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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:46:32 UTC

Update Date

2022-03-07 02:54:37 UTC

HMDB ID

HMDB0035754

Secondary Accession Numbers

HMDB35754

Metabolite Identification

Common Name

Phytuberin

Description

Phytuberin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Phytuberin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0035754
     RDKit          3D
Phytuberin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.2024    2.5735    0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175    1.2566    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809    0.6126   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5188    0.8316    0.5375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.4156    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.3663   -1.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254   -1.4931    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.5959    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.9120   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -2.2354    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -1.0095    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.5607    1.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4470   -1.0609   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916    0.2521   -0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.9832   -0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.2051    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    1.3045   -2.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483    0.3984   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -0.5203   -1.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    0.0601   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    0.5708   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1743    3.3082    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    2.4589    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4989    2.8857    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    0.4805   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.3510   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -1.3079   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -1.9561    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -2.2316   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -1.0502    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6410   -0.6647    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -2.6958    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4056   -2.0126   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -2.8596    1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -2.8759   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -0.6344    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.4213    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104   -1.2877    2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848   -1.5254    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044   -1.6051   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    2.6784    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2504    2.9816   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    2.0571    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534    2.1410   -2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    0.4000   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.3137    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.0526   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 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  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  8  1  0
 20 11  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
M  END


  Mrv0541 05061308422D          

 21 23  0  0  0  0            999 V2000
    2.9046    4.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4105    2.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0314    2.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3233   -0.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7225   -0.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915    1.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877    1.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504    4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209    2.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582    0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1335    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    3.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447    1.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -0.4225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752    3.5113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 12  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  5  1  0  0  0  0
 16  8  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  2  0  0  0  0
 19  9  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035754

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC(C)(C)C1CCC2(C)COC3(C)C=COC23C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O4/c1-12(18)21-14(2,3)13-6-7-15(4)11-20-16(5)8-9-19-17(15,16)10-13/h8-9,13H,6-7,10-11H2,1-5H3

> <INCHI_KEY>
YARAJYKHRCCDLG-UHFFFAOYSA-N

> <FORMULA>
C17H26O4

> <MOLECULAR_WEIGHT>
294.3859

> <EXACT_MASS>
294.18310932

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.16241056270249

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5,8-dimethyl-2,6-dioxatricyclo[6.4.0.0¹,⁵]dodec-3-en-11-yl}propan-2-yl acetate

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
2.317423118333332

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11312517597911

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
79.1392

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{5,8-dimethyl-2,6-dioxatricyclo[6.4.0.0¹,⁵]dodec-3-en-11-yl}propan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035754
     RDKit          3D
Phytuberin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.2024    2.5735    0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175    1.2566    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809    0.6126   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5188    0.8316    0.5375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.4156    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.3663   -1.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254   -1.4931    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.5959    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.9120   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -2.2354    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -1.0095    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.5607    1.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4470   -1.0609   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916    0.2521   -0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.9832   -0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.2051    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    1.3045   -2.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483    0.3984   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -0.5203   -1.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    0.0601   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    0.5708   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1743    3.3082    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    2.4589    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4989    2.8857    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    0.4805   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.3510   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -1.3079   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -1.9561    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -2.2316   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -1.0502    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6410   -0.6647    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -2.6958    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4056   -2.0126   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -2.8596    1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -2.8759   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -0.6344    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.4213    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104   -1.2877    2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848   -1.5254    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044   -1.6051   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    2.6784    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2504    2.9816   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    2.0571    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534    2.1410   -2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    0.4000   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.3137    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.0526   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 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  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  8  1  0
 20 11  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  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       5.422   9.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.500   5.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.525   4.754   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.203  -0.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.349  -0.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.891   2.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.603   1.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.499   1.716   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.096   3.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.270   3.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.553  -0.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.134   7.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.725   3.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.012   5.042   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.149   0.503   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.666   0.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.983   1.509   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.680   7.053   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.630   3.008   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.018  -0.789   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.300   6.554   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6    7   13                                                       
CONECT    7    6   15                                                       
CONECT    8    9   16                                                       
CONECT    9    8   19                                                       
CONECT   10   13   17                                                       
CONECT   11   15   20                                                       
CONECT   12    1   18   21                                                  
CONECT   13    6   10   14                                                  
CONECT   14    2    3   13   21                                             
CONECT   15    4    7   11   17                                             
CONECT   16    5    8   17   20                                             
CONECT   17   10   15   16   19                                             
CONECT   18   12                                                            
CONECT   19    9   17                                                       
CONECT   20   11   16                                                       
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0035754
HETATM    1  C1  UNL     1       4.202   2.574   0.929  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.818   1.257   0.355  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.681   0.613  -0.255  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.519   0.832   0.537  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.115  -0.416   0.006  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.315  -0.366  -1.486  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.925  -1.493   0.658  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.658  -0.596   0.383  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.206  -1.912  -0.169  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.236  -2.235   0.165  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.059  -1.010   0.381  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.085  -0.561   1.820  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.447  -1.061  -0.191  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.792   0.252  -0.411  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.627   0.983  -0.680  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.618   2.205   0.142  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.577   1.304  -2.131  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.848   0.398  -2.758  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.399  -0.520  -1.824  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.483   0.060  -0.538  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.186   0.571  -0.126  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.174   3.308   0.101  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.188   2.459   1.391  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.499   2.886   1.734  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.943   0.481  -1.813  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.358  -0.351  -2.043  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.826  -1.308  -1.779  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.335  -1.956   1.468  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.311  -2.232  -0.074  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.839  -1.050   1.150  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.641  -0.665   1.491  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.821  -2.696   0.321  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.406  -2.013  -1.262  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.312  -2.860   1.097  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.645  -2.876  -0.645  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.135  -0.634   2.170  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.624   0.421   1.987  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.510  -1.288   2.440  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.185  -1.525   0.486  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.404  -1.605  -1.163  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.652   2.678   0.319  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.250   2.982  -0.382  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.155   2.057   1.126  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.053   2.141  -2.613  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.649   0.400  -3.845  1.00  0.00           H  
HETATM   46  H25 UNL     1      -0.186   1.314   0.702  1.00  0.00           H  
HETATM   47  H26 UNL     1       0.337   1.053  -0.971  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    7    8
CONECT    6   25   26   27
CONECT    7   28   29   30
CONECT    8    9   21   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   13   20
CONECT   12   36   37   38
CONECT   13   14   39   40
CONECT   14   15
CONECT   15   16   17   20
CONECT   16   41   42   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20
CONECT   20   21
CONECT   21   46   47
END

HMDB0035754
     RDKit          3D
Phytuberin
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.2024    2.5735    0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8175    1.2566    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6809    0.6126   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5188    0.8316    0.5375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154   -0.4156    0.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.3663   -1.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9254   -1.4931    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.5959    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.9120   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -2.2354    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0592   -1.0095    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -0.5607    1.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4470   -1.0609   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916    0.2521   -0.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.9832   -0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185    2.2051    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    1.3045   -2.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8483    0.3984   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3995   -0.5203   -1.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    0.0601   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865    0.5708   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1743    3.3082    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    2.4589    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4989    2.8857    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433    0.4805   -1.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581   -0.3510   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262   -1.3079   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -1.9561    1.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3115   -2.2316   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393   -1.0502    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6410   -0.6647    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -2.6958    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4056   -2.0126   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -2.8596    1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -2.8759   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1351   -0.6344    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.4213    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104   -1.2877    2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1848   -1.5254    0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044   -1.6051   -1.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    2.6784    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2504    2.9816   -0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1545    2.0571    1.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534    2.1410   -2.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6491    0.4000   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    1.3137    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.0526   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 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  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  8  1  0
 20 11  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Phytuberin	HMDB
(3AR,5as,8R,9ar)-5,5a,6,7,8,9-hexahydro-a,a,3a,5a-tetramethyl-3ah-furo[3,2-c]isobenzofuran-8-methanol acetate	HMDB
2-{5,8-dimethyl-2,6-dioxatricyclo[6.4.0.0¹,⁵]dodec-3-en-11-yl}propan-2-yl acetic acid	Generator
Phytuberin	MeSH

Chemical Formula

C₁₇H₂₆O₄

Average Molecular Weight

294.3859

Monoisotopic Molecular Weight

294.18310932

IUPAC Name

2-{5,8-dimethyl-2,6-dioxatricyclo[6.4.0.0¹,⁵]dodec-3-en-11-yl}propan-2-yl acetate

Traditional Name

2-{5,8-dimethyl-2,6-dioxatricyclo[6.4.0.0¹,⁵]dodec-3-en-11-yl}propan-2-yl acetate

CAS Registry Number

37209-50-0

SMILES

CC(=O)OC(C)(C)C1CCC2(C)COC3(C)C=COC23C1

InChI Identifier

InChI=1S/C17H26O4/c1-12(18)21-14(2,3)13-6-7-15(4)11-20-16(5)8-9-19-17(15,16)10-13/h8-9,13H,6-7,10-11H2,1-5H3

InChI Key

YARAJYKHRCCDLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Furofuran
Dihydrofuran
Tetrahydrofuran
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035754)
Cell membrane (HMDB: HMDB0035754)

Cellular substructure

Extracellular (HMDB: HMDB0035754)
Membrane (HMDB: HMDB0035754)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035754)

Source

Endogenous

Endogenous (HMDB: HMDB0035754)

Plant

Plant (HMDB: HMDB0035754)

Animal

Animal (HMDB: HMDB0035754)

Exogenous

Food

Food (HMDB: HMDB0035754)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035754)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035754)

Cellular process

Cell signaling (HMDB: HMDB0035754)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035754)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035754)

Nutrient

Nutrient (HMDB: HMDB0035754)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035754)

Emulsifier (HMDB: HMDB0035754)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0082 g/L	ALOGPS
logP	3.66	ALOGPS
logP	2.32	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.14 m³·mol⁻¹	ChemAxon
Polarizability	32.16 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]+	169.043	31661259
DarkChem	[M-H]-	164.095	31661259
DeepCCS	[M-2H]-	198.741	30932474
DeepCCS	[M+Na]+	173.968	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.8	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	177.7	32859911
AllCCS	[M+HCOO]-	178.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phytuberin	CC(=O)OC(C)(C)C1CCC2(C)COC3(C)C=COC23C1	2555.1	Standard polar	33892256
Phytuberin	CC(=O)OC(C)(C)C1CCC2(C)COC3(C)C=COC23C1	1753.9	Standard non polar	33892256
Phytuberin	CC(=O)OC(C)(C)C1CCC2(C)COC3(C)C=COC23C1	1862.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phytuberin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8790000000-204f18f03337448806bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phytuberin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phytuberin 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 - Phytuberin 10V, Positive-QTOF	splash10-0002-0090000000-cc76c763cbe31dfdd96d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 20V, Positive-QTOF	splash10-0f7a-0290000000-5b04d6d01ecfb38f4027	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 40V, Positive-QTOF	splash10-0k9l-9470000000-c2b72c5c1de2ed990b8a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 10V, Negative-QTOF	splash10-0006-1090000000-82afbf69bdcfb43dd30a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 20V, Negative-QTOF	splash10-0udl-2090000000-97ea2256b67bbbd6f922	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 40V, Negative-QTOF	splash10-05fr-3090000000-a9065826352da11fcf26	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 10V, Positive-QTOF	splash10-000i-0090000000-5f8ee6859cac66bfcaaf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 20V, Positive-QTOF	splash10-000i-3690000000-28de909c0b3cd35a9d2b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 40V, Positive-QTOF	splash10-0gdu-9720000000-b5aa3acb717923280f3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 10V, Negative-QTOF	splash10-001i-0090000000-46f655010b6b64c43b61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 20V, Negative-QTOF	splash10-0a59-6090000000-8fce51c00773e97d8713	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phytuberin 40V, Negative-QTOF	splash10-0c2c-2090000000-e2c6f8948b470842d2a3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

315114

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Phytuberin (HMDB0035754)

MOL for HMDB0035754 (Phytuberin)

3D MOL for HMDB0035754 (Phytuberin)

3D SDF for HMDB0035754 (Phytuberin)

3D-SDF for HMDB0035754 (Phytuberin)

PDB for HMDB0035754 (Phytuberin)

3D PDB for HMDB0035754 (Phytuberin)

SMILES for HMDB0035754 (Phytuberin)

INCHI for HMDB0035754 (Phytuberin)

Structure for HMDB0035754 (Phytuberin)

3D Structure for HMDB0035754 (Phytuberin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra