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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:10:19 UTC

Update Date

2022-03-07 02:54:25 UTC

HMDB ID

HMDB0035220

Secondary Accession Numbers

HMDB35220

Metabolite Identification

Common Name

Cryptotanshinone

Description

Cryptotanshinone 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 a significant number of articles have been published on Cryptotanshinone.

Structure

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

HMDB0035220
     RDKit          3D
Cryptotanshinone
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.2078    0.2066    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.8260   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200   -0.3169   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928    0.5727   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.0395   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -0.8701    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -1.6491    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.4490    1.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -1.4811    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962   -2.1220    2.0188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177   -0.5566    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.1421   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5075    1.0263   -1.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2038   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    0.4914   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -0.3971    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -1.1735    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976   -0.7940    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453   -0.4186    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716    0.7373   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    2.0333    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913    0.8602   -2.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.5748    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -0.2121    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    1.0806    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749   -1.8113   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -1.1780   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5429    0.2165   -1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    1.5537   -2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.8978   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782   -2.2735    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9079    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    0.0665    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194   -1.6270    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794   -0.0490    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2685   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4368    2.0350    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    2.1401    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    2.8968   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857    0.2559   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    1.9402   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4893   -2.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END


  Mrv0541 05061308182D          

 22 25  0  0  0  0            999 V2000
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21 17  2  0  0  0  0
 22  9  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035220

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3

> <INCHI_KEY>
GVKKJJOMQCNPGB-UHFFFAOYSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.3603

> <EXACT_MASS>
296.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.224457059161736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15)-tetraene-16,17-dione

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
3.8918905059999997

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.86023128899661

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
86.41149999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cryptotanshinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035220
     RDKit          3D
Cryptotanshinone
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.2078    0.2066    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.8260   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200   -0.3169   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928    0.5727   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.0395   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -0.8701    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -1.6491    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.4490    1.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -1.4811    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962   -2.1220    2.0188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177   -0.5566    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.1421   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5075    1.0263   -1.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2038   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    0.4914   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -0.3971    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -1.1735    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976   -0.7940    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453   -0.4186    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716    0.7373   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    2.0333    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913    0.8602   -2.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.5748    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -0.2121    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    1.0806    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749   -1.8113   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -1.1780   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5429    0.2165   -1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    1.5537   -2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.8978   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782   -2.2735    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9079    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    0.0665    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194   -1.6270    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794   -0.0490    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2685   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4368    2.0350    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    2.1401    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    2.8968   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857    0.2559   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    1.9402   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4893   -2.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.791   0.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.929  -0.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.943   1.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.373   6.011   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.180   1.533   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8    4   19                                                       
CONECT    9   10   22                                                       
CONECT   10    1    9   14                                                  
CONECT   11    5   13   15                                                  
CONECT   12    6   15   18                                                  
CONECT   13    7   11   19                                                  
CONECT   14   10   16   18                                                  
CONECT   15   11   12   17                                                  
CONECT   16   14   17   20                                                  
CONECT   17   15   16   21                                                  
CONECT   18   12   14   22                                                  
CONECT   19    2    3    8   13                                             
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22    9   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0035220
HETATM    1  C1  UNL     1       5.208   0.207   0.802  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.597  -0.826  -0.145  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.620  -0.317  -1.568  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.493   0.573  -1.513  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.541  -0.039  -0.671  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.142  -0.870   0.147  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.436  -1.649   1.130  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.937  -2.449   1.930  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.959  -1.481   1.197  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.296  -2.122   2.019  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.318  -0.557   0.283  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.097   0.142  -0.624  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.507   1.026  -1.507  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.840   1.204  -1.477  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.609   0.491  -0.555  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.081  -0.397   0.343  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.838  -1.174   1.345  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.298  -0.794   1.347  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.845  -0.419   0.004  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.072   0.737  -0.595  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.372   2.033   0.119  1.00  0.00           C  
HETATM   22  C19 UNL     1      -3.491   0.860  -2.041  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.471   0.575   1.538  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.062  -0.212   1.353  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.511   1.081   0.195  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.075  -1.811  -0.026  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.409  -1.178  -2.230  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.543   0.216  -1.823  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.145   1.554  -2.200  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.315   1.898  -2.168  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.778  -2.273   1.165  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.509  -0.908   2.399  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.486   0.067   2.021  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.919  -1.627   1.737  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.879  -0.049   0.169  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.924  -1.268  -0.702  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.437   2.035   0.455  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.699   2.140   0.997  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.266   2.897  -0.562  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.386   0.256  -2.260  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.633   1.940  -2.306  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.690   0.489  -2.723  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    6   26
CONECT    3    4   27   28
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   16
CONECT   12   13
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   20
CONECT   16   17
CONECT   17   18   31   32
CONECT   18   19   33   34
CONECT   19   20   35   36
CONECT   20   21   22
CONECT   21   37   38   39
CONECT   22   40   41   42
END

HMDB0035220
     RDKit          3D
Cryptotanshinone
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.2078    0.2066    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5968   -0.8260   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200   -0.3169   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928    0.5727   -1.5125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -0.0395   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416   -0.8701    0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4357   -1.6491    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -2.4490    1.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -1.4811    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2962   -2.1220    2.0188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177   -0.5566    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    0.1421   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5075    1.0263   -1.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401    1.2038   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    0.4914   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810   -0.3971    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8384   -1.1735    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976   -0.7940    1.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8453   -0.4186    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716    0.7373   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3718    2.0333    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913    0.8602   -2.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.5748    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0624   -0.2121    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5114    1.0806    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749   -1.8113   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -1.1780   -2.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5429    0.2165   -1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449    1.5537   -2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.8978   -2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782   -2.2735    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5089   -0.9079    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4860    0.0665    2.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194   -1.6270    1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794   -0.0490    0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9239   -1.2685   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4368    2.0350    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6990    2.1401    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    2.8968   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3857    0.2559   -2.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    1.9402   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4893   -2.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Cryptotanshinone	HMDB
Cryptotanshinone	MeSH

Chemical Formula

C₁₉H₂₀O₃

Average Molecular Weight

296.3603

Monoisotopic Molecular Weight

296.141244506

IUPAC Name

6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15)-tetraene-16,17-dione

Traditional Name

cryptotanshinone

CAS Registry Number

35825-57-1

SMILES

CC1COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)C

InChI Identifier

InChI=1S/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3

InChI Key

GVKKJJOMQCNPGB-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
11-oxosteroid
12-oxosteroid
Oxosteroid
Delta-5-steroid
Delta-7-steroid
15-oxasteroid
Steroid
Phenanthrene
Naphthofuran
Naphthoquinone
Naphthalene
Tetralin
Aryl ketone
Quinone
Benzenoid
Vinylogous ester
Dihydrofuran
Ketone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035220)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035220)

Source

Endogenous

Endogenous (HMDB: HMDB0035220)

Plant

Plant (HMDB: HMDB0035220)

Animal

Animal (HMDB: HMDB0035220)

Exogenous

Food

Food (HMDB: HMDB0035220)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035220)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035220)

Cellular process

Cell signaling (HMDB: HMDB0035220)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035220)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035220)

Nutrient

Nutrient (HMDB: HMDB0035220)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0035220)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 °C	Not Available
Boiling Point	459.03 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.52 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.130 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0098 g/L	ALOGPS
logP	4.32	ALOGPS
logP	3.89	ChemAxon
logS	-4.5	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	86.41 m³·mol⁻¹	ChemAxon
Polarizability	33.22 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
DarkChem	[M+H]+	170.918	31661259
DarkChem	[M-H]-	171.039	31661259
DeepCCS	[M+H]+	172.042	30932474
DeepCCS	[M-H]-	169.683	30932474
DeepCCS	[M-2H]-	203.187	30932474
DeepCCS	[M+Na]+	178.414	30932474
AllCCS	[M+H]+	169.4	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	172.6	32859911
AllCCS	[M+Na]+	173.5	32859911
AllCCS	[M-H]-	179.8	32859911
AllCCS	[M+Na-2H]-	179.5	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cryptotanshinone	CC1COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)C	3456.2	Standard polar	33892256
Cryptotanshinone	CC1COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)C	2550.0	Standard non polar	33892256
Cryptotanshinone	CC1COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)C	2691.3	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 - Cryptotanshinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1290000000-f7743f6d06f474b84ea0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cryptotanshinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cryptotanshinone 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 - Cryptotanshinone 10V, Positive-QTOF	splash10-0002-0090000000-6c008adace2f8f56e0f4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 20V, Positive-QTOF	splash10-0a6s-2290000000-ec20e442b4567e2f6f11	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 40V, Positive-QTOF	splash10-0a4i-6930000000-d08515026608b82d6a54	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 10V, Negative-QTOF	splash10-0002-0090000000-cd3cc2fb7ff68d188783	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 20V, Negative-QTOF	splash10-0002-0090000000-8c45a9b3b1be6fcdf320	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 40V, Negative-QTOF	splash10-0gw0-1390000000-5cd643541f2f8a50cfbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 10V, Positive-QTOF	splash10-0002-0090000000-227502f8cadf6b5e8f26	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 20V, Positive-QTOF	splash10-0002-0090000000-8219942a4fecc9126f24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 40V, Positive-QTOF	splash10-014l-0190000000-0e5b44be65a2a7a226cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 10V, Negative-QTOF	splash10-0002-0090000000-db72210c281b6deac77d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 20V, Negative-QTOF	splash10-00kb-0090000000-cc16cf326343e6a2f756	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cryptotanshinone 40V, Negative-QTOF	splash10-00n0-0190000000-001e2e19034ee4a15c10	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB013869

KNApSAcK ID

C00031697

Chemspider ID

434562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

496348

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1665471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim EJ, Jung SN, Son KH, Kim SR, Ha TY, Park MG, Jo IG, Park JG, Choe W, Kim SS, Ha J: Antidiabetes and antiobesity effect of cryptotanshinone via activation of AMP-activated protein kinase. Mol Pharmacol. 2007 Jul;72(1):62-72. Epub 2007 Apr 11. [PubMed:17429005 ]
Shin DS, Kim HN, Shin KD, Yoon YJ, Kim SJ, Han DC, Kwon BM: Cryptotanshinone inhibits constitutive signal transducer and activator of transcription 3 function through blocking the dimerization in DU145 prostate cancer cells. Cancer Res. 2009 Jan 1;69(1):193-202. doi: 10.1158/0008-5472.CAN-08-2575. [PubMed:19118003 ]
Jin DZ, Yin LL, Ji XQ, Zhu XZ: Cryptotanshinone inhibits cyclooxygenase-2 enzyme activity but not its expression. Eur J Pharmacol. 2006 Nov 7;549(1-3):166-72. Epub 2006 Aug 17. [PubMed:16989810 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Cryptotanshinone (HMDB0035220)

MOL for HMDB0035220 (Cryptotanshinone)

3D MOL for HMDB0035220 (Cryptotanshinone)

3D SDF for HMDB0035220 (Cryptotanshinone)

3D-SDF for HMDB0035220 (Cryptotanshinone)

PDB for HMDB0035220 (Cryptotanshinone)

3D PDB for HMDB0035220 (Cryptotanshinone)

SMILES for HMDB0035220 (Cryptotanshinone)

INCHI for HMDB0035220 (Cryptotanshinone)

Structure for HMDB0035220 (Cryptotanshinone)

3D Structure for HMDB0035220 (Cryptotanshinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra