NP-MRD: Showing NP-Card for (r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid (NP0237591)

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Record Information

Version

1.0

Created at

2022-09-06 20:46:56 UTC

Updated at

2022-09-06 20:46:56 UTC

NP-MRD ID

NP0237591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid

Description

(2R)-2-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl]-2-(3,4,5-trihydroxybenzoyloxy)acetic acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid is found in Phyllanthus emblica. Based on a literature review very few articles have been published on (2R)-2-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl]-2-(3,4,5-trihydroxybenzoyloxy)acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222462D          

 35 37  0  0  1  0            999 V2000
    6.1022   -0.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2737   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8760   -1.5346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6211   -0.7500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1060   -0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -1.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -2.0195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2086   -2.8445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4941   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941   -4.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -5.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -5.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -6.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -5.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -5.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -4.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -4.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230   -3.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -2.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230   -4.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6714   -0.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4561   -1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0692   -0.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6276   -2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4122   -2.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0145   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860   -3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299   -2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -3.3597   -0.9921   -2.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007   -0.6756   -0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    0.0740   -0.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2723    0.5054   -1.1331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2194    2.0370   -1.1309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7663    2.5427   -2.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029    2.2968    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877    3.4705    0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2623    1.1145    0.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0212    0.0772   -0.4758 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1378    0.1942   -1.4790 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4075    0.0771   -0.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    1.0927   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455    2.1699   -1.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5920    0.8801   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5696    1.8502   -0.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7794    1.6555    0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7180    2.6621    0.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0376    0.4499    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2555    0.2728    1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -0.5269    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3684   -1.7352    1.7978 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751   -0.3157    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -0.7841   -2.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486   -1.5714   -2.7800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085   -0.9483   -3.4617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -1.0997   -0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5603   -1.8460   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6031   -2.2322    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6064   -2.9756   -0.1656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6053   -1.8697    1.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6044   -2.2257    2.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5382   -1.1072    2.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5314   -0.7386    3.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5071   -0.7314    1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336    0.1328   -2.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537    2.3724   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    3.2025   -2.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1089   -0.9066   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1061    1.2083   -1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3480    2.7928   -0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5279    3.5296    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4856   -0.5896    2.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -2.4708    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1221   -1.1075    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809   -0.6369   -4.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5755   -2.1419   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4238   -3.3313    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3786   -2.7690    2.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7933   -0.1892    3.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882   -0.1427    1.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  2  0
  4 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 11 24  1  0
 24 26  1  0
 24 25  2  0
  7  5  1  0
 23 15  1  0
 35 27  1  0
  6 38  1  0
  5 37  1  1
  4 36  1  6
 28 47  1  0
 30 48  1  0
 32 49  1  0
 34 50  1  0
 35 51  1  0
 10 39  1  1
 11 40  1  6
 16 41  1  0
 18 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 26 46  1  0
M  END


  Mrv1652309062222462D          

 35 37  0  0  1  0            999 V2000
    6.1022   -0.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2737   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8760   -1.5346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6211   -0.7500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1060   -0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111   -0.0825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -1.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -2.0195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2086   -2.8445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4941   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4941   -4.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -4.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -5.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -5.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -6.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -5.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -5.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3507   -4.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -4.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0652   -4.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230   -3.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6375   -2.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230   -4.0820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0583   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6714   -0.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4561   -1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0692   -0.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6276   -2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4122   -2.2573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0145   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1860   -3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299   -2.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 15 23  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC1=O)[C@@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O15/c21-7-1-5(2-8(22)11(7)25)18(30)33-14-13(27)20(32)34-15(14)16(17(28)29)35-19(31)6-3-9(23)12(26)10(24)4-6/h1-4,13-16,21-27H,(H,28,29)/t13-,14-,15-,16+/m0/s1

> <INCHI_KEY>
DRESSPOLWVWPPB-YHUYYLMFSA-N

> <FORMULA>
C20H16O15

> <MOLECULAR_WEIGHT>
496.333

> <EXACT_MASS>
496.048919815

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.390490744439774

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl]-2-(3,4,5-trihydroxybenzoyloxy)acetic acid

> <JCHEM_LOGP>
0.7442091193333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.803670479217135

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.38956690764076

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548942536537049

> <JCHEM_POLAR_SURFACE_AREA>
257.80999999999995

> <JCHEM_REFRACTIVITY>
106.17559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(R)-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      11.391  -0.804   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.711  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.567  -3.340   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.102  -2.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.626  -1.400   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.531  -0.154   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.086  -1.400   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.181  -0.154   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.610  -2.865   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.856  -3.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.856  -5.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.522  -6.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.522  -7.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.856  -8.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.189  -8.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.189  -9.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.855 -10.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.855 -12.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.521  -9.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.188 -10.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.521  -8.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.188  -7.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.855  -7.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.190  -6.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.523  -5.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.190  -7.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.176  -2.786   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.320  -1.755   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.785  -2.231   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.929  -1.201   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.105  -3.738   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.569  -4.214   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.960  -4.768   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.281  -6.274   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.496  -4.292   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15                                                       
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    2   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   27                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(2S,3S,4S)-4-Hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl]-2-(3,4,5-trihydroxybenzoyloxy)acetate	Generator

Chemical Formula

C₂₀H₁₆O₁₅

Average Mass

496.3330 Da

Monoisotopic Mass

496.04892 Da

IUPAC Name

(2R)-2-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl]-2-(3,4,5-trihydroxybenzoyloxy)acetic acid

Traditional Name

(R)-[(2S,3S,4S)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC1=O)[C@@H](OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C20H16O15/c21-7-1-5(2-8(22)11(7)25)18(30)33-14-13(27)20(32)34-15(14)16(17(28)29)35-19(31)6-3-9(23)12(26)10(24)4-6/h1-4,13-16,21-27H,(H,28,29)/t13-,14-,15-,16+/m0/s1

InChI Key

DRESSPOLWVWPPB-YHUYYLMFSA-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
Phyllanthus emblica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Pyrogallol derivative
Benzenetriol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	0.74	ChemAxon
pKa (Strongest Acidic)	2.39	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	257.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.18 m³·mol⁻¹	ChemAxon
Polarizability	43.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162986714

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid (NP0237591)

MOL for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

3D MOL for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

3D SDF for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

3D-SDF for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

PDB for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

3D PDB for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

SMILES for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

INCHI for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

Structure for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)

3D Structure for NP0237591 ((r)-[(2s,3s,4s)-4-hydroxy-5-oxo-3-(3,4,5-trihydroxybenzoyloxy)oxolan-2-yl](3,4,5-trihydroxybenzoyloxy)acetic acid)