NP-MRD: Showing NP-Card for (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate (NP0149254)

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Record Information

Version

2.0

Created at

2022-09-02 05:07:23 UTC

Updated at

2022-09-02 05:07:23 UTC

NP-MRD ID

NP0149254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

Description

ZINC31157210 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. (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate is found in Populus balsamifera, Salix purpurea and Salix sericea. Based on a literature review very few articles have been published on ZINC31157210.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207072D          

 30 32  0  0  1  0            999 V2000
    3.2452   -4.8534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -4.8534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -4.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664   -3.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -1.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -1.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8422   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -1.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3156   -0.5116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8785    0.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    0.9164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8286    1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    1.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    0.9452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4776    1.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275    0.2456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3520    0.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401   -0.4828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5773   -1.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    5.9491   -0.5110    1.7336 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5860   -0.3418    0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8489    0.9240   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5344    0.6001   -1.4718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0974   -0.6659   -2.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -1.5579   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8539   -1.4081   -0.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9268   -2.6313    0.5994 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4261   -0.9698   -0.1909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922    0.0844   -0.7786 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -1.7398    0.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1030   -1.3153    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -0.0380    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7539    0.6282    1.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4531    1.8198    2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971    2.3194    2.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729    1.6465    1.5513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5030    0.4749    0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598   -0.1638    0.1781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    0.1207   -0.0632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6671   -0.8541    0.4054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9383   -0.2974    0.4522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9235   -1.1748    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5474   -1.4182    2.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4496   -0.0934   -0.9697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7406    0.3820   -0.9482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4855    0.9092   -1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8693    1.2760   -2.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1080    0.2835   -1.5412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2327    1.1672   -2.1611 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9097    1.4733   -0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4993    1.5879    0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6446    0.5707   -1.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3368    1.4137   -2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4401   -0.8433   -3.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0895   -2.4708   -2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1365   -3.3201   -0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -2.0982    0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.3192   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    0.2722    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2046    2.3477    2.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0302    3.2527    2.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472    2.0761    1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755    1.0568    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8982    0.7073    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8900   -0.6174    1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1283   -2.0981    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1049   -0.6122    2.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3310   -1.0418   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2406   -0.0323   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4580    1.7721   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1862    0.4553   -3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1326   -0.7137   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252    0.7260   -2.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  7  1  0
  7  8  1  1
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
 20 29  1  0
 29 30  1  0
 29 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 22  1  0
 13 18  1  0
  2  7  1  0
 24 48  1  0
 23 46  1  0
 23 47  1  0
 22 45  1  1
 20 44  1  1
 17 43  1  0
 16 42  1  0
 15 41  1  0
 14 40  1  0
 12 38  1  0
 12 39  1  0
  8 37  1  0
  6 36  1  0
  5 35  1  0
  4 33  1  0
  4 34  1  0
  3 31  1  0
  3 32  1  0
 29 53  1  6
 30 54  1  0
 27 51  1  1
 28 52  1  0
 25 49  1  6
 26 50  1  0
M  END


  Mrv1652309022207072D          

 30 32  0  0  1  0            999 V2000
    3.2452   -4.8534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -6.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -5.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -4.8534    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0281   -4.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7664   -3.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537   -2.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -1.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4548   -1.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8422   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6666   -0.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1038   -1.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9283   -1.2401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3156   -0.5116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8785    0.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2658    0.9164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8286    1.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    1.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    0.9452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4776    1.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5275    0.2456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3520    0.2744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401   -0.4828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5773   -1.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0149254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=CC=C2COC(=O)[C@@]2(O)C=CCCC2=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O10/c21-9-13-15(23)16(24)17(25)18(30-13)29-12-6-2-1-5-11(12)10-28-19(26)20(27)8-4-3-7-14(20)22/h1-2,4-6,8,13,15-18,21,23-25,27H,3,7,9-10H2/t13-,15-,16+,17-,18-,20-/m1/s1

> <INCHI_KEY>
CZDNLUMNELLDDD-ORRCJIOJSA-N

> <FORMULA>
C20H24O10

> <MOLECULAR_WEIGHT>
424.402

> <EXACT_MASS>
424.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.76130520073292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-0.43183241933333355

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.205273323610774

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.317590195981262

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092344897183

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
100.40870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       6.058  -9.060   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.724  -9.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.724 -11.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.390 -12.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.057 -11.370   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.057  -9.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.390  -9.060   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.113  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.652  -7.646   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.297  -6.394   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.020  -5.034   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.204  -3.728   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.665  -3.782   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.849  -2.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.572  -1.116   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.111  -1.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.927  -2.369   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.466  -2.315   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.189  -0.955   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.373   0.351   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.096   1.711   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.280   3.017   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.741   2.963   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.635   1.764   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.358   3.124   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.451   0.458   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.990   0.512   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.728  -0.901   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.544  -2.207   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₁₀

Average Mass

424.4020 Da

Monoisotopic Mass

424.13695 Da

IUPAC Name

(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

Traditional Name

(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=CC=C2COC(=O)[C@@]2(O)C=CCCC2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H24O10/c21-9-13-15(23)16(24)17(25)18(30-13)29-12-6-2-1-5-11(12)10-28-19(26)20(27)8-4-3-7-14(20)22/h1-2,4-6,8,13,15-18,21,23-25,27H,3,7,9-10H2/t13-,15-,16+,17-,18-,20-/m1/s1

InChI Key

CZDNLUMNELLDDD-ORRCJIOJSA-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
Populus balsamifera	LOTUS Database	35616633
Salix purpurea	LOTUS Database	35616633
Salix sericea	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Cyclohexenone
Acyloin
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Tertiary alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Aldehyde
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
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	-0.18	ALOGPS
logP	-0.43	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.41 m³·mol⁻¹	ChemAxon
Polarizability	40.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

34995475

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38348839

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate (NP0149254)

MOL for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

3D MOL for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

3D SDF for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

3D-SDF for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

PDB for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

3D PDB for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

SMILES for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

INCHI for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

Structure for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)

3D Structure for NP0149254 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (1r)-1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate)