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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:12:53 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036151

Secondary Accession Numbers

HMDB36151

Metabolite Identification

Common Name

Arabsin

Description

Arabsin 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 Arabsin.

Structure

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

HMDB0036151
     RDKit          3D
Arabsin
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.1804    0.1042   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217    0.4320    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.8789    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201    2.8035    0.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2258    2.0409   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    0.7754    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -0.1070   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -1.5485   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864   -2.0122    0.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025   -1.8278   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.9331   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263   -1.3087    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -1.2767   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3141   -0.1142   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513    0.8172    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    1.1549    1.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6780    1.3252    0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6543    2.7768    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    0.5473   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    0.5329   -0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2955   -0.9834   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.4519   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379    0.0601    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    0.6268    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    0.1537   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -2.1182   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141   -2.9950    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -2.8617   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.6275   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.0824    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -2.4177    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -0.8517    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.6394   -1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811   -2.1695   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.4644   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3469   -0.5502   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    1.2705    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6841    2.7748   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5413    3.3273    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    3.2977    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419    0.8085   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 19 11  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

  Mrv0541 05061308542D          

 19 21  0  0  0  0            999 V2000
    0.7800    3.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    0.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446    0.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    0.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3900    2.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    1.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346    2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938    0.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0838    1.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8246    1.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    1.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456    2.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8692    3.0525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -0.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468    2.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1818    2.3316    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
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  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>
HMDB0036151

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(OC1=O)C1C(C)C(=O)CCC1(C)CC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h7-8,10-13,17H,4-6H2,1-3H3

> <INCHI_KEY>
SCHUPVUUEKIZGP-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.824595150684523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
1.373507815333333

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.79780767152534

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.820196431635086

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8774224459969115

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
68.7775

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036151
     RDKit          3D
Arabsin
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.1804    0.1042   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217    0.4320    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.8789    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201    2.8035    0.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2258    2.0409   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    0.7754    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -0.1070   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -1.5485   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864   -2.0122    0.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025   -1.8278   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.9331   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263   -1.3087    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -1.2767   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3141   -0.1142   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513    0.8172    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    1.1549    1.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6780    1.3252    0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6543    2.7768    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    0.5473   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    0.5329   -0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2955   -0.9834   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.4519   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379    0.0601    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    0.6268    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    0.1537   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -2.1182   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141   -2.9950    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -2.8617   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.6275   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.0824    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -2.4177    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -0.8517    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.6394   -1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811   -2.1695   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.4644   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3469   -0.5502   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    1.2705    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6841    2.7748   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5413    3.3273    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    3.2977    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419    0.8085   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 19 11  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.456   5.794   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.562   1.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.083   0.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.539   3.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.728   1.723   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.623   0.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.728   4.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.385   2.234   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.811   4.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.162   0.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.890   1.867   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.539   3.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.079   3.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.498   3.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.811   1.771   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.623   5.698   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.973  -0.799   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.807   4.581   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.073   4.352   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   15                                                       
CONECT    7    1    9   12                                                  
CONECT    8    2   11   14                                                  
CONECT    9    4    7   16                                                  
CONECT   10    6   11   17                                                  
CONECT   11    8   10   13                                                  
CONECT   12    7   13   15                                                  
CONECT   13   11   12   19                                                  
CONECT   14    8   18   19                                                  
CONECT   15    3    5    6   12                                             
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036151
HETATM    1  C1  UNL     1       4.180   0.104  -0.548  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.922   0.432   0.198  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.592   1.879   0.174  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.420   2.803   0.306  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.226   2.041  -0.017  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.661   0.775   0.258  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.684  -0.107  -0.476  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.418  -1.548  -0.283  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.686  -2.012   0.997  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.002  -1.828  -0.720  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.019  -0.933  -0.085  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.126  -1.309   1.373  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.364  -1.277  -0.720  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.314  -0.114  -0.704  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.051   0.817   0.414  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.949   1.155   1.151  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.678   1.325   0.612  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.654   2.777   0.202  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.701   0.547  -0.252  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.028   0.533  -0.012  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.295  -0.983  -0.565  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.082   0.452  -1.595  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.938   0.060   1.228  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.694   0.627   1.338  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.688   0.154  -1.531  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.076  -2.118  -0.973  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.814  -2.995   0.917  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.278  -2.862  -0.518  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.029  -1.628  -1.829  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.231  -1.082   1.958  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.254  -2.418   1.402  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.986  -0.852   1.882  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.186  -1.639  -1.758  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.781  -2.170  -0.170  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.296   0.464  -1.642  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.347  -0.550  -0.592  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.336   1.270   1.660  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.684   2.775  -0.926  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.541   3.327   0.584  1.00  0.00           H  
HETATM   40  H21 UNL     1      -0.757   3.298   0.583  1.00  0.00           H  
HETATM   41  H22 UNL     1      -0.842   0.808  -1.320  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    7   23
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   24
CONECT    7    8   25
CONECT    8    9   10   26
CONECT    9   27
CONECT   10   11   28   29
CONECT   11   12   13   19
CONECT   12   30   31   32
CONECT   13   14   33   34
CONECT   14   15   35   36
CONECT   15   16   16   17
CONECT   17   18   19   37
CONECT   18   38   39   40
CONECT   19   41
END

HMDB0036151
     RDKit          3D
Arabsin
 41 43  0  0  0  0  0  0  0  0999 V2000
    4.1804    0.1042   -0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217    0.4320    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924    1.8789    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4201    2.8035    0.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2258    2.0409   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614    0.7754    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -0.1070   -0.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -1.5485   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864   -2.0122    0.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025   -1.8278   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -0.9331   -0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263   -1.3087    1.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -1.2767   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3141   -0.1142   -0.7043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513    0.8172    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    1.1549    1.1508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6780    1.3252    0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6543    2.7768    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    0.5473   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    0.5329   -0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2955   -0.9834   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.4519   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9379    0.0601    1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6937    0.6268    1.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    0.1537   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -2.1182   -0.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141   -2.9950    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -2.8617   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.6275   -1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.0824    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -2.4177    1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858   -0.8517    1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.6394   -1.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7811   -2.1695   -0.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.4644   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3469   -0.5502   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360    1.2705    1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6841    2.7748   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5413    3.3273    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7570    3.2977    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419    0.8085   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 19 11  1  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
[3R-(3alpha,3Abeta,5aalpha,6alpha,9beta,9abeta,9balpha)]-octahydro-6-hydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione	HMDB

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

4-hydroxy-3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione

Traditional Name

4-hydroxy-3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

38412-44-1

SMILES

CC1C2C(OC1=O)C1C(C)C(=O)CCC1(C)CC2O

InChI Identifier

InChI=1S/C15H22O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h7-8,10-13,17H,4-6H2,1-3H3

InChI Key

SCHUPVUUEKIZGP-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
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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: HMDB0036151)

Source

Endogenous

Endogenous (HMDB: HMDB0036151)

Plant

Plant (HMDB: HMDB0036151)

Animal

Animal (HMDB: HMDB0036151)

Exogenous

Food

Food (HMDB: HMDB0036151)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0036151)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036151)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036151)

Lipid metabolism pathway (HMDB: HMDB0036151)

Cellular process

Cell signaling (HMDB: HMDB0036151)

Biochemical process

Lipid transport (HMDB: HMDB0036151)

Role

Biological role

Energy source (HMDB: HMDB0036151)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036151)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188 - 189 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	48920 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	2.79 g/L	ALOGPS
logP	0.76	ALOGPS
logP	1.37	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	-2.9	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	68.78 m³·mol⁻¹	ChemAxon
Polarizability	28.82 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]+	162.507	31661259
DarkChem	[M-H]-	162.14	31661259
DeepCCS	[M+H]+	164.658	30932474
DeepCCS	[M-H]-	162.3	30932474
DeepCCS	[M-2H]-	195.186	30932474
DeepCCS	[M+Na]+	170.751	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+NH4]+	165.8	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	168.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arabsin	CC1C2C(OC1=O)C1C(C)C(=O)CCC1(C)CC2O	3119.9	Standard polar	33892256
Arabsin	CC1C2C(OC1=O)C1C(C)C(=O)CCC1(C)CC2O	2200.2	Standard non polar	33892256
Arabsin	CC1C2C(OC1=O)C1C(C)C(=O)CCC1(C)CC2O	2308.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arabsin,1TMS,isomer #1	CC1C(=O)OC2C1C(O[Si](C)(C)C)CC1(C)CCC(=O)C(C)C21	2261.4	Semi standard non polar	33892256
Arabsin,1TMS,isomer #2	CC1=C(O[Si](C)(C)C)CCC2(C)CC(O)C3C(C)C(=O)OC3C12	2293.8	Semi standard non polar	33892256
Arabsin,1TMS,isomer #3	CC1C(=O)OC2C1C(O)CC1(C)CC=C(O[Si](C)(C)C)C(C)C21	2292.6	Semi standard non polar	33892256
Arabsin,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCC2(C)CC(O[Si](C)(C)C)C3C(C)C(=O)OC3C12	2322.2	Semi standard non polar	33892256
Arabsin,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCC2(C)CC(O[Si](C)(C)C)C3C(C)C(=O)OC3C12	2279.5	Standard non polar	33892256
Arabsin,2TMS,isomer #2	CC1C(=O)OC2C1C(O[Si](C)(C)C)CC1(C)CC=C(O[Si](C)(C)C)C(C)C21	2314.6	Semi standard non polar	33892256
Arabsin,2TMS,isomer #2	CC1C(=O)OC2C1C(O[Si](C)(C)C)CC1(C)CC=C(O[Si](C)(C)C)C(C)C21	2243.4	Standard non polar	33892256
Arabsin,1TBDMS,isomer #1	CC1C(=O)OC2C1C(O[Si](C)(C)C(C)(C)C)CC1(C)CCC(=O)C(C)C21	2501.6	Semi standard non polar	33892256
Arabsin,1TBDMS,isomer #2	CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CC(O)C3C(C)C(=O)OC3C12	2529.7	Semi standard non polar	33892256
Arabsin,1TBDMS,isomer #3	CC1C(=O)OC2C1C(O)CC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21	2538.3	Semi standard non polar	33892256
Arabsin,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CC(O[Si](C)(C)C(C)(C)C)C3C(C)C(=O)OC3C12	2759.1	Semi standard non polar	33892256
Arabsin,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CC(O[Si](C)(C)C(C)(C)C)C3C(C)C(=O)OC3C12	2790.6	Standard non polar	33892256
Arabsin,2TBDMS,isomer #2	CC1C(=O)OC2C1C(O[Si](C)(C)C(C)(C)C)CC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21	2752.6	Semi standard non polar	33892256
Arabsin,2TBDMS,isomer #2	CC1C(=O)OC2C1C(O[Si](C)(C)C(C)(C)C)CC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21	2671.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arabsin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fr-5790000000-d4e49584004ba76987f2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arabsin GC-MS (1 TMS) - 70eV, Positive	splash10-00el-2293000000-192901fe84c62534d720	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arabsin 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 - Arabsin 10V, Positive-QTOF	splash10-00kb-0190000000-92df0f1d1dd937388ff9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 20V, Positive-QTOF	splash10-00te-0690000000-522c6f6c2ff42fcf94cf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 40V, Positive-QTOF	splash10-014l-9800000000-2ad79d0a275865957336	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 10V, Negative-QTOF	splash10-014i-0090000000-0602e36b54bf075f0388	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 20V, Negative-QTOF	splash10-01ba-0090000000-ea79eae8c632f872f99c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 40V, Negative-QTOF	splash10-0ktf-6940000000-95dc589bc2fe63fbe06f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 10V, Positive-QTOF	splash10-00l2-0090000000-10f1eeda2e60c84aa816	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 20V, Positive-QTOF	splash10-05ub-0490000000-b072e040f74349d5b3ba	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 40V, Positive-QTOF	splash10-0592-2920000000-134b21db64430890a373	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 10V, Negative-QTOF	splash10-014i-0090000000-c6cc318d73093d112373	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 20V, Negative-QTOF	splash10-014i-0090000000-ba9dd5b70bc01f8443c3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arabsin 40V, Negative-QTOF	splash10-052f-9870000000-8eb255343338493586f7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB015002

KNApSAcK ID

C00013068

Chemspider ID

35014104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751919

PDB ID

Not Available

ChEBI ID

174506

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853781

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 Arabsin (HMDB0036151)

MOL for HMDB0036151 (Arabsin)

3D MOL for HMDB0036151 (Arabsin)

3D SDF for HMDB0036151 (Arabsin)

3D-SDF for HMDB0036151 (Arabsin)

PDB for HMDB0036151 (Arabsin)

3D PDB for HMDB0036151 (Arabsin)

SMILES for HMDB0036151 (Arabsin)

INCHI for HMDB0036151 (Arabsin)

Structure for HMDB0036151 (Arabsin)

3D Structure for HMDB0036151 (Arabsin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra