NP-MRD: Showing NP-Card for 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0157865)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 15:21:15 UTC

Updated at

2022-09-02 15:21:15 UTC

NP-MRD ID

NP0157865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Description

3-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is found in Manilkara zapota. 3-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241513572D          

 36 38  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    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
    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    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 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
    6.4302   -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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   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
    2.8579   -4.9500    0.0000 O   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
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   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 O   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
    1.9592   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0678    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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
  7 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 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
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 25 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    1.9801   -0.5728    0.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3350   -0.1798   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5602    1.0040   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735    1.9689   -1.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173    2.4287   -0.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533    3.6356   -0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491    4.1383   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848    3.4820    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8972    3.9634    1.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2177    2.3115    1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6034    2.2662 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1064    1.8268    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -1.0364   -0.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0172   -2.2253   -0.1696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1406   -3.3835   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -4.6796   -0.5920 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8627   -5.4023   -1.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5985   -5.4957    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1931   -5.0943    1.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9087   -6.7535   -0.3650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5796   -4.5014    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731   -3.2090   -0.1138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4727   -3.1564    0.6018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3950   -2.0905    0.4080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0108   -0.8668    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754    0.0534    0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365   -0.2251    2.2032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1058    1.3057    0.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5320    2.1504    1.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    3.3659    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5753    4.2194    2.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3448    3.7640    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543    4.9731   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    2.8990   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195    3.3188   -2.2960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038    1.6993   -0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    1.1367   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221    2.7108   -2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233    4.1553   -1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966    5.0569   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3745    4.8229    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5234    1.9676    2.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6877    0.9084    0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -2.3009    0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3154   -3.1090   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278   -3.5224   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -5.7361   -2.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010   -7.4668    0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085   -4.3066    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -5.3491    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -3.1830   -1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8720   -4.0556    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -2.2378    1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4268    1.9408    2.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4744    4.0184    3.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2514    5.5621    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154    2.7156   -3.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9674    1.0326   -1.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 16  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 13  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
 14 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 16 18  1  0
 18 20  1  0
 18 19  2  0
 24 22  1  0
 36 28  1  0
 12  5  1  0
 23 52  1  0
 22 51  1  6
 21 49  1  0
 21 50  1  0
 17 47  1  0
 15 45  1  0
 15 46  1  0
 14 44  1  1
  3 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
 11 42  1  0
 12 43  1  0
 24 53  1  1
 29 54  1  0
 31 55  1  0
 33 56  1  0
 35 57  1  0
 36 58  1  0
 20 48  1  0
M  END


  Mrv1533004241513572D          

 36 38  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    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
    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    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 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
    6.4302   -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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   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
    2.8579   -4.9500    0.0000 O   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
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   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 O   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
    1.9592   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0678    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  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 13 20  1  0  0  0  0
  7 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 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
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 25 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O13/c24-12-3-1-10(5-13(12)25)2-4-18(29)35-17-9-23(34,22(32)33)8-16(28)20(17)36-21(31)11-6-14(26)19(30)15(27)7-11/h1-7,16-17,20,24-28,30,34H,8-9H2,(H,32,33)

> <INCHI_KEY>
JODSXMBDAMZIDL-UHFFFAOYSA-N

> <FORMULA>
C23H22O13

> <MOLECULAR_WEIGHT>
506.416

> <EXACT_MASS>
506.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.52479355514683

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.3160741256666662

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.070502682301262

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9680369349639455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2468923999223795

> <JCHEM_POLAR_SURFACE_AREA>
231.50999999999996

> <JCHEM_REFRACTIVITY>
118.99939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.677  -3.440   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.657  -3.440   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.174  -3.708   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.131  -1.993   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   34                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
CONECT   21    7    2   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25                                                       
CONECT   34    4   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₃H₂₂O₁₃

Average Mass

506.4160 Da

Monoisotopic Mass

506.10604 Da

IUPAC Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1CC(O)(CC(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C23H22O13/c24-12-3-1-10(5-13(12)25)2-4-18(29)35-17-9-23(34,22(32)33)8-16(28)20(17)36-21(31)11-6-14(26)19(30)15(27)7-11/h1-7,16-17,20,24-28,30,34H,8-9H2,(H,32,33)

InChI Key

JODSXMBDAMZIDL-UHFFFAOYSA-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
Manilkara zapota	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Galloyl ester
Gallic acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Pyrogallol derivative
Benzenetriol
Tricarboxylic acid or derivatives
Catechol
Styrene
Benzoyl
Phenol
Cyclohexanol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alpha-hydroxy acid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	1.52	ALOGPS
logP	1.32	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	231.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	119 m³·mol⁻¹	ChemAxon
Polarizability	46.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0157865)

MOL for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D MOL for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D SDF for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D-SDF for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

PDB for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D PDB for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

SMILES for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

INCHI for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

Structure for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D Structure for NP0157865 (3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)