NP-MRD: Showing NP-Card for 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside (NP0027696)

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Record Information

Version

2.0

Created at

2021-06-19 19:46:53 UTC

Updated at

2021-06-29 23:53:57 UTC

NP-MRD ID

NP0027696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside is found in Upuna borneensis. 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside was first documented in 2004 (Ali, Z., et al.). Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121463D          

 58 60  0  0  0  0            999 V2000
    3.2390    1.6463   -3.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    1.9424   -2.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4897    0.8665   -1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910   -0.3447   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1189   -0.5879   -2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770   -1.3272   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0638   -1.1057    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293   -2.1150    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.0867    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    0.2942    1.8415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7060   -0.3329    3.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087   -0.1370    4.1472 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4304   -0.7068    5.4226 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5906   -2.1236    5.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -0.8083    3.8155 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.5630    0.4780    0.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4091   -0.1312   -0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  4  2  0  0  0  0
  4 33  1  0  0  0  0
 12 11  1  0  0  0  0
  5  6  1  0  0  0  0
  4  2  1  0  0  0  0
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  2  3  2  0  0  0  0
 18 19  1  0  0  0  0
  2  1  1  0  0  0  0
 20 21  1  0  0  0  0
 33 34  1  0  0  0  0
  8  9  1  0  0  0  0
 21 22  1  0  0  0  0
 14 15  1  0  0  0  0
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 24 25  2  0  0  0  0
 24 22  1  0  0  0  0
 33 10  2  0  0  0  0
 22 23  2  0  0  0  0
 20 18  1  0  0  0  0
 25 26  1  0  0  0  0
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 18 16  1  0  0  0  0
 27 28  1  0  0  0  0
  8  7  2  0  0  0  0
 28 29  2  0  0  0  0
 16 13  1  0  0  0  0
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M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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    3.1910   -0.3447   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9293   -2.1150    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2087   -0.1370    4.1472 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192121463D          

 58 60  0  0  0  0            999 V2000
    3.2390    1.6463   -3.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    1.9424   -2.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2378    3.0769   -2.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.8665   -1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910   -0.3447   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5697    4.1761   -5.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647    4.9370   -6.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382    3.4084   -5.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    2.6425   -4.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.0745   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    2.2566   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.7135   -4.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291    1.6205   -3.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538    2.4441   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280   -1.4583   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -2.2704   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974   -1.7167    2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    1.3668    2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477    0.9404    4.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.4682    6.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.2831    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.5177    5.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -1.8900    3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -0.8824    4.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.7961    2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -1.2584    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536   -1.3468    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    0.1665   -2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    2.3276   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    3.4605   -3.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    4.8036   -5.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566    4.8350   -7.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    3.3962   -5.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3476    2.0643   -3.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2655    2.9059   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  4 33  1  0  0  0  0
 12 11  1  0  0  0  0
  5  6  1  0  0  0  0
  4  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2  3  2  0  0  0  0
 18 19  1  0  0  0  0
  2  1  1  0  0  0  0
 20 21  1  0  0  0  0
 33 34  1  0  0  0  0
  8  9  1  0  0  0  0
 21 22  1  0  0  0  0
 14 15  1  0  0  0  0
 11 20  1  0  0  0  0
 24 25  2  0  0  0  0
 24 22  1  0  0  0  0
 33 10  2  0  0  0  0
 22 23  2  0  0  0  0
 20 18  1  0  0  0  0
 25 26  1  0  0  0  0
 10  8  1  0  0  0  0
 26 27  2  0  0  0  0
 18 16  1  0  0  0  0
 27 28  1  0  0  0  0
  8  7  2  0  0  0  0
 28 29  2  0  0  0  0
 16 13  1  0  0  0  0
 29 31  1  0  0  0  0
  7  5  1  0  0  0  0
 31 32  2  0  0  0  0
 32 26  1  0  0  0  0
 13 12  1  0  0  0  0
 29 30  1  0  0  0  0
 13 14  1  0  0  0  0
 11 10  1  0  0  0  0
 11 41  1  1  0  0  0
 16 46  1  6  0  0  0
 17 47  1  0  0  0  0
 18 48  1  1  0  0  0
 19 49  1  0  0  0  0
 20 50  1  6  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 13 42  1  1  0  0  0
 15 45  1  0  0  0  0
  7 39  1  0  0  0  0
  6 38  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
 34 58  1  0  0  0  0
  9 40  1  0  0  0  0
 24 51  1  0  0  0  0
 25 52  1  0  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
 31 56  1  0  0  0  0
 32 57  1  0  0  0  0
 30 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[C@@]2([H])C2=C(O[H])C(C(=O)C([H])([H])[H])=C(O[H])C([H])=C2O[H])C([H])([H])O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O11/c1-10(25)17-13(27)8-14(28)18(20(17)31)22-23(21(32)19(30)15(9-24)33-22)34-16(29)7-4-11-2-5-12(26)6-3-11/h2-8,15,19,21-24,26-28,30-32H,9H2,1H3/b7-4+/t15-,19-,21+,22+,23-/m1/s1

> <INCHI_KEY>
MYDUGZXQDHTEJB-YTPWZWQBSA-N

> <FORMULA>
C23H24O11

> <MOLECULAR_WEIGHT>
476.434

> <EXACT_MASS>
476.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.85217611407595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.8932018609999997

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.107676533923781

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.552107229735751

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979193257133341

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
117.07039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    3.2390    1.6463   -3.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2574    0.2942    1.8415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7060   -0.3329    3.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4304   -0.7068    5.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -2.1236    5.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0942   -0.3013    1.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.9358   -1.2181   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6406    0.6596   -1.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958    1.8648   -2.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    2.6343   -3.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269    3.4300   -3.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676    4.1945   -4.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697    4.1761   -5.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6382    3.4084   -5.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    2.6425   -4.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.0745   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    2.2566   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.7135   -4.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291    1.6205   -3.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538    2.4441   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280   -1.4583   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -2.2704   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974   -1.7167    2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    1.3668    2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477    0.9404    4.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.4682    6.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.2831    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.5177    5.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -1.8900    3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -0.8824    4.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.7961    2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -1.2584    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536   -1.3468    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    0.1665   -2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    2.3276   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    3.4605   -3.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    4.8036   -5.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566    4.8350   -7.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    3.3962   -5.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3476    2.0643   -3.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2655    2.9059   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  4 33  1  0
 12 11  1  0
  5  6  1  0
  4  2  1  0
 16 17  1  0
  2  3  2  0
 18 19  1  0
  2  1  1  0
 20 21  1  0
 33 34  1  0
  8  9  1  0
 21 22  1  0
 14 15  1  0
 11 20  1  0
 24 25  2  0
 24 22  1  0
 33 10  2  0
 22 23  2  0
 20 18  1  0
 25 26  1  0
 10  8  1  0
 26 27  2  0
 18 16  1  0
 27 28  1  0
  8  7  2  0
 28 29  2  0
 16 13  1  0
 29 31  1  0
  7  5  1  0
 31 32  2  0
 32 26  1  0
 13 12  1  0
 29 30  1  0
 13 14  1  0
 11 10  1  0
 11 41  1  1
 16 46  1  6
 17 47  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  6
 14 43  1  0
 14 44  1  0
 13 42  1  1
 15 45  1  0
  7 39  1  0
  6 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 34 58  1  0
  9 40  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 28 54  1  0
 31 56  1  0
 32 57  1  0
 30 55  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.239   1.646  -3.630  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.644   1.942  -2.281  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.238   3.077  -2.008  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.490   0.867  -1.252  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.191  -0.345  -1.301  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.119  -0.588  -2.275  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.977  -1.327  -0.334  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.064  -1.106   0.693  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.929  -2.115   1.606  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.336   0.087   0.788  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.257   0.294   1.841  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.706  -0.333   3.057  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.209  -0.137   4.147  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.430  -0.707   5.423  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.591  -2.124   5.347  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.542  -0.808   3.816  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.486  -0.626   4.874  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.122  -0.240   2.515  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.327  -0.986   2.256  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.094  -0.301   1.370  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.563   0.478   0.242  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.409  -0.131  -0.614  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.936  -1.218  -0.423  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.641   0.660  -1.838  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.096   1.865  -2.067  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.285   2.634  -3.304  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.227   3.430  -3.767  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.368   4.194  -4.928  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.570   4.176  -5.622  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.665   4.937  -6.749  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.638   3.408  -5.173  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.496   2.643  -4.011  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.583   1.075  -0.186  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.890   2.257  -0.051  0.00  0.00           O+0
HETATM   35  H   UNK     0       2.840   0.714  -4.037  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.329   1.621  -3.565  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.954   2.444  -4.324  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.528  -1.458  -2.123  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.516  -2.270  -0.354  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.597  -1.717   2.441  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.153   1.367   2.047  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.348   0.940   4.307  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.162  -0.468   6.312  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.431  -0.283   5.555  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.250  -2.518   5.642  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.408  -1.890   3.688  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.350  -0.882   4.486  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.450   0.796   2.666  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.340  -1.258   1.314  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.954  -1.347   1.062  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.276   0.167  -2.565  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.442   2.328  -1.331  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.279   3.461  -3.234  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.541   4.804  -5.283  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.557   4.835  -7.119  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.585   3.396  -5.703  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.348   2.064  -3.662  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.266   2.906  -0.691  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5   33    2                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   38                                                       
CONECT    7    8    5   39                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8   40                                                       
CONECT   10   33    8   11                                                  
CONECT   11   12   20   10   41                                             
CONECT   12   11   13                                                       
CONECT   13   16   12   14   42                                             
CONECT   14   15   13   43   44                                             
CONECT   15   14   45                                                       
CONECT   16   17   18   13   46                                             
CONECT   17   16   47                                                       
CONECT   18   19   20   16   48                                             
CONECT   19   18   49                                                       
CONECT   20   21   11   18   50                                             
CONECT   21   20   22                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22                                                            
CONECT   24   25   22   51                                                  
CONECT   25   24   26   52                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   53                                                  
CONECT   28   27   29   54                                                  
CONECT   29   28   31   30                                                  
CONECT   30   29   55                                                       
CONECT   31   29   32   56                                                  
CONECT   32   31   26   57                                                  
CONECT   33    4   34   10                                                  
CONECT   34   33   58                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   31                                                            
CONECT   57   32                                                            
CONECT   58   34                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    3.2390    1.6463   -3.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6437    1.9424   -2.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2378    3.0769   -2.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.8665   -1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1910   -0.3447   -1.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1189   -0.5879   -2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770   -1.3272   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0638   -1.1057    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293   -2.1150    1.6058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.0867    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    0.2942    1.8415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7060   -0.3329    3.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087   -0.1370    4.1472 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4304   -0.7068    5.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -2.1236    5.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -0.8083    3.8155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4863   -0.6260    4.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218   -0.2395    2.5152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3267   -0.9855    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0942   -0.3013    1.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5630    0.4780    0.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4091   -0.1312   -0.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9358   -1.2181   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6406    0.6596   -1.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958    1.8648   -2.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    2.6343   -3.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2269    3.4300   -3.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3676    4.1945   -4.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697    4.1761   -5.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647    4.9370   -6.7489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382    3.4084   -5.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    2.6425   -4.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.0745   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    2.2566   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8400    0.7135   -4.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291    1.6205   -3.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538    2.4441   -4.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280   -1.4583   -2.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -2.2704   -0.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5974   -1.7167    2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    1.3668    2.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477    0.9404    4.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.4682    6.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4313   -0.2831    5.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.5177    5.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4081   -1.8900    3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -0.8824    4.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.7961    2.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -1.2584    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9536   -1.3468    1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2758    0.1665   -2.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    2.3276   -1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    3.4605   -3.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414    4.8036   -5.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5566    4.8350   -7.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850    3.3962   -5.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3476    2.0643   -3.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2655    2.9059   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  4 33  1  0
 12 11  1  0
  5  6  1  0
  4  2  1  0
 16 17  1  0
  2  3  2  0
 18 19  1  0
  2  1  1  0
 20 21  1  0
 33 34  1  0
  8  9  1  0
 21 22  1  0
 14 15  1  0
 11 20  1  0
 24 25  2  0
 24 22  1  0
 33 10  2  0
 22 23  2  0
 20 18  1  0
 25 26  1  0
 10  8  1  0
 26 27  2  0
 18 16  1  0
 27 28  1  0
  8  7  2  0
 28 29  2  0
 16 13  1  0
 29 31  1  0
  7  5  1  0
 31 32  2  0
 32 26  1  0
 13 12  1  0
 29 30  1  0
 13 14  1  0
 11 10  1  0
 11 41  1  1
 16 46  1  6
 17 47  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  6
 14 43  1  0
 14 44  1  0
 13 42  1  1
 15 45  1  0
  7 39  1  0
  6 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 34 58  1  0
  9 40  1  0
 24 51  1  0
 25 52  1  0
 27 53  1  0
 28 54  1  0
 31 56  1  0
 32 57  1  0
 30 55  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-2-(3-Acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₃H₂₄O₁₁

Average Mass

476.4340 Da

Monoisotopic Mass

476.13186 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-2-(3-acetyl-2,4,6-trihydroxyphenyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)O[C@]2([H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[C@@]2([H])C2=C(O[H])C(C(=O)C([H])([H])[H])=C(O[H])C([H])=C2O[H])C([H])([H])O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C23H24O11/c1-10(25)17-13(27)8-14(28)18(20(17)31)22-23(21(32)19(30)15(9-24)33-22)34-16(29)7-4-11-2-5-12(26)6-3-11/h2-8,15,19,21-24,26-28,30-32H,9H2,1H3/b7-4+/t15-,19-,21+,22+,23-/m1/s1

InChI Key

MYDUGZXQDHTEJB-YTPWZWQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Upuna borneensis	JEOL database	Ali, Z., et al, Phytochemistry 65, 2141 (2004)

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
Coumaric acid ester
Alkyl-phenylketone
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
C-glycosyl compound
Acylphloroglucinol derivative
Phloroglucinol derivative
Benzenetriol
Phenylketone
Acetophenone
Benzoyl
Styrene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Ketone
Secondary alcohol
1,2-diol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Organic oxide
Primary alcohol
Carbonyl group
Alcohol
Hydrocarbon derivative
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	1.15	ALOGPS
logP	1.89	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.07 m³·mol⁻¹	ChemAxon
Polarizability	46.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

10191066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21579248

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ali, Z., et al. (2004). Ali, Z., et al, Phytochemistry 65, 2141 (2004). Phytochem..

Showing NP-Card for 2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside (NP0027696)

MOL for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

3D MOL for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

3D SDF for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

3D-SDF for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

PDB for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

3D PDB for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

SMILES for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

INCHI for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

Structure for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)

3D Structure for NP0027696 (2,4,6-trihydroxyacetophenone 3-C-beta-(2'-O-E-coumaroyl)-glucopyranoside)