NP-MRD: Showing NP-Card for Amorfrutin A (NP0001742)

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Record Information

Version

2.0

Created at

2020-10-14 21:10:02 UTC

Updated at

2021-03-18 16:11:39 UTC

NP-MRD ID

NP0001742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Amorfrutin A

Description

3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid, also known as amorfrutin a, 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. Based on a literature review very few articles have been published on 3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylic acid.

Structure

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

NP0001742
     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
   -1.0805    2.7373   -2.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    2.1024   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2326    1.1568   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919    0.8235   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -0.1301   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670   -0.3452   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452    0.4217    0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786    0.1883    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999   -0.8121    0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415   -0.9922    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2033   -0.1632   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    0.8654   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1869    0.9874   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.7642    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -1.7668    1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8249   -2.1094    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -2.4224    2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.4265    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.9885    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9712    0.5392    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    0.8978    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    0.3000   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -0.4785   -0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -1.1060   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067   -0.7873    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    3.1299   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    3.6202   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    2.0140   -3.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    1.3270   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -1.4119   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.0421   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    1.5183    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571    0.3260    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092   -1.4746    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133   -1.7921    1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.2623   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.5167   -1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    1.7974   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -3.2402    3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -1.6418    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.9969    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    0.5662    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    0.5152   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.1314   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1857   -1.0939   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402   -0.4236   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6569    0.1273    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -1.3104    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8146   -1.4425    1.4487 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  1  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
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20  3  1  0
 13  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
M  END


  Mrv0541 02241212152D          

 25 26  0  0  0  0            999 V2000
   -5.0384    2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7529    1.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7529    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0384    0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3239    1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3239    1.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6095    2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6095    3.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    1.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4660    3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    3.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4660    1.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7516    3.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    4.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4660    4.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0371    3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0371    4.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918    4.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0371    1.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16  8  1  0  0  0  0
 16 17  2  0  0  0  0
 11 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCC2=CC=CC=C2)=C(C(O)=O)C(O)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)

> <INCHI_KEY>
CTNFTPUIYFUXBE-UHFFFAOYSA-N

> <FORMULA>
C21H24O4

> <MOLECULAR_WEIGHT>
340.4129

> <EXACT_MASS>
340.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.991302699327306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
6.084521828000001

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.292687966546831

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.893312903655431

> <JCHEM_PKA_STRONGEST_BASIC>
-4.866777609855168

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
100.33930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001742
     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
   -1.0805    2.7373   -2.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    2.1024   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2326    1.1568   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919    0.8235   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -0.1301   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670   -0.3452   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452    0.4217    0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786    0.1883    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999   -0.8121    0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415   -0.9922    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2033   -0.1632   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    0.8654   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1869    0.9874   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.7642    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -1.7668    1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8249   -2.1094    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -2.4224    2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.4265    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.9885    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9712    0.5392    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    0.8978    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    0.3000   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -0.4785   -0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -1.1060   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067   -0.7873    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    3.1299   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    3.6202   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    2.0140   -3.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    1.3270   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -1.4119   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.0421   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    1.5183    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571    0.3260    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092   -1.4746    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133   -1.7921    1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.2623   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.5167   -1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    1.7974   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -3.2402    3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -1.6418    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.9969    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    0.5662    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    0.5152   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.1314   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1857   -1.0939   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402   -0.4236   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6569    0.1273    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -1.3104    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8146   -1.4425    1.4487 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  1  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
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20  3  1  0
 13  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.405   4.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.739   3.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.739   1.980   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.405   1.210   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.071   1.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.071   3.520   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.738   4.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.738   5.830   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.404   3.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.070   4.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.737   6.600   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.070   5.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.737   3.520   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.403   4.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.403   5.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.404   6.600   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.404   8.140   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.737   8.140   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.069   6.600   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.069   8.140   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.264   8.910   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.264  10.450   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.598   8.140   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.069   3.520   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.264   4.290   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    9                                                       
CONECT    8   16                                                            
CONECT    9    7   10                                                       
CONECT   10    9   12   13                                                  
CONECT   11   12   15   18                                                  
CONECT   12   10   11   16                                                  
CONECT   13   10   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   11   14   19                                                  
CONECT   16   12    8   17                                                  
CONECT   17   16                                                            
CONECT   18   11                                                            
CONECT   19   15   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   14   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    NP0001742
HETATM    1  C1  UNL     1      -1.080   2.737  -2.603  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.851   2.102  -1.604  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.233   1.157  -0.789  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.092   0.824  -0.925  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.724  -0.130  -0.107  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.167  -0.345  -0.350  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.045   0.422   0.602  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.479   0.188   0.374  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.200  -0.812   0.991  1.00  0.00           C  
HETATM   10  C9  UNL     1       6.542  -0.992   0.745  1.00  0.00           C  
HETATM   11  C10 UNL     1       7.203  -0.163  -0.137  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.516   0.865  -0.788  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.187   0.987  -0.497  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.024  -0.764   0.882  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.621  -1.767   1.715  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.825  -2.109   1.631  1.00  0.00           O  
HETATM   17  O3  UNL     1      -0.128  -2.422   2.696  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.361  -0.426   1.019  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.166  -0.989   1.953  1.00  0.00           O  
HETATM   20  C16 UNL     1      -1.971   0.539   0.179  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.406   0.898   0.332  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.256   0.300  -0.720  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.264  -0.478  -0.374  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.152  -1.106  -1.429  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.607  -0.787   1.039  1.00  0.00           C  
HETATM   26  H1  UNL     1      -0.115   3.130  -2.244  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.627   3.620  -3.036  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.862   2.014  -3.410  1.00  0.00           H  
HETATM   29  H4  UNL     1       0.641   1.327  -1.694  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.387  -1.412  -0.316  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.384   0.042  -1.413  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.880   1.518   0.329  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.757   0.326   1.656  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.709  -1.475   1.684  1.00  0.00           H  
HETATM   35  H10 UNL     1       7.113  -1.792   1.239  1.00  0.00           H  
HETATM   36  H11 UNL     1       8.251  -0.262  -0.365  1.00  0.00           H  
HETATM   37  H12 UNL     1       7.035   1.517  -1.480  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.645   1.797  -1.008  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.176  -3.240   3.185  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.017  -1.642   2.626  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.490   1.997   0.247  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.702   0.566   1.352  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.027   0.515  -1.750  1.00  0.00           H  
HETATM   44  H19 UNL     1      -5.845  -2.131  -1.661  1.00  0.00           H  
HETATM   45  H20 UNL     1      -7.186  -1.094  -1.028  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.140  -0.424  -2.303  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.657   0.127   1.670  1.00  0.00           H  
HETATM   48  H23 UNL     1      -6.598  -1.310   1.115  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.815  -1.443   1.449  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   29
CONECT    5    6   14   14
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9    9   13
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   38
CONECT   14   15   18
CONECT   15   16   16   17
CONECT   17   39
CONECT   18   19   20   20
CONECT   19   40
CONECT   20   21
CONECT   21   22   41   42
CONECT   22   23   23   43
CONECT   23   24   25
CONECT   24   44   45   46
CONECT   25   47   48   49
END

NP0001742
     RDKit          3D

49 50  0  0  0  0  0  0  0  0999 V2000
   -1.0805    2.7373   -2.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    2.1024   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2326    1.1568   -0.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0919    0.8235   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7244   -0.1301   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1670   -0.3452   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0452    0.4217    0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786    0.1883    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999   -0.8121    0.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415   -0.9922    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2033   -0.1632   -0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5159    0.8654   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1869    0.9874   -0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0237   -0.7642    0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206   -1.7668    1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8249   -2.1094    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276   -2.4224    2.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -0.4265    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.9885    1.9528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9712    0.5392    0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4056    0.8978    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2556    0.3000   -0.7198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -0.4785   -0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1516   -1.1060   -1.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6067   -0.7873    1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1146    3.1299   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6273    3.6202   -3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    2.0140   -3.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    1.3270   -1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -1.4119   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844    0.0421   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    1.5183    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7571    0.3260    1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092   -1.4746    1.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133   -1.7921    1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2512   -0.2623   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.5167   -1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    1.7974   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755   -3.2402    3.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -1.6418    2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    1.9969    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7024    0.5662    1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0273    0.5152   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449   -2.1314   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1857   -1.0939   -1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402   -0.4236   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6569    0.1273    1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5983   -1.3104    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8146   -1.4425    1.4487 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  1  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
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 23 25  1  0
 20  3  1  0
 13  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 17 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
3-Hydroxy-4-isopentenyl-5-methoxybibenzyl-2-carboxylate	Generator
Amorfrutin a	HMDB

Chemical Formula

C₂₁H₂₄O₄

Average Mass

340.4129 Da

Monoisotopic Mass

340.16746 Da

IUPAC Name

2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

Traditional Name

2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(CCC2=CC=CC=C2)=C(C(O)=O)C(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C21H24O4/c1-14(2)9-12-17-18(25-3)13-16(19(20(17)22)21(23)24)11-10-15-7-5-4-6-8-15/h4-9,13,22H,10-12H2,1-3H3,(H,23,24)

InChI Key

CTNFTPUIYFUXBE-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400Mz, CHCL₃(Solvent-Peak), simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-10-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa	KNApSAcK Database	22123792
Cajanus cajan	KNApSAcK Database	22123792
Glycyrrhiza acanthocarpa	KNApSAcK Database	22123792

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
P-methoxybenzoic acid or derivatives
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid or derivatives
Benzoic acid
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Benzoyl
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	4.37	ALOGPS
logP	6.08	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.34 m³·mol⁻¹	ChemAxon
Polarizability	37.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302011

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001743

KNApSAcK ID

C00015437

Chemspider ID

16430153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17950432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Amorfrutin A (NP0001742)

MOL for NP0001742 (Amorfrutin A)

3D MOL for NP0001742 (Amorfrutin A)

3D SDF for NP0001742 (Amorfrutin A)

3D-SDF for NP0001742 (Amorfrutin A)

PDB for NP0001742 (Amorfrutin A)

3D PDB for NP0001742 (Amorfrutin A)

SMILES for NP0001742 (Amorfrutin A)

INCHI for NP0001742 (Amorfrutin A)

Structure for NP0001742 (Amorfrutin A)

3D Structure for NP0001742 (Amorfrutin A)