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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:07:46 UTC

Update Date

2022-03-07 02:55:55 UTC

HMDB ID

HMDB0038784

Secondary Accession Numbers

HMDB38784

Metabolite Identification

Common Name

(E)-Arachidin II

Description

(E)-Arachidin II 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 (E)-Arachidin II has been detected, but not quantified in, nuts and peanuts (Arachis hypogaea). This could make (e)-arachidin II a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-Arachidin II.

Structure

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

HMDB0038784
     RDKit          3D
(E)-Arachidin II
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2446   -2.0689    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5749   -0.6308    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.2627    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.2690   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.0843   -1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    0.5660   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    1.8829   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    2.6215   -1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4423   -0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0215    1.7218    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416    2.4600    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380    2.0187    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101    0.7011    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8122    0.1952    1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -0.9910    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -1.7107   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6743   -2.9221   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -1.2646   -0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.0459   -0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.4170    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018   -0.1522   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -1.5041    0.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836   -2.7091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.3099   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869   -2.3388    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6357   -0.8471    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201    0.8315    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345   -0.4517    2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239    1.3076   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    0.2144   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -1.1749   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    2.2606   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220    3.4787   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    3.5637    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234    2.7123    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.7400    2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2380   -1.3810    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480   -3.7498    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7262   -1.8356   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6941    0.2889   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.2040    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -2.0540    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
M  END


  Mrv0541 05061310392D          

 22 23  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  2  0  0  0  0
 14  4  1  0  0  0  0
 14  6  2  0  0  0  0
 14  7  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038784

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-13(2)3-10-17-18(21)11-15(12-19(17)22)5-4-14-6-8-16(20)9-7-14/h3-9,11-12,20-22H,10H2,1-2H3/b5-4-

> <INCHI_KEY>
WWFOQQIWOKJBSJ-PLNGDYQASA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.3603

> <EXACT_MASS>
296.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.97412620177429

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.1309578856666676

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.558414852542533

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.850513898033979

> <JCHEM_PKA_STRONGEST_BASIC>
-5.730185642386695

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
91.69829999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038784
     RDKit          3D
(E)-Arachidin II
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2446   -2.0689    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5749   -0.6308    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.2627    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.2690   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.0843   -1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    0.5660   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    1.8829   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    2.6215   -1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4423   -0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0215    1.7218    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416    2.4600    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380    2.0187    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101    0.7011    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8122    0.1952    1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -0.9910    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -1.7107   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6743   -2.9221   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -1.2646   -0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.0459   -0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.4170    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018   -0.1522   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -1.5041    0.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836   -2.7091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.3099   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869   -2.3388    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6357   -0.8471    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201    0.8315    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345   -0.4517    2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239    1.3076   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    0.2144   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -1.1749   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    2.2606   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220    3.4787   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    3.5637    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234    2.7123    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.7400    2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2380   -1.3810    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480   -3.7498    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7262   -1.8356   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6941    0.2889   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.2040    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -2.0540    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   10   13                                                       
CONECT    4    5   14                                                       
CONECT    5    4   15                                                       
CONECT    6    8   14                                                       
CONECT    7    9   14                                                       
CONECT    8    6   16                                                       
CONECT    9    7   16                                                       
CONECT   10    3   17                                                       
CONECT   11   15   18                                                       
CONECT   12   15   19                                                       
CONECT   13    1    2    3                                                  
CONECT   14    4    6    7                                                  
CONECT   15    5   11   12                                                  
CONECT   16    8    9   20                                                  
CONECT   17   10   18   19                                                  
CONECT   18   11   17   21                                                  
CONECT   19   12   17   22                                                  
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0038784
HETATM    1  C1  UNL     1       4.245  -2.069   0.157  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.575  -0.631   0.290  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.757  -0.263   1.146  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.850   0.269  -0.325  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.702  -0.084  -1.156  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.437   0.566  -0.750  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.144   1.883  -1.027  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.088   2.621  -1.727  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.043   2.442  -0.623  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.021   1.722   0.086  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.142   2.460   0.568  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.338   2.019   0.749  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.810   0.701   0.477  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.812   0.195   1.267  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.427  -0.991   0.996  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.031  -1.711  -0.109  1.00  0.00           C  
HETATM   17  O2  UNL     1      -5.674  -2.922  -0.365  1.00  0.00           O  
HETATM   18  C16 UNL     1      -4.037  -1.265  -0.944  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.444  -0.046  -0.620  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.682   0.417   0.338  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.502  -0.152  -0.062  1.00  0.00           C  
HETATM   22  O3  UNL     1       0.736  -1.504   0.253  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.084  -2.709   0.524  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.140  -2.310  -0.938  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.287  -2.339   0.638  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.636  -0.847   0.803  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.920   0.832   1.059  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.534  -0.452   2.218  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.124   1.308  -0.202  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.903   0.214  -2.216  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.501  -1.175  -1.205  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.965   2.261  -2.047  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.222   3.479  -0.865  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.980   3.564   0.831  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.123   2.712   1.155  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.155   0.740   2.156  1.00  0.00           H  
HETATM   37  H15 UNL     1      -6.238  -1.381   1.653  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.248  -3.750   0.068  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.726  -1.836  -1.815  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.694   0.289  -1.347  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.352  -0.204   0.927  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.069  -2.054   0.754  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    4
CONECT    3   26   27   28
CONECT    4    5   29
CONECT    5    6   30   31
CONECT    6    7    7   21
CONECT    7    8    9
CONECT    8   32
CONECT    9   10   10   33
CONECT   10   11   20
CONECT   11   12   12   34
CONECT   12   13   35
CONECT   13   14   14   19
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   18
CONECT   17   38
CONECT   18   19   19   39
CONECT   19   40
CONECT   20   21   21   41
CONECT   21   22
CONECT   22   42
END

HMDB0038784
     RDKit          3D
(E)-Arachidin II
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.2446   -2.0689    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5749   -0.6308    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.2627    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501    0.2690   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021   -0.0843   -1.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    0.5660   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1438    1.8829   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879    2.6215   -1.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426    2.4423   -0.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0215    1.7218    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416    2.4600    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3380    2.0187    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8101    0.7011    0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8122    0.1952    1.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -0.9910    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313   -1.7107   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6743   -2.9221   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0367   -1.2646   -0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4441   -0.0459   -0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820    0.4170    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018   -0.1522   -0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361   -1.5041    0.2527 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836   -2.7091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405   -2.3099   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869   -2.3388    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6357   -0.8471    0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201    0.8315    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5345   -0.4517    2.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239    1.3076   -0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    0.2144   -2.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -1.1749   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9652    2.2606   -2.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220    3.4787   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9800    3.5637    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234    2.7123    1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1549    0.7400    2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2380   -1.3810    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480   -3.7498    0.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7262   -1.8356   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6941    0.2889   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.2040    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0692   -2.0540    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  6  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Isopentenyl-3,4',5-trihydroxystilbene	HMDB
4-Prenylresveratrol	HMDB
Arachidin II	HMDB

Chemical Formula

C₁₉H₂₀O₃

Average Molecular Weight

296.3603

Monoisotopic Molecular Weight

296.141244506

IUPAC Name

5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

Traditional Name

5-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

CAS Registry Number

61517-87-1

SMILES

CC(C)=CCC1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C19H20O3/c1-13(2)3-10-17-18(21)11-15(12-19(17)22)5-4-14-6-8-16(20)9-7-14/h3-9,11-12,20-22H,10H2,1-2H3/b5-4-

InChI Key

WWFOQQIWOKJBSJ-PLNGDYQASA-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
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
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

Cell membrane (HMDB: HMDB0038784)

Cellular substructure

Membrane (HMDB: HMDB0038784)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038784)

Source

Exogenous

Food

Food (HMDB: HMDB0038784)

Nut

Peanut (FooDB: FOOD00016)
Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0038784)

Not Available

Nutrient (HMDB: HMDB0038784)

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	1.12 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	4.16	ALOGPS
logP	5.13	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.7 m³·mol⁻¹	ChemAxon
Polarizability	32.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DeepCCS	[M+H]+	171.763	30932474
DeepCCS	[M-H]-	169.405	30932474
DeepCCS	[M-2H]-	203.144	30932474
DeepCCS	[M+Na]+	178.371	30932474
AllCCS	[M+H]+	173.2	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	176.6	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-Arachidin II	CC(C)=CCC1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O	4562.2	Standard polar	33892256
(E)-Arachidin II	CC(C)=CCC1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O	2863.8	Standard non polar	33892256
(E)-Arachidin II	CC(C)=CCC1=C(O)C=C(\C=C/C2=CC=C(O)C=C2)C=C1O	3106.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-Arachidin II,1TMS,isomer #1	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O)C=C2)C=C1O[Si](C)(C)C	3005.3	Semi standard non polar	33892256
(E)-Arachidin II,1TMS,isomer #2	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O[Si](C)(C)C)C=C2)C=C1O	3050.8	Semi standard non polar	33892256
(E)-Arachidin II,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(/C=C\C2=CC=C(O)C=C2)C=C1O[Si](C)(C)C	2942.7	Semi standard non polar	33892256
(E)-Arachidin II,2TMS,isomer #2	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O[Si](C)(C)C)C=C2)C=C1O[Si](C)(C)C	2924.9	Semi standard non polar	33892256
(E)-Arachidin II,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=C(/C=C\C2=CC=C(O[Si](C)(C)C)C=C2)C=C1O[Si](C)(C)C	2928.5	Semi standard non polar	33892256
(E)-Arachidin II,1TBDMS,isomer #1	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O)C=C2)C=C1O[Si](C)(C)C(C)(C)C	3286.2	Semi standard non polar	33892256
(E)-Arachidin II,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1O	3339.7	Semi standard non polar	33892256
(E)-Arachidin II,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(/C=C\C2=CC=C(O)C=C2)C=C1O[Si](C)(C)C(C)(C)C	3480.4	Semi standard non polar	33892256
(E)-Arachidin II,2TBDMS,isomer #2	CC(C)=CCC1=C(O)C=C(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1O[Si](C)(C)C(C)(C)C	3471.5	Semi standard non polar	33892256
(E)-Arachidin II,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=C1O[Si](C)(C)C(C)(C)C	3675.8	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 - (E)-Arachidin II GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-4190000000-f4e2586d997ddff2bc24	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-Arachidin II GC-MS (3 TMS) - 70eV, Positive	splash10-0002-2000900000-87f78af86d091584128b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-Arachidin II GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-Arachidin II 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 - (E)-Arachidin II 10V, Positive-QTOF	splash10-0002-0290000000-99c8e1979206dd8578c0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 20V, Positive-QTOF	splash10-00kp-2890000000-dce0a22d3ff634c456d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 40V, Positive-QTOF	splash10-016r-7930000000-9b6ae18c6d0c24ccf75f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 10V, Negative-QTOF	splash10-0002-0090000000-5ec5f484f53082746e3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 20V, Negative-QTOF	splash10-0002-0090000000-f295bb69b8e51ead3ab7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 40V, Negative-QTOF	splash10-0a6r-4690000000-28d59dd31c6d51d36023	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 10V, Negative-QTOF	splash10-0002-0090000000-db72210c281b6deac77d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 20V, Negative-QTOF	splash10-002b-0190000000-b871a75b8cb4e47d9249	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 40V, Negative-QTOF	splash10-0006-2950000000-706f0ce5b4f8f0d7f42f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 10V, Positive-QTOF	splash10-0006-0090000000-108bbc9577392fd311e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 20V, Positive-QTOF	splash10-0076-0290000000-2bb30c4d36bdcee85d85	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Arachidin II 40V, Positive-QTOF	splash10-0nu0-1690000000-a1e745afbdd89899734f	2021-09-23	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

FDB018205

KNApSAcK ID

C00002901

Chemspider ID

30777291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92012758

PDB ID

Not Available

ChEBI ID

174824

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1871321

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 (E)-Arachidin II (HMDB0038784)

MOL for HMDB0038784 ((E)-Arachidin II)

3D MOL for HMDB0038784 ((E)-Arachidin II)

3D SDF for HMDB0038784 ((E)-Arachidin II)

3D-SDF for HMDB0038784 ((E)-Arachidin II)

PDB for HMDB0038784 ((E)-Arachidin II)

3D PDB for HMDB0038784 ((E)-Arachidin II)

SMILES for HMDB0038784 ((E)-Arachidin II)

INCHI for HMDB0038784 ((E)-Arachidin II)

Structure for HMDB0038784 ((E)-Arachidin II)

3D Structure for HMDB0038784 ((E)-Arachidin II)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra