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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:53:35 UTC

Update Date

2022-11-23 22:25:18 UTC

HMDB ID

HMDB0253978

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lapachol

Description

lapachol belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Based on a literature review very few articles have been published on lapachol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lapachol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lapachol 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

HMDB0253978
     RDKit          3D
lapachol
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8280   -0.1154   -1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986    0.1336    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5312   -0.1515    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    0.6005    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.8880   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.1609   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151    0.9168   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148    2.3202   -0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.3638   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355    1.2015    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7830    0.6620    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258   -0.7260    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -1.5590    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026   -1.0090   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.8913   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -3.1540   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411   -1.2878   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8939   -1.9720   -0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828   -0.4510   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130   -0.8678   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6398    0.8373   -1.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1723    0.1048    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -1.2350    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4690    0.4236    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.7677    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448    0.5383   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    1.9764   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8222    2.7166   -1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    2.2760    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584    1.2851    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -1.1212    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -2.6318    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  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
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17  6  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1652309112114532D          

 18 19  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  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
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 17  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253978

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C2=CC=CC=C2C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3

> <INCHI_KEY>
CWPGNVFCJOPXFB-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.960161821089578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
3.0634483610000003

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.682315814328933

> <JCHEM_PKA_STRONGEST_BASIC>
-6.874355062812531

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
71.61599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lapachol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253978
     RDKit          3D
lapachol
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8280   -0.1154   -1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986    0.1336    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5312   -0.1515    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    0.6005    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.8880   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.1609   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151    0.9168   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148    2.3202   -0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.3638   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355    1.2015    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7830    0.6620    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258   -0.7260    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -1.5590    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026   -1.0090   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.8913   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -3.1540   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411   -1.2878   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8939   -1.9720   -0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828   -0.4510   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130   -0.8678   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6398    0.8373   -1.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1723    0.1048    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -1.2350    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4690    0.4236    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.7677    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448    0.5383   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    1.9764   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8222    2.7166   -1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    2.2760    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584    1.2851    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -1.1212    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -2.6318    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  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
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17  6  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    5   16                                                  
CONECT   16   15                                                            
CONECT   17    6                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0253978
HETATM    1  C1  UNL     1      -3.828  -0.115  -1.368  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.499   0.134   0.058  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.531  -0.151   1.077  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.290   0.600   0.341  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.253   0.888  -0.653  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.016   0.161  -0.460  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.115   0.917  -0.283  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.015   2.320  -0.290  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.439   0.364  -0.080  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.535   1.201   0.096  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.783   0.662   0.287  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.926  -0.726   0.301  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.854  -1.559   0.128  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.603  -1.009  -0.063  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.459  -1.891  -0.247  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.558  -3.154  -0.240  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.141  -1.288  -0.449  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.894  -1.972  -0.615  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.883  -0.451  -1.490  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.113  -0.868  -1.755  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.640   0.837  -1.907  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.172   0.105   2.105  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.806  -1.235   1.123  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.469   0.424   0.927  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.101   0.768   1.419  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.645   0.538  -1.654  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.093   1.976  -0.759  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.822   2.717  -1.222  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.413   2.276   0.084  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.658   1.285   0.428  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.906  -1.121   0.451  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.973  -2.632   0.140  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22   23   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   28
CONECT    9   10   10   14
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   18
END

HMDB0253978
     RDKit          3D
lapachol
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8280   -0.1154   -1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986    0.1336    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5312   -0.1515    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898    0.6005    0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.8880   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    0.1609   -0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151    0.9168   -0.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0148    2.3202   -0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.3638   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355    1.2015    0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7830    0.6620    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258   -0.7260    0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -1.5590    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6026   -1.0090   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593   -1.8913   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5577   -3.1540   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411   -1.2878   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8939   -1.9720   -0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828   -0.4510   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130   -0.8678   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6398    0.8373   -1.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1723    0.1048    2.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8059   -1.2350    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4690    0.4236    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    0.7677    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448    0.5383   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    1.9764   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8222    2.7166   -1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4128    2.2760    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584    1.2851    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9060   -1.1212    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -2.6318    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  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
 15 16  2  0
 15 17  1  0
 17 18  2  0
 17  6  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtho-quinone	MeSH
Lapachol, sodium salt	MeSH

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.274

Monoisotopic Molecular Weight

242.094294311

IUPAC Name

4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

Traditional Name

lapachol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=CC=CC=C2C(=O)C1=O

InChI Identifier

InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3

InChI Key

CWPGNVFCJOPXFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
1-naphthol
Aryl ketone
Quinone
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.26	ALOGPS
logP	3.06	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.68	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.62 m³·mol⁻¹	ChemAxon
Polarizability	25.96 Å³	ChemAxon
Number of Rings	2	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]+	153.532	30932474
DeepCCS	[M-H]-	151.174	30932474
DeepCCS	[M-2H]-	184.108	30932474
DeepCCS	[M+Na]+	159.625	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.3	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	158.5	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
lapachol	CC(C)=CCC1=C(O)C2=CC=CC=C2C(=O)C1=O	3175.2	Standard polar	33892256
lapachol	CC(C)=CCC1=C(O)C2=CC=CC=C2C(=O)C1=O	1985.4	Standard non polar	33892256
lapachol	CC(C)=CCC1=C(O)C2=CC=CC=C2C(=O)C1=O	2027.6	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 - Lapachol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06si-4890000000-3abaa04f11a56fc4cd16	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lapachol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lapachol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lapachol 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 - Lapachol 10V, Positive-QTOF	splash10-000i-0930000000-11b8b7563aa93456c382	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapachol 20V, Positive-QTOF	splash10-000i-0900000000-a72fcf10ff0c4a7b867c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapachol 40V, Positive-QTOF	splash10-0a4i-1900000000-6a465269ba8c748c73b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapachol 10V, Negative-QTOF	splash10-0006-0090000000-b72122e63043a3d3aeba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapachol 20V, Negative-QTOF	splash10-0006-0290000000-cc90a54e9a65dde464c9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lapachol 40V, Negative-QTOF	splash10-05g1-2900000000-66074d5a86530f6a6937	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

C00002813

Chemspider ID

3747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lapachol

METLIN ID

Not Available

PubChem Compound

3884

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 Lapachol (HMDB0253978)

MOL for HMDB0253978 (Lapachol)

3D MOL for HMDB0253978 (Lapachol)

3D SDF for HMDB0253978 (Lapachol)

3D-SDF for HMDB0253978 (Lapachol)

PDB for HMDB0253978 (Lapachol)

3D PDB for HMDB0253978 (Lapachol)

SMILES for HMDB0253978 (Lapachol)

INCHI for HMDB0253978 (Lapachol)

Structure for HMDB0253978 (Lapachol)

3D Structure for HMDB0253978 (Lapachol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra