NP-MRD: Showing NP-Card for [(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate (NP0172043)

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Record Information

Version

2.0

Created at

2022-09-03 08:49:33 UTC

Updated at

2022-09-03 08:49:33 UTC

NP-MRD ID

NP0172043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate

Description

10-Benzoylcatalpol 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. [(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate is found in Globularia davisiana, Penstemon albidus, Penstemon auriberbis, Pinguicula moranensis, Plantago hookeriana, Plantago lagopus and Plantago patagonica. [(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate was first documented in 2000 (PMID: 21214473). Based on a literature review very few articles have been published on 10-Benzoylcatalpol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210492D          

 33 37  0  0  1  0            999 V2000
    2.4054    3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2647    3.2656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    3.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    4.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619    3.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    2.6998    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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  5  7  1  0  0  0  0
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  8  9  1  1  0  0  0
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 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
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   -0.3853   -1.8254   -3.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -1.7104   -1.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7494   -0.3835   -0.1211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034    0.2232   -0.0630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9494    1.3497    0.6934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9134    1.5712    1.6226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4355    1.1163    3.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    1.3481    3.9592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870    1.0891    1.3156 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1460    2.1333    0.9195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3867    0.0165    0.2899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4880   -0.8152    0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0869   -0.7606    0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1724   -1.6787   -0.7699 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681    0.3486   -1.5170 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1867   -0.7511    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5714   -1.1109    1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6821   -0.0433    2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3204    0.3045    1.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7998    2.0682   -2.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162    0.9695   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2470    1.2542   -3.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121   -0.9691   -4.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.7632   -3.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    0.0996   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    0.5493   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9978    2.6971    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1009    0.0594    2.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5659    1.7134    3.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8828    0.4699    4.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7302    0.6954    2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5903    2.9390    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4229    0.5251   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1930   -0.4815   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092   -1.3198    1.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0022   -2.2255   -0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780    1.3212   -1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2516   -2.2721   -0.0072 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4558    0.8499    2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
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 31 32  1  0
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 27 14  1  0
 27 10  1  0
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 33 28  1  0
 20 47  1  0
 19 45  1  0
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 18 44  1  1
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 29 55  1  0
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 31 57  1  0
 32 58  1  0
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 27 54  1  1
 25 52  1  1
 26 53  1  0
 23 50  1  6
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 21 48  1  1
 22 49  1  0
M  END


  Mrv1652309032210492D          

 33 37  0  0  1  0            999 V2000
    2.4054    3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    3.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    4.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619    3.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    2.6998    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
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  5  7  1  0  0  0  0
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 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=CC3[C@H](O)[C@@H]4O[C@]4(COC(=O)C4=CC=CC=C4)C23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c23-8-12-15(25)16(26)17(27)21(31-12)32-20-13-11(6-7-29-20)14(24)18-22(13,33-18)9-30-19(28)10-4-2-1-3-5-10/h1-7,11-18,20-21,23-27H,8-9H2/t11?,12-,13?,14+,15-,16+,17-,18+,20+,21+,22-/m1/s1

> <INCHI_KEY>
JADZPWILSJVZBO-ASZLBAKKSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.30805052672689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,4S,5S,10S)-5-hydroxy-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl benzoate

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-0.9365037610000005

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.107361024996731

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195332440710969

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601929344

> <JCHEM_POLAR_SURFACE_AREA>
167.67000000000002

> <JCHEM_REFRACTIVITY>
107.01350000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,4S,5S,10S)-5-hydroxy-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       4.490   5.932   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.799   5.122   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.752   3.582   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.395   2.854   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.348   1.314   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.874   1.107   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.931  -0.111   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.755  -1.106   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.869  -2.642   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.446  -0.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.967  -0.726   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.145   0.339   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.221   1.835   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.700   2.266   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.066   3.762   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.954   4.827   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.524   4.396   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.637   5.461   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.115   5.031   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.227   6.096   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.270   6.957   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.383   8.022   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.208   7.388   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.575   8.883   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.320   6.323   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.799   6.753   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.812   1.201   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.156   5.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.203   7.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.560   8.118   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.870   7.308   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.822   5.768   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.466   5.040   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   27                                             
CONECT    6    5    7                                                       
CONECT    7    6    5    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   10    5                                                  
CONECT   28    2   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

[(2S,4S,5S,10S)-5-hydroxy-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl benzoate

Traditional Name

[(2S,4S,5S,10S)-5-hydroxy-10-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=CC3[C@H](O)[C@@H]4O[C@]4(COC(=O)C4=CC=CC=C4)C23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C22H26O11/c23-8-12-15(25)16(26)17(27)21(31-12)32-20-13-11(6-7-29-20)14(24)18-22(13,33-18)9-30-19(28)10-4-2-1-3-5-10/h1-7,11-18,20-21,23-27H,8-9H2/t11?,12-,13?,14+,15-,16+,17-,18+,20+,21+,22-/m1/s1

InChI Key

JADZPWILSJVZBO-ASZLBAKKSA-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
Globularia davisiana	LOTUS Database	35616633
Penstemon albidus	LOTUS Database	35616633
Penstemon auriberbis	LOTUS Database	35616633
Pinguicula moranensis	LOTUS Database	35616633
Plantago hookeriana	LOTUS Database	35616633
Plantago lagopus	LOTUS Database	35616633
Plantago patagonica	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

Hexose monosaccharide
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.45	ALOGPS
logP	-0.94	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	167.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	107.01 m³·mol⁻¹	ChemAxon
Polarizability	44.31 Å³	ChemAxon
Number of Rings	5	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

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

101637375

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Velazquez-Fiz MP, Diaz-Lanza AM, Fernandez-Matellano L: Iridoids from plantago lagopus. Pharm Biol. 2000;38(4):268-70. doi: 10.1076/1388-0209(200009)3841-AFT268. [PubMed:21214473 ]
LOTUS database [Link]

Showing NP-Card for [(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate (NP0172043)

MOL for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

3D MOL for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

3D SDF for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

3D-SDF for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

PDB for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

3D PDB for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

SMILES for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

INCHI for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

Structure for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)

3D Structure for NP0172043 ([(2s,4s,5s,10s)-5-hydroxy-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl benzoate)