NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0280750)

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Record Information

Version

2.0

Created at

2022-09-09 06:42:55 UTC

Updated at

2022-09-09 06:42:55 UTC

NP-MRD ID

NP0280750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Description

Glochidacuminoside D belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. (2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate is found in Phyllanthus meghalayensis. Based on a literature review very few articles have been published on Glochidacuminoside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208422D          

 33 35  0  0  1  0            999 V2000
   -2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -1.9207   -3.8875   -0.1888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155   -2.7826    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832   -1.3771    0.4446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9253   -0.6040   -0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8570    0.2330   -0.2373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3541    1.5357   -0.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.4647   -0.2335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9258    3.8319    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923    4.1698   -0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    2.5718   -1.5645 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7300    2.9725   -1.4154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    1.2099   -2.2114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9557    1.1802   -2.8299 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    0.1069   -1.1383 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5604   -0.0304   -0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3970   -1.0994   -0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9476   -1.9941   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197   -1.2073   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1811   -0.1880    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4040   -0.2176    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8784    0.7963    2.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2134   -1.3457    1.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4313   -1.3741    1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7592   -2.3631    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325   -3.4792    0.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -2.2896   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8417   -1.2063    0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3620   -1.0273    1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -0.8741    2.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5532   -0.8973    0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9291   -0.7373    1.1537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0590   -1.0737   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -1.2264   -0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -1.1636    1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6821    0.0332    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4365    2.1905    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3599    3.8884    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0683    4.5485    0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5873    4.6195   -0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0675    3.2961   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    3.3514   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0683    1.0262   -2.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9095    0.5136   -3.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1480   -0.8228   -1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5660    0.7012    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    1.6345    2.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0630   -2.1174    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -3.5943    0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594   -3.0991   -0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7161   -1.0054    2.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1106   -0.7329    3.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3469   -0.6058    2.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7459   -1.0861   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3268   -1.3662   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  3 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  2  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 14 12  1  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  7  1  0
 33 27  1  0
 26 18  1  0
  9 39  1  0
  8 37  1  0
  8 38  1  0
  7 36  1  1
  5 35  1  1
  3 34  1  1
 28 50  1  0
 29 51  1  0
 31 52  1  0
 32 53  1  0
 33 54  1  0
 14 44  1  6
 19 45  1  0
 21 46  1  0
 23 47  1  0
 25 48  1  0
 26 49  1  0
 12 42  1  6
 13 43  1  0
 10 40  1  6
 11 41  1  0
M  END


  Mrv1652309092208422D          

 33 35  0  0  1  0            999 V2000
   -2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280750

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H21NO11/c22-7-14(9-1-3-11(24)4-2-9)31-21-19(18(29)17(28)15(8-23)32-21)33-20(30)10-5-12(25)16(27)13(26)6-10/h1-6,14-15,17-19,21,23-29H,8H2/t14-,15-,17-,18+,19-,21-/m1/s1

> <INCHI_KEY>
BPGKGGZOJNCPKJ-IHGRRFEYSA-N

> <FORMULA>
C21H21NO11

> <MOLECULAR_WEIGHT>
463.395

> <EXACT_MASS>
463.1114605

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.8666852587663

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-[(S)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
0.46398742766666645

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.469216415020275

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.082658316304116

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849122470584

> <JCHEM_POLAR_SURFACE_AREA>
210.15999999999997

> <JCHEM_REFRACTIVITY>
107.84200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-[(S)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  N   UNK     0      -4.001   5.390   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18                                                       
CONECT   27    3   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₁NO₁₁

Average Mass

463.3950 Da

Monoisotopic Mass

463.11146 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-[(S)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3R,4S,5S,6R)-2-[(S)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@H](C#N)C2=CC=C(O)C=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H21NO11/c22-7-14(9-1-3-11(24)4-2-9)31-21-19(18(29)17(28)15(8-23)32-21)33-20(30)10-5-12(25)16(27)13(26)6-10/h1-6,14-15,17-19,21,23-29H,8H2/t14-,15-,17-,18+,19-,21-/m1/s1

InChI Key

BPGKGGZOJNCPKJ-IHGRRFEYSA-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
Glochidion acuminatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Galloyl ester
Hexose monosaccharide
Gallic acid or derivatives
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Secondary alcohol
Nitrile
Carbonitrile
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Cyanide
Organopnictogen compound
Organic nitrogen compound
Primary 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	0.46	ChemAxon
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	210.16 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.84 m³·mol⁻¹	ChemAxon
Polarizability	42.87 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

C00031820

Chemspider ID

10187345

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21577092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0280750)

MOL for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0280750 ((2r,3r,4s,5s,6r)-2-[(s)-cyano(4-hydroxyphenyl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)