NP-MRD: Showing NP-Card for [(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate (NP0319003)

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Record Information

Version

2.0

Created at

2022-09-11 19:48:55 UTC

Updated at

2022-09-11 19:48:55 UTC

NP-MRD ID

NP0319003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate

Description

Alpha-benzoyloxypaeoniflorin, also known as alpha-oxypaeoniflorin 6'-benzoate, belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. [(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate is found in Paeonia suffruticosa. [(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate was first documented in 2001 (PMID: 11339628). Based on a literature review very few articles have been published on alpha-benzoyloxypaeoniflorin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112221492D          

 43 49  0  0  1  0            999 V2000
    2.1764    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2775    0.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0869    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055   -0.3328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7297   -0.3700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.8550    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4587    0.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844   -0.6341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6895   -1.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -1.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -2.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -1.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -3.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302   -3.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680   -4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -4.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -5.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405   -4.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -3.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -0.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9856   -0.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.3344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0589    0.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402    0.8906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0809    0.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.0288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2207   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -1.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629   -2.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -2.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767   -1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3972    0.6868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2159    0.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    1.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5737    2.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    1.5486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0637    2.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 25 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END


  Mrv1652309112221492D          

 43 49  0  0  1  0            999 V2000
    2.1764    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2775    0.8305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0869    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055   -0.3328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7297   -0.3700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -1.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.8550    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4587    0.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844   -0.6341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6895   -1.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7273   -1.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -2.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1547   -1.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -3.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2302   -3.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680   -4.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -4.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109   -5.5790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405   -4.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8028   -3.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -0.2077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9856   -0.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    0.3344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0589    0.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402    0.8906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0809    0.1306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.0288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2207   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -1.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629   -2.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -2.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767   -1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3972    0.6868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2159    0.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    1.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5737    2.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    1.5486    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0637    2.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 25 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0319003

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@@]3(O)O[C@@H](O1)[C@]1(COC(=O)C4=CC=C(O)C=C4)[C@H]3C[C@]21O[C@H]1O[C@H](COC(=O)C2=CC=CC=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O13/c1-27-13-29(37)19-11-30(27,28(19,26(42-27)43-29)14-39-24(36)16-7-9-17(31)10-8-16)41-25-22(34)21(33)20(32)18(40-25)12-38-23(35)15-5-3-2-4-6-15/h2-10,18-22,25-26,31-34,37H,11-14H2,1H3/t18-,19-,20-,21+,22-,25-,26-,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
VIWQCBZFJFSCLC-PEROMJSHSA-N

> <FORMULA>
C30H32O13

> <MOLECULAR_WEIGHT>
600.573

> <EXACT_MASS>
600.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,3R,5R,6R,8S)-3-{[(2R,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl 4-hydroxybenzoate

> <JCHEM_LOGP>
1.8051845516666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.544484258952155

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.498921889718698

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490929336008993

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
141.10660000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,3R,5R,6R,8S)-3-{[(2R,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.063   3.079   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.251   1.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.762   0.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.424  -0.621   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.962  -0.691   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.608  -2.184   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.158  -1.596   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.590   0.054   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.584  -1.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.287  -2.014   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.358  -3.552   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.725  -4.261   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.022  -3.430   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.796  -5.799   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.163  -6.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.234  -8.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.937  -8.876   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.007 -10.414   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.569  -8.168   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.499  -6.629   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.632  -0.388   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.840  -0.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.905   0.624   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.977   1.853   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.448   1.662   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.151   0.244   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.679   0.054   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.279  -1.365   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.807  -1.555   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.406  -2.974   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.477  -4.202   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.934  -3.164   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.534  -4.582   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.062  -4.773   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.991  -3.544   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.391  -2.126   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.863  -1.936   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.608   1.282   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.136   1.092   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.009   2.701   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.937   3.929   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.480   2.891   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.119   4.309   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   23                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6   21                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   21   23                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21    9    4   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    2    9   24                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   42                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   27   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   25   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
alpha-6'-Benzoyloxypaeoniflorin	ChEBI
alpha-Oxypaeoniflorin 6'-benzoate	ChEBI
Benzoyloxypaeoniflorin	ChEBI
a-6'-Benzoyloxypaeoniflorin	Generator
Α-6'-benzoyloxypaeoniflorin	Generator
a-Oxypaeoniflorin 6'-benzoate	Generator
a-Oxypaeoniflorin 6'-benzoic acid	Generator
alpha-Oxypaeoniflorin 6'-benzoic acid	Generator
Α-oxypaeoniflorin 6'-benzoate	Generator
Α-oxypaeoniflorin 6'-benzoic acid	Generator
a-Benzoyloxypaeoniflorin	Generator
Α-benzoyloxypaeoniflorin	Generator

Chemical Formula

C₃₀H₃₂O₁₃

Average Mass

600.5730 Da

Monoisotopic Mass

600.18429 Da

IUPAC Name

[(1R,2S,3R,5R,6R,8S)-3-{[(2R,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl 4-hydroxybenzoate

Traditional Name

[(1R,2S,3R,5R,6R,8S)-3-{[(2R,3R,4S,5S,6R)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@@]3(O)O[C@@H](O1)[C@]1(COC(=O)C4=CC=C(O)C=C4)[C@H]3C[C@]21O[C@H]1O[C@H](COC(=O)C2=CC=CC=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H32O13/c1-27-13-29(37)19-11-30(27,28(19,26(42-27)43-29)14-39-24(36)16-7-9-17(31)10-8-16)41-25-22(34)21(33)20(32)18(40-25)12-38-23(35)15-5-3-2-4-6-15/h2-10,18-22,25-26,31-34,37H,11-14H2,1H3/t18-,19-,20-,21+,22-,25-,26-,27+,28+,29-,30+/m1/s1

InChI Key

VIWQCBZFJFSCLC-PEROMJSHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paeonia suffruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Pinane monoterpenoid
Nopinane monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Furofuran
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Phenol
Monocyclic benzene moiety
Meta-dioxane
Monosaccharide
Benzenoid
Oxane
Dicarboxylic acid or derivatives
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Carboxylic acid derivative
Organooxygen compound
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	1.81	ChemAxon
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.11 m³·mol⁻¹	ChemAxon
Polarizability	0 Å³	ChemAxon
Number of Rings	7	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

58827442

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102597515

PDB ID

Not Available

ChEBI ID

132790

Good Scents ID

Not Available

References

General References

Ryu G, Park EK, Joo JH, Lee BH, Choi BW, Jung DS, Lee NH: A new antioxidant monoterpene glycoside, alpha-benzoyloxypaeoniflorin from Paeonia suffruticosa. Arch Pharm Res. 2001 Apr;24(2):105-8. doi: 10.1007/BF02976476. [PubMed:11339628 ]
LOTUS database [Link]

Showing NP-Card for [(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate (NP0319003)

MOL for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

3D MOL for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

3D SDF for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

3D-SDF for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

PDB for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

3D PDB for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

SMILES for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

INCHI for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

Structure for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)

3D Structure for NP0319003 ([(1r,2s,3r,5r,6r,8s)-3-{[(2r,3r,4s,5s,6r)-6-[(benzoyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl 4-hydroxybenzoate)