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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:04:11 UTC

Update Date

2022-03-07 02:54:44 UTC

HMDB ID

HMDB0036005

Secondary Accession Numbers

HMDB36005

Metabolite Identification

Common Name

Istanbulin B

Description

Istanbulin B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Istanbulin B.

Structure

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

HMDB0036005
     RDKit          3D
Istanbulin B
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3815   -1.8335    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776   -0.4151    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    0.0318    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.5557    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -0.2469   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -0.7929   -1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8387   -0.9058    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.0951    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -0.2719   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    1.2131   -0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.7466   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    2.5242   -1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973    1.2511   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    1.7681   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    1.5106    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.8690   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081    0.7204   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231    0.6405   -0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -2.1978    1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.4898   -0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4499   -1.9290    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -0.0126    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936   -1.6281    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2120   -0.7062   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441   -0.3716   -2.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -1.9039   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -1.9580   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2702   -1.4269    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574   -0.2107    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.9352    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9398   -0.7351   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325   -0.5401   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.5680   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.4704    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615    1.6279    0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854    1.2961   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346    2.8471   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    2.0771    1.1763 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  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 15  3  1  0
 13  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
M  END

  Mrv0541 05061308502D          

 18 20  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036005

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(=O)C2CC3OC(=O)C(C)=C3CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-12(16)11-6-13-10(7-15(8,11)3)9(2)14(17)18-13/h8,11,13H,4-7H2,1-3H3

> <INCHI_KEY>
IXMDYOSMFGVWJY-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.071694932031466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2,8-dione

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.758732824666667

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.80072645897151

> <JCHEM_PKA_STRONGEST_BASIC>
-6.773805241877606

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.8161

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,5-trimethyl-4H,5H,6H,7H,8aH,9H,9aH-naphtho[2,3-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036005
     RDKit          3D
Istanbulin B
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3815   -1.8335    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776   -0.4151    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    0.0318    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.5557    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -0.2469   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -0.7929   -1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8387   -0.9058    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.0951    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -0.2719   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    1.2131   -0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.7466   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    2.5242   -1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973    1.2511   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    1.7681   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    1.5106    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.8690   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081    0.7204   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231    0.6405   -0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -2.1978    1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.4898   -0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4499   -1.9290    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -0.0126    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936   -1.6281    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2120   -0.7062   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441   -0.3716   -2.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -1.9039   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -1.9580   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2702   -1.4269    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574   -0.2107    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.9352    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9398   -0.7351   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325   -0.5401   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.5680   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.4704    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615    1.6279    0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854    1.2961   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346    2.8471   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    2.0771    1.1763 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  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 15  3  1  0
 13  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.578  -1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   12                                                       
CONECT    6   11   13                                                       
CONECT    7   10   15                                                       
CONECT    8    1    4   15                                                  
CONECT    9    2   10   14                                                  
CONECT   10    7    9   13                                                  
CONECT   11    6   12   15                                                  
CONECT   12    5   11   16                                                  
CONECT   13    6   10   18                                                  
CONECT   14    9   17   18                                                  
CONECT   15    3    7    8   11                                             
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0036005
HETATM    1  C1  UNL     1       3.382  -1.833   0.464  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.978  -0.415   0.313  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.773   0.032   0.538  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.459  -0.556   0.974  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.536  -0.247  -0.153  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.101  -0.793  -1.420  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.839  -0.906   0.082  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.148  -1.095   1.568  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.024  -0.272  -0.547  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.080   1.213  -0.453  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.787   1.747  -0.943  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.734   2.524  -1.843  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.597   1.251  -0.245  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.702   1.768  -0.792  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.750   1.511   0.280  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.036   1.869  -0.109  1.00  0.00           O  
HETATM   17  C15 UNL     1       3.808   0.720  -0.099  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.023   0.641  -0.392  1.00  0.00           O  
HETATM   19  H1  UNL     1       3.247  -2.198   1.502  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.813  -2.490  -0.221  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.450  -1.929   0.204  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.185  -0.013   1.903  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.594  -1.628   1.117  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.212  -0.706  -1.396  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.344  -0.372  -2.332  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.099  -1.904  -1.398  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.767  -1.958  -0.325  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.270  -1.427   2.127  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.657  -0.211   1.970  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.899  -1.935   1.626  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.940  -0.735  -0.086  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.032  -0.540  -1.640  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.947   1.568  -1.036  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.193   1.470   0.640  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.661   1.628   0.818  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.985   1.296  -1.758  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.635   2.847  -0.951  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.425   2.077   1.176  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4   15
CONECT    4    5   22   23
CONECT    5    6    7   13
CONECT    6   24   25   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   13
CONECT   13   14   35
CONECT   14   15   36   37
CONECT   15   16   38
CONECT   16   17
CONECT   17   18   18
END

HMDB0036005
     RDKit          3D
Istanbulin B
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.3815   -1.8335    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9776   -0.4151    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7730    0.0318    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.5557    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -0.2469   -0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1007   -0.7929   -1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8387   -0.9058    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.0951    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -0.2719   -0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    1.2131   -0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867    1.7466   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    2.5242   -1.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973    1.2511   -0.2449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    1.7681   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7503    1.5106    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    1.8690   -0.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081    0.7204   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231    0.6405   -0.3917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -2.1978    1.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -2.4898   -0.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4499   -1.9290    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -0.0126    1.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5936   -1.6281    1.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2120   -0.7062   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441   -0.3716   -2.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995   -1.9039   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670   -1.9580   -0.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2702   -1.4269    2.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574   -0.2107    1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994   -1.9352    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9398   -0.7351   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0325   -0.5401   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    1.5680   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929    1.4704    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615    1.6279    0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854    1.2961   -1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346    2.8471   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    2.0771    1.1763 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  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17  2  1  0
 15  3  1  0
 13  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2,8-dione

Traditional Name

3,4a,5-trimethyl-4H,5H,6H,7H,8aH,9H,9aH-naphtho[2,3-b]furan-2,8-dione

CAS Registry Number

12656-97-2

SMILES

CC1CCC(=O)C2CC3OC(=O)C(C)=C3CC12C

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-12(16)11-6-13-10(7-15(8,11)3)9(2)14(17)18-13/h8,11,13H,4-7H2,1-3H3

InChI Key

IXMDYOSMFGVWJY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036005)

Source

Endogenous

Endogenous (HMDB: HMDB0036005)

Plant

Plant (HMDB: HMDB0036005)

Animal

Animal (HMDB: HMDB0036005)

Exogenous

Food

Food (HMDB: HMDB0036005)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0036005)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036005)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036005)

Lipid metabolism pathway (HMDB: HMDB0036005)

Cellular process

Cell signaling (HMDB: HMDB0036005)

Biochemical process

Lipid transport (HMDB: HMDB0036005)

Role

Biological role

Energy source (HMDB: HMDB0036005)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036005)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	848.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.76	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.8	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.82 m³·mol⁻¹	ChemAxon
Polarizability	27.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.71	31661259
DarkChem	[M-H]-	155.215	31661259
DeepCCS	[M-2H]-	192.947	30932474
DeepCCS	[M+Na]+	168.261	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Istanbulin B	CC1CCC(=O)C2CC3OC(=O)C(C)=C3CC12C	3066.1	Standard polar	33892256
Istanbulin B	CC1CCC(=O)C2CC3OC(=O)C(C)=C3CC12C	2062.8	Standard non polar	33892256
Istanbulin B	CC1CCC(=O)C2CC3OC(=O)C(C)=C3CC12C	2286.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Istanbulin B,1TMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2OC1=O	2252.3	Semi standard non polar	33892256
Istanbulin B,1TMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2OC1=O	2056.8	Standard non polar	33892256
Istanbulin B,1TMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2OC1=O	2238.7	Semi standard non polar	33892256
Istanbulin B,1TMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2OC1=O	2011.7	Standard non polar	33892256
Istanbulin B,1TBDMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2OC1=O	2457.4	Semi standard non polar	33892256
Istanbulin B,1TBDMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2OC1=O	2317.9	Standard non polar	33892256
Istanbulin B,1TBDMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2OC1=O	2440.4	Semi standard non polar	33892256
Istanbulin B,1TBDMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2OC1=O	2209.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Istanbulin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kg9-1950000000-11cdf9bcdc5ffa69e84a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Istanbulin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Istanbulin B 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 - Istanbulin B 10V, Positive-QTOF	splash10-002b-0890000000-41562d7c14d90b7bf32c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 20V, Positive-QTOF	splash10-004i-1910000000-c94159b76c22b92a39ba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 40V, Positive-QTOF	splash10-0k96-9500000000-99d108768c84354e9374	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 10V, Negative-QTOF	splash10-0002-0190000000-fdd99c78a54b2e3b7362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 20V, Negative-QTOF	splash10-0f6t-0090000000-f010e21e684a96f277a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 40V, Negative-QTOF	splash10-0udr-2930000000-32fa9f1067c1577ff221	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 10V, Positive-QTOF	splash10-0002-0090000000-49680131e353d9de1199	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 20V, Positive-QTOF	splash10-0002-0290000000-018d7e62bed33a4e42c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 40V, Positive-QTOF	splash10-03di-1910000000-6eb8f8fa40007c44f8e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 20V, Negative-QTOF	splash10-0002-0090000000-3ef26a39d49de07a33cd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin B 40V, Negative-QTOF	splash10-0002-0590000000-b400755cba5892ca3540	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB014818

KNApSAcK ID

C00017440

Chemspider ID

35014062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751897

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853121

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 Istanbulin B (HMDB0036005)

MOL for HMDB0036005 (Istanbulin B)

3D MOL for HMDB0036005 (Istanbulin B)

3D SDF for HMDB0036005 (Istanbulin B)

3D-SDF for HMDB0036005 (Istanbulin B)

PDB for HMDB0036005 (Istanbulin B)

3D PDB for HMDB0036005 (Istanbulin B)

SMILES for HMDB0036005 (Istanbulin B)

INCHI for HMDB0036005 (Istanbulin B)

Structure for HMDB0036005 (Istanbulin B)

3D Structure for HMDB0036005 (Istanbulin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra