NP-MRD: Showing NP-Card for [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0148147)

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Record Information

Version

2.0

Created at

2022-09-02 03:51:33 UTC

Updated at

2022-09-02 03:51:33 UTC

NP-MRD ID

NP0148147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Kelampayoside B belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Ilex macropoda and Neolamarckia cadamba. [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate was first documented in 1996 (PMID: 8814946). Based on a literature review very few articles have been published on Kelampayoside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205512D          

 45 48  0  0  1  0            999 V2000
    5.1886  -12.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7037  -11.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392  -10.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5543  -10.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8899   -9.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049   -8.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405   -8.0565    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2556   -7.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911   -6.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1062   -5.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4418   -5.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9568   -4.5468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1318   -4.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -3.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443   -3.2773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9923   -2.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964   -2.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -2.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4554   -2.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -1.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2623   -2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8144   -1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6213   -1.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1734   -1.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9804   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353   -2.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0423   -2.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7103   -9.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1953  -10.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0157   -9.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5007  -10.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8597  -10.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446  -11.4799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0091  -12.2336    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
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  9 10  1  6  0  0  0
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 31 32  1  1  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  1  0  0  0
  5 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  2  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
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   -8.5375   -0.3478   -0.7796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2491   -0.4558   -0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1886    0.3088   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9221    0.1990   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.9037   -0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5841    1.8018   -1.6580 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3037    1.7965   -2.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8611   -0.6573   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6360    3.7687   -0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.5791   -2.3653    2.3735 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1684   -2.7335    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -2.0992   -1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2921   -2.5591    1.9489 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.7717   -1.2871    2.1613 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 11 12  1  0
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M  END


  Mrv1652309022205512D          

 45 48  0  0  1  0            999 V2000
    5.1886  -12.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7037  -11.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5543  -10.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8899   -9.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049   -8.8102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2556   -7.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5911   -6.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1062   -5.9680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4418   -5.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1318   -4.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769   -3.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443   -3.2773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9923   -2.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964   -2.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -2.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4554   -2.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -1.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2623   -2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8144   -1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6213   -1.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1734   -1.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9804   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2353   -2.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0423   -2.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6833   -2.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9382   -3.6934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8763   -2.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118   -3.7622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9964   -3.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4116   -6.5492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7472   -5.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -7.2166    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7170   -7.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5610   -7.9703    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0459   -8.6377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7103   -9.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1953  -10.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0157   -9.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5007  -10.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8597  -10.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446  -11.4799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0091  -12.2336    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
 15 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  1  0  0  0
  5 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  2  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(COC(=O)\C=C\C4=CC=C(O)C(O)=C4)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O16/c1-38-18-9-15(10-19(39-2)25(18)40-3)44-27-24(35)23(34)22(33)20(45-27)11-41-28-26(36)29(37,13-43-28)12-42-21(32)7-5-14-4-6-16(30)17(31)8-14/h4-10,20,22-24,26-28,30-31,33-37H,11-13H2,1-3H3/b7-5+/t20-,22-,23+,24-,26+,27-,28-,29-/m1/s1

> <INCHI_KEY>
CKCXDLPHBUFZPH-YVQWANQJSA-N

> <FORMULA>
C29H36O16

> <MOLECULAR_WEIGHT>
640.591

> <EXACT_MASS>
640.200335079

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
62.52954635243231

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.07885961866666619

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.64236201293002

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207204168029826

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486859944966694

> <JCHEM_POLAR_SURFACE_AREA>
232.51999999999995

> <JCHEM_REFRACTIVITY>
149.7726

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.685 -22.997   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.780 -21.751   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.407 -20.344   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.501 -19.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.128 -17.692   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.223 -16.446   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.849 -15.039   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.944 -13.793   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.570 -12.386   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.665 -11.140   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.291  -9.733   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.386  -8.487   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.846  -8.487   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.370  -7.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.616  -6.118   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.586  -4.973   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.647  -4.973   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.153  -5.293   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.183  -4.149   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.707  -2.684   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.690  -4.469   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.720  -3.325   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.227  -3.645   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.257  -2.500   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.763  -2.821   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.239  -4.285   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.746  -4.605   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.209  -5.430   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.685  -6.894   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.702  -5.109   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.862  -7.023   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.327  -6.547   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.102 -12.225   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.728 -10.818   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.007 -13.471   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.538 -13.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.380 -14.878   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.286 -16.124   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.659 -17.531   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.564 -18.776   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.096 -18.616   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      14.001 -19.861   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.938 -20.183   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      11.843 -21.429   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      11.217 -22.836   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   31                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31   15   12   32                                                  
CONECT   32   31                                                            
CONECT   33    9   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    7   38                                                  
CONECT   38   37                                                            
CONECT   39    5   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40    3   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₆

Average Mass

640.5910 Da

Monoisotopic Mass

640.20034 Da

IUPAC Name

[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(3S,4R,5R)-3,4-dihydroxy-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](CO[C@@H]3OC[C@](O)(COC(=O)\C=C\C4=CC=C(O)C(O)=C4)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C29H36O16/c1-38-18-9-15(10-19(39-2)25(18)40-3)44-27-24(35)23(34)22(33)20(45-27)11-41-28-26(36)29(37,13-43-28)12-42-21(32)7-5-14-4-6-16(30)17(31)8-14/h4-10,20,22-24,26-28,30-31,33-37H,11-13H2,1-3H3/b7-5+/t20-,22-,23+,24-,26+,27-,28-,29-/m1/s1

InChI Key

CKCXDLPHBUFZPH-YVQWANQJSA-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
Ilex macropoda	LOTUS Database	35616633
Neolamarckia cadamba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Disaccharide
O-glycosyl compound
Anisole
Catechol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Oxolane
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.77	ALOGPS
logP	0.079	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	232.52 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	149.77 m³·mol⁻¹	ChemAxon
Polarizability	62.53 Å³	ChemAxon
Number of Rings	4	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

C00058562

Chemspider ID

9017113

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10841818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kitagawa I, Wei H, Nagao S, Mahmud T, Hori K, Kobayashi M, Uji T, Shibuya H: Indonesian Medicinal Plants. XIV. Characterization of 3'-O-Caffeoylsweroside, a new secoiridoid glucoside, and kelampayosides A and B, two new phenolic apioglucosides, from the bark of Anthocephalus chinensis (Rubiaceae). Chem Pharm Bull (Tokyo). 1996 Jun;44(6):1162-7. doi: 10.1248/cpb.44.1162. [PubMed:8814946 ]
LOTUS database [Link]

Showing NP-Card for [(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0148147)

MOL for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0148147 ([(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)