NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0153915)

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Record Information

Version

2.0

Created at

2022-09-02 10:39:19 UTC

Updated at

2022-09-02 10:39:19 UTC

NP-MRD ID

NP0153915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. (2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Balanophora tobiracola. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212392D          

 33 35  0  0  1  0            999 V2000
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  2  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
    5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    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    5.7750    0.0000 C   0  0  0  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    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  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  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 31  1  0  0  0  0
 21 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -2.3500   -0.6895    1.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -0.1562    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375   -0.0341   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6098   -0.4718    0.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8421   -0.3949   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9247    0.1498   -1.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1111    0.2058   -2.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2751   -0.3002   -1.8479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4739   -0.2577   -2.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2103   -0.8528   -0.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3869   -1.3513   -0.0466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0065   -0.9005    0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    0.2887    0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1790    0.2026    1.1239 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7508    1.4610    1.3401 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042    1.3250    2.4340 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4104    2.5808    2.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5872    3.6540    2.9338 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622    0.1074    2.3271 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0121   -0.9606    3.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348   -0.4114    0.8885 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1728    0.4867    0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.1967   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883    1.1780   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0315    0.9504   -2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5896    1.9357   -3.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6883   -0.2595   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8492   -0.5038   -2.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1661   -1.2437   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7946   -2.4860   -1.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9950   -0.9986   -0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1318   -0.7027    0.3719 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7564   -2.0212    0.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3777    0.4181   -1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6113   -0.9230    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0456    0.5529   -2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1362    0.6425   -3.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5260    0.1408   -3.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3483   -1.7556    0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0070   -1.3376    1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0072   -0.2785    2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401    1.1858    3.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0043    2.3964    3.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    2.7537    1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8688    3.7199    2.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5257    0.2848    2.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -1.8274    2.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -1.3942    0.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4048    2.1406   -1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1963    2.8451   -3.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3082   -1.3885   -2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4475   -3.2355   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398   -1.8292    0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0587   -0.4809   -0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236   -2.3564   -0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 14 32  1  0
 32 33  1  0
 32 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
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 25 26  1  0
 25 27  2  0
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 21 19  1  0
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 12  5  1  0
 31 23  1  0
 18 45  1  0
 17 43  1  0
 17 44  1  0
 16 42  1  1
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  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 32 54  1  6
 33 55  1  0
 21 48  1  1
 24 49  1  0
 26 50  1  0
 28 51  1  0
 30 52  1  0
 31 53  1  0
 19 46  1  1
 20 47  1  0
M  END


  Mrv1652309022212392D          

 33 35  0  0  1  0            999 V2000
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  2  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
    5.0013    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    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    5.7750    0.0000 C   0  0  0  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    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  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  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 23 31  1  0  0  0  0
 21 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0153915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](OC2=CC(O)=C(O)C(O)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O12/c22-8-15-18(29)20(31-10-6-13(25)17(28)14(26)7-10)19(30)21(32-15)33-16(27)4-2-9-1-3-11(23)12(24)5-9/h1-7,15,18-26,28-30H,8H2/b4-2+/t15-,18-,19-,20+,21+/m1/s1

> <INCHI_KEY>
JFRZUQRYFPPNMG-GGYMIXDKSA-N

> <FORMULA>
C21H22O12

> <MOLECULAR_WEIGHT>
466.395

> <EXACT_MASS>
466.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.12166731404773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.9176765106666659

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.448587908797794

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.849117327238922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981112170262742

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
109.6555

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (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  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  13.090   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003  13.090   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670  11.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.672  10.780   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.005  11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.672   9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      20.005   8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.338   6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.670   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23                                                       
CONECT   32   21   14   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₁H₂₂O₁₂

Average Mass

466.3950 Da

Monoisotopic Mass

466.11113 Da

IUPAC Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](OC2=CC(O)=C(O)C(O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O12/c22-8-15-18(29)20(31-10-6-13(25)17(28)14(26)7-10)19(30)21(32-15)33-16(27)4-2-9-1-3-11(23)12(24)5-9/h1-7,15,18-26,28-30H,8H2/b4-2+/t15-,18-,19-,20+,21+/m1/s1

InChI Key

JFRZUQRYFPPNMG-GGYMIXDKSA-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
Balanophora tobiracola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Benzenetriol
4-alkoxyphenol
Pyrogallol derivative
Phenoxy compound
Catechol
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	0.98	ALOGPS
logP	0.92	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.66 m³·mol⁻¹	ChemAxon
Polarizability	44.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163194152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0153915)

MOL for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0153915 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyphenoxy)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)