NP-MRD: Showing NP-Card for 2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl (NP0001744)

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Record Information

Version

1.0

Created at

2020-10-15 18:55:53 UTC

Updated at

2020-11-24 22:27:37 UTC

NP-MRD ID

NP0001744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl

Description

4-Hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid 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. 2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl is found in Amorpha fruticosa. Based on a literature review very few articles have been published on 4-hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid.

Structure

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

NP0001744
     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
   -2.0373    3.2109   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151    2.2722   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029    1.0053   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -0.1288   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432   -0.0336   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.3818    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9815   -0.3703    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6305    0.0245    2.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183   -1.6280    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -1.3755   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -2.4781   -0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.4874   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126   -0.3423   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737   -0.5079   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -0.1917    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.4408    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450    0.5554   -0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948    0.3624   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1296   -0.8776   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2819   -1.8673    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287   -1.6886    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877    0.8468   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470    2.0650   -1.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    2.4333   -2.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    2.8140   -0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    4.0923   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8862    2.8640    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    3.5265   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    0.7014   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073   -1.0452   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    1.2945    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5553    1.1298    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -0.5214    2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3783   -1.9834    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7073   -2.4548    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -3.4111   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.4401   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    0.1475   -1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -1.5445   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.8536    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -0.9009    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8033    1.5327   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2438    1.1478   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1983   -1.0251   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7059   -2.8558    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -2.4982    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    2.6015    0.8429 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  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
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 23 25  1  0
 22  3  1  0
 21 16  1  0
  1 26  1  0
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  1 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
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 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 25 49  1  0
M  END


  Mrv1533004241500092D          

 25 26  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    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
    2.8579   -1.6500    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -4.1250    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
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -4.9500    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
  1  2  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 13 22  2  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C(O)=CC(CCC2=CC=CC=C2)=C1C(O)=O

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

> <INCHI_KEY>
LWTSBJAZSUSNIF-UHFFFAOYSA-N

> <FORMULA>
C21H24O4

> <MOLECULAR_WEIGHT>
340.419

> <EXACT_MASS>
340.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.56923491873235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.31

> <JCHEM_LOGP>
5.434521828

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.626181846453498

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.84543081774763

> <JCHEM_PKA_STRONGEST_BASIC>
-4.914113164909894

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
100.3393

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.79e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001744
     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
   -2.0373    3.2109   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151    2.2722   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029    1.0053   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -0.1288   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432   -0.0336   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.3818    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9815   -0.3703    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6305    0.0245    2.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183   -1.6280    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -1.3755   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -2.4781   -0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.4874   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126   -0.3423   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737   -0.5079   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -0.1917    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.4408    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450    0.5554   -0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948    0.3624   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1296   -0.8776   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2819   -1.8673    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287   -1.6886    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877    0.8468   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470    2.0650   -1.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    2.4333   -2.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    2.8140   -0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7059   -2.8558    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -2.4982    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    2.6015    0.8429 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  3
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  4 10  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
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 13 22  2  0
 22 23  1  0
 23 24  2  0
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 22  3  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   13    3   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    NP0001744
HETATM    1  C1  UNL     1      -2.037   3.211  -0.322  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.715   2.272  -1.284  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.203   1.005  -1.122  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.969  -0.129  -1.015  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.443  -0.034  -1.068  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.059   0.382   0.206  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.982  -0.370   0.775  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.630   0.024   2.078  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.418  -1.628   0.134  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.351  -1.376  -0.853  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.172  -2.478  -0.752  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.018  -1.487  -0.799  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.813  -0.342  -0.906  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.274  -0.508  -0.845  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.922  -0.192   0.451  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.400  -0.441   0.260  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.245   0.555  -0.172  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.595   0.362  -0.358  1.00  0.00           C  
HETATM   19  C17 UNL     1       7.130  -0.878  -0.104  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.282  -1.867   0.327  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.929  -1.689   0.518  1.00  0.00           C  
HETATM   22  C20 UNL     1       0.188   0.847  -1.061  1.00  0.00           C  
HETATM   23  C21 UNL     1       0.947   2.065  -1.205  1.00  0.00           C  
HETATM   24  O3  UNL     1       1.321   2.433  -2.334  1.00  0.00           O  
HETATM   25  O4  UNL     1       1.250   2.814  -0.087  1.00  0.00           O  
HETATM   26  H1  UNL     1      -1.346   4.092  -0.463  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.886   2.864   0.713  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.098   3.526  -0.422  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.765   0.701  -1.863  1.00  0.00           H  
HETATM   30  H5  UNL     1      -3.807  -1.045  -1.359  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.790   1.294   0.721  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.555   1.130   2.196  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.185  -0.521   2.931  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.713  -0.257   2.058  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.713  -1.508  -0.939  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.378  -1.983   0.630  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.707  -2.455   0.204  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.815  -3.411  -0.635  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.512  -2.440  -0.675  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.757   0.148  -1.634  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.565  -1.544  -1.177  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.840   0.854   0.771  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.539  -0.901   1.221  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.803   1.533  -0.368  1.00  0.00           H  
HETATM   45  H20 UNL     1       7.244   1.148  -0.696  1.00  0.00           H  
HETATM   46  H21 UNL     1       8.198  -1.025  -0.253  1.00  0.00           H  
HETATM   47  H22 UNL     1       6.706  -2.856   0.530  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.306  -2.498   0.858  1.00  0.00           H  
HETATM   49  H24 UNL     1       0.954   2.601   0.843  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   10
CONECT    5    6   29   30
CONECT    6    7    7   31
CONECT    7    8    9
CONECT    8   32   33   34
CONECT    9   35   36   37
CONECT   10   11   12   12
CONECT   11   38
CONECT   12   13   39
CONECT   13   14   22   22
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   17   21
CONECT   17   18   44
CONECT   18   19   19   45
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   48
CONECT   22   23
CONECT   23   24   24   25
CONECT   25   49
END

NP0001744
     RDKit          3D

49 50  0  0  0  0  0  0  0  0999 V2000
   -2.0373    3.2109   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7151    2.2722   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029    1.0053   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9694   -0.1288   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432   -0.0336   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0587    0.3818    0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9815   -0.3703    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6305    0.0245    2.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4183   -1.6280    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -1.3755   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1718   -2.4781   -0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177   -1.4874   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126   -0.3423   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2737   -0.5079   -0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222   -0.1917    0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.4408    0.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450    0.5554   -0.1716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5948    0.3624   -0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1296   -0.8776   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2819   -1.8673    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9287   -1.6886    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877    0.8468   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470    2.0650   -1.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    2.4333   -2.3338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    2.8140   -0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    4.0923   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8862    2.8640    0.7126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0976    3.5265   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    0.7014   -1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073   -1.0452   -1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900    1.2945    0.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5553    1.1298    2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -0.5214    2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7125   -0.2568    2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7126   -1.5076   -0.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3783   -1.9834    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7073   -2.4548    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -3.4111   -0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.4401   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    0.1475   -1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -1.5445   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.8536    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -0.9009    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8033    1.5327   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2438    1.1478   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1983   -1.0251   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7059   -2.8558    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -2.4982    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    2.6015    0.8429 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  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22  3  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 25 49  1  0
M  END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-2-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoate	Generator

Chemical Formula

C₂₁H₂₄O₄

Average Mass

340.4190 Da

Monoisotopic Mass

340.16746 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C(O)=CC(CCC2=CC=CC=C2)=C1C(O)=O

InChI Identifier

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

InChI Key

LWTSBJAZSUSNIF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400Mz, CHCL₃(Solvent-Peak), simulated)	Rgf8b			2020-10-15	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Amorpha fruticosa	LOTUS Database	35616633

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
O-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid or derivatives
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	4.31	ALOGPS
logP	5.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.85	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	37.57 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24705714

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25135578

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl (NP0001744)

MOL for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

3D MOL for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

3D SDF for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

3D-SDF for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

PDB for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

3D PDB for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

SMILES for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

INCHI for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

Structure for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)

3D Structure for NP0001744 (2-Carboxy-3-methoxy-5-hydroxy-4-prenylbibenzyl)