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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:37:47 UTC

Update Date

2021-09-26 22:59:48 UTC

HMDB ID

HMDB0249138

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Lapachone

Description

Lapachone, also known as ARQ 501 or beta-lap, 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. Lapachone 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 Lapachone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-lapachone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-Lapachone 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

HMDB0249138
     RDKit          3D
beta-Lapachone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.2919   -0.4906   -1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -0.5485   -0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -1.6998    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990    0.7278    0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    1.8041    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    1.3253    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831    0.0861    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043   -0.8826    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5918   -0.2976    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -1.6487   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -2.0579   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.1277   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.2111    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291    0.6285    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    2.0215    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    2.8610    0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622    2.3689    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755    3.5765    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.0945   -1.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    0.1297   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.5359   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160   -1.6551    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9956   -1.5880    1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -2.6321    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    0.5035    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    1.0993   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.3345    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    2.5794   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388   -2.3627   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -3.1247   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -1.4719   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    0.9611    0.1097 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  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
  8  2  1  0
 14  9  1  0
 17  6  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
  4 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1533004151519002D          

 18 20  0  0  0  0            999 V2000
    4.3772   -0.5841    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
    3.4587   -1.1144    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    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249138

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O

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

> <INCHI_KEY>
QZPQTZZNNJUOLS-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.647652145475725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.629317615333333

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8851459719292745

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
69.09200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-lapachone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249138
     RDKit          3D
beta-Lapachone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.2919   -0.4906   -1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -0.5485   -0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -1.6998    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990    0.7278    0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    1.8041    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    1.3253    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831    0.0861    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043   -0.8826    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5918   -0.2976    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -1.6487   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -2.0579   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.1277   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.2111    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291    0.6285    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    2.0215    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    2.8610    0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622    2.3689    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755    3.5765    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.0945   -1.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    0.1297   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.5359   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160   -1.6551    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9956   -1.5880    1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -2.6321    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    0.5035    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    1.0993   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.3345    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    2.5794   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388   -2.3627   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -3.1247   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -1.4719   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    0.9611    0.1097 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  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
  8  2  1  0
 14  9  1  0
 17  6  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
  4 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
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   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0249138
HETATM    1  C1  UNL     1      -2.292  -0.491  -1.653  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.128  -0.548  -0.130  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.987  -1.700   0.412  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.599   0.728   0.477  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.565   1.804   0.552  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.184   1.325   0.413  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.183   0.086   0.223  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.804  -0.883   0.141  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.592  -0.298   0.098  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.870  -1.649  -0.103  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.163  -2.058  -0.226  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.180  -1.128  -0.150  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.942   0.211   0.046  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.629   0.629   0.171  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.272   2.021   0.382  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.201   2.861   0.449  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.862   2.369   0.503  1.00  0.00           C  
HETATM   18  O3  UNL     1       0.575   3.576   0.684  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.289  -0.094  -1.937  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.456   0.130  -2.041  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.129  -1.536  -2.008  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.016  -1.655   0.028  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.996  -1.588   1.522  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.455  -2.632   0.188  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.023   0.504   1.491  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.459   1.099  -0.123  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.681   2.334   1.525  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.718   2.579  -0.255  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.039  -2.363  -0.158  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.361  -3.125  -0.383  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.198  -1.472  -0.250  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.711   0.961   0.110  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    8
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7    7   17
CONECT    7    8    9
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

HMDB0249138
     RDKit          3D
beta-Lapachone
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.2919   -0.4906   -1.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280   -0.5485   -0.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -1.6998    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990    0.7278    0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647    1.8041    0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    1.3253    0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831    0.0861    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043   -0.8826    0.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5918   -0.2976    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -1.6487   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626   -2.0579   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1797   -1.1277   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    0.2111    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291    0.6285    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    2.0215    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    2.8610    0.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8622    2.3689    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5755    3.5765    0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887   -0.0945   -1.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    0.1297   -2.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.5359   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160   -1.6551    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9956   -1.5880    1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -2.6321    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    0.5035    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4587    1.0993   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.3345    1.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7183    2.5794   -0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388   -2.3627   -0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -3.1247   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -1.4719   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111    0.9611    0.1097 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  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
  8  2  1  0
 14  9  1  0
 17  6  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
  4 26  1  0
  5 27  1  0
  5 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
3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione	ChEBI
ARQ 501	ChEBI
beta-Lap	ChEBI
b-Lap	Generator
Β-lap	Generator
b-Lapachone	Generator
β-lapachone	Generator

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.274

Monoisotopic Molecular Weight

242.094294311

IUPAC Name

2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

Traditional Name

β-lapachone

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O

InChI Identifier

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

InChI Key

QZPQTZZNNJUOLS-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
Quinone
Aryl ketone
Benzenoid
Pyran
Vinylogous ester
Ketone
Oxacycle
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:10429 )
benzochromenone (CHEBI:10429 )

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	2.82	ALOGPS
logP	2.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	25.65 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]+	160.348	30932474
DeepCCS	[M-H]-	157.99	30932474
DeepCCS	[M-2H]-	190.876	30932474
DeepCCS	[M+Na]+	166.442	30932474
AllCCS	[M+H]+	153.8	32859911
AllCCS	[M+H-H2O]+	149.8	32859911
AllCCS	[M+NH4]+	157.5	32859911
AllCCS	[M+Na]+	158.6	32859911
AllCCS	[M-H]-	160.8	32859911
AllCCS	[M+Na-2H]-	160.5	32859911
AllCCS	[M+HCOO]-	160.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Lapachone	CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O	3079.3	Standard polar	33892256
beta-Lapachone	CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O	2020.4	Standard non polar	33892256
beta-Lapachone	CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O	2157.6	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 - beta-Lapachone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-4980000000-93a44e3902f7e083ce89	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Lapachone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone DI-ESI-qTof , Positive-QTOF	splash10-004i-0490000000-9dbf4ce893a2feaca176	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone LC-ESI-QTOF , positive-QTOF	splash10-0006-0090000000-4a26146991318c5f1e1c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone LC-ESI-QTOF , positive-QTOF	splash10-000i-0950000000-fc19149826e6662b522d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone LC-ESI-QTOF , positive-QTOF	splash10-052r-0900000000-47530e7c0f8b6bf3c398	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-bc6b197a7ba33ff3caf9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0900000000-9b23674b37357d81e688	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 50V, Positive-QTOF	splash10-0a4i-0900000000-9f017f4dbfdd84cf26f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 40V, Positive-QTOF	splash10-0a4i-0900000000-f2933e7a9e7dd8750f36	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 50V, Positive-QTOF	splash10-0a4i-0900000000-9b23674b37357d81e688	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 10V, Positive-QTOF	splash10-0006-0090000000-4a26146991318c5f1e1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 20V, Positive-QTOF	splash10-000i-0950000000-fc19149826e6662b522d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 40V, Positive-QTOF	splash10-0a4i-0900000000-bc6b197a7ba33ff3caf9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Lapachone 30V, Positive-QTOF	splash10-052r-0900000000-47530e7c0f8b6bf3c398	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 10V, Positive-QTOF	splash10-0006-0190000000-0eb470cfdec2155a8463	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 20V, Positive-QTOF	splash10-000l-2790000000-8c8bdd620a2501eb594c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 40V, Positive-QTOF	splash10-0kui-4910000000-6462bb462f0065818aa5	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 10V, Negative-QTOF	splash10-0006-0090000000-d4cd1050ce2d6e224022	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 20V, Negative-QTOF	splash10-0006-0490000000-e106ead431bbe2f52fb0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 40V, Negative-QTOF	splash10-053i-0910000000-a98b0c2c500fcd555c16	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 10V, Positive-QTOF	splash10-0006-0090000000-a810a7788942d2c00b91	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 20V, Positive-QTOF	splash10-000i-0960000000-85938be19c32581de1d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 40V, Positive-QTOF	splash10-0a5i-1910000000-6641a286c1851df8c22a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 10V, Negative-QTOF	splash10-0006-0090000000-b72122e63043a3d3aeba	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 20V, Negative-QTOF	splash10-0006-0090000000-e714c7405a7d58deac7b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Lapachone 40V, Negative-QTOF	splash10-022j-0930000000-14bfb0c47e6856e208f5	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

DB11948

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002836

Chemspider ID

3748

KEGG Compound ID

C10367

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3885

PDB ID

Not Available

ChEBI ID

10429

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1529071

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 beta-Lapachone (HMDB0249138)

MOL for HMDB0249138 (beta-Lapachone)

3D MOL for HMDB0249138 (beta-Lapachone)

3D SDF for HMDB0249138 (beta-Lapachone)

3D-SDF for HMDB0249138 (beta-Lapachone)

PDB for HMDB0249138 (beta-Lapachone)

3D PDB for HMDB0249138 (beta-Lapachone)

SMILES for HMDB0249138 (beta-Lapachone)

INCHI for HMDB0249138 (beta-Lapachone)

Structure for HMDB0249138 (beta-Lapachone)

3D Structure for HMDB0249138 (beta-Lapachone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra