Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:17:54 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037055

Secondary Accession Numbers

HMDB37055

Metabolite Identification

Common Name

Istanbulin A

Description

Istanbulin A 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 significant number of articles have been published on Istanbulin A.

Structure

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

HMDB0037055
     RDKit          3D
Istanbulin A
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1785   -1.7838    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -0.4356    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932   -0.1442   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319   -0.9427   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.1404   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -0.0799   -2.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.0429   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256   -0.8133   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -0.9271    1.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576    0.4333    1.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    1.3817    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330    2.3759    1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    1.2203   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    1.9124    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    1.2585   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    1.4039   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.7509    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.7557    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7938    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -2.2295    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082   -2.4662    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.6158    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486   -1.5443   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -1.7100    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -0.6206   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    0.9957   -2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222   -0.5206   -2.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -2.1132   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -1.6332   -1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.9352   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169    0.1854   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -1.0580    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -1.6737    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.6287    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.6171    2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2068    1.8887   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6303    2.9851   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    1.9508    1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594    1.8925   -2.1164 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
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
M  END


  Mrv0541 05061309322D          

 19 21  0  0  0  0            999 V2000
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -1.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    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  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037055

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h8,11,18H,4-7H2,1-3H3

> <INCHI_KEY>
HYBIDSYXKTYHCM-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.875887724665006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.340347317000001

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.272160350718174

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.241428917722313

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4427988906254265

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
69.3938

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.89e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037055
     RDKit          3D
Istanbulin A
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1785   -1.7838    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -0.4356    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932   -0.1442   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319   -0.9427   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.1404   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -0.0799   -2.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.0429   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256   -0.8133   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -0.9271    1.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576    0.4333    1.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    1.3817    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330    2.3759    1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    1.2203   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    1.9124    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    1.2585   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    1.4039   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.7509    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.7557    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7938    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -2.2295    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082   -2.4662    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.6158    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486   -1.5443   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -1.7100    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -0.6206   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    0.9957   -2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222   -0.5206   -2.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -2.1132   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -1.6332   -1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.9352   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169    0.1854   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -1.0580    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -1.6737    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.6287    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.6171    2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2068    1.8887   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6303    2.9851   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    1.9508    1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594    1.8925   -2.1164 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
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  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       7.591   1.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   1.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.429  -3.604   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    5    8                                                       
CONECT    5    4   12                                                       
CONECT    6   10   14                                                       
CONECT    7   11   15                                                       
CONECT    8    1    4   14                                                  
CONECT    9    2   10   13                                                  
CONECT   10    6    9   15                                                  
CONECT   11    7   12   14                                                  
CONECT   12    5   11   16                                                  
CONECT   13    9   17   19                                                  
CONECT   14    3    6    8   11                                             
CONECT   15    7   10   18   19                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0037055
HETATM    1  C1  UNL     1       3.178  -1.784   1.263  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.865  -0.436   0.670  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.793  -0.144  -0.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.632  -0.943  -0.393  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.613  -0.140  -0.658  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.768  -0.080  -2.168  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.770  -1.043  -0.199  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.026  -0.813  -0.999  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.990  -0.927   1.291  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.558   0.433   1.547  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.517   1.382   1.108  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.333   2.376   1.799  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.674   1.220  -0.111  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.617   1.912   0.172  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.821   1.258  -0.441  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.873   1.404  -1.821  1.00  0.00           O  
HETATM   17  O3  UNL     1       3.010   1.751   0.085  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.696   0.756   0.764  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.801   0.794   1.359  1.00  0.00           O  
HETATM   20  H1  UNL     1       2.207  -2.229   1.582  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.608  -2.466   0.518  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.828  -1.616   2.147  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.949  -1.544  -1.298  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.474  -1.710   0.399  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.629  -0.621  -2.561  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.757   0.996  -2.513  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.122  -0.521  -2.704  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.486  -2.113  -0.363  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.198  -1.633  -1.758  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.910  -0.935  -0.305  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.117   0.185  -1.424  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.024  -1.058   1.779  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.748  -1.674   1.564  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.454   0.629   0.913  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.816   0.617   2.602  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.207   1.889  -0.861  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.630   2.985  -0.142  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.828   1.951   1.282  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.659   1.892  -2.116  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   15
CONECT    4    5   23   24
CONECT    5    6    7   13
CONECT    6   25   26   27
CONECT    7    8    9   28
CONECT    8   29   30   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   12   13
CONECT   13   14   36
CONECT   14   15   37   38
CONECT   15   16   17
CONECT   16   39
CONECT   17   18
CONECT   18   19   19
END

HMDB0037055
     RDKit          3D
Istanbulin A
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1785   -1.7838    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -0.4356    0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7932   -0.1442   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319   -0.9427   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -0.1404   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -0.0799   -2.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.0429   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256   -0.8133   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9902   -0.9271    1.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5576    0.4333    1.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167    1.3817    1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3330    2.3759    1.7989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742    1.2203   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6173    1.9124    0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8207    1.2585   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    1.4039   -1.8212 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.7509    0.0846 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962    0.7557    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8006    0.7938    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -2.2295    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6082   -2.4662    0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8280   -1.6158    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486   -1.5443   -1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743   -1.7100    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -0.6206   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565    0.9957   -2.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222   -0.5206   -2.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -2.1132   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1982   -1.6332   -1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -0.9352   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169    0.1854   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243   -1.0580    1.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7479   -1.6737    1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.6287    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.6171    2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2068    1.8887   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6303    2.9851   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    1.9508    1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594    1.8925   -2.1164 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
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 15  3  1  0
 13  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
ent-8a-Hydroxy-1-oxo-7(11)-eremophilen-12,8-olide	HMDB
Istanbulin-a	HMDB, MeSH
Istanbulin a	MeSH

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

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

Traditional Name

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

CAS Registry Number

35481-83-5

SMILES

CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C

InChI Identifier

InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h8,11,18H,4-7H2,1-3H3

InChI Key

HYBIDSYXKTYHCM-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
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
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: HMDB0037055)

Source

Endogenous

Endogenous (HMDB: HMDB0037055)

Plant

Plant (HMDB: HMDB0037055)

Animal

Animal (HMDB: HMDB0037055)

Exogenous

Food

Food (HMDB: HMDB0037055)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0037055)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037055)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037055)

Lipid metabolism pathway (HMDB: HMDB0037055)

Cellular process

Cell signaling (HMDB: HMDB0037055)

Biochemical process

Lipid transport (HMDB: HMDB0037055)

Role

Biological role

Energy source (HMDB: HMDB0037055)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037055)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1013 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	0.89 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2.34	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.39 m³·mol⁻¹	ChemAxon
Polarizability	27.88 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]+	162.566	31661259
DarkChem	[M-H]-	155.603	31661259
DeepCCS	[M-2H]-	193.176	30932474
DeepCCS	[M+Na]+	168.595	30932474
AllCCS	[M+H]+	161.1	32859911
AllCCS	[M+H-H2O]+	157.5	32859911
AllCCS	[M+NH4]+	164.4	32859911
AllCCS	[M+Na]+	165.4	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	167.4	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.	6.24 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3901 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2397.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	332.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	162.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	515.0 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	654.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	67.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1057.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	436.2 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	1365.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	284.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	223.4 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	63.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Istanbulin A	CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C	3381.9	Standard polar	33892256
Istanbulin A	CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C	2130.0	Standard non polar	33892256
Istanbulin A	CC1CCC(=O)C2CC3(O)OC(=O)C(C)=C3CC12C	2301.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Istanbulin A,1TMS,isomer #1	CC1=C2CC3(C)C(C)CCC(=O)C3CC2(O[Si](C)(C)C)OC1=O	2294.3	Semi standard non polar	33892256
Istanbulin A,1TMS,isomer #2	CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O)OC1=O	2292.3	Semi standard non polar	33892256
Istanbulin A,1TMS,isomer #3	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O)OC1=O	2250.9	Semi standard non polar	33892256
Istanbulin A,2TMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O[Si](C)(C)C)OC1=O	2386.2	Semi standard non polar	33892256
Istanbulin A,2TMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C)CCC3C)CC2(O[Si](C)(C)C)OC1=O	2257.7	Standard non polar	33892256
Istanbulin A,2TMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O[Si](C)(C)C)OC1=O	2364.9	Semi standard non polar	33892256
Istanbulin A,2TMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C)C3CC2(O[Si](C)(C)C)OC1=O	2172.6	Standard non polar	33892256
Istanbulin A,1TBDMS,isomer #1	CC1=C2CC3(C)C(C)CCC(=O)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2524.1	Semi standard non polar	33892256
Istanbulin A,1TBDMS,isomer #2	CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O)OC1=O	2512.5	Semi standard non polar	33892256
Istanbulin A,1TBDMS,isomer #3	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O)OC1=O	2470.2	Semi standard non polar	33892256
Istanbulin A,2TBDMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2836.5	Semi standard non polar	33892256
Istanbulin A,2TBDMS,isomer #1	CC1=C2CC3(C)C(=C(O[Si](C)(C)C(C)(C)C)CCC3C)CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2785.6	Standard non polar	33892256
Istanbulin A,2TBDMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2804.7	Semi standard non polar	33892256
Istanbulin A,2TBDMS,isomer #2	CC1=C2CC3(C)C(C)CC=C(O[Si](C)(C)C(C)(C)C)C3CC2(O[Si](C)(C)C(C)(C)C)OC1=O	2568.3	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1960000000-61907d8d15b1cbc582d5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Istanbulin A GC-MS (1 TMS) - 70eV, Positive	splash10-009i-8594000000-e3d285e622927e744842	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Istanbulin A 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 A 10V, Positive-QTOF	splash10-014i-0390000000-4bbdc72d7be928afeddd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 20V, Positive-QTOF	splash10-00ke-2960000000-2441ad518e158dd2ba9f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 40V, Positive-QTOF	splash10-0k97-9300000000-ea930d4bee3a28712293	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 10V, Negative-QTOF	splash10-03di-0090000000-ca8ed823a3d7b408e00c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 20V, Negative-QTOF	splash10-0900-0090000000-2beb80d806f8e4bfb86b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 40V, Negative-QTOF	splash10-00l6-5690000000-c385f2ffc88d58522478	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 10V, Negative-QTOF	splash10-03di-0090000000-16d43704d08f3756e03a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 20V, Negative-QTOF	splash10-03di-0090000000-cf4dd69ba3cf077e83ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 40V, Negative-QTOF	splash10-03ki-2890000000-0da57c6995395368a5c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 10V, Positive-QTOF	splash10-014i-0090000000-8d9e65027e815d92f341	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 20V, Positive-QTOF	splash10-014i-0290000000-dc1ee00146a9b0d0427c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Istanbulin A 40V, Positive-QTOF	splash10-00si-3920000000-48bfbf4c83ccd0e454ab	2021-09-24	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

FDB016038

KNApSAcK ID

C00017304

Chemspider ID

35014361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304519

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1858991

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 A (HMDB0037055)

MOL for HMDB0037055 (Istanbulin A)

3D MOL for HMDB0037055 (Istanbulin A)

3D SDF for HMDB0037055 (Istanbulin A)

3D-SDF for HMDB0037055 (Istanbulin A)

PDB for HMDB0037055 (Istanbulin A)

3D PDB for HMDB0037055 (Istanbulin A)

SMILES for HMDB0037055 (Istanbulin A)

INCHI for HMDB0037055 (Istanbulin A)

Structure for HMDB0037055 (Istanbulin A)

3D Structure for HMDB0037055 (Istanbulin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra