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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:25:01 UTC

Update Date

2021-09-26 23:15:50 UTC

HMDB ID

HMDB0258714

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tanshinone I

Description

6,14-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2,4,6,8,11(15),13-heptaene-16,17-dione belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Based on a literature review very few articles have been published on 6,14-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2,4,6,8,11(15),13-heptaene-16,17-dione. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tanshinone i is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tanshinone I 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

HMDB0258714
     RDKit          3D
Tanshinone I
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.3529   -0.1921   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    0.1788    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122    0.8322    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.9477    1.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808    0.4174    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8328   -0.0732   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -0.7243   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142   -1.1735   -2.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.8392   -1.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -1.4040   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500   -0.2899   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    0.3280    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649    0.8515    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    0.7825    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.1823    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902    0.1182    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4146    0.6928    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -0.4876   -0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.0209   -1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -0.9554   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -0.3614   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3090   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    0.2782   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327   -1.2659   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.1856    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207    1.3251    2.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1845    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    0.1131    2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4726    0.7174    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1320    1.7689    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2608   -0.5397   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137   -1.5043   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -1.3819   -2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6  2  1  0
 21 11  1  0
 12  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
 13 26  1  0
 14 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END


  Mrv1533004241518332D          

 21 24  0  0  0  0            999 V2000
    6.1996    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258714

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C=CC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-8H,1-2H3

> <INCHI_KEY>
AIGAZQPHXLWMOJ-UHFFFAOYSA-N

> <FORMULA>
C18H12O3

> <MOLECULAR_WEIGHT>
276.291

> <EXACT_MASS>
276.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.694120117582504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),3,5,8,11(15),13-heptaene-16,17-dione

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
3.9952722539999996

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9580119974750465

> <JCHEM_POLAR_SURFACE_AREA>
47.28

> <JCHEM_REFRACTIVITY>
80.0745

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tanshinone I

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258714
     RDKit          3D
Tanshinone I
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.3529   -0.1921   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    0.1788    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122    0.8322    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.9477    1.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808    0.4174    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8328   -0.0732   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -0.7243   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142   -1.1735   -2.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.8392   -1.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -1.4040   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500   -0.2899   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    0.3280    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649    0.8515    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    0.7825    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.1823    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902    0.1182    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4146    0.6928    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -0.4876   -0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.0209   -1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -0.9554   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -0.3614   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3090   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    0.2782   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327   -1.2659   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.1856    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207    1.3251    2.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1845    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    0.1131    2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4726    0.7174    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1320    1.7689    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2608   -0.5397   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137   -1.5043   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -1.3819   -2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6  2  1  0
 21 11  1  0
 12  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
 13 26  1  0
 14 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      11.573   3.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.964  -2.398   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.770   2.079   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0258714
HETATM    1  C1  UNL     1       5.353  -0.192  -0.601  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.137   0.179   0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.012   0.832   1.359  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.736   0.948   1.643  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.981   0.417   0.710  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.833  -0.073  -0.241  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.225  -0.724  -1.406  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.014  -1.173  -2.277  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.772  -0.839  -1.536  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.371  -1.404  -2.553  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.050  -0.290  -0.479  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.511   0.328   0.627  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.265   0.852   1.634  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.618   0.783   1.583  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.205   0.182   0.511  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.590   0.118   0.470  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.415   0.693   1.574  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.183  -0.488  -0.611  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.445  -1.021  -1.634  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.037  -0.955  -1.593  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.444  -0.361  -0.532  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.218   0.309  -0.087  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.334   0.278  -1.623  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.533  -1.266  -0.659  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.832   1.186   1.964  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.221   1.325   2.479  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.270   1.184   2.360  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.286   0.113   2.496  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.473   0.717   1.247  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.132   1.769   1.765  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.261  -0.540  -0.647  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.914  -1.504  -2.498  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.497  -1.382  -2.408  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    6
CONECT    3    4   25
CONECT    4    5
CONECT    5    6    6   12
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   11
CONECT   11   12   12   21
CONECT   12   13
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16   21
CONECT   16   17   18
CONECT   17   28   29   30
CONECT   18   19   19   31
CONECT   19   20   32
CONECT   20   21   21   33
END

HMDB0258714
     RDKit          3D
Tanshinone I
 33 36  0  0  0  0  0  0  0  0999 V2000
    5.3529   -0.1921   -0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    0.1788    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122    0.8322    1.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.9477    1.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808    0.4174    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8328   -0.0732   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246   -0.7243   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142   -1.1735   -2.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724   -0.8392   -1.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3714   -1.4040   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500   -0.2899   -0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    0.3280    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649    0.8515    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6176    0.7825    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.1823    0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902    0.1182    0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4146    0.6928    1.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1829   -0.4876   -0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448   -1.0209   -1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0371   -0.9554   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437   -0.3614   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3090   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3336    0.2782   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5327   -1.2659   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.1856    1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207    1.3251    2.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    1.1845    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    0.1131    2.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4726    0.7174    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1320    1.7689    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2608   -0.5397   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137   -1.5043   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4971   -1.3819   -2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  6  2  1  0
 21 11  1  0
 12  5  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
 13 26  1  0
 14 27  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₂O₃

Average Molecular Weight

276.291

Monoisotopic Molecular Weight

276.078644246

IUPAC Name

6,14-dimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),3,5,8,11(15),13-heptaene-16,17-dione

Traditional Name

tanshinone I

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C=CC=C2C

InChI Identifier

InChI=1S/C18H12O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-8H,1-2H3

InChI Key

AIGAZQPHXLWMOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tanshinones, isotanshinones, and derivatives

Alternative Parents

Substituents

Tanshinone skeleton
Phenanthrene
Naphthofuran
Naphthalene
Aryl ketone
Quinone
O-quinone
Benzenoid
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	3.38	ALOGPS
logP	4	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.28 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.07 m³·mol⁻¹	ChemAxon
Polarizability	29.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.918	30932474
DeepCCS	[M-H]-	158.56	30932474
DeepCCS	[M-2H]-	192.153	30932474
DeepCCS	[M+Na]+	167.369	30932474
AllCCS	[M+H]+	163.3	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	163.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tanshinone I	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C=CC=C2C	3749.7	Standard polar	33892256
Tanshinone I	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C=CC=C2C	2487.3	Standard non polar	33892256
Tanshinone I	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C=CC=C2C	2790.0	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 - Tanshinone I GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-0590000000-6892e72733ac49044461	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tanshinone I GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

C00031401

Chemspider ID

102863

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

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 Tanshinone I (HMDB0258714)

MOL for HMDB0258714 (Tanshinone I)

3D MOL for HMDB0258714 (Tanshinone I)

3D SDF for HMDB0258714 (Tanshinone I)

3D-SDF for HMDB0258714 (Tanshinone I)

PDB for HMDB0258714 (Tanshinone I)

3D PDB for HMDB0258714 (Tanshinone I)

SMILES for HMDB0258714 (Tanshinone I)

INCHI for HMDB0258714 (Tanshinone I)

Structure for HMDB0258714 (Tanshinone I)

3D Structure for HMDB0258714 (Tanshinone I)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra