NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0257313)

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Record Information

Version

2.0

Created at

2022-09-07 22:24:42 UTC

Updated at

2022-09-07 22:24:42 UTC

NP-MRD ID

NP0257313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Scrophuloside A 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. [(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Neopicrorhiza scrophulariiflora. [(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate was first documented in 2017 (PMID: 28496487). Based on a literature review very few articles have been published on Scrophuloside A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200242D          

 34 36  0  0  1  0            999 V2000
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -2.6922   -3.1672   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5306   -1.7772   -0.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724   -1.0519   -0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3731   -1.7545    0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2602   -1.1202    1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2916   -1.8585    2.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2256   -1.1295    3.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4165   -3.0848    2.0966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1032    0.2474    1.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1506    0.9373    1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2225    0.3135    0.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.0951   -0.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3001    0.7949   -1.3437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0092    1.1167   -0.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146    2.3538   -1.2408 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3850    2.9150   -0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5627    2.2260   -0.0587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7690    0.9672    0.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850    0.2905    0.7542 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1272    0.4105    0.5668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929   -0.8039    1.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -1.4015    1.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7591   -0.7588    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0013   -1.3916    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0841   -2.6708    1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3308   -3.2900    1.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -3.3126    1.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6910   -2.6930    1.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294    3.3608   -1.3653 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1237    4.5900   -1.6470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557    2.9774   -2.5634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8520    3.4703   -2.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274    1.4879   -2.6952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6075    1.0228   -3.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0294   -3.6101   -1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7549   -3.3302   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -3.6938    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692   -2.8296    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6391   -0.2143    2.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0775   -1.7455    3.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6059   -0.7860    3.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8227    0.7378    2.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0532    2.0184    1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2392   -0.2715   -1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757    2.3494   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844    3.9623   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    3.1175    0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9512    1.0377    0.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702   -1.3361    1.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7517    0.2528    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9143   -0.8752    0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8592   -3.2147    2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9787   -4.3225    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612   -3.1881    1.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    3.4538   -0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834    4.4484   -2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    3.4067   -3.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288    3.3543   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5499    1.1648   -3.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    0.8025   -4.4621 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  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 15 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
 11  3  1  0
 33 13  1  0
 28 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  9 42  1  0
 10 43  1  0
 13 44  1  6
 15 45  1  6
 16 46  1  0
 16 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 29 55  1  1
 30 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
M  END


  Mrv1652309082200242D          

 34 36  0  0  1  0            999 V2000
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 13 14  1  0  0  0  0
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 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0257313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O10/c1-13(25)15-6-9-17(18(11-15)31-2)33-24-23(30)22(29)21(28)19(34-24)12-32-20(27)10-5-14-3-7-16(26)8-4-14/h3-11,19,21-24,26,28-30H,12H2,1-2H3/b10-5+/t19-,21-,22+,23-,24-/m1/s1

> <INCHI_KEY>
ZZDJNPFVWSOKTO-TULNHCNLSA-N

> <FORMULA>
C24H26O10

> <MOLECULAR_WEIGHT>
474.462

> <EXACT_MASS>
474.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.520281646680615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.5319140503333326

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20214169056911

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397961030437141

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491103097396866

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
118.59790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.005 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.674 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.674 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      28.007 -14.630   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.338 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   15   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   13   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(e)-6-O-(2''-Acetyl-3'', 4''-di-O,O-p-methoxycinnamoyl)-alpha-L-rhamnopyranosyl catalpol	MeSH
Scrophuloside a(4)	MeSH

Chemical Formula

C₂₄H₂₆O₁₀

Average Mass

474.4620 Da

Monoisotopic Mass

474.15260 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O)C(C)=O

InChI Identifier

InChI=1S/C24H26O10/c1-13(25)15-6-9-17(18(11-15)31-2)33-24-23(30)22(29)21(28)19(34-24)12-32-20(27)10-5-14-3-7-16(26)8-4-14/h3-11,19,21-24,26,28-30H,12H2,1-2H3/b10-5+/t19-,21-,22+,23-,24-/m1/s1

InChI Key

ZZDJNPFVWSOKTO-TULNHCNLSA-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
Neopicrorhiza scrophulariiflora	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
Coumaric acid ester
Alkyl-phenylketone
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Phenylketone
Acetophenone
Anisole
Methoxybenzene
Benzoyl
Phenol ether
Aryl alkyl ketone
Aryl ketone
Phenoxy compound
Styrene
Fatty acid ester
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Ketone
Ether
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aldehyde
Alcohol
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	1.53	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.6 m³·mol⁻¹	ChemAxon
Polarizability	47.52 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

C00031323

Chemspider ID

9678608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11503806

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pasdaran A, Delazar A, Ayatollahi SA, Pasdaran A: Chemical Composition and Biological Activities of Methanolic Extract of Scrophularia Oxysepala Boiss. Iran J Pharm Res. 2017 Winter;16(1):338-346. [PubMed:28496487 ]
LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0257313)

MOL for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0257313 ([(2r,3s,4s,5r,6s)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)