NP-MRD: Showing NP-Card for 6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin (NP0034249)

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Record Information

Version

2.0

Created at

2021-06-20 18:01:58 UTC

Updated at

2021-06-30 00:04:30 UTC

NP-MRD ID

NP0034249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin

Provided By

JEOL Database JEOL Logo

Description

CHEMBL563403 belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. 6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin is found in Hintonia standleyana. 6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin was first documented in 2009 (Cristians, S., et al.). Based on a literature review very few articles have been published on CHEMBL563403.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120013D          

 56 59  0  0  0  0            999 V2000
   -3.6462    3.7478    1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    2.5158    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2119   -0.1976   -0.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0984   -1.0381    0.0865 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.5209   -0.8867    2.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 29  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120013D          

 56 59  0  0  0  0            999 V2000
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   -1.9921   -0.4891   -2.6377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2001   -1.2417   -2.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044    4.6382    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    3.7044    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    3.8029    2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329    1.7860   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    0.8238   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215    1.1365   -1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817   -0.4362    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -0.6914    1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.0177    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.6642    5.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -1.0493    4.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -3.7283    3.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -5.6701    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353   -5.3094    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7514   -3.0619    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999   -1.1213    1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8062   -2.8022   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -3.2924    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -0.9269   -2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -3.1497   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.0467   -3.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.9848   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0  0  0  0
 14 15  1  0  0  0  0
 23 24  1  0  0  0  0
 15 16  1  0  0  0  0
 24 26  2  0  0  0  0
 28 20  1  0  0  0  0
 26 27  1  0  0  0  0
 27 21  2  0  0  0  0
 24 25  1  0  0  0  0
 20 19  2  0  0  0  0
 19 17  1  0  0  0  0
 17 16  1  0  0  0  0
 15 28  2  0  0  0  0
 17 18  2  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 28 10  1  0  0  0  0
 10  9  1  0  0  0  0
 11 12  1  0  0  0  0
  8 29  1  0  0  0  0
 29 31  1  0  0  0  0
 31 33  1  0  0  0  0
 33  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 33 34  1  0  0  0  0
 31 32  1  0  0  0  0
 29 30  1  0  0  0  0
 20 21  1  0  0  0  0
  5  4  1  0  0  0  0
  4  2  1  0  0  0  0
 21 22  1  0  0  0  0
  2  3  2  0  0  0  0
 12 14  2  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 25 48  1  0  0  0  0
 11 42  1  0  0  0  0
 14 44  1  0  0  0  0
 19 45  1  0  0  0  0
 13 43  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 26 49  1  0  0  0  0
 27 50  1  0  0  0  0
 34 56  1  0  0  0  0
  8 41  1  1  0  0  0
 33 55  1  6  0  0  0
 31 53  1  1  0  0  0
 32 54  1  0  0  0  0
 29 51  1  6  0  0  0
 30 52  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  6 40  1  1  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)OC2=C1C(O[C@]1([H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])=C([H])C(O[H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O11/c1-10(24)31-9-17-20(28)21(29)22(30)23(34-17)33-16-7-13(26)6-15-19(16)14(8-18(27)32-15)11-2-4-12(25)5-3-11/h2-8,17,20-23,25-26,28-30H,9H2,1H3/t17-,20+,21+,22-,23-/m1/s1

> <INCHI_KEY>
WBCRDJIBCGCYEI-SUHOFRIBSA-N

> <FORMULA>
C23H22O11

> <MOLECULAR_WEIGHT>
474.418

> <EXACT_MASS>
474.116211528

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.98389160528134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-hydroxy-4-(4-hydroxyphenyl)-2-oxo-2H-chromen-5-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
0.4789195449999998

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.22836886942524

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.749631797478649

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491028194739554

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
122.33990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-hydroxy-4-(4-hydroxyphenyl)-2-oxochromen-5-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -3.6462    3.7478    1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    2.5158    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7426    1.6496    0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    2.5221   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    1.3816   -1.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136    0.4985   -1.4693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2119   -0.1976   -0.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0984   -1.0381    0.0865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2508   -1.7409    1.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -0.8867    2.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.3798    2.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1470    0.5483    3.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3796    1.1282    3.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2039    0.9338    4.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    0.3741    4.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0147    0.8427    5.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2921    0.4028    5.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264    0.8485    6.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -0.6571    4.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.1365    3.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -2.2824    2.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -3.5715    2.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -4.6712    2.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4321   -4.4846    1.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -5.5861    0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400   -3.2138    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947   -2.1117    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -0.5632    3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -2.1160   -1.0057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2215   -2.9255   -0.8273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.4558   -2.3813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8400   -2.4681   -3.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -0.4891   -2.6377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2001   -1.2417   -2.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044    4.6382    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    3.7044    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    3.8029    2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329    1.7860   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    0.8238   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215    1.1365   -1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817   -0.4362    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -0.6914    1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.0177    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.6642    5.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -1.0493    4.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -3.7283    3.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -5.6701    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353   -5.3094    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7514   -3.0619    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999   -1.1213    1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8062   -2.8022   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -3.2924    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -0.9269   -2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -3.1497   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.0467   -3.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.9848   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0
 14 15  1  0
 23 24  1  0
 15 16  1  0
 24 26  2  0
 28 20  1  0
 26 27  1  0
 27 21  2  0
 24 25  1  0
 20 19  2  0
 19 17  1  0
 17 16  1  0
 15 28  2  0
 17 18  2  0
 10 11  2  0
 12 13  1  0
 28 10  1  0
 10  9  1  0
 11 12  1  0
  8 29  1  0
 29 31  1  0
 31 33  1  0
 33  6  1  0
  6  7  1  0
  7  8  1  0
 33 34  1  0
 31 32  1  0
 29 30  1  0
 20 21  1  0
  5  4  1  0
  4  2  1  0
 21 22  1  0
  2  3  2  0
 12 14  2  0
  2  1  1  0
  6  5  1  0
  8  9  1  0
 25 48  1  0
 11 42  1  0
 14 44  1  0
 19 45  1  0
 13 43  1  0
 22 46  1  0
 23 47  1  0
 26 49  1  0
 27 50  1  0
 34 56  1  0
  8 41  1  1
 33 55  1  6
 31 53  1  1
 32 54  1  0
 29 51  1  6
 30 52  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  1 35  1  0
  1 36  1  0
  1 37  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.646   3.748   1.216  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.958   2.516   0.420  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.743   1.650   0.786  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.230   2.522  -0.729  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.362   1.382  -1.607  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.114   0.499  -1.469  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.212  -0.198  -0.219  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.098  -1.038   0.087  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.251  -1.741   1.348  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.521  -0.887   2.391  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.826  -0.380   2.487  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.147   0.548   3.467  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.380   1.128   3.503  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.204   0.934   4.400  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.926   0.374   4.333  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.015   0.843   5.301  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.292   0.403   5.321  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.126   0.849   6.100  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.645  -0.657   4.371  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.808  -1.137   3.434  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.345  -2.282   2.670  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.847  -3.571   2.909  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.391  -4.671   2.243  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.432  -4.485   1.342  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.928  -5.586   0.712  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.940  -3.214   1.090  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.395  -2.112   1.755  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.553  -0.563   3.358  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.951  -2.116  -1.006  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.222  -2.926  -0.827  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.838  -1.456  -2.381  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.840  -2.468  -3.402  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.992  -0.489  -2.638  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.200  -1.242  -2.802  0.00  0.00           O+0
HETATM   35  H   UNK     0      -3.804   4.638   0.602  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.615   3.704   1.573  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.318   3.803   2.078  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.433   1.786  -2.622  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.281   0.824  -1.398  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.222   1.137  -1.422  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.182  -0.436   0.152  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.579  -0.691   1.766  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.791   1.018   2.617  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.453   1.664   5.164  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.647  -1.049   4.510  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.040  -3.728   3.621  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.007  -5.670   2.432  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.635  -5.309   0.106  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.751  -3.062   0.385  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.800  -1.121   1.559  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.806  -2.802  -0.985  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.161  -3.292   0.078  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.120  -0.927  -2.463  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.213  -3.150  -3.083  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.832   0.047  -3.580  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.961  -1.985  -3.395  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    4    6   38   39                                             
CONECT    6   33    7    5   40                                             
CONECT    7    6    8                                                       
CONECT    8   29    7    9   41                                             
CONECT    9   10    8                                                       
CONECT   10   11   28    9                                                  
CONECT   11   10   12   42                                                  
CONECT   12   13   11   14                                                  
CONECT   13   12   43                                                       
CONECT   14   15   12   44                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   19   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20   17   45                                                  
CONECT   20   28   19   21                                                  
CONECT   21   27   20   22                                                  
CONECT   22   23   21   46                                                  
CONECT   23   22   24   47                                                  
CONECT   24   23   26   25                                                  
CONECT   25   24   48                                                       
CONECT   26   24   27   49                                                  
CONECT   27   26   21   50                                                  
CONECT   28   20   15   10                                                  
CONECT   29    8   31   30   51                                             
CONECT   30   29   52                                                       
CONECT   31   29   33   32   53                                             
CONECT   32   31   54                                                       
CONECT   33   31    6   34   55                                             
CONECT   34   33   56                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   19                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   27                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
CONECT   54   32                                                            
CONECT   55   33                                                            
CONECT   56   34                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
   -3.6462    3.7478    1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    2.5158    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7426    1.6496    0.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    2.5221   -0.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3617    1.3816   -1.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136    0.4985   -1.4693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2119   -0.1976   -0.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5209   -0.8867    2.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -0.3798    2.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3796    1.1282    3.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1264    0.8485    6.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6445   -0.6571    4.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.1365    3.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452   -2.2824    2.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -3.5715    2.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -4.6712    2.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4321   -4.4846    1.3416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280   -5.5861    0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400   -3.2138    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947   -2.1117    1.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5532   -0.5632    3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9506   -2.1160   -1.0057 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2215   -2.9255   -0.8273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.4558   -2.3813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8400   -2.4681   -3.4020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -0.4891   -2.6377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2001   -1.2417   -2.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044    4.6382    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    3.7044    1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3176    3.8029    2.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4329    1.7860   -2.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    0.8238   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215    1.1365   -1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817   -0.4362    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788   -0.6914    1.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7909    1.0177    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.6642    5.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474   -1.0493    4.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -3.7283    3.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -5.6701    2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353   -5.3094    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7514   -3.0619    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999   -1.1213    1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8062   -2.8022   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1612   -3.2924    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -0.9269   -2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -3.1497   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320    0.0467   -3.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -1.9848   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  2  0
 14 15  1  0
 23 24  1  0
 15 16  1  0
 24 26  2  0
 28 20  1  0
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 27 21  2  0
 24 25  1  0
 20 19  2  0
 19 17  1  0
 17 16  1  0
 15 28  2  0
 17 18  2  0
 10 11  2  0
 12 13  1  0
 28 10  1  0
 10  9  1  0
 11 12  1  0
  8 29  1  0
 29 31  1  0
 31 33  1  0
 33  6  1  0
  6  7  1  0
  7  8  1  0
 33 34  1  0
 31 32  1  0
 29 30  1  0
 20 21  1  0
  5  4  1  0
  4  2  1  0
 21 22  1  0
  2  3  2  0
 12 14  2  0
  2  1  1  0
  6  5  1  0
  8  9  1  0
 25 48  1  0
 11 42  1  0
 14 44  1  0
 19 45  1  0
 13 43  1  0
 22 46  1  0
 23 47  1  0
 26 49  1  0
 27 50  1  0
 34 56  1  0
  8 41  1  1
 33 55  1  6
 31 53  1  1
 32 54  1  0
 29 51  1  6
 30 52  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  1
  1 35  1  0
  1 36  1  0
  1 37  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₁₁

Average Mass

474.4180 Da

Monoisotopic Mass

474.11621 Da

IUPAC Name

[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-hydroxy-4-(4-hydroxyphenyl)-2-oxo-2H-chromen-5-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[7-hydroxy-4-(4-hydroxyphenyl)-2-oxochromen-5-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)OC2=C1C(O[C@]1([H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H])=C([H])C(O[H])=C2[H]

InChI Identifier

InChI=1S/C23H22O11/c1-10(24)31-9-17-20(28)21(29)22(30)23(34-17)33-16-7-13(26)6-15-19(16)14(8-18(27)32-15)11-2-4-12(25)5-3-11/h2-8,17,20-23,25-26,28-30H,9H2,1H3/t17-,20+,21+,22-,23-/m1/s1

InChI Key

WBCRDJIBCGCYEI-SUHOFRIBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hintonia standleyana	JEOL database	Cristians, S., et al, J. Nat. Prod. 72, 408 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-5-o-glycoside
4-phenylcoumarin
Neoflavonoid skeleton
Phenolic glycoside
7-hydroxycoumarin
Hydroxycoumarin
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
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	1.18	ALOGPS
logP	0.48	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.34 m³·mol⁻¹	ChemAxon
Polarizability	44.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24628155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45270512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cristians, S., et al. (2009). Cristians, S., et al, J. Nat. Prod. 72, 408 (2009). J. Nat. Prod..

Showing NP-Card for 6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin (NP0034249)

MOL for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

3D MOL for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

3D SDF for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

3D-SDF for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

PDB for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

3D PDB for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

SMILES for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

INCHI for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

Structure for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)

3D Structure for NP0034249 (6''-O-acetyl-5-O-beta-D-galactopyranosyl-7,4'-dihydroxy-4-phenylcoumarin)