NP-MRD: Showing NP-Card for [(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate (NP0279263)

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Record Information

Version

2.0

Created at

2022-09-09 04:35:24 UTC

Updated at

2022-09-09 04:35:24 UTC

NP-MRD ID

NP0279263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate

Description

[(1R,4aS,5S,7aR)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl benzoate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. [(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate is found in Lathraea squamaria. Based on a literature review very few articles have been published on [(1R,4aS,5S,7aR)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092206352D          

 43 47  0  0  1  0            999 V2000
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 37  5  1  1  0  0  0
  9 37  1  0  0  0  0
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 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092206352D          

 43 47  0  0  1  0            999 V2000
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6378   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0681   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0681   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -2.7604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  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
 17 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  1  0  0  0
 13 37  1  0  0  0  0
 37  5  1  1  0  0  0
  9 37  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0279263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H]3OC=C[C@@H]4[C@H](O)C=C(COC(=O)C5=CC=CC=C5)[C@H]34)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O15/c29-9-16-19(31)21(33)23(35)27(41-16)40-11-17-20(32)22(34)24(36)28(42-17)43-26-18-13(8-15(30)14(18)6-7-38-26)10-39-25(37)12-4-2-1-3-5-12/h1-8,14-24,26-36H,9-11H2/t14-,15-,16-,17-,18+,19-,20-,21+,22+,23-,24-,26-,27-,28+/m1/s1

> <INCHI_KEY>
QFOXOSPKPYCKKH-CJYICXALSA-N

> <FORMULA>
C28H36O15

> <MOLECULAR_WEIGHT>
612.581

> <EXACT_MASS>
612.205420459

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.697627296601766

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,4aS,5S,7aR)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl benzoate

> <JCHEM_LOGP>
-2.457405699333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.428437097767652

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.907580486933886

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
141.4121

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4aS,5S,7aR)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]methyl benzoate

> <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  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.258  -2.073   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591  -4.383   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.926  -4.383   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.926  -2.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.260  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.260  -0.533   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.593   0.237   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.593  -2.843   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.927  -2.073   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.593  -4.383   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.927  -5.153   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.260  -5.153   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.260  -6.693   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.591  -9.003   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.924  -7.463   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.376  -5.294   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   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                                                            
CONECT   31   17   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   15   36                                                  
CONECT   36   35                                                            
CONECT   37   13    5    9                                                  
CONECT   38    2   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   38                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
[(1R,4AS,5S,7ar)-5-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-7-yl]methyl benzoic acid	Generator

Chemical Formula

C₂₈H₃₆O₁₅

Average Mass

612.5810 Da

Monoisotopic Mass

612.20542 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@H]3OC=C[C@@H]4[C@H](O)C=C(COC(=O)C5=CC=CC=C5)[C@H]34)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C28H36O15/c29-9-16-19(31)21(33)23(35)27(41-16)40-11-17-20(32)22(34)24(36)28(42-17)43-26-18-13(8-15(30)14(18)6-7-38-26)10-39-25(37)12-4-2-1-3-5-12/h1-8,14-24,26-36H,9-11H2/t14-,15-,16-,17-,18+,19-,20-,21+,22+,23-,24-,26-,27-,28+/m1/s1

InChI Key

QFOXOSPKPYCKKH-CJYICXALSA-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
Lathraea squamaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Disaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Bicyclic monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Oxane
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	-2.5	ChemAxon
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.41 m³·mol⁻¹	ChemAxon
Polarizability	59.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163037622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate (NP0279263)

MOL for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

3D MOL for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

3D SDF for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

3D-SDF for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

PDB for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

3D PDB for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

SMILES for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

INCHI for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

Structure for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)

3D Structure for NP0279263 ([(1r,4as,5s,7ar)-5-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl benzoate)