NP-MRD: Showing NP-Card for N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+ (NP0031068)

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Record Information

Version

1.0

Created at

2021-06-19 22:15:18 UTC

Updated at

2021-06-29 23:59:26 UTC

NP-MRD ID

NP0031068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+

Provided By

JEOL Database JEOL Logo

Description

N-[2-(beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilic acid methyl ester 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. N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+ is found in Delphinium staphisagria L. It was first documented in 2005 (Diaz, J. G., et al.). Based on a literature review very few articles have been published on N-[2-(beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilic acid methyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100153D          

 56 58  0  0  0  0            999 V2000
   -0.5264   -2.1155    3.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517   -1.4866    3.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -0.7250    1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0543   -0.5665    1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.1076    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -0.3338    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.2313    2.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -0.0208    3.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    1.0236    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    1.2558    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.7023    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9035    1.7106   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8297    4.3234   -4.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161    2.0744   -4.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1030    0.6695   -2.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0  0  0  0
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 26 27  1  0  0  0  0
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 15 21  2  0  0  0  0
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  9 10  2  0  0  0  0
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  8 38  1  0  0  0  0
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M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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    4.8309    1.0236    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    1.2558    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202100153D          

 56 58  0  0  0  0            999 V2000
   -0.5264   -2.1155    3.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517   -1.4866    3.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -0.7250    1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0543   -0.5665    1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1740   -0.3338    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.2313    2.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -0.0208    3.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    1.0236    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    1.2558    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1614   -5.1742   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053   -2.8466   -1.5714 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3619   -3.1280   -2.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -1.3635    3.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380   -2.6968    4.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -2.7973    2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.9479    3.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    0.4411    3.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    1.4714    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.8807   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    0.4677   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668    3.8431   -2.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    4.9707   -4.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    2.1979   -4.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.0327   -3.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7234   -1.8502   -3.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -2.7838   -2.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0117   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584   -3.0249   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -0.3867   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.6618   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -5.7396   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -4.4508   -2.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -5.1970   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -2.6295   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -2.2948   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0  0  0  0
 24 23  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  3  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
 30 31  1  0  0  0  0
  2  1  1  0  0  0  0
 32 33  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 26 27  1  0  0  0  0
 13 15  1  0  0  0  0
 23 32  1  0  0  0  0
 15 21  2  0  0  0  0
 32 30  1  0  0  0  0
 21 20  1  0  0  0  0
  7  9  1  0  0  0  0
 20 19  2  0  0  0  0
 30 28  1  0  0  0  0
 19 17  1  0  0  0  0
  9 10  2  0  0  0  0
 17 16  2  0  0  0  0
 16 15  1  0  0  0  0
 21 22  1  0  0  0  0
 28 25  1  0  0  0  0
  3  4  2  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  0  0  0  0
 25 24  1  0  0  0  0
 17 18  1  0  0  0  0
 25 26  1  0  0  0  0
 23 22  1  0  0  0  0
 23 46  1  6  0  0  0
 28 51  1  1  0  0  0
 29 52  1  0  0  0  0
 30 53  1  6  0  0  0
 31 54  1  0  0  0  0
 32 55  1  1  0  0  0
 33 56  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 25 47  1  6  0  0  0
 27 50  1  0  0  0  0
  9 39  1  0  0  0  0
 10 40  1  0  0  0  0
  6 37  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
 12 41  1  0  0  0  0
 20 45  1  0  0  0  0
 19 44  1  0  0  0  0
 16 42  1  0  0  0  0
  8 38  1  0  0  0  0
 18 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(C(=O)OC([H])([H])[H])=C(N([H])C(=O)C2=C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C([H])=C([H])C(O[H])=C2[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H23NO11/c1-31-20(30)11-6-9(24)2-4-13(11)22-19(29)12-7-10(25)3-5-14(12)32-21-18(28)17(27)16(26)15(8-23)33-21/h2-7,15-18,21,23-28H,8H2,1H3,(H,22,29)/t15-,16-,17+,18-,21-/m1/s1

> <INCHI_KEY>
BIQSZYHQDBWCMC-ZIKOTGLESA-N

> <FORMULA>
C21H23NO11

> <MOLECULAR_WEIGHT>
465.411

> <EXACT_MASS>
465.127110565

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.9449719736962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)benzoate

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
0.5398435273333331

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.466664882679286

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.863578309213565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346251889

> <JCHEM_POLAR_SURFACE_AREA>
195.23999999999998

> <JCHEM_REFRACTIVITY>
111.70390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -0.5264   -2.1155    3.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517   -1.4866    3.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -0.7250    1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0543   -0.5665    1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.1076    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -0.3338    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.2313    2.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -0.0208    3.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    1.0236    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    1.2558    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.7023    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343    0.9330   -0.3149 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    1.7106   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    2.3793   -1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7340    1.7717   -2.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041    3.0055   -3.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    3.1438   -3.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8297    4.3234   -4.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161    2.0744   -4.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833    0.8390   -3.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030    0.6695   -2.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -0.5147   -2.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -1.6577   -2.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9012   -1.4599   -1.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -2.6014   -1.7705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1207   -2.2293   -1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -1.0456   -1.7945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1597   -3.8288   -1.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9749   -4.9850   -1.2751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -4.0970   -1.6526 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1614   -5.1742   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053   -2.8466   -1.5714 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3619   -3.1280   -2.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -1.3635    3.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380   -2.6968    4.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -2.7973    2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.9479    3.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    0.4411    3.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    1.4714    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.8807   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    0.4677   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668    3.8431   -2.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    4.9707   -4.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    2.1979   -4.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.0327   -3.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7234   -1.8502   -3.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -2.7838   -2.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0117   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584   -3.0249   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -0.3867   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.6618   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -5.7396   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -4.4508   -2.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -5.1970   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -2.6295   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -2.2948   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
 24 23  1  0
  5  6  1  0
  6  7  2  0
  5  3  1  0
 28 29  1  0
  3  2  1  0
 30 31  1  0
  2  1  1  0
 32 33  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 26 27  1  0
 13 15  1  0
 23 32  1  0
 15 21  2  0
 32 30  1  0
 21 20  1  0
  7  9  1  0
 20 19  2  0
 30 28  1  0
 19 17  1  0
  9 10  2  0
 17 16  2  0
 16 15  1  0
 21 22  1  0
 28 25  1  0
  3  4  2  0
 10 11  1  0
  7  8  1  0
 25 24  1  0
 17 18  1  0
 25 26  1  0
 23 22  1  0
 23 46  1  6
 28 51  1  1
 29 52  1  0
 30 53  1  6
 31 54  1  0
 32 55  1  1
 33 56  1  0
 26 48  1  0
 26 49  1  0
 25 47  1  6
 27 50  1  0
  9 39  1  0
 10 40  1  0
  6 37  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 12 41  1  0
 20 45  1  0
 19 44  1  0
 16 42  1  0
  8 38  1  0
 18 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.526  -2.115   3.130  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.752  -1.487   3.018  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.906  -0.725   1.906  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.054  -0.567   1.042  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.265  -0.108   1.848  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.174  -0.334   2.898  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.441   0.231   2.860  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.281  -0.021   3.903  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.831   1.024   1.793  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.936   1.256   0.743  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.647   0.702   0.748  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.734   0.933  -0.315  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.904   1.711  -1.444  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.892   2.379  -1.728  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.734   1.772  -2.373  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.504   3.006  -3.006  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.569   3.144  -3.874  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.830   4.323  -4.503  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.416   2.074  -4.126  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.183   0.839  -3.515  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.103   0.670  -2.640  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.223  -0.515  -2.037  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.623  -1.658  -2.231  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.901  -1.460  -1.625  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.765  -2.601  -1.771  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.121  -2.229  -1.162  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.615  -1.046  -1.795  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.160  -3.829  -1.082  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.975  -4.985  -1.275  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.766  -4.097  -1.653  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.161  -5.174  -0.919  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.105  -2.847  -1.571  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.362  -3.128  -2.210  0.00  0.00           O+0
HETATM   34  H   UNK     0      -1.320  -1.363   3.181  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.538  -2.697   4.056  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.692  -2.797   2.289  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.910  -0.948   3.755  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.122   0.441   3.749  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.819   1.471   1.750  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.285   1.881  -0.073  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.827   0.468  -0.223  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.167   3.843  -2.804  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.148   4.971  -4.256  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.257   2.198  -4.804  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.871   0.033  -3.750  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.723  -1.850  -3.308  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.915  -2.784  -2.843  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.029  -2.012  -0.092  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.858  -3.025  -1.300  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.900  -0.387  -1.704  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.082  -3.662  -0.001  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.431  -5.740  -0.969  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.839  -4.451  -2.689  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.770  -5.197  -1.221  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.337  -2.630  -0.523  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.873  -2.295  -2.183  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   11    6    3                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7   38                                                       
CONECT    9    7   10   39                                                  
CONECT   10    9   11   40                                                  
CONECT   11    5   12   10                                                  
CONECT   12   11   13   41                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   21   16                                                  
CONECT   16   17   15   42                                                  
CONECT   17   19   16   18                                                  
CONECT   18   17   43                                                       
CONECT   19   20   17   44                                                  
CONECT   20   21   19   45                                                  
CONECT   21   15   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   24   32   22   46                                             
CONECT   24   23   25                                                       
CONECT   25   28   24   26   47                                             
CONECT   26   27   25   48   49                                             
CONECT   27   26   50                                                       
CONECT   28   29   30   25   51                                             
CONECT   29   28   52                                                       
CONECT   30   31   32   28   53                                             
CONECT   31   30   54                                                       
CONECT   32   33   23   30   55                                             
CONECT   33   32   56                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   16                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   23                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   28                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -0.5264   -2.1155    3.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7517   -1.4866    3.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9055   -0.7250    1.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0543   -0.5665    1.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.1076    1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -0.3338    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.2313    2.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2805   -0.0208    3.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309    1.0236    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    1.2558    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.7023    0.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343    0.9330   -0.3149 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    1.7106   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    2.3793   -1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7340    1.7717   -2.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5041    3.0055   -3.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5693    3.1438   -3.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8297    4.3234   -4.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4161    2.0744   -4.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833    0.8390   -3.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030    0.6695   -2.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2227   -0.5147   -2.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -1.6577   -2.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9012   -1.4599   -1.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -2.6014   -1.7705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1207   -2.2293   -1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149   -1.0456   -1.7945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1597   -3.8288   -1.0823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9749   -4.9850   -1.2751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -4.0970   -1.6526 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1614   -5.1742   -0.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053   -2.8466   -1.5714 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3619   -3.1280   -2.2102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -1.3635    3.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380   -2.6968    4.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -2.7973    2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -0.9479    3.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1219    0.4411    3.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    1.4714    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853    1.8807   -0.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    0.4677   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668    3.8431   -2.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1478    4.9707   -4.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    2.1979   -4.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8710    0.0327   -3.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7234   -1.8502   -3.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9152   -2.7838   -2.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0117   -0.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8584   -3.0249   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8995   -0.3867   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -3.6618   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306   -5.7396   -0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8394   -4.4508   -2.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -5.1970   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -2.6295   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -2.2948   -2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  5  2  0
 24 23  1  0
  5  6  1  0
  6  7  2  0
  5  3  1  0
 28 29  1  0
  3  2  1  0
 30 31  1  0
  2  1  1  0
 32 33  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 26 27  1  0
 13 15  1  0
 23 32  1  0
 15 21  2  0
 32 30  1  0
 21 20  1  0
  7  9  1  0
 20 19  2  0
 30 28  1  0
 19 17  1  0
  9 10  2  0
 17 16  2  0
 16 15  1  0
 21 22  1  0
 28 25  1  0
  3  4  2  0
 10 11  1  0
  7  8  1  0
 25 24  1  0
 17 18  1  0
 25 26  1  0
 23 22  1  0
 23 46  1  6
 28 51  1  1
 29 52  1  0
 30 53  1  6
 31 54  1  0
 32 55  1  1
 33 56  1  0
 26 48  1  0
 26 49  1  0
 25 47  1  6
 27 50  1  0
  9 39  1  0
 10 40  1  0
  6 37  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 12 41  1  0
 20 45  1  0
 19 44  1  0
 16 42  1  0
  8 38  1  0
 18 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
N-[2-(b-D-Glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilate methyl ester	Generator
N-[2-(b-D-Glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilic acid methyl ester	Generator
N-[2-(beta-D-Glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilate methyl ester	Generator
N-[2-(Β-D-glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilate methyl ester	Generator
N-[2-(Β-D-glucopyranosyloxy)-5-hydroxybenzoyl]-5-hydroxyanthanilic acid methyl ester	Generator

Chemical Formula

C₂₁H₂₃NO₁₁

Average Mass

465.4110 Da

Monoisotopic Mass

465.12711 Da

IUPAC Name

methyl 5-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)benzoate

Traditional Name

methyl 5-hydroxy-2-(5-hydroxy-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzamido)benzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(C(=O)OC([H])([H])[H])=C(N([H])C(=O)C2=C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C([H])=C([H])C(O[H])=C2[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C21H23NO11/c1-31-20(30)11-6-9(24)2-4-13(11)22-19(29)12-7-10(25)3-5-14(12)32-21-18(28)17(27)16(26)15(8-23)33-21/h2-7,15-18,21,23-28H,8H2,1H3,(H,22,29)/t15-,16-,17+,18-,21-/m1/s1

InChI Key

BIQSZYHQDBWCMC-ZIKOTGLESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Staphisagria macrosperma	JEOL database	Diaz, J. G., et al, Phytochemistry 66, 733 (2005)

Chemical Taxonomy

Classification

Not classified

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	0.09	ALOGPS
logP	0.54	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.24 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.7 m³·mol⁻¹	ChemAxon
Polarizability	44.94 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

8109819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9934191

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Diaz, J. G., et al. (2005). Diaz, J. G., et al, Phytochemistry 66, 733 (2005) . Phytochem..

Showing NP-Card for N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+ (NP0031068)

MOL for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

3D MOL for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

3D SDF for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

3D-SDF for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

PDB for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

3D PDB for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

SMILES for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

INCHI for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

Structure for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)

3D Structure for NP0031068 ( N-(2'-beta-glucopyranosyl-5'-hydroxysalicyl)-5-hydroxyanthranilic acid m+)