NP-MRD: Showing NP-Card for (1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione (NP0233892)

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Record Information

Version

2.0

Created at

2022-09-06 15:39:46 UTC

Updated at

2022-09-06 15:39:46 UTC

NP-MRD ID

NP0233892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione

Description

Dicaffeoylglycerol belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. (1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione is found in Ananas comosus. (1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione was first documented in 2010 (PMID: 20677784). Based on a literature review a small amount of articles have been published on dicaffeoylglycerol (PMID: 32245029) (PMID: 35566208).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217392D          

 30 31  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   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
  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  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
M  END

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
   -2.4073   -3.4292    1.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365   -2.3981    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6053   -1.7494    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -0.7056   -0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2225   -0.1126   -0.7461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3540   -0.5731   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5657    0.0746   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6829    1.1705   -1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9128    1.8158   -1.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5478    1.6342   -1.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5990    2.7464   -2.6068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3456    0.9925   -1.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -2.0675   -0.2281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0639   -0.9744   -1.0532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.8041    0.8516 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0701   -2.8996    1.7127 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3781   -1.7877    0.1408 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4470   -0.7505   -0.7172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -1.8630    1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -2.8102    1.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286   -1.0307    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9350   -0.0639    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1529    0.7605    0.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0787    0.5552    1.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2071    1.3849    1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3762    2.3815    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4984    3.2050    0.6071 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4516    2.5895   -0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6118    3.5857   -1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3479    1.7613   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4843   -2.1773    0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0953   -0.2430   -1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3058   -1.4503    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4523   -0.2927    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9434    2.6211   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575    3.0817   -3.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815    1.4127   -2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084   -2.9129   -0.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646   -1.2190   -2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0897   -0.8384    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -3.7062    1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -2.7731   -0.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9143    0.0508   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -1.2181    1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833    0.1895   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0011   -0.2082    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9701    1.2639    2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2271    3.1091    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9057    3.7069   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    1.9652   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 12  5  1  0
 30 23  1  0
 16 41  1  0
 15 40  1  1
 13 38  1  6
 14 39  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 17 42  1  6
 18 43  1  0
 21 44  1  0
 22 45  1  0
 24 46  1  0
 25 47  1  0
 27 48  1  0
 29 49  1  0
 30 50  1  0
M  END


  Mrv1652309062217392D          

 30 31  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   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
  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  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233892

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c22-13-5-1-11(9-17(13)26)3-7-15(24)19(28)21(30)20(29)16(25)8-4-12-2-6-14(23)18(27)10-12/h1-10,19-23,26-30H/b7-3+,8-4+

> <INCHI_KEY>
PKJKQOJIQKRUEM-FCXRPNKRSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.382

> <EXACT_MASS>
416.110732224

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.06483992933358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,8E)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione

> <JCHEM_LOGP>
1.7047188766666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.302086333457494

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.701023441407397

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7375776076080927

> <JCHEM_POLAR_SURFACE_AREA>
175.75

> <JCHEM_REFRACTIVITY>
108.03409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1E,8E)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₉

Average Mass

416.3820 Da

Monoisotopic Mass

416.11073 Da

IUPAC Name

(1E,8E)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione

Traditional Name

(1E,8E)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H20O9/c22-13-5-1-11(9-17(13)26)3-7-15(24)19(28)21(30)20(29)16(25)8-4-12-2-6-14(23)18(27)10-12/h1-10,19-23,26-30H/b7-3+,8-4+

InChI Key

PKJKQOJIQKRUEM-FCXRPNKRSA-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
Ananas comosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Fatty alcohol
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Phenol
Fatty acyl
Benzenoid
Monosaccharide
Beta-hydroxy ketone
Monocyclic benzene moiety
Acyloin
Alpha,beta-unsaturated ketone
Enone
Alpha-hydroxy ketone
Acryloyl-group
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.7	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	175.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	108.03 m³·mol⁻¹	ChemAxon
Polarizability	41.06 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

C00054145

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129847896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han HJ, Park SK, Kang JY, Kim JM, Yoo SK, Heo HJ: Anti-Melanogenic Effect of Ethanolic Extract of Sorghum bicolor on IBMX-Induced Melanogenesis in B16/F10 Melanoma Cells. Nutrients. 2020 Mar 20;12(3). pii: nu12030832. doi: 10.3390/nu12030832. [PubMed:32245029 ]
Wang H, Zhang R, Zhang K, Chen X, Zhang Y: Antioxidant, Hypoglycemic and Molecular Docking Studies of Methanolic Extract, Fractions and Isolated Compounds from Aerial Parts of Cymbopogon citratus (DC.) Stapf. Molecules. 2022 Apr 30;27(9):2858. doi: 10.3390/molecules27092858. [PubMed:35566208 ]
Svensson L, Sekwati-Monang B, Lutz DL, Schieber A, Ganzle MG: Phenolic acids and flavonoids in nonfermented and fermented red sorghum (Sorghum bicolor (L.) Moench). J Agric Food Chem. 2010 Aug 25;58(16):9214-20. doi: 10.1021/jf101504v. Epub 2010 Aug 2. [PubMed:20677784 ]
LOTUS database [Link]

Showing NP-Card for (1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione (NP0233892)

MOL for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

3D MOL for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

3D SDF for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

3D-SDF for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

PDB for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

3D PDB for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

SMILES for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

INCHI for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

Structure for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)

3D Structure for NP0233892 ((1e,8e)-1,9-bis(3,4-dihydroxyphenyl)-4,5,6-trihydroxynona-1,8-diene-3,7-dione)