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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:18:37 UTC

Update Date

2021-09-26 23:09:08 UTC

HMDB ID

HMDB0254836

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mollugin

Description

rubimaillin, also known as mollugin, belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. rubimaillin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on rubimaillin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mollugin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mollugin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254836
     RDKit          3D
Mollugin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.4512   -2.3069    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668   -1.7317    0.3041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.4339   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989    0.2262   -0.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    0.2677   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -0.3825    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    0.3051   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    1.6427   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    2.3006   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340    3.6370   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    4.2692   -1.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    3.6155   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    2.2792   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284    1.6077   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    2.3552   -0.8503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -0.2877    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -1.6106    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944   -2.3138   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477   -1.6291    1.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913   -2.3272    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -1.7732    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -1.6010    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -2.7307    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795   -3.1119   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9057    1.7587   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901    4.1570   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    5.3040   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    4.1266   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649    2.2629   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -3.3726   -0.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868   -2.2864   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -1.7187   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323   -0.7379    2.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -2.5773    2.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162   -1.4683    1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -3.3634    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -2.3504    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 14  5  1  0
 21  6  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1533004171507232D          

 21 23  0  0  0  0            999 V2000
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 O   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
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   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
    3.6020    1.1270    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
    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
    2.3645    0.4125    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
    1.1270   -0.3020    0.0000 O   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
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    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
    0.3020    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  2  0  0  0  0
 14 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254836

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=C2C=CC(C)(C)OC2=C2C=CC=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-9,18H,1-3H3

> <INCHI_KEY>
VLGATXOTCNBWIT-UHFFFAOYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.311

> <EXACT_MASS>
284.104858995

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.253468350575865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.213257617

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.753453161670587

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352502490674884

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
80.90780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-hydroxy-2,2-dimethylbenzo[h]chromene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254836
     RDKit          3D
Mollugin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.4512   -2.3069    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668   -1.7317    0.3041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.4339   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989    0.2262   -0.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    0.2677   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -0.3825    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    0.3051   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    1.6427   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    2.3006   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340    3.6370   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    4.2692   -1.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    3.6155   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    2.2792   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284    1.6077   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    2.3552   -0.8503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -0.2877    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -1.6106    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944   -2.3138   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477   -1.6291    1.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913   -2.3272    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -1.7732    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -1.6010    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -2.7307    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795   -3.1119   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9057    1.7587   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901    4.1570   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    5.3040   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    4.1266   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649    2.2629   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -3.3726   -0.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868   -2.2864   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -1.7187   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323   -0.7379    2.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -2.5773    2.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162   -1.4683    1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -3.3634    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -2.3504    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 14  5  1  0
 21  6  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.564   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.874   6.105   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184   2.104   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       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    5   14                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0254836
HETATM    1  C1  UNL     1       4.451  -2.307   0.384  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.167  -1.732   0.304  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.928  -0.434  -0.056  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.999   0.226  -0.320  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.676   0.268  -0.174  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.488  -0.383   0.095  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.728   0.305  -0.022  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.782   1.643  -0.406  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.995   2.301  -0.514  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.034   3.637  -0.899  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.842   4.269  -1.163  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.382   3.615  -1.056  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.398   2.279  -0.670  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.628   1.608  -0.559  1.00  0.00           C  
HETATM   15  O3  UNL     1       2.727   2.355  -0.850  1.00  0.00           O  
HETATM   16  O4  UNL     1      -1.932  -0.288   0.231  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.062  -1.611   0.624  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.894  -2.314  -0.446  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.848  -1.629   1.920  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.791  -2.327   0.745  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.386  -1.773   0.505  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.253  -1.601   0.139  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.569  -2.731   1.402  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.479  -3.112  -0.397  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.906   1.759  -0.295  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.990   4.157  -0.985  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.831   5.304  -1.463  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.299   4.127  -1.267  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.665   2.263  -0.887  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.073  -3.373  -0.198  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.287  -2.286  -1.392  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.807  -1.719  -0.589  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.532  -0.738   2.501  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.736  -2.577   2.472  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.916  -1.468   1.632  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.802  -3.363   1.046  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.292  -2.350   0.610  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   14
CONECT    6    7   21
CONECT    7    8    8   16
CONECT    8    9   13
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14
CONECT   14   15
CONECT   15   29
CONECT   16   17
CONECT   17   18   19   20
CONECT   18   30   31   32
CONECT   19   33   34   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0254836
     RDKit          3D
Mollugin
 37 39  0  0  0  0  0  0  0  0999 V2000
    4.4512   -2.3069    0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668   -1.7317    0.3041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9281   -0.4339   -0.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9989    0.2262   -0.3196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6760    0.2677   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -0.3825    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    0.3051   -0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    1.6427   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    2.3006   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340    3.6370   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8422    4.2692   -1.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    3.6155   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    2.2792   -0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284    1.6077   -0.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266    2.3552   -0.8503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322   -0.2877    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -1.6106    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944   -2.3138   -0.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477   -1.6291    1.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913   -2.3272    0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3860   -1.7732    0.5047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2527   -1.6010    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -2.7307    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4795   -3.1119   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9057    1.7587   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901    4.1570   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    5.3040   -1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    4.1266   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6649    2.2629   -0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -3.3726   -0.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2868   -2.2864   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070   -1.7187   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323   -0.7379    2.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -2.5773    2.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162   -1.4683    1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -3.3634    1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925   -2.3504    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 14  5  1  0
 21  6  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 15 29  1  0
 18 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mollugin	ChEBI
3'-Carbomethoxy-4'-hydroxy-6,6-dimethylnaphtho(1',2'-2,3)pyran	MeSH
Rubimaillin	MeSH

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.311

Monoisotopic Molecular Weight

284.104858995

IUPAC Name

methyl 6-hydroxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate

Traditional Name

methyl 6-hydroxy-2,2-dimethylbenzo[h]chromene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2C=CC(C)(C)OC2=C2C=CC=CC2=C1O

InChI Identifier

InChI=1S/C17H16O4/c1-17(2)9-8-12-13(16(19)20-3)14(18)10-6-4-5-7-11(10)15(12)21-17/h4-9,18H,1-3H3

InChI Key

VLGATXOTCNBWIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
2-naphthalenecarboxylic acid
2-naphthalenecarboxylic acid or derivatives
2,2-dimethyl-1-benzopyran
1-naphthol
Benzopyran
1-benzopyran
Salicylic acid or derivatives
Naphthalene
Alkyl aryl ether
Benzenoid
Pyran
Vinylogous acid
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	3.74	ALOGPS
logP	4.21	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.75	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.91 m³·mol⁻¹	ChemAxon
Polarizability	30.25 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
DeepCCS	[M+H]+	164.365	30932474
DeepCCS	[M-H]-	162.007	30932474
DeepCCS	[M-2H]-	195.382	30932474
DeepCCS	[M+Na]+	170.609	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.5	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	168.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mollugin	COC(=O)C1=C2C=CC(C)(C)OC2=C2C=CC=CC2=C1O	3177.5	Standard polar	33892256
Mollugin	COC(=O)C1=C2C=CC(C)(C)OC2=C2C=CC=CC2=C1O	2161.1	Standard non polar	33892256
Mollugin	COC(=O)C1=C2C=CC(C)(C)OC2=C2C=CC=CC2=C1O	2234.7	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 - Mollugin GC-MS (Non-derivatized) - 70eV, Positive	splash10-1000-0290000000-16dd173d86cde0c9e6ce	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mollugin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mollugin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mollugin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Mollugin 10V, Positive-QTOF	splash10-000i-0090000000-76ca0e4141658a95b447	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mollugin 20V, Positive-QTOF	splash10-0udr-0090000000-8b5ca62a0fba1c305e87	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mollugin 40V, Positive-QTOF	splash10-00or-0190000000-0b4f5e8d5d19d4fa1c6e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mollugin 10V, Negative-QTOF	splash10-001i-0090000000-c5832dccd44e0984ddaa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mollugin 20V, Negative-QTOF	splash10-001i-0090000000-b0fe6494d2ef45133f30	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mollugin 40V, Negative-QTOF	splash10-001i-0090000000-8b837471a9e17aaa77c5	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00030781

Chemspider ID

110674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

141063

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Mollugin (HMDB0254836)

MOL for HMDB0254836 (Mollugin)

3D MOL for HMDB0254836 (Mollugin)

3D SDF for HMDB0254836 (Mollugin)

3D-SDF for HMDB0254836 (Mollugin)

PDB for HMDB0254836 (Mollugin)

3D PDB for HMDB0254836 (Mollugin)

SMILES for HMDB0254836 (Mollugin)

INCHI for HMDB0254836 (Mollugin)

Structure for HMDB0254836 (Mollugin)

3D Structure for HMDB0254836 (Mollugin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra