NP-MRD: Showing NP-Card for (1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0244778)

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Record Information

Version

2.0

Created at

2022-09-07 05:39:06 UTC

Updated at

2022-09-07 05:39:06 UTC

NP-MRD ID

NP0244778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL517628 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. (1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid is found in Ipomoea pes-caprae. Based on a literature review very few articles have been published on CHEMBL517628.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207392D          

 36 38  0  0  1  0            999 V2000
    5.0013    1.2375    0.0000 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    6.4302    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8999    4.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9605    4.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730    4.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    5.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    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  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
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 17 19  1  6  0  0  0
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 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
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 34 35  1  0  0  0  0
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 29 36  1  0  0  0  0
M  END

     RDKit          3D

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   -6.7244   -1.2761   -2.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7501   -0.1982    1.3854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7097    0.3396    2.2159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2305    0.1791    3.6501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6627    1.2182    4.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256   -1.1340    4.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7627   -2.2539    3.2240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0294   -2.5670    2.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997   -3.4388    3.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -3.3793    4.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9330   -4.6141    3.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789   -1.9207    2.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -0.4542    2.1185 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3224   -0.1691    0.9782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6387    0.2558    1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357    0.3823    2.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4358    0.5501   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0850    1.5078   -3.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0729    2.4203   -1.5477 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8794    1.6870   -0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031   -1.0062   -0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057    1.8810   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6304    2.3937   -2.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4214    1.6920   -4.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3467   -0.7307   -4.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0509   -2.3057   -3.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2753   -1.6697   -1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    1.4175    2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3339    0.3118    3.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    2.0352    3.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -1.4413    5.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1637   -1.0532    4.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910   -2.9912    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -4.8510    3.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -2.1052    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
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 10 42  1  0
 11 43  1  0
 21 50  1  0
M  END


  Mrv1652309072207392D          

 36 38  0  0  1  0            999 V2000
    5.0013    1.2375    0.0000 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8999    4.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9605    4.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7730    4.2012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6784    5.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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 30 31  1  0  0  0  0
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 32 33  1  0  0  0  0
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 29 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O11/c26-16-6-1-14(2-7-16)4-9-22(31)36-23-19(29)12-25(34,24(32)33)13-20(23)35-21(30)10-5-15-3-8-17(27)18(28)11-15/h1-11,19-20,23,26-29,34H,12-13H2,(H,32,33)/b9-4+,10-5+/t19-,20-,23+,25-/m1/s1

> <INCHI_KEY>
PCMWSBGTYOCQCP-UMHPNHICSA-N

> <FORMULA>
C25H24O11

> <MOLECULAR_WEIGHT>
500.456

> <EXACT_MASS>
500.131861593

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
49.368240978356326

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.4617956383333324

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.992251476759618

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3189920303452682

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246879196378349

> <JCHEM_POLAR_SURFACE_AREA>
191.04999999999998

> <JCHEM_REFRACTIVITY>
124.78329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.013   8.110   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.993   8.110   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.510   7.842   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.466   9.557   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.339   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.673   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      24.006   1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      21.339   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      21.339   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   13   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₁

Average Mass

500.4560 Da

Monoisotopic Mass

500.13186 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C25H24O11/c26-16-6-1-14(2-7-16)4-9-22(31)36-23-19(29)12-25(34,24(32)33)13-20(23)35-21(30)10-5-15-3-8-17(27)18(28)11-15/h1-11,19-20,23,26-29,34H,12-13H2,(H,32,33)/b9-4+,10-5+/t19-,20-,23+,25-/m1/s1

InChI Key

PCMWSBGTYOCQCP-UMHPNHICSA-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
Ipomoea pes-caprae	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

Coumaric acid ester
Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Fatty acyl
Hydroxy acid
Monocyclic benzene moiety
Alpha-hydroxy acid
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.46	ChemAxon
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.78 m³·mol⁻¹	ChemAxon
Polarizability	49.37 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

24717310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42598865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid (NP0244778)

MOL for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D MOL for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D SDF for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D-SDF for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

PDB for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D PDB for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

SMILES for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

INCHI for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

Structure for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)

3D Structure for NP0244778 ((1r,3r,4s,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid)