NP-MRD: Showing NP-Card for butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate (NP0274263)

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Record Information

Version

2.0

Created at

2022-09-08 21:35:44 UTC

Updated at

2022-09-08 21:35:44 UTC

NP-MRD ID

NP0274263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

Description

Butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-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. butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate is found in Hydrastis canadensis. Butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181503262D          

 30 31  0  0  0  0            999 V2000
   -1.7869   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -6.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855   -7.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7821   -7.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -5.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2518   -5.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -4.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -4.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -3.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037   -3.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680   -2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502   -1.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4145    0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967    0.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9448   -0.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7573   -0.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626   -1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946   -5.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070   -5.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -6.4162    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  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
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 19 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  8 30  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -7.3057    2.8431    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2823    2.2800    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7870    0.9106    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8369    0.2675   -0.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5590    0.1212   -0.3960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2659   -0.6050    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1997   -1.2060    1.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -0.6921    1.2569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9100   -1.4956    2.3921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -1.3337    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -0.3141   -0.6734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5039   -0.9960   -1.5611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862    0.6950    0.0541 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8584    0.2606    0.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    0.9673   -0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605    2.0473   -1.1797 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610    0.4829   -0.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -0.6396   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9576   -1.1510   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2079   -2.3627    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4646   -2.9092    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5370   -2.2818    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8195   -2.8161    0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2885   -1.0798   -0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3935   -0.4494   -1.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1378    0.7709   -1.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0223   -0.5367   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9638    0.9246    1.4716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3145    0.1013    2.3817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.7191    1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3139    2.4622    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3206    3.9471    1.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0220    2.5401    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2655    2.9675   -0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3218    2.2148    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7920    0.9942   -0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9180    0.3106    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7876    0.8179   -1.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2476   -0.7478   -1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2782   -2.3689    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527   -2.0180   -0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1611   -1.9443    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148    0.1750   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7090   -1.9723   -1.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182    1.6695   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.0639   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8289   -1.2004    0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3975   -2.8705    1.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6620   -3.8580    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5717   -2.3310   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188    0.7342   -2.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8849    1.5567   -1.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0506    1.0941   -2.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8916    0.4035   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671    1.9713    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.4771    1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0267    1.4413    0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7207    0.9021    2.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  2  0
 13 28  1  0
 28 29  1  0
 28 30  1  0
 30  8  1  0
 27 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  6
 12 44  1  0
 13 45  1  6
 17 46  1  0
 18 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  1
 29 56  1  0
 30 57  1  0
 30 58  1  0
M  END


  Mrv1533004181503262D          

 30 31  0  0  0  0            999 V2000
   -1.7869   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3579   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -6.5594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855   -6.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7855   -7.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -6.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7821   -7.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696   -5.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2518   -5.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7215   -4.5202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643   -5.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -4.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161   -3.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0037   -3.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680   -2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502   -1.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4145    0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967    0.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9448   -0.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7573   -0.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626   -1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5946   -5.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4070   -5.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -6.4162    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  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
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 19 27  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
  8 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0274263

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-3-4-9-29-20(26)21(27)11-15(23)19(16(24)12-21)30-18(25)8-6-13-5-7-14(22)17(10-13)28-2/h5-8,10,15-16,19,22-24,27H,3-4,9,11-12H2,1-2H3

> <INCHI_KEY>
CFSGXVCRNZCANZ-UHFFFAOYSA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.446

> <EXACT_MASS>
424.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.232006217120244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.3471573686666665

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.177916973199633

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865600484177914

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246164950483471

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
106.35969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -3.336 -12.244   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.002 -13.014   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.668 -12.244   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.666 -13.014   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.999 -12.244   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.333 -13.014   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.333 -14.554   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.667 -12.244   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.193 -13.691   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.677 -11.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.203  -9.617   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.213  -8.438   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.720  -9.350   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.247  -7.903   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.257  -6.723   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.740  -6.991   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.783  -5.276   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.794  -4.096   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.320  -2.649   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.330  -1.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.857  -0.022   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.374   0.245   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.900   1.692   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.364  -0.935   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.880  -0.667   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.870  -1.847   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.837  -2.382   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.710 -10.530   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.226 -10.262   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.183 -11.977   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   19                                                       
CONECT   28   13   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    8                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
Butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₈O₉

Average Mass

424.4460 Da

Monoisotopic Mass

424.17333 Da

IUPAC Name

butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

Traditional Name

butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)C1(O)CC(O)C(OC(=O)C=CC2=CC=C(O)C(OC)=C2)C(O)C1

InChI Identifier

InChI=1S/C21H28O9/c1-3-4-9-29-20(26)21(27)11-15(23)19(16(24)12-21)30-18(25)8-6-13-5-7-14(22)17(10-13)28-2/h5-8,10,15-16,19,22-24,27H,3-4,9,11-12H2,1-2H3

InChI Key

CFSGXVCRNZCANZ-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
Hydrastis canadensis	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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Fatty acid ester
Phenol
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ether
Carboxylic acid derivative
Polyol
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	1.28	ALOGPS
logP	1.35	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.36 m³·mol⁻¹	ChemAxon
Polarizability	43.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

470422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate (NP0274263)

MOL for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

3D MOL for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

3D SDF for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

3D-SDF for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

PDB for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

3D PDB for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

SMILES for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

INCHI for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

Structure for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)

3D Structure for NP0274263 (butyl 1,3,5-trihydroxy-4-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate)