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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:01:27 UTC

Update Date

2022-03-07 02:54:21 UTC

HMDB ID

HMDB0035080

Secondary Accession Numbers

HMDB35080

Metabolite Identification

Common Name

Miltirone

Description

Miltirone 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 small amount of articles have been published on Miltirone.

Structure

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

HMDB0035080
     RDKit          3D
Miltirone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.2734    0.9568    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672    0.0286   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620   -1.3714   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1087    0.1473   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085   -0.8386   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -0.7660   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934   -1.8783    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -1.7730    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -0.5869    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    0.5371   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    0.4764   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.6380   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.7444   -0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4945    1.4431   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689    2.4747   -0.8889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    1.7590   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8163    1.9920    0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087    0.8739    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.3950    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -1.5434    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -0.6100   -1.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    2.0137    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427    0.8068    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3573    0.6708    0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.3052   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089   -2.0721   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652   -1.3927   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -1.7795    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401   -1.8119    0.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.8282    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.6439    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005    2.6303   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    1.4265   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    2.0797    1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    2.9427    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    1.1870    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    0.6615    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -1.2501    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -2.4840    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357   -1.6298    1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494   -0.7686   -1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -1.5838   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6779    0.2115   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 14  4  1  0
 11  6  1  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END


  Mrv0541 05061308132D          

 21 23  0  0  0  0            999 V2000
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  9  1  0  0  0  0
 19 15  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035080

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h7-8,10-11H,5-6,9H2,1-4H3

> <INCHI_KEY>
FEFAIBOZOKSLJR-UHFFFAOYSA-N

> <FORMULA>
C19H22O2

> <MOLECULAR_WEIGHT>
282.3768

> <EXACT_MASS>
282.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.915966393007395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,8-dimethyl-2-(propan-2-yl)-3,4,5,6,7,8-hexahydrophenanthrene-3,4-dione

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
5.372757833666666

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.675596180199223

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
86.17759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
miltirone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035080
     RDKit          3D
Miltirone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.2734    0.9568    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672    0.0286   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620   -1.3714   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1087    0.1473   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085   -0.8386   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -0.7660   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934   -1.8783    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -1.7730    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -0.5869    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    0.5371   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    0.4764   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.6380   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.7444   -0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4945    1.4431   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689    2.4747   -0.8889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    1.7590   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8163    1.9920    0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087    0.8739    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.3950    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -1.5434    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -0.6100   -1.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    2.0137    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427    0.8068    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3573    0.6708    0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.3052   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089   -2.0721   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652   -1.3927   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -1.7795    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401   -1.8119    0.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.8282    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.6439    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005    2.6303   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    1.4265   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    2.0797    1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    2.9427    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    1.1870    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    0.6615    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -1.2501    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -2.4840    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357   -1.6298    1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494   -0.7686   -1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -1.5838   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6779    0.2115   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 14  4  1  0
 11  6  1  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  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      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6    9                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   15                                                       
CONECT    9    5   19                                                       
CONECT   10   12   14                                                       
CONECT   11    1    2   14                                                  
CONECT   12    7   10   16                                                  
CONECT   13    6   15   16                                                  
CONECT   14   10   11   17                                                  
CONECT   15    8   13   19                                                  
CONECT   16   12   13   18                                                  
CONECT   17   14   18   20                                                  
CONECT   18   16   17   21                                                  
CONECT   19    3    4    9   15                                             
CONECT   20   17                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0035080
HETATM    1  C1  UNL     1       5.273   0.957   0.533  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.567   0.029  -0.433  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.062  -1.371  -0.152  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.109   0.147  -0.367  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.309  -0.839  -0.097  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.849  -0.766  -0.021  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.093  -1.878   0.281  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.279  -1.773   0.350  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.923  -0.587   0.127  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.137   0.537  -0.180  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.228   0.476  -0.258  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.035   1.638  -0.567  1.00  0.00           C  
HETATM   13  O1  UNL     1       0.519   2.744  -0.779  1.00  0.00           O  
HETATM   14  C13 UNL     1       2.495   1.443  -0.617  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.169   2.475  -0.889  1.00  0.00           O  
HETATM   16  C14 UNL     1      -1.883   1.759  -0.416  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.816   1.992   0.766  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.809   0.874   0.882  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.387  -0.395   0.195  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.882  -1.543   1.107  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.062  -0.610  -1.132  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.240   2.014   0.200  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.943   0.807   1.563  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.357   0.671   0.501  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.917   0.305  -1.454  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.809  -2.072  -0.975  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.165  -1.393  -0.039  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.653  -1.779   0.793  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.740  -1.812   0.092  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.597  -2.828   0.460  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.906  -2.644   0.589  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.500   2.630  -0.859  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.655   1.426  -1.217  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.280   2.080   1.729  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.366   2.943   0.623  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.777   1.187   0.421  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.007   0.661   1.940  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.845  -1.250   1.592  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.939  -2.484   0.553  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.136  -1.630   1.926  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.249  -0.769  -1.896  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.612  -1.584  -1.133  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.678   0.212  -1.489  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   25
CONECT    3   26   27   28
CONECT    4    5    5   14
CONECT    5    6   29
CONECT    6    7    7   11
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   19
CONECT   10   11   11   16
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15
CONECT   16   17   32   33
CONECT   17   18   34   35
CONECT   18   19   36   37
CONECT   19   20   21
CONECT   20   38   39   40
CONECT   21   41   42   43
END

HMDB0035080
     RDKit          3D
Miltirone
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.2734    0.9568    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672    0.0286   -0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0620   -1.3714   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1087    0.1473   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085   -0.8386   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491   -0.7660   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0934   -1.8783    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791   -1.7730    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9232   -0.5869    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369    0.5371   -0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2281    0.4764   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347    1.6380   -0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.7444   -0.7794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4945    1.4431   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689    2.4747   -0.8889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    1.7590   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8163    1.9920    0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8087    0.8739    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873   -0.3950    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -1.5434    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0617   -0.6100   -1.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2399    2.0137    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9427    0.8068    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3573    0.6708    0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.3052   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8089   -2.0721   -0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652   -1.3927   -0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6532   -1.7795    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401   -1.8119    0.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5968   -2.8282    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.6439    0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5005    2.6303   -0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    1.4265   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799    2.0797    1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3659    2.9427    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773    1.1870    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    0.6615    1.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8451   -1.2501    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -2.4840    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1357   -1.6298    1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494   -0.7686   -1.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6122   -1.5838   -1.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6779    0.2115   -1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 14  4  1  0
 11  6  1  0
 19  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rosmariquinone	ChEMBL, HMDB
20-Nor-5,7,9,13-abietatetraene-11,12-dione	HMDB
5,6,7,8-tetrahydro-2-Isopropyl-8,8-dimethyl-3,4-phenanthraquinone	HMDB
5,6,7,8-tetrahydro-8,8-Dimethyl-2-(1-methylethyl)-3,4-phenanthrenedione, 9ci	HMDB
5,6,7,8-Tetrahydro-8,8-dimethyl-2-isopropyl-3,4-phenanthrenedione	MeSH

Chemical Formula

C₁₉H₂₂O₂

Average Molecular Weight

282.3768

Monoisotopic Molecular Weight

282.161979948

IUPAC Name

8,8-dimethyl-2-(propan-2-yl)-3,4,5,6,7,8-hexahydrophenanthrene-3,4-dione

Traditional Name

miltirone

CAS Registry Number

27210-57-7

SMILES

CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1

InChI Identifier

InChI=1S/C19H22O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h7-8,10-11H,5-6,9H2,1-4H3

InChI Key

FEFAIBOZOKSLJR-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
Hydrophenanthrene
Phenanthrene
Naphthoquinone
Naphthalene
Tetralin
Aryl ketone
Quinone
Benzenoid
Ketone
Cyclic ketone
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:34851 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035080)

Source

Endogenous

Endogenous (HMDB: HMDB0035080)

Plant

Plant (HMDB: HMDB0035080)

Animal

Animal (HMDB: HMDB0035080)

Exogenous

Food

Food (HMDB: HMDB0035080)

Herb and spice

Herb

Rosemary (FooDB: FOOD00159)
Common sage (FooDB: FOOD00165)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035080)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035080)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035080)

Lipid metabolism pathway (HMDB: HMDB0035080)

Cellular process

Cell signaling (HMDB: HMDB0035080)

Biochemical process

Lipid transport (HMDB: HMDB0035080)

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0035080)
Antioxidant (HMDB: HMDB0035080)

Pharmaceutical industry

Antineoplastic agent

Cancer preventive (HMDB: HMDB0035080)

Biological role

Energy source (HMDB: HMDB0035080)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 °C	Not Available
Boiling Point	421.00 to 422.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.053 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.916 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	4.84	ALOGPS
logP	5.37	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-8.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.18 m³·mol⁻¹	ChemAxon
Polarizability	32.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.549	31661259
DarkChem	[M-H]-	163.009	31661259
DeepCCS	[M+H]+	175.688	30932474
DeepCCS	[M-H]-	173.33	30932474
DeepCCS	[M-2H]-	207.057	30932474
DeepCCS	[M+Na]+	182.284	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	177.6	32859911
AllCCS	[M+Na-2H]-	177.5	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.24 minutes	32390414
Predicted by Siyang on May 30, 2022	19.1201 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2730.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	622.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	316.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	834.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	989.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1568.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	648.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1720.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	496.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Miltirone	CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1	3269.0	Standard polar	33892256
Miltirone	CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1	2332.0	Standard non polar	33892256
Miltirone	CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1	2403.0	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 - Miltirone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fri-0190000000-8b591eeeaf484d670821	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Miltirone 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 - Miltirone 10V, Positive-QTOF	splash10-001i-0090000000-9ec2564b6f9b90213adb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 20V, Positive-QTOF	splash10-015c-5390000000-343c6dd5681dbd8e06c8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 40V, Positive-QTOF	splash10-066u-9530000000-219319b405d5b00e0aa3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 10V, Negative-QTOF	splash10-001i-0090000000-90744d07cfd9ecf1fce8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 20V, Negative-QTOF	splash10-001i-0090000000-aa4478128c678b8319e4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 40V, Negative-QTOF	splash10-000i-1190000000-989595d18fd0f462fcce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 10V, Positive-QTOF	splash10-001i-0090000000-4260633e72f1d76ede8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 20V, Positive-QTOF	splash10-001i-0090000000-4b9d59566f55ff1ebc6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 40V, Positive-QTOF	splash10-05di-0290000000-edb318f8cfd778fb275f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 10V, Negative-QTOF	splash10-001i-0090000000-f2a094898ac4cb43c575	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 20V, Negative-QTOF	splash10-001i-0090000000-e1aa81f3aa3960c43fa2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltirone 40V, Negative-QTOF	splash10-00di-0090000000-42777c473da28859b03c	2021-09-24	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160142

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1057461

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 Miltirone (HMDB0035080)

MOL for HMDB0035080 (Miltirone)

3D MOL for HMDB0035080 (Miltirone)

3D SDF for HMDB0035080 (Miltirone)

3D-SDF for HMDB0035080 (Miltirone)

PDB for HMDB0035080 (Miltirone)

3D PDB for HMDB0035080 (Miltirone)

SMILES for HMDB0035080 (Miltirone)

INCHI for HMDB0035080 (Miltirone)

Structure for HMDB0035080 (Miltirone)

3D Structure for HMDB0035080 (Miltirone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra