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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:52:08 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038544

Secondary Accession Numbers

HMDB38544

Metabolite Identification

Common Name

Longistylin C

Description

Longistylin C belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Longistylin C has been detected, but not quantified in, pulses. This could make longistylin C a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Longistylin C.

Structure

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

HMDB0038544
     RDKit          3D
Longistylin C
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.7937    4.2222    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    2.9008   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.9138    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497    2.2008    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    1.2350    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.5778    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.0957    1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.1054    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8228   -0.7402    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443   -1.6520    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.7711   -1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.9491   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197   -0.0169   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.0348    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156   -0.3359   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520    0.6411   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.3048   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.1407   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -1.9518   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -3.3910   -1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881   -1.4663    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    4.9098    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    4.1450    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.5378   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    3.2225    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.3754    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333    1.4983    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1752   -0.7016    2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2373   -2.3037    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5642   -2.4968   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.0184   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    0.6213   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -0.8863    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -1.3654   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    0.9383   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5858    0.5164   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.5383   -1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9848   -3.5704   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -3.7242   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510   -3.9811   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2738   -0.6165   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424   -1.0463    1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5016   -2.2634    0.2935 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16  3  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END


  Mrv0541 05061310312D          

 21 22  0  0  0  0            999 V2000
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14 12  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  9  2  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  2  0  0  0  0
 21  3  1  0  0  0  0
 21 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038544

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC=C(C)C)C=CC(\C=C/C2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O/c1-16(2)9-13-19-14-12-18(15-20(19)21-3)11-10-17-7-5-4-6-8-17/h4-12,14-15H,13H2,1-3H3/b11-10-

> <INCHI_KEY>
HPQIYBHUJSJOMV-KHPPLWFESA-N

> <FORMULA>
C20H22O

> <MOLECULAR_WEIGHT>
278.3881

> <EXACT_MASS>
278.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.51001130971582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxy-1-(3-methylbut-2-en-1-yl)-4-[(Z)-2-phenylethenyl]benzene

> <ALOGPS_LOGP>
6.33

> <JCHEM_LOGP>
5.883982585

> <ALOGPS_LOGS>
-5.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.837712002379985

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
92.2188

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.79e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-1-(3-methylbut-2-en-1-yl)-4-[(Z)-2-phenylethenyl]benzene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038544
     RDKit          3D
Longistylin C
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.7937    4.2222    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    2.9008   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.9138    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497    2.2008    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    1.2350    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.5778    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.0957    1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.1054    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8228   -0.7402    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443   -1.6520    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.7711   -1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.9491   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197   -0.0169   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.0348    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156   -0.3359   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520    0.6411   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.3048   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.1407   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -1.9518   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -3.3910   -1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881   -1.4663    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    4.9098    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    4.1450    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.5378   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    3.2225    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.3754    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333    1.4983    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1752   -0.7016    2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2373   -2.3037    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5642   -2.4968   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.0184   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    0.6213   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -0.8863    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -1.3654   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    0.9383   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5858    0.5164   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.5383   -1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9848   -3.5704   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -3.7242   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510   -3.9811   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2738   -0.6165   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424   -1.0463    1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5016   -2.2634    0.2935 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16  3  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  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      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   21                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   17                                                       
CONECT    8    6   17                                                       
CONECT    9   13   16                                                       
CONECT   10   11   17                                                       
CONECT   11   10   18                                                       
CONECT   12   14   18                                                       
CONECT   13    9   19                                                       
CONECT   14   12   19                                                       
CONECT   15   18   20                                                       
CONECT   16    1    2    9                                                  
CONECT   17    7    8   10                                                  
CONECT   18   11   12   15                                                  
CONECT   19   13   14   20                                                  
CONECT   20   15   19   21                                                  
CONECT   21    3   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0038544
HETATM    1  C1  UNL     1      -1.794   4.222   0.217  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.098   2.901  -0.185  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.143   1.914   0.062  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.050   2.201   0.670  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.036   1.235   0.936  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.177   1.578   1.711  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.360   1.096   1.628  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.792   0.105   0.688  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.823  -0.740   1.127  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.444  -1.652   0.309  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.062  -1.771  -1.018  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.063  -0.949  -1.441  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.420  -0.017  -0.630  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.707  -0.035   0.535  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.516  -0.336  -0.092  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.452   0.641  -0.333  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.739   0.305  -0.997  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.782  -1.141  -1.306  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.703  -1.952  -0.820  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.666  -3.391  -1.186  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.788  -1.466   0.092  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.639   4.910   0.093  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.504   4.145   1.305  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.895   4.538  -0.375  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.287   3.222   0.982  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.029   2.375   2.502  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.133   1.498   2.367  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.175  -0.702   2.158  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.237  -2.304   0.647  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.564  -2.497  -1.645  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.745  -1.018  -2.465  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.672   0.621  -1.073  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.366  -0.886   0.733  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.727  -1.365  -0.393  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.926   0.938  -1.887  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.586   0.516  -0.293  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.022  -1.538  -1.959  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.985  -3.570  -2.042  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.711  -3.724  -1.451  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.351  -3.981  -0.276  1.00  0.00           H  
HETATM   41  H20 UNL     1      -5.274  -0.616  -0.460  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.342  -1.046   1.014  1.00  0.00           H  
HETATM   43  H22 UNL     1      -5.502  -2.263   0.294  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   25
CONECT    5    6   14   14
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   13
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   32
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17
CONECT   17   18   35   36
CONECT   18   19   19   37
CONECT   19   20   21
CONECT   20   38   39   40
CONECT   21   41   42   43
END

HMDB0038544
     RDKit          3D
Longistylin C
 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.7937    4.2222    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    2.9008   -0.1854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1426    1.9138    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497    2.2008    0.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0355    1.2350    0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    1.5778    1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.0957    1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.1054    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8228   -0.7402    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4443   -1.6520    0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623   -1.7711   -1.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0628   -0.9491   -1.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197   -0.0169   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7069   -0.0348    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156   -0.3359   -0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520    0.6411   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.3048   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7819   -1.1407   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -1.9518   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6656   -3.3910   -1.1857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881   -1.4663    0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6389    4.9098    0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    4.1450    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8953    4.5378   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2869    3.2225    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.3754    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333    1.4983    2.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1752   -0.7016    2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2373   -2.3037    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5642   -2.4968   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -1.0184   -2.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6719    0.6213   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3663   -0.8863    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -1.3654   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    0.9383   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5858    0.5164   -0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.5383   -1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9848   -3.5704   -2.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109   -3.7242   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510   -3.9811   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2738   -0.6165   -0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424   -1.0463    1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5016   -2.2634    0.2935 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  5 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 16  3  1  0
 13  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methoxy-4-prenylstilbene	HMDB
5-Hydroxy-2-isopentenyl-3-methoxystilbene	HMDB
Longistyline C	HMDB

Chemical Formula

C₂₀H₂₂O

Average Molecular Weight

278.3881

Monoisotopic Molecular Weight

278.167065326

IUPAC Name

2-methoxy-1-(3-methylbut-2-en-1-yl)-4-[(Z)-2-phenylethenyl]benzene

Traditional Name

2-methoxy-1-(3-methylbut-2-en-1-yl)-4-[(Z)-2-phenylethenyl]benzene

CAS Registry Number

64125-60-6

SMILES

COC1=C(CC=C(C)C)C=CC(\C=C/C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C20H22O/c1-16(2)9-13-19-14-12-18(15-20(19)21-3)11-10-17-7-5-4-6-8-17/h4-12,14-15H,13H2,1-3H3/b11-10-

InChI Key

HPQIYBHUJSJOMV-KHPPLWFESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038544)
Cell membrane (HMDB: HMDB0038544)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038544)

Source

Exogenous

Exogenous (HMDB: HMDB0038544)

Food

Food (HMDB: HMDB0038544)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0038544)
Fabaceae (HMDB: HMDB0038544)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038544)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	99 - 100 °C	Not Available
Boiling Point	457.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.15 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.430 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	6.33	ALOGPS
logP	5.88	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.22 m³·mol⁻¹	ChemAxon
Polarizability	33.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.18	31661259
DarkChem	[M-H]-	169.709	31661259
DeepCCS	[M+H]+	178.169	30932474
DeepCCS	[M-H]-	175.811	30932474
DeepCCS	[M-2H]-	208.698	30932474
DeepCCS	[M+Na]+	184.263	30932474
AllCCS	[M+H]+	168.2	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	168.9	32859911
AllCCS	[M+Na-2H]-	168.4	32859911
AllCCS	[M+HCOO]-	168.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.64 minutes	32390414
Predicted by Siyang on May 30, 2022	21.7946 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3407.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	755.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	292.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	439.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	927.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	914.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2031.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	827.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1695.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	662.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	602.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	436.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	518.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Longistylin C	COC1=C(CC=C(C)C)C=CC(\C=C/C2=CC=CC=C2)=C1	3095.4	Standard polar	33892256
Longistylin C	COC1=C(CC=C(C)C)C=CC(\C=C/C2=CC=CC=C2)=C1	2346.9	Standard non polar	33892256
Longistylin C	COC1=C(CC=C(C)C)C=CC(\C=C/C2=CC=CC=C2)=C1	2395.3	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 - Longistylin C GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2090000000-c01c5bf760bc23b0ed67	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Longistylin C 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 - Longistylin C 10V, Positive-QTOF	splash10-004i-1290000000-3d8dc975edccbb023439	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 20V, Positive-QTOF	splash10-009i-4690000000-e720d80f201556f494c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 40V, Positive-QTOF	splash10-0fr6-8910000000-c0c3394e3269144cae1e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 10V, Negative-QTOF	splash10-004i-0090000000-76578462ab1f615e7ce8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 20V, Negative-QTOF	splash10-004i-0090000000-8245082b9fed9c080c3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 40V, Negative-QTOF	splash10-03dv-4590000000-f00dd4ab8cc7959faf20	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 10V, Positive-QTOF	splash10-00di-0090000000-c7f75f73aa26fd56f84a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 20V, Positive-QTOF	splash10-00di-0590000000-3f12bc4835094f4d452c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 40V, Positive-QTOF	splash10-004l-1930000000-17e5699d5a68c1f4f0da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 10V, Negative-QTOF	splash10-004i-0090000000-9292df548caa7b864781	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 20V, Negative-QTOF	splash10-004i-0090000000-eab7a58f0757a588f532	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Longistylin C 40V, Negative-QTOF	splash10-004i-0390000000-002a5924f0c29adf0370	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017930

KNApSAcK ID

C00015604

Chemspider ID

30777268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752398

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1501411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Longistylin C (HMDB0038544)

MOL for HMDB0038544 (Longistylin C)

3D MOL for HMDB0038544 (Longistylin C)

3D SDF for HMDB0038544 (Longistylin C)

3D-SDF for HMDB0038544 (Longistylin C)

PDB for HMDB0038544 (Longistylin C)

3D PDB for HMDB0038544 (Longistylin C)

SMILES for HMDB0038544 (Longistylin C)

INCHI for HMDB0038544 (Longistylin C)

Structure for HMDB0038544 (Longistylin C)

3D Structure for HMDB0038544 (Longistylin C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra