NP-MRD: Showing NP-Card for (2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid (NP0207263)

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Record Information

Version

2.0

Created at

2022-09-05 03:48:30 UTC

Updated at

2022-09-05 03:48:30 UTC

NP-MRD ID

NP0207263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid

Description

CHEMBL3112597 belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid is found in Plectranthus amboinicus. Based on a literature review very few articles have been published on CHEMBL3112597.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205482D          

 27 28  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 O   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
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.5195   -0.5101    2.1693 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -0.1523    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    0.5431    1.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1456   -0.4798   -0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9986   -0.1526   -0.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2552    0.4826   -0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6073    1.7123   -1.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8251    2.3074   -1.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801    1.6537   -0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    2.2385   -0.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    0.4421    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3791   -0.2601    1.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2280   -0.1174    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.1597   -0.4572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2517   -0.2556   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540   -0.5651    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0920    0.2741    1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3286    1.4393    0.7703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3439    2.3312    1.1254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    1.7365   -0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7563    2.9242   -0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5033    0.9289   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216   -2.5010    0.1613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5696   -3.0069   -0.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   -3.4602   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -3.2071    0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5453   -4.6143   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4979    1.5631    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613   -0.3666   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828    2.2340   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0988    3.2716   -1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7741    1.8891    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899    0.1197    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378   -1.0982    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -1.2183   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.4788    1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026    0.0001    2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110    2.0724    1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    3.5333   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8568    1.1448   -1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -2.4787    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225   -3.1060   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310   -4.6534   -1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 14  1  0
 14  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 23 25  1  0
 25 27  1  0
 25 26  2  0
 13  6  1  0
 22 15  1  0
 24 42  1  0
 23 41  1  1
 14 35  1  6
  5 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
  3 28  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
 27 43  1  0
M  END


  Mrv1652309052205482D          

 27 28  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 O   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
    4.2868   -2.4750    0.0000 O   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
    2.8579   -1.6500    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(\C(=C\C1=CC=C(O)C(O)=C1)C(O)=O)C1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O9/c19-11-3-1-8(6-13(11)21)5-10(17(24)25)15(16(23)18(26)27)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-23H,(H,24,25)(H,26,27)/b10-5-

> <INCHI_KEY>
GRVCQHNOZLCUEA-YHYXMXQVSA-N

> <FORMULA>
C18H16O9

> <MOLECULAR_WEIGHT>
376.317

> <EXACT_MASS>
376.079432095

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.10858792219947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid

> <JCHEM_LOGP>
1.5139819059999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.34809619906738

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6685650588145613

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9774761241541183

> <JCHEM_POLAR_SURFACE_AREA>
175.75

> <JCHEM_REFRACTIVITY>
92.26679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
CONECT   14    4   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   14   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₉

Average Mass

376.3170 Da

Monoisotopic Mass

376.07943 Da

IUPAC Name

(2Z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid

Traditional Name

(2Z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid

CAS Registry Number

Not Available

SMILES

OC(C(\C(=C\C1=CC=C(O)C(O)=C1)C(O)=O)C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C18H16O9/c19-11-3-1-8(6-13(11)21)5-10(17(24)25)15(16(23)18(26)27)9-2-4-12(20)14(22)7-9/h1-7,15-16,19-23H,(H,24,25)(H,26,27)/b10-5-

InChI Key

GRVCQHNOZLCUEA-YHYXMXQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coleus amboinicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Linear 1,3-diarylpropanoid
Cinnamylphenol
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
3-phenylpropanoic-acid
Medium-chain hydroxy acid
Catechol
Medium-chain fatty acid
Branched fatty acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Hydroxy fatty acid
1-hydroxy-4-unsubstituted benzenoid
Unsaturated fatty acid
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Hydroxy acid
Fatty acid
Benzenoid
Alpha-hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	1.51	ChemAxon
pKa (Strongest Acidic)	2.67	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	175.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	92.27 m³·mol⁻¹	ChemAxon
Polarizability	35.11 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

31136790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57620293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid (NP0207263)

MOL for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

3D MOL for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

3D SDF for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

3D-SDF for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

PDB for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

3D PDB for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

SMILES for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

INCHI for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

Structure for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)

3D Structure for NP0207263 ((2z)-3-(3,4-dihydroxyphenyl)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxypentanedioic acid)