.922   0.195  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.550   0.374  -0.269  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.440   1.215  -0.422  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.670   2.501  -0.886  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.833   0.803  -0.131  1.00  0.00           C  
HETATM   11  O2  UNL     1       1.880   1.613  -0.281  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.110   1.256  -0.013  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.167   2.154  -0.192  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.459   1.748   0.100  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.685   0.468   0.561  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.984   0.071   0.851  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.615  -0.401   0.729  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.319  -0.026   0.447  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.265  -0.903   0.619  1.00  0.00           C  
HETATM   20  O4  UNL     1       2.436  -2.076   1.037  1.00  0.00           O  
HETATM   21  C17 UNL     1       0.980  -0.483   0.323  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.078  -1.376   0.500  1.00  0.00           C  
HETATM   23  O5  UNL     1       0.155  -2.653   0.962  1.00  0.00           O  
HETATM   24  O6  UNL     1      -2.812   0.820  -0.571  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.025   1.783   0.380  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.521   0.489   1.603  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.903   0.238   0.469  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.011  -1.096  -1.976  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.678   0.532  -1.721  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.084   0.304  -2.587  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.569  -2.001   0.177  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.386  -2.783   0.703  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.068   3.178  -1.028  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.978   3.158  -0.555  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.279   2.441  -0.037  1.00  0.00           H  
HETATM   36  H12 UNL     1       7.497  -0.352   0.066  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.759  -1.418   1.091  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.571  -3.310   1.098  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   22
CONECT    7    8   24
CONECT    8    9   10   10
CONECT    9   33
CONECT   10   11   21
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   34
CONECT   14   15   15   35
CONECT   15   16   17
CONECT   16   36
CONECT   17   18   18   37
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22
CONECT   22   23
CONECT   23   38
END

HMDB0033100
     RDKit          3D
Atroviridin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -4.9029    0.7022    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615    0.0632   -0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7255   -0.0305   -1.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093   -1.2940    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5252   -1.7544    0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3463   -0.9217    0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499    0.3737   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    1.2145   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    2.5013   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328    0.8026   -0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8803    1.6130   -0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    1.2558   -0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    2.1540   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    1.7483    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853    0.4679    0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9841    0.0706    0.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6154   -0.4011    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.0263    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -0.9026    0.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356   -2.0756    1.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9798   -0.4832    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778   -1.3756    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1554   -2.6530    0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8123    0.8204   -0.5710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0250    1.7831    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5207    0.4893    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9025    0.2377    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0111   -1.0960   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6780    0.5316   -1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    0.3041   -2.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5694   -2.0010    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861   -2.7830    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0682    3.1776   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9778    3.1576   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2791    2.4407   -0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4967   -0.3515    0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -1.4180    1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710   -3.3096    1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  7 24  1  0
 24  2  1  0
 22  6  1  0
 21 10  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  9 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Atroviridin	MeSH

Chemical Formula

C₁₈H₁₄O₆

Average Molecular Weight

326.3002

Monoisotopic Molecular Weight

326.07903818

IUPAC Name

5,8,12-trihydroxy-2,2-dimethyl-2,6-dihydro-1,11-dioxatetracen-6-one

Traditional Name

5,8,12-trihydroxy-2,2-dimethyl-1,11-dioxatetracen-6-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(O)C3=C(C(O)=C2C=C1)C(=O)C1=C(O3)C=CC(O)=C1

InChI Identifier

InChI=1S/C18H14O6/c1-18(2)6-5-9-13(20)12-14(21)10-7-8(19)3-4-11(10)23-17(12)15(22)16(9)24-18/h3-7,19-20,22H,1-2H3

InChI Key

LPOCFPIHJNBUIN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Polyol
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033100)
Cell membrane (HMDB: HMDB0033100)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033100)

Source

Exogenous

Exogenous (HMDB: HMDB0033100)

Food

Food (HMDB: HMDB0033100)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033100)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033100)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	257 - 259 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.6	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.15 m³·mol⁻¹	ChemAxon
Polarizability	33.03 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]+	173.728	31661259
DarkChem	[M-H]-	172.976	31661259
DeepCCS	[M+H]+	183.864	30932474
DeepCCS	[M-H]-	181.506	30932474
DeepCCS	[M-2H]-	215.631	30932474
DeepCCS	[M+Na]+	190.859	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.7	32859911
AllCCS	[M+Na]+	179.6	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	176.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.49 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9895 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2302.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	150.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	532.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	518.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	318.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	824.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	349.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1129.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	307.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	39.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atroviridin	CC1(C)OC2=C(O)C3=C(C(O)=C2C=C1)C(=O)C1=C(O3)C=CC(O)=C1	4106.6	Standard polar	33892256
Atroviridin	CC1(C)OC2=C(O)C3=C(C(O)=C2C=C1)C(=O)C1=C(O3)C=CC(O)=C1	2884.0	Standard non polar	33892256
Atroviridin	CC1(C)OC2=C(O)C3=C(C(O)=C2C=C1)C(=O)C1=C(O3)C=CC(O)=C1	3091.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Atroviridin,1TMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O	3064.9	Semi standard non polar	33892256
Atroviridin,1TMS,isomer #2	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O[Si](C)(C)C	3079.1	Semi standard non polar	33892256
Atroviridin,1TMS,isomer #3	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O[Si](C)(C)C)C=C3C(=O)C1=C2O	3124.1	Semi standard non polar	33892256
Atroviridin,2TMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C)=C1OC3=CC=C(O[Si](C)(C)C)C=C3C(=O)C1=C2O	3038.2	Semi standard non polar	33892256
Atroviridin,2TMS,isomer #2	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O[Si](C)(C)C	3067.8	Semi standard non polar	33892256
Atroviridin,2TMS,isomer #3	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O[Si](C)(C)C)C=C3C(=O)C1=C2O[Si](C)(C)C	3111.1	Semi standard non polar	33892256
Atroviridin,3TMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C)=C1OC3=CC=C(O[Si](C)(C)C)C=C3C(=O)C1=C2O[Si](C)(C)C	3065.9	Semi standard non polar	33892256
Atroviridin,1TBDMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C(C)(C)C)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O	3314.1	Semi standard non polar	33892256
Atroviridin,1TBDMS,isomer #2	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O[Si](C)(C)C(C)(C)C	3325.6	Semi standard non polar	33892256
Atroviridin,1TBDMS,isomer #3	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C1=C2O	3341.6	Semi standard non polar	33892256
Atroviridin,2TBDMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C(C)(C)C)=C1OC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C1=C2O	3521.5	Semi standard non polar	33892256
Atroviridin,2TBDMS,isomer #2	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C(C)(C)C)=C1OC3=CC=C(O)C=C3C(=O)C1=C2O[Si](C)(C)C(C)(C)C	3561.9	Semi standard non polar	33892256
Atroviridin,2TBDMS,isomer #3	CC1(C)C=CC2=C(O1)C(O)=C1OC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C1=C2O[Si](C)(C)C(C)(C)C	3608.5	Semi standard non polar	33892256
Atroviridin,3TBDMS,isomer #1	CC1(C)C=CC2=C(O1)C(O[Si](C)(C)C(C)(C)C)=C1OC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C(=O)C1=C2O[Si](C)(C)C(C)(C)C	3762.7	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 - Atroviridin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0695000000-bd5d3c138563d42b7cf2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atroviridin GC-MS (3 TMS) - 70eV, Positive	splash10-00b9-6325970000-c6ac71b954b7a34fd0cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atroviridin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atroviridin 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 - Atroviridin 10V, Positive-QTOF	splash10-004i-1019000000-8c3f9028171a56704e52	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 20V, Positive-QTOF	splash10-004i-2098000000-fa752c0d3299a64c6cf2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 40V, Positive-QTOF	splash10-014i-5390000000-255f63eab7b83305132b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 10V, Negative-QTOF	splash10-004i-0009000000-0b2f33546d7dd1010aa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 20V, Negative-QTOF	splash10-004i-0049000000-57e180ba6cf5f833a0b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 40V, Negative-QTOF	splash10-000l-3790000000-e42e5fbd3ab84122eead	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 10V, Negative-QTOF	splash10-004i-0009000000-eb8469b649b7c5d99242	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 20V, Negative-QTOF	splash10-004i-0009000000-edc8ab5624e030d04937	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 40V, Negative-QTOF	splash10-001i-0290000000-4e654ed435b60dd5c4f1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 10V, Positive-QTOF	splash10-004i-0009000000-fdece4c688aa8992d2ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 20V, Positive-QTOF	splash10-004i-0009000000-1933d6b27f39dad20a5d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atroviridin 40V, Positive-QTOF	splash10-014r-2491000000-e874d1bf2423e09a5005	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011095

KNApSAcK ID

C00049039

Chemspider ID

9442359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11267348

PDB ID

Not Available

ChEBI ID

174366

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 Atroviridin (HMDB0033100)

MOL for HMDB0033100 (Atroviridin)

3D MOL for HMDB0033100 (Atroviridin)

3D SDF for HMDB0033100 (Atroviridin)

3D-SDF for HMDB0033100 (Atroviridin)

PDB for HMDB0033100 (Atroviridin)

3D PDB for HMDB0033100 (Atroviridin)

SMILES for HMDB0033100 (Atroviridin)

INCHI for HMDB0033100 (Atroviridin)

Structure for HMDB0033100 (Atroviridin)

3D Structure for HMDB0033100 (Atroviridin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra