NP-MRD: Showing NP-Card for methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate (NP0201000)

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Record Information

Version

2.0

Created at

2022-09-04 19:57:54 UTC

Updated at

2022-09-04 19:57:54 UTC

NP-MRD ID

NP0201000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

Description

Methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate 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. methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate is found in Helianthus annuus. Based on a literature review very few articles have been published on methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221572D          

 30 31  0  0  1  0            999 V2000
    2.9218   -1.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -2.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -3.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6131   -3.0805    0.0000 O   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 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    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
    1.4289   -6.6000    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
    0.0000   -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
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    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
   -2.8579   -7.4250    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
   -3.5724   -7.8375    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 25 29  2  0  0  0  0
 18 29  1  0  0  0  0
 12 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -3.8636    3.7031   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5165    2.5377    0.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1106    1.2584   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290    1.1818   -0.9332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716    0.0228    0.3535 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8176    0.4594    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4414   -0.7471   -0.7512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0165   -2.1992   -0.7727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3948   -2.7283    0.4832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5033   -2.1781   -0.8849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0336   -3.4630   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985   -1.7682    0.4813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6462   -1.3450    0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -2.0189    0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647   -3.0676    1.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8181   -1.5623    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -0.4787   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.0026   -0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6173    1.1668   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8677    1.6730   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.0210   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2916    1.5246   -1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292    2.9060   -1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3554    0.9203   -1.0751 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8838   -0.1092    0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9408   -0.7362    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2697   -0.3267    1.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6453   -1.9361    1.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5522   -0.6009    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8340   -0.7691    1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6373    4.3297    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481    3.4701   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6213    4.2587   -0.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5225    0.8566    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0879   -0.3016   -1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5299   -0.7000   -0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5103   -2.7117   -1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2970   -2.3392    0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -1.4617   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -3.4917   -2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022   -2.7182    1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -2.1428    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2446    0.0688   -0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759    1.7062   -1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144    2.5824   -1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7017    3.5338   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9585    2.8645   -2.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3465    3.2945   -1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4013   -0.7225    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -0.7071    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3294    0.7623    1.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730   -1.5116    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914   -1.2254    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1317   -0.0369    1.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 30  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  1  0
 25 29  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 30  5  1  0
 29 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  6
  9 38  1  0
 10 39  1  6
 11 40  1  0
 12 41  1  1
 30 53  1  0
 30 54  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 29 52  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
M  END


  Mrv1652309042221572D          

 30 31  0  0  1  0            999 V2000
    2.9218   -1.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915   -2.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -3.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6131   -3.0805    0.0000 O   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 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    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
    1.4289   -6.6000    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
    0.0000   -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
   -0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    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
   -2.8579   -7.4250    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
   -3.5724   -7.8375    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 25 29  2  0  0  0  0
 18 29  1  0  0  0  0
 12 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201000

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O9/c1-11(22)14-6-4-13(8-15(14)12(2)23)5-7-18(25)30-17-10-21(28,20(27)29-3)9-16(24)19(17)26/h4-8,16-17,19,24,26,28H,9-10H2,1-3H3/b7-5+/t16-,17-,19-,21+/m0/s1

> <INCHI_KEY>
YVEPWSQLAFZXEG-JBTCCLEGSA-N

> <FORMULA>
C21H24O9

> <MOLECULAR_WEIGHT>
420.414

> <EXACT_MASS>
420.142032353

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.18478804355941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

> <JCHEM_LOGP>
-0.4002100213333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.197104676882944

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.142053819114953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.231828400944721

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
104.84759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.454  -3.123   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.464  -4.303   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.991  -5.750   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.508  -6.018   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.011  -5.750   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335 -12.320   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      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   30                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   18                                                       
CONECT   30   12    5                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄O₉

Average Mass

420.4140 Da

Monoisotopic Mass

420.14203 Da

IUPAC Name

methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

Traditional Name

methyl (1R,3S,4S,5S)-3-{[(2E)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H24O9/c1-11(22)14-6-4-13(8-15(14)12(2)23)5-7-18(25)30-17-10-21(28,20(27)29-3)9-16(24)19(17)26/h4-8,16-17,19,24,26,28H,9-10H2,1-3H3/b7-5+/t16-,17-,19-,21+/m0/s1

InChI Key

YVEPWSQLAFZXEG-JBTCCLEGSA-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
Helianthus annuus	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

Alkyl-phenylketone
Quinic acid
Cinnamic acid or derivatives
Cinnamic acid ester
Acetophenone
Phenylketone
Benzoyl
Aryl alkyl ketone
Aryl ketone
Styrene
Cyclohexanol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
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	-0.4	ChemAxon
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.85 m³·mol⁻¹	ChemAxon
Polarizability	42.18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

163185984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate (NP0201000)

MOL for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

3D MOL for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

3D SDF for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

3D-SDF for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

PDB for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

3D PDB for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

SMILES for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

INCHI for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

Structure for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)

3D Structure for NP0201000 (methyl (1r,3s,4s,5s)-3-{[(2e)-3-(3,4-diacetylphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylate)