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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:47:52 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036635

Secondary Accession Numbers

HMDB36635

Metabolite Identification

Common Name

Hydroxytanshinone

Description

Hydroxytanshinone belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Hydroxytanshinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0036635
     RDKit          3D
Hydroxytanshinone
 41 44  0  0  0  0  0  0  0  0999 V2000
    6.0568   -0.1078    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8327   -0.0099   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    0.1358   -1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.1809   -2.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    0.0760   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -0.0454    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.1794    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185   -0.2889    2.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916   -0.1805    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.2981    2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -0.0504    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    0.0748   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.2004   -2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.2009   -1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.0753   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.0524    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.1927    1.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349    0.9541    2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -0.3941    1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.6520    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233    0.0863   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5944   -1.2709   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.0372   -1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -0.2193   -0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.9416    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.8521    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.1949   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.2996   -2.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5135    0.3024   -2.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538   -1.1311    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.6914    3.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.2330    2.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -1.4331    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7672    1.5664    0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666    0.8319    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5511   -1.3693   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -2.0971   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883   -1.3871   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    1.2052   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    2.0134   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447    0.5916   -2.6297 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
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv0541 05061309152D          

 23 26  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
    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
    4.2475    2.1537    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
    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
    3.4354    2.2989    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
    2.9035    1.6682    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
    3.1551    3.0748    0.0000 O   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  2  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23  8  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036635

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O4/c1-9-8-23-18-10-4-5-11-15(12(20)6-7-19(11,2)3)14(10)17(22)16(21)13(9)18/h4-5,8,12,20H,6-7H2,1-3H3

> <INCHI_KEY>
UPCWCCRFMPIOAP-UHFFFAOYSA-N

> <FORMULA>
C19H18O4

> <MOLECULAR_WEIGHT>
310.3438

> <EXACT_MASS>
310.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.46542280542824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.3008834633333333

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.115854840667883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.185525092691867

> <JCHEM_POLAR_SURFACE_AREA>
67.50999999999999

> <JCHEM_REFRACTIVITY>
86.60449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036635
     RDKit          3D
Hydroxytanshinone
 41 44  0  0  0  0  0  0  0  0999 V2000
    6.0568   -0.1078    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8327   -0.0099   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    0.1358   -1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.1809   -2.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    0.0760   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -0.0454    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.1794    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185   -0.2889    2.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916   -0.1805    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.2981    2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -0.0504    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    0.0748   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.2004   -2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.2009   -1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.0753   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.0524    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.1927    1.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349    0.9541    2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -0.3941    1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.6520    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233    0.0863   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5944   -1.2709   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.0372   -1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -0.2193   -0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.9416    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.8521    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.1949   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.2996   -2.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5135    0.3024   -2.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538   -1.1311    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.6914    3.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.2330    2.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -1.4331    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7672    1.5664    0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666    0.8319    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5511   -1.3693   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -2.0971   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883   -1.3871   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    1.2052   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    2.0134   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447    0.5916   -2.6297 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
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  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       3.434   0.759   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.943   1.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.420   3.114   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       5.890   5.740   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.373   6.011   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.180   1.533   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   19                                                       
CONECT    8    9   23                                                       
CONECT    9    1    8   13                                                  
CONECT   10    4   14   18                                                  
CONECT   11    5   15   19                                                  
CONECT   12    6   15   20                                                  
CONECT   13    9   16   18                                                  
CONECT   14   10   15   17                                                  
CONECT   15   11   12   14                                                  
CONECT   16   13   17   21                                                  
CONECT   17   14   16   22                                                  
CONECT   18   10   13   23                                                  
CONECT   19    2    3    7   11                                             
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0036635
HETATM    1  C1  UNL     1       6.057  -0.108   0.477  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.833  -0.010  -0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.722   0.136  -1.735  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.464   0.181  -2.065  1.00  0.00           O  
HETATM    5  C4  UNL     1       2.683   0.076  -1.004  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.521  -0.045   0.084  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.955  -0.179   1.405  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.719  -0.289   2.387  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.492  -0.181   1.531  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.049  -0.298   2.688  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.616  -0.050   0.360  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.230   0.075  -0.879  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.436   0.200  -2.000  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.929   0.201  -1.888  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.511   0.075  -0.647  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.758  -0.052   0.496  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.358  -0.193   1.849  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.235   0.954   2.626  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.882  -0.394   1.737  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.378   0.652   0.760  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.023   0.086  -0.601  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.594  -1.271  -0.840  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.575   1.037  -1.634  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.920  -0.219  -0.221  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.006  -0.942   1.210  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.258   0.852   1.027  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.606   0.195  -2.368  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.929   0.300  -2.983  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.514   0.302  -2.798  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.054  -1.131   2.371  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.460   0.691   3.551  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.341  -0.233   2.716  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.062  -1.433   1.347  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.767   1.566   0.905  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.467   0.832   0.862  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.551  -1.369  -0.272  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.890  -2.097  -0.633  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.888  -1.387  -1.917  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.644   1.205  -1.372  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.069   2.013  -1.543  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.545   0.592  -2.630  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    6
CONECT    3    4   27
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   28
CONECT   14   15   29
CONECT   15   16   16   21
CONECT   16   17
CONECT   17   18   19   30
CONECT   18   31
CONECT   19   20   32   33
CONECT   20   21   34   35
CONECT   21   22   23
CONECT   22   36   37   38
CONECT   23   39   40   41
END

HMDB0036635
     RDKit          3D
Hydroxytanshinone
 41 44  0  0  0  0  0  0  0  0999 V2000
    6.0568   -0.1078    0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8327   -0.0099   -0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    0.1358   -1.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.1809   -2.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6832    0.0760   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -0.0454    0.0840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9550   -0.1794    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185   -0.2889    2.3870 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916   -0.1805    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -0.2981    2.6882 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -0.0504    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    0.0748   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.2004   -2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.2009   -1.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107    0.0753   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581   -0.0524    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585   -0.1927    1.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349    0.9541    2.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -0.3941    1.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785    0.6520    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233    0.0863   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5944   -1.2709   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.0372   -1.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -0.2193   -0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0062   -0.9416    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2582    0.8521    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6063    0.1949   -2.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.2996   -2.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5135    0.3024   -2.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538   -1.1311    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4595    0.6914    3.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.2330    2.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -1.4331    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7672    1.5664    0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666    0.8319    0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5511   -1.3693   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905   -2.0971   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8883   -1.3871   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    1.2052   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0687    2.0134   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5447    0.5916   -2.6297 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
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6  2  1  0
 16 11  1  0
 12  5  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Hydroxy-14,16-epoxy-20-nor-5(10),6,8,13,15-abietapentaene-11,12-dione	HMDB

Chemical Formula

C₁₉H₁₈O₄

Average Molecular Weight

310.3438

Monoisotopic Molecular Weight

310.120509064

IUPAC Name

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

Traditional Name

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

CAS Registry Number

18887-18-8

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C

InChI Identifier

InChI=1S/C19H18O4/c1-9-8-23-18-10-4-5-11-15(12(20)6-7-19(11,2)3)14(10)17(22)16(21)13(9)18/h4-5,8,12,20H,6-7H2,1-3H3

InChI Key

UPCWCCRFMPIOAP-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036635)
Cell membrane (HMDB: HMDB0036635)

Cellular substructure

Extracellular (HMDB: HMDB0036635)
Membrane (HMDB: HMDB0036635)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036635)

Source

Endogenous

Endogenous (HMDB: HMDB0036635)

Plant

Plant (HMDB: HMDB0036635)

Animal

Animal (HMDB: HMDB0036635)

Exogenous

Food

Food (HMDB: HMDB0036635)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036635)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036635)

Cellular process

Cell signaling (HMDB: HMDB0036635)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036635)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036635)

Nutrient

Nutrient (HMDB: HMDB0036635)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036635)

Emulsifier (HMDB: HMDB0036635)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 °C	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
Water Solubility	0.033 g/L	ALOGPS
logP	3.14	ALOGPS
logP	3.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.6 m³·mol⁻¹	ChemAxon
Polarizability	33.47 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]+	172.201	31661259
DarkChem	[M-H]-	170.105	31661259
DeepCCS	[M+H]+	173.132	30932474
DeepCCS	[M-H]-	170.774	30932474
DeepCCS	[M-2H]-	204.738	30932474
DeepCCS	[M+Na]+	179.966	30932474
AllCCS	[M+H]+	172.5	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.6	32859911
AllCCS	[M+Na]+	176.5	32859911
AllCCS	[M-H]-	180.6	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxytanshinone	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C	3696.5	Standard polar	33892256
Hydroxytanshinone	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C	2667.6	Standard non polar	33892256
Hydroxytanshinone	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C	2944.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxytanshinone,1TMS,isomer #1	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O[Si](C)(C)C)CCC2(C)C	2842.6	Semi standard non polar	33892256
Hydroxytanshinone,1TBDMS,isomer #1	CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O[Si](C)(C)C(C)(C)C)CCC2(C)C	3063.9	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 - Hydroxytanshinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0190000000-303b948cd84ab5b3c3c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxytanshinone GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-4039000000-f23fce8c9e528aaac142	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxytanshinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxytanshinone 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 - Hydroxytanshinone 10V, Positive-QTOF	splash10-01ox-0095000000-1459090115953e2d8ada	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Positive-QTOF	splash10-0006-1091000000-9b160e8f70ba1ebd0e8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Positive-QTOF	splash10-0v4l-4290000000-673a83937492b73d2faf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Negative-QTOF	splash10-0a4i-0029000000-857494f71efc4fd3d067	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Negative-QTOF	splash10-0a4i-0069000000-e26deb1c0ad2f400236e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Negative-QTOF	splash10-004j-0190000000-fc4e16c2c20e31bada31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Negative-QTOF	splash10-0a4i-0029000000-fac4878c9215b2cd3161	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Negative-QTOF	splash10-0a4l-0069000000-4fb07203823f1c3c868f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Negative-QTOF	splash10-004l-0191000000-b9d77947a2efacfb4303	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 10V, Positive-QTOF	splash10-03di-0049000000-095cdc9f44d9d61d2906	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 20V, Positive-QTOF	splash10-040r-0091000000-91de6cd8c46488f5e66a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxytanshinone 40V, Positive-QTOF	splash10-0ue9-0090000000-cd483d43e8533af44a90	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB015555

KNApSAcK ID

Not Available

Chemspider ID

4476947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318349

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

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 Hydroxytanshinone (HMDB0036635)

MOL for HMDB0036635 (Hydroxytanshinone)

3D MOL for HMDB0036635 (Hydroxytanshinone)

3D SDF for HMDB0036635 (Hydroxytanshinone)

3D-SDF for HMDB0036635 (Hydroxytanshinone)

PDB for HMDB0036635 (Hydroxytanshinone)

3D PDB for HMDB0036635 (Hydroxytanshinone)

SMILES for HMDB0036635 (Hydroxytanshinone)

INCHI for HMDB0036635 (Hydroxytanshinone)

Structure for HMDB0036635 (Hydroxytanshinone)

3D Structure for HMDB0036635 (Hydroxytanshinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra