NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0179056)

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Record Information

Version

2.0

Created at

2022-09-03 17:10:29 UTC

Updated at

2022-09-03 17:10:29 UTC

NP-MRD ID

NP0179056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Neocalceolarioside D belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. [(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Abeliophyllum distichum. [(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate was first documented in 2019 (PMID: 29911890). Based on a literature review very few articles have been published on Neocalceolarioside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219102D          

 33 35  0  0  1  0            999 V2000
    5.8138   -9.3442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8138   -8.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -8.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -7.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8138   -6.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835   -6.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3441   -6.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1565   -6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6868   -5.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4993   -5.8918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0296   -5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8421   -5.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3724   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1848   -4.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -4.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4330   -3.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5276   -4.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0579   -3.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8704   -3.9369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4007   -3.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2131   -3.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4953   -4.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3078   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -4.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1525   -4.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1242   -6.1783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9367   -6.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5939   -6.8103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8761   -7.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7815   -6.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2512   -7.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -7.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -8.1067    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
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 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  1  0  0  0
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 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  2  0  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -9.5115    0.7480    2.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6226    0.4326    1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3980   -0.9445    1.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4676   -1.2635    0.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5847   -0.2857   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6199   -0.4120   -1.8755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1699   -0.6477    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1172    0.2537   -0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -0.1807   -0.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323    0.5811   -0.5409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0040   -0.2285   -1.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2971   -0.3083   -0.7416 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0605   -1.2695   -1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3900   -1.4549   -1.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3323   -0.4770   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133    0.6962   -1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7210   -0.7208   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949    0.2636   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9779    0.1309   -0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5608   -1.0566    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9020   -1.1029    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6587    0.0341    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0050   -0.0198    1.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1104    1.2360    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7938    1.2433   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1543   -0.7682    0.6700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3246   -1.3018    1.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.3979    1.4888 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1688   -0.1296    2.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1650    1.2863    0.5944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4339    2.4144    0.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8485    1.0870   -0.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7697    1.4425    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0486   -1.6919    1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3368   -2.3099   -0.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9549   -1.1283   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2202   -0.5795    1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0150   -1.7063   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1548    0.2913   -1.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    1.2945   -0.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    1.3721   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    0.6836   -0.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643   -0.9390   -2.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -2.2578   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473   -1.7085   -0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413    1.2425   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9589   -1.9547    0.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3193   -2.0674    0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5597    0.8229    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7368    2.1162    0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3726    2.1985   -0.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5909   -1.6131    0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470   -2.0638    1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.9071    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2950    0.6092    3.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    1.7151    1.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7431    2.6945   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2378    1.8888   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8980    2.5082    1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 12  1  0
 12 13  1  0
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 12 11  1  0
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 10  9  1  0
  9  8  1  0
  8  7  1  0
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  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 33  1  0
 33 32  2  0
 10 30  1  0
 30 31  1  0
 30 28  1  0
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 25 19  1  0
 32  5  1  0
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 26 52  1  6
 12 42  1  1
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 13 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 21 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 10 41  1  6
  8 39  1  0
  8 40  1  0
  7 37  1  0
  7 38  1  0
  6 36  1  0
  4 35  1  0
  3 34  1  0
 33 59  1  0
 32 58  1  0
 30 56  1  1
 31 57  1  0
 28 54  1  1
 29 55  1  0
M  END


  Mrv1652309032219102D          

 33 35  0  0  1  0            999 V2000
    5.8138   -9.3442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8138   -8.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -8.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -7.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8138   -6.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835   -6.2373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3441   -6.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1565   -6.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6868   -5.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4993   -5.8918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0296   -5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8421   -5.4031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3724   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1848   -4.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7151   -4.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4330   -3.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4953   -4.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3078   -4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9650   -4.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1525   -4.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9367   -6.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5939   -6.8103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8761   -7.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7815   -6.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2512   -7.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -7.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5282   -8.1067    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  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
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 32 33  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0179056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OCCC2(O)C=CC(=O)C=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O10/c24-15-4-1-14(2-5-15)3-6-18(26)32-13-17-19(27)20(28)21(29)22(33-17)31-12-11-23(30)9-7-16(25)8-10-23/h1-10,17,19-22,24,27-30H,11-13H2/b6-3+/t17-,19-,20+,21-,22-/m1/s1

> <INCHI_KEY>
IWMPEDMJSGFILP-FPULVWICSA-N

> <FORMULA>
C23H26O10

> <MOLECULAR_WEIGHT>
462.451

> <EXACT_MASS>
462.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.84446656606619

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
0.662053828333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.203611187376096

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397963359505312

> <JCHEM_PKA_STRONGEST_BASIC>
-3.295591434612313

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
116.80470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0      10.852 -17.443   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.852 -15.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.519 -15.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.519 -13.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.852 -12.823   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.862 -11.643   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.842 -11.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.359 -11.910   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.349 -10.731   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      15.865 -10.998   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.855  -9.818   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      18.372 -10.086   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.362  -8.906   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.878  -9.173   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.868  -7.994   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.342  -6.547   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      23.385  -8.261   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.375  -7.081   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.891  -7.349   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.881  -6.169   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.398  -6.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.925  -7.884   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      30.441  -8.151   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      27.935  -9.063   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.418  -8.796   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.899 -11.533   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.415 -11.800   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      17.909 -12.713   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.435 -14.160   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.392 -12.445   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.402 -13.625   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.186 -13.593   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.186 -15.133   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   32                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26   12   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10   31                                                  
CONECT   31   30                                                            
CONECT   32    5   33                                                       
CONECT   33   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₁₀

Average Mass

462.4510 Da

Monoisotopic Mass

462.15260 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OCCC2(O)C=CC(=O)C=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C23H26O10/c24-15-4-1-14(2-5-15)3-6-18(26)32-13-17-19(27)20(28)21(29)22(33-17)31-12-11-23(30)9-7-16(25)8-10-23/h1-10,17,19-22,24,27-30H,11-13H2/b6-3+/t17-,19-,20+,21-,22-/m1/s1

InChI Key

IWMPEDMJSGFILP-FPULVWICSA-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
Abeliophyllum distichum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Aldehyde
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	0.66	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.8 m³·mol⁻¹	ChemAxon
Polarizability	45.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8542523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10367075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bardakci H, Turkoz Acar E, Kirmizibekmez H: Simultaneous quantification of six phenylethanoid glycosides in some Turkish Scutellaria species by a new HPLC-DAD method. Nat Prod Res. 2019 Jul;33(14):2116-2119. doi: 10.1080/14786419.2018.1486309. Epub 2018 Jun 18. [PubMed:29911890 ]
LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0179056)

MOL for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0179056 ([(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)ethoxy]oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)