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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:22:26 UTC

Update Date

2021-09-26 23:08:00 UTC

HMDB ID

HMDB0254184

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pterocarpanquinone

Description

Pterocarpanquinone, also known as LQB 118, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review a significant number of articles have been published on Pterocarpanquinone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pterocarpanquinone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pterocarpanquinone 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

HMDB0254184
     RDKit          3D
Pterocarpanquinone
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.5655    2.0541   -2.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2867    1.1223   -1.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.7056   -1.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.2585   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -0.9233    0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.8487    1.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167   -0.5419    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946   -1.2032    1.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3226   -0.8492    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6529    0.1675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8234   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    0.4738   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.6831   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.4766    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7119   -0.3317    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -0.3994    2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326   -0.2220    1.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750    0.0270    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102    0.0934   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622   -0.0836   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -0.0639   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.3650   -1.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    1.3385   -1.8659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020   -2.0015    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937   -1.3552    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.4575   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185    1.6224   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -1.8053   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953   -0.5962    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015   -0.2746    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400    0.1699    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    0.2916   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073   -0.5982   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    1.8824   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    1.9215   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 21 13  1  0
 23  3  1  0
 12  7  1  0
 20 15  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 21 33  1  0
 22 34  1  0
 22 35  1  0
M  END


  Mrv1652309112115222D          

 23 27  0  0  0  0            999 V2000
    2.4254    1.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533    1.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5023    0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7744    1.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360    2.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850    1.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8571    2.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1234    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9339    1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723    0.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002   -0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896   -0.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8512    0.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -0.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924    0.8826    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254184

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C2=C(C3OC4=CC=CC=C4C3CO2)C(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O4/c20-16-11-6-1-2-7-12(11)17(21)19-15(16)18-13(9-22-19)10-5-3-4-8-14(10)23-18/h1-8,13,18H,9H2

> <INCHI_KEY>
BUEHOQICFGQBNY-UHFFFAOYSA-N

> <FORMULA>
C19H12O4

> <MOLECULAR_WEIGHT>
304.301

> <EXACT_MASS>
304.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.540668277290322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,12-dioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(13),4,6,8,15,17,19-heptaene-14,21-dione

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.1255021919999995

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.83635065118242

> <JCHEM_PKA_STRONGEST_BASIC>
-4.633096897779509

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
84.31350000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,12-dioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(13),4,6,8,15,17,19-heptaene-14,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254184
     RDKit          3D
Pterocarpanquinone
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.5655    2.0541   -2.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2867    1.1223   -1.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.7056   -1.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.2585   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -0.9233    0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.8487    1.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167   -0.5419    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946   -1.2032    1.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3226   -0.8492    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6529    0.1675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8234   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    0.4738   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.6831   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.4766    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7119   -0.3317    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -0.3994    2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326   -0.2220    1.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750    0.0270    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102    0.0934   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622   -0.0836   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -0.0639   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.3650   -1.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    1.3385   -1.8659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020   -2.0015    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937   -1.3552    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.4575   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185    1.6224   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -1.8053   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953   -0.5962    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015   -0.2746    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400    0.1699    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    0.2916   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073   -0.5982   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    1.8824   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    1.9215   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 21 13  1  0
 23  3  1  0
 12  7  1  0
 20 15  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 21 33  1  0
 22 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.527   3.697   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.019   2.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.025   1.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.538   1.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.046   2.817   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.041   3.984   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.559   3.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.067   4.557   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.564   1.937   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.077   2.224   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.082   1.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.574  -0.397   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.061  -0.684   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.056   0.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.543   0.196   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.035  -1.258   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.225  -0.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.726   0.113   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.461  -0.765   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.068  -0.108   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.059   1.427   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.206   2.305   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.599   1.648   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17    3   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   18                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0254184
HETATM    1  O1  UNL     1      -2.565   2.054  -2.101  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.287   1.122  -1.298  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.870   0.706  -1.138  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.546  -0.258  -0.313  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.624  -0.923   0.456  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.309  -1.849   1.247  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.017  -0.542   0.324  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.995  -1.203   1.075  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.323  -0.849   0.958  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.653   0.167   0.086  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.679   0.823  -0.659  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.352   0.474  -0.546  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.840  -0.683  -0.140  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.332  -0.477   1.178  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.712  -0.332   1.114  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.699  -0.399   2.111  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.033  -0.222   1.824  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.375   0.027   0.512  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.410   0.093  -0.465  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.062  -0.084  -0.188  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.839  -0.064  -1.045  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.438   1.365  -1.343  1.00  0.00           C  
HETATM   23  O4  UNL     1       0.124   1.338  -1.866  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.702  -2.001   1.754  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.094  -1.355   1.536  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.691   0.458  -0.018  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.919   1.622  -1.348  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.843  -1.805  -0.296  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.395  -0.596   3.128  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.801  -0.275   2.600  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.440   0.170   0.275  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.697   0.292  -1.500  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.007  -0.598  -1.997  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.147   1.882  -1.986  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.427   1.922  -0.361  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   23
CONECT    4    5   13
CONECT    5    6    6    7
CONECT    7    8    8   12
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   13   14   21   28
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   21
CONECT   21   22   33
CONECT   22   23   34   35
END

HMDB0254184
     RDKit          3D
Pterocarpanquinone
 35 39  0  0  0  0  0  0  0  0999 V2000
   -2.5655    2.0541   -2.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2867    1.1223   -1.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8696    0.7056   -1.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456   -0.2585   -0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -0.9233    0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.8487    1.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167   -0.5419    0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946   -1.2032    1.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3226   -0.8492    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6529    0.1675    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8234   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    0.4738   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.6831   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.4766    1.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7119   -0.3317    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6990   -0.3994    2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0326   -0.2220    1.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750    0.0270    0.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102    0.0934   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622   -0.0836   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -0.0639   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.3650   -1.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    1.3385   -1.8659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020   -2.0015    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0937   -1.3552    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6905    0.4575   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9185    1.6224   -1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426   -1.8053   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953   -0.5962    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8015   -0.2746    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4400    0.1699    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    0.2916   -1.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0073   -0.5982   -1.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    1.8824   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4268    1.9215   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 21 13  1  0
 23  3  1  0
 12  7  1  0
 20 15  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 21 33  1  0
 22 34  1  0
 22 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
LQB 118	MeSH
LQB-118	MeSH

Chemical Formula

C₁₉H₁₂O₄

Average Molecular Weight

304.301

Monoisotopic Molecular Weight

304.073558866

IUPAC Name

3,12-dioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(13),4,6,8,15,17,19-heptaene-14,21-dione

Traditional Name

3,12-dioxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-1(13),4,6,8,15,17,19-heptaene-14,21-dione

CAS Registry Number

Not Available

SMILES

O=C1C2=C(C3OC4=CC=CC=C4C3CO2)C(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C19H12O4/c20-16-11-6-1-2-7-12(11)17(21)19-15(16)18-13(9-22-19)10-5-3-4-8-14(10)23-18/h1-8,13,18H,9H2

InChI Key

BUEHOQICFGQBNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Naphthalene
Coumaran
Aryl ketone
Quinone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Vinylogous ester
Ketone
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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)

Source

Exogenous

Exogenous (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	ALOGPS
logP	2.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	17.84	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.31 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	5	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-2H]-	205.45	30932474
DeepCCS	[M+Na]+	180.677	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	17.324 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2727.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	541.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	295.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	738.5 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	918.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1522.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	574.0 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	1727.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	514.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	530.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	430.1 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	104.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pterocarpanquinone	O=C1C2=C(C3OC4=CC=CC=C4C3CO2)C(=O)C2=CC=CC=C12	4002.0	Standard polar	33892256
Pterocarpanquinone	O=C1C2=C(C3OC4=CC=CC=C4C3CO2)C(=O)C2=CC=CC=C12	2615.2	Standard non polar	33892256
Pterocarpanquinone	O=C1C2=C(C3OC4=CC=CC=C4C3CO2)C(=O)C2=CC=CC=C12	2914.4	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 - Pterocarpanquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0950000000-0c309aeef35f9b8de73a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pterocarpanquinone 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 - Pterocarpanquinone 10V, Positive-QTOF	splash10-0a4i-0009000000-65f36650821dd11e29ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pterocarpanquinone 20V, Positive-QTOF	splash10-0a4i-0009000000-e3c61e50f75ff59dfc98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pterocarpanquinone 40V, Positive-QTOF	splash10-0a4i-0926000000-9f32931e89afc9eb1df2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pterocarpanquinone 10V, Negative-QTOF	splash10-0udi-0009000000-dee7626e8c41931932f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pterocarpanquinone 20V, Negative-QTOF	splash10-0udi-0009000000-dee7626e8c41931932f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pterocarpanquinone 40V, Negative-QTOF	splash10-0udi-0209000000-55f2265ceec28c143a1e	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

Not Available

Chemspider ID

58921478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53330933

PDB ID

Not Available

ChEBI ID

Not Available

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 Pterocarpanquinone (HMDB0254184)

MOL for HMDB0254184 (Pterocarpanquinone)

3D MOL for HMDB0254184 (Pterocarpanquinone)

3D SDF for HMDB0254184 (Pterocarpanquinone)

3D-SDF for HMDB0254184 (Pterocarpanquinone)

PDB for HMDB0254184 (Pterocarpanquinone)

3D PDB for HMDB0254184 (Pterocarpanquinone)

SMILES for HMDB0254184 (Pterocarpanquinone)

INCHI for HMDB0254184 (Pterocarpanquinone)

Structure for HMDB0254184 (Pterocarpanquinone)

3D Structure for HMDB0254184 (Pterocarpanquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra