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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:15:40 UTC

Update Date

2022-03-07 02:54:49 UTC

HMDB ID

HMDB0036202

Secondary Accession Numbers

HMDB36202

Metabolite Identification

Common Name

Alkhanin

Description

Alkhanin belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Alkhanin.

Structure

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

HMDB0036202
     RDKit          3D
Alkhanin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4840    3.0886   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    1.7976   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    0.6932    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.7322    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    1.5149   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    1.0309   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    1.6655   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871   -0.3102   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.2898   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -0.6575   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.7013    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.5762    1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -0.6283    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2890   -1.1931   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -0.4451    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -0.1200    2.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3786    0.5305   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    1.7893   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    2.8198   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    3.9522   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124    3.2261    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403    3.1881   -1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    1.0174    1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.1877    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821   -1.4347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.2624   -0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -0.9348   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2936   -0.8348   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956   -2.6999    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.7533    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.5589    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -1.1857    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -2.1380   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453   -0.4409   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728   -1.3592   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.4661    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -0.6574    2.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7415    0.0555   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907    0.7335    0.5992 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 13  3  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061308562D          

 19 21  0  0  0  0            999 V2000
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036202

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC3(C)C(O)CC(=O)C(C)=C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7,9,11,13,17H,4-6H2,1-3H3

> <INCHI_KEY>
RARZBOWMYCHUMB-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.049581493451644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.5284496143333333

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.48094471573675

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.442525939972263

> <JCHEM_PKA_STRONGEST_BASIC>
-3.040846152156649

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
69.1006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3,5a,9-trimethyl-3H,3aH,4H,5H,6H,7H,9bH-naphtho[1,2-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036202
     RDKit          3D
Alkhanin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4840    3.0886   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    1.7976   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    0.6932    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.7322    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    1.5149   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    1.0309   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    1.6655   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871   -0.3102   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.2898   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -0.6575   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.7013    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.5762    1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -0.6283    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2890   -1.1931   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -0.4451    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -0.1200    2.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3786    0.5305   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    1.7893   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    2.8198   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    3.9522   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124    3.2261    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403    3.1881   -1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    1.0174    1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.1877    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821   -1.4347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.2624   -0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -0.9348   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2936   -0.8348   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956   -2.6999    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.7533    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.5589    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -1.1857    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -2.1380   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453   -0.4409   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728   -1.3592   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.4661    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -0.6574    2.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7415    0.0555   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907    0.7335    0.5992 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 13  3  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 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       7.895   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790  -1.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.417   3.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   15                                                       
CONECT    6   10   11                                                       
CONECT    7    1    9   14                                                  
CONECT    8    2   10   12                                                  
CONECT    9    4    7   13                                                  
CONECT   10    6    8   16                                                  
CONECT   11    6   15   17                                                  
CONECT   12    8   13   15                                                  
CONECT   13    9   12   19                                                  
CONECT   14    7   18   19                                                  
CONECT   15    3    5   11   12                                             
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036202
HETATM    1  C1  UNL     1      -0.484   3.089  -0.155  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.193   1.798  -0.104  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.488   0.693   0.053  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.945   0.732   0.175  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.666   1.515  -0.736  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.969   1.031  -0.689  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.954   1.666  -1.138  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.987  -0.310  -0.042  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.855  -1.290  -0.779  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.497  -0.657  -0.187  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.024  -1.701   0.743  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.424  -1.576   1.057  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.163  -0.628   0.112  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.289  -1.193  -1.264  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.548  -0.445   0.755  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.365  -0.120   2.085  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.379   0.531  -0.007  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.649   1.789  -0.227  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.312   2.820  -0.515  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.189   3.952  -0.096  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.212   3.226   0.712  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.040   3.188  -1.126  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.312   1.017   1.196  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.255  -0.188   1.005  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.782  -1.435  -0.187  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.326  -2.262  -0.789  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.135  -0.935  -1.783  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.294  -0.835  -1.241  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.196  -2.700   0.245  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.593  -1.753   1.688  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.928  -2.559   0.968  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.607  -1.186   2.080  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.709  -2.138  -1.408  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.945  -0.441  -2.000  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.373  -1.359  -1.475  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.007  -1.466   0.729  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.958  -0.657   2.690  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.741   0.056  -0.942  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.291   0.733   0.599  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   13
CONECT    4    5   10   23
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   24
CONECT    9   25   26   27
CONECT   10   11   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15
CONECT   14   33   34   35
CONECT   15   16   17   36
CONECT   16   37
CONECT   17   18   38   39
CONECT   18   19   19
END

HMDB0036202
     RDKit          3D
Alkhanin
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4840    3.0886   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1934    1.7976   -0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    0.6932    0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.7322    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663    1.5149   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9692    1.0309   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    1.6655   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871   -0.3102   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -1.2898   -0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4970   -0.6575   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.7013    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -1.5762    1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1634   -0.6283    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2890   -1.1931   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479   -0.4451    0.7553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3646   -0.1200    2.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3786    0.5305   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6495    1.7893   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3117    2.8198   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    3.9522   -0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2124    3.2261    0.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403    3.1881   -1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    1.0174    1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -0.1877    1.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7821   -1.4347   -0.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -2.2624   -0.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1354   -0.9348   -1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2936   -0.8348   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956   -2.6999    0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.7533    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.5589    0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6071   -1.1857    2.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087   -2.1380   -1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453   -0.4409   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728   -1.3592   -1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -1.4661    0.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -0.6574    2.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7415    0.0555   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907    0.7335    0.5992 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
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18  2  1  0
 13  3  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1a-Hydroxy-3-oxo-4-eudesmen-12,6a-olide	HMDB
Alhanin	HMDB
Dehydroisoerivanin	HMDB
[3S-(3alpha,3Aalpha,5abeta,6alpha,9bbeta)]-3a,5,5a,6,7,9b-hexahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

6-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9bH-naphtho[1,2-b]furan-2,8-dione

Traditional Name

6-hydroxy-3,5a,9-trimethyl-3H,3aH,4H,5H,6H,7H,9bH-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

71327-31-6

SMILES

CC1C2CCC3(C)C(O)CC(=O)C(C)=C3C2OC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7,9,11,13,17H,4-6H2,1-3H3

InChI Key

RARZBOWMYCHUMB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036202)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036202)

Source

Endogenous

Endogenous (HMDB: HMDB0036202)

Plant

Plant (HMDB: HMDB0036202)

Animal

Animal (HMDB: HMDB0036202)

Exogenous

Food

Food (HMDB: HMDB0036202)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036202)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036202)

Cellular process

Cell signaling (HMDB: HMDB0036202)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036202)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036202)

Nutrient

Nutrient (HMDB: HMDB0036202)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036202)

Emulsifier (HMDB: HMDB0036202)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	201 - 203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	26090 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	1.26 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.53	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-3	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	69.1 m³·mol⁻¹	ChemAxon
Polarizability	28.05 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]+	160.822	31661259
DarkChem	[M-H]-	158.929	31661259
DeepCCS	[M+H]+	164.629	30932474
DeepCCS	[M-H]-	162.271	30932474
DeepCCS	[M-2H]-	195.157	30932474
DeepCCS	[M+Na]+	170.722	30932474
AllCCS	[M+H]+	161.6	32859911
AllCCS	[M+H-H2O]+	158.1	32859911
AllCCS	[M+NH4]+	164.9	32859911
AllCCS	[M+Na]+	165.9	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alkhanin	CC1C2CCC3(C)C(O)CC(=O)C(C)=C3C2OC1=O	3416.9	Standard polar	33892256
Alkhanin	CC1C2CCC3(C)C(O)CC(=O)C(C)=C3C2OC1=O	2223.8	Standard non polar	33892256
Alkhanin	CC1C2CCC3(C)C(O)CC(=O)C(C)=C3C2OC1=O	2325.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alkhanin,1TMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C)CC1=O	2304.0	Semi standard non polar	33892256
Alkhanin,1TMS,isomer #2	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O)C=C1O[Si](C)(C)C	2336.2	Semi standard non polar	33892256
Alkhanin,2TMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2368.1	Semi standard non polar	33892256
Alkhanin,2TMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C)C=C1O[Si](C)(C)C	2270.8	Standard non polar	33892256
Alkhanin,1TBDMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C(C)(C)C)CC1=O	2515.0	Semi standard non polar	33892256
Alkhanin,1TBDMS,isomer #2	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O)C=C1O[Si](C)(C)C(C)(C)C	2548.8	Semi standard non polar	33892256
Alkhanin,2TBDMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2782.9	Semi standard non polar	33892256
Alkhanin,2TBDMS,isomer #1	CC1=C2C3OC(=O)C(C)C3CCC2(C)C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2714.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alkhanin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-3970000000-822afb4532f2c21cd7d8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alkhanin GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-3192000000-1a359eaddb46f72bf1c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alkhanin 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 - Alkhanin 10V, Positive-QTOF	splash10-00kb-0290000000-e89b395d9956abe0d007	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 20V, Positive-QTOF	splash10-02be-0970000000-bfca4fa39656074f9703	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 40V, Positive-QTOF	splash10-0gb9-6910000000-93b6d80fc56db49dd4fd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 10V, Negative-QTOF	splash10-03di-0090000000-4b316544253947dfdf7f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 20V, Negative-QTOF	splash10-03xs-0190000000-1bd9e6a267dd8c6f8813	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 40V, Negative-QTOF	splash10-0uxv-3960000000-0c28f11ba303ad9d1c8f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 10V, Positive-QTOF	splash10-014i-0290000000-4fe3b5fcb23523aac5f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 20V, Positive-QTOF	splash10-014l-0490000000-0ab6c071f03453fe12d0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 40V, Positive-QTOF	splash10-0080-2900000000-85c2ebb73c3c754a1767	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 10V, Negative-QTOF	splash10-03di-0090000000-44b2d00a730e3afe0cae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 20V, Negative-QTOF	splash10-03di-0090000000-ee70c056c6b8bd8208b3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alkhanin 40V, Negative-QTOF	splash10-000f-6980000000-63c57529c2a460c54cdc	2021-09-25	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

FDB015060

KNApSAcK ID

C00013061

Chemspider ID

35014109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13944243

PDB ID

Not Available

ChEBI ID

174479

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853881

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 Alkhanin (HMDB0036202)

MOL for HMDB0036202 (Alkhanin)

3D MOL for HMDB0036202 (Alkhanin)

3D SDF for HMDB0036202 (Alkhanin)

3D-SDF for HMDB0036202 (Alkhanin)

PDB for HMDB0036202 (Alkhanin)

3D PDB for HMDB0036202 (Alkhanin)

SMILES for HMDB0036202 (Alkhanin)

INCHI for HMDB0036202 (Alkhanin)

Structure for HMDB0036202 (Alkhanin)

3D Structure for HMDB0036202 (Alkhanin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra