NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol (NP0291462)

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Record Information

Version

1.0

Created at

2022-09-09 22:34:10 UTC

Updated at

2022-09-09 22:34:10 UTC

NP-MRD ID

NP0291462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol

Description

Cuneataside C belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol is found in Fraxinus sieboldiana and Sargentodoxa cuneata. It was first documented in 2022 (PMID: 36115695). Based on a literature review a significant number of articles have been published on Cuneataside C (PMID: 36115691) (PMID: 36115694) (PMID: 36115693) (PMID: 36115692).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200342D          

 31 33  0  0  1  0            999 V2000
    3.8694   -4.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -5.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0203   -5.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -6.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -7.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -7.4570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6749   -8.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0105   -8.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -9.5456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8611  -10.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762  -10.9667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7118  -11.7204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2268  -12.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624  -13.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775  -13.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130  -14.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281  -15.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076  -15.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227  -15.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7721  -14.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484  -14.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570  -13.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557  -10.8805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0708  -11.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202  -10.1268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3997  -10.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -9.4594    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3695   -8.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049   -6.6724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1203   -6.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 16 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
  7 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -4.9255    3.0731    1.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1688    2.2830    1.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9536    1.6878    1.2537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0953    2.6446    0.7584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488    0.8360    2.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8075   -0.4235    2.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958   -0.5675    0.6887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1173   -1.7345    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2117   -2.5953   -0.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4879   -2.1233   -1.5456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7065   -1.0383   -1.4432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6177   -1.1676   -1.8114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3543   -1.6695   -0.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505   -0.8215   -0.1913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6867    0.4333    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781    1.2657    0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4541    2.2175    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4640    2.9853    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    2.8294    2.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    3.6077    2.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1718    1.8829    2.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5595    1.7364    4.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636    1.1178    2.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773   -1.8443   -3.1103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1879   -0.9515   -4.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2872   -2.7098   -3.5366 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1115   -3.6954   -4.4344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8127   -3.3080   -2.2370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6871   -4.3428   -2.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468    0.6593    0.2150 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8895    1.0718   -1.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8929    2.8797    1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737    2.8140    2.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8067    1.4317    2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247    3.4654    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317    1.2224    3.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675    0.7572    2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204   -0.4021    0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8051   -3.5378   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733   -2.9511    0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073   -1.8463   -2.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9725   -0.0992   -1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360   -1.3794    0.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951   -0.5296   -0.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142    0.1906    1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209    1.0657   -0.2797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1462    2.3272   -0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893    3.7324    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1190    3.4700    3.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    1.0659    4.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6377    0.3706    2.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -2.5491   -3.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -0.4873   -3.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -2.0700   -3.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -3.4753   -4.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570   -3.5983   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -5.1640   -1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4451    0.4938    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916    1.4637   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 12 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
  7 30  1  0
 30 31  1  0
 30  3  1  0
 28 10  1  0
 23 16  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  6
 12 42  1  6
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 20 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  1
 25 53  1  0
 26 54  1  6
 27 55  1  0
 28 56  1  1
 29 57  1  0
 30 58  1  6
 31 59  1  0
M  END


  Mrv1652309102200342D          

 31 33  0  0  1  0            999 V2000
    3.8694   -4.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -5.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0203   -5.5744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -6.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -7.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -7.4570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6749   -8.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0105   -8.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5256   -9.5456    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8611  -10.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762  -10.9667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7118  -11.7204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2268  -12.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624  -13.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775  -13.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130  -14.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281  -15.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076  -15.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227  -15.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7721  -14.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484  -14.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570  -13.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557  -10.8805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0708  -11.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202  -10.1268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3997  -10.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7051   -9.4594    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3695   -8.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049   -6.6724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1203   -6.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 16 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  6  0  0  0
  7 30  1  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0291462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O12/c20-7-19(27)8-30-18(16(19)26)29-6-12-13(23)14(24)15(25)17(31-12)28-4-3-9-1-2-10(21)11(22)5-9/h1-2,5,12-18,20-27H,3-4,6-8H2/t12-,13-,14+,15-,16+,17-,18-,19-/m1/s1

> <INCHI_KEY>
LBHKVQMODMELAS-OTCFHACESA-N

> <FORMULA>
C19H28O12

> <MOLECULAR_WEIGHT>
448.421

> <EXACT_MASS>
448.158076342

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.37227246220445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol

> <JCHEM_LOGP>
-2.1599080953333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.679189924484925

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.444707633716408

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
198.76

> <JCHEM_REFRACTIVITY>
100.67420000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6R)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       7.223  -8.941   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.699 -10.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.638 -10.406   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.914 -12.455   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.438 -13.920   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.898 -13.920   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.993 -15.166   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.620 -16.573   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.714 -17.818   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.341 -19.225   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.436 -20.471   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.062 -21.878   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.157 -23.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.783 -24.531   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.878 -25.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.504 -27.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.599 -28.429   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.068 -28.268   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.162 -29.514   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.441 -26.862   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.090 -26.701   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.346 -25.616   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.904 -20.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.999 -21.556   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.278 -18.903   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.746 -18.742   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.183 -17.657   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.556 -16.251   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.423 -12.455   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.958 -11.979   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   30                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24   12   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   10   29                                                  
CONECT   29   28                                                            
CONECT   30    7    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₁₂

Average Mass

448.4210 Da

Monoisotopic Mass

448.15808 Da

IUPAC Name

(2R,3S,4S,5R,6R)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6R)-2-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C19H28O12/c20-7-19(27)8-30-18(16(19)26)29-6-12-13(23)14(24)15(25)17(31-12)28-4-3-9-1-2-10(21)11(22)5-9/h1-2,5,12-18,20-27H,3-4,6-8H2/t12-,13-,14+,15-,16+,17-,18-,19-/m1/s1

InChI Key

LBHKVQMODMELAS-OTCFHACESA-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
Fraxinus sieboldiana	LOTUS Database	35616633
Sargentodoxa cuneata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Disaccharide
O-glycosyl compound
Tyrosol derivative
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Oxolane
Tertiary alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Alcohol
Hydrocarbon derivative
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	-2.2	ChemAxon
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	100.67 m³·mol⁻¹	ChemAxon
Polarizability	43.37 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

9678079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11503277

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hosokawa K, Nakao S: Somatic mutations and clonal expansions in paroxysmal nocturnal hemoglobinuria. Semin Hematol. 2022 Jul;59(3):143-149. doi: 10.1053/j.seminhematol.2022.08.004. Epub 2022 Aug 22. [PubMed:36115691 ]
eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695 ]
Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694 ]
Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693 ]
Todisco G, Moura PL, Hellstrom-Lindberg E: Clinical manifestations of clonal hematopoiesis: What has SF3B1-mutant MDS taught us? Semin Hematol. 2022 Jul;59(3):150-155. doi: 10.1053/j.seminhematol.2022.08.002. Epub 2022 Aug 11. [PubMed:36115692 ]
LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol (NP0291462)

MOL for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D MOL for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D SDF for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D-SDF for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

PDB for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D PDB for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

SMILES for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

INCHI for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

Structure for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)

3D Structure for NP0291462 ((2r,3s,4s,5r,6r)-2-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(3,4-dihydroxyphenyl)ethoxy]oxane-3,4,5-triol)