NP-MRD: Showing NP-Card for Benzoyloxypeoniflorin (NP0141226)

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Record Information

Version

1.0

Created at

2022-06-29 22:18:35 UTC

Updated at

2022-06-29 22:18:35 UTC

NP-MRD ID

NP0141226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzoyloxypeoniflorin

Description

Beta-benzoyloxypaeoniflorin, also known as beta-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. Benzoyloxypeoniflorin is found in Paeonia suffruticosa. It was first documented in 2001 (PMID: 11339628). Based on a literature review a significant number of articles have been published on beta-benzoyloxypaeoniflorin (PMID: 17067761) (PMID: 19586602) (PMID: 16270571) (PMID: 20824965).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306302200182D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306302200182D          

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   -0.5212   -0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926    0.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4115    1.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    0.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -0.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398    0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    0.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -2.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1166   -2.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688   -1.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1798   -1.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  2 10  1  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  8 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
  7 23  1  6  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 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
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 27 40  1  6  0  0  0
 26 41  1  1  0  0  0
 25 42  1  6  0  0  0
  4 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0141226

> <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-HRCYFWENSA-N

> <FORMULA>
C30H32O13

> <MOLECULAR_WEIGHT>
600.573

> <EXACT_MASS>
600.18429109

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       7.539   2.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.966   1.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.305  -0.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.794  -0.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.448   0.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.382   1.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.175   1.275   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.127   2.071   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.700   2.484   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.150   3.071   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.132   0.834   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.943   3.206   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.804   4.779   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.066   5.663   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.462   5.013   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.931   7.197   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.535   7.847   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.400   9.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.661  10.265   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.057   9.615   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.192   8.081   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.526  11.799   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.060  -0.471   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.080  -1.157   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.213  -2.691   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.951  -3.574   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.556  -2.922   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.422  -1.388   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.684  -0.505   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.973  -0.736   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.106   0.798   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.502   1.450   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.635   2.984   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -3.764   0.567   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.630  -0.967   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.892  -1.849   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.288  -1.198   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.421   0.336   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.159   1.219   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.706  -3.804   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.084  -5.108   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.608  -3.343   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.069  -2.319   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   11   43                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8   23                                             
CONECT    8    7    5    9   12                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    2                                                       
CONECT   11    9    4                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
CONECT   23    7   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   42                                                  
CONECT   26   25   27   41                                                  
CONECT   27   26   28   40                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   27                                                            
CONECT   41   26                                                            
CONECT   42   25                                                            
CONECT   43    4                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
Benzoyloxypaeoniflorin	ChEBI
beta-6'-Benzoyloxypaeoniflorin	ChEBI
beta-Oxypaeoniflorin 6'-benzoate	ChEBI
b-6'-Benzoyloxypaeoniflorin	Generator
Β-6'-benzoyloxypaeoniflorin	Generator
b-Oxypaeoniflorin 6'-benzoate	Generator
b-Oxypaeoniflorin 6'-benzoic acid	Generator
beta-Oxypaeoniflorin 6'-benzoic acid	Generator
Β-oxypaeoniflorin 6'-benzoate	Generator
Β-oxypaeoniflorin 6'-benzoic acid	Generator
b-Benzoyloxypaeoniflorin	Generator
Β-benzoyloxypaeoniflorin	Generator
alpha-Benzoyloxypaeoniflorin	MeSH
Benzoyloxy-paeoniflorin	MeSH

Chemical Formula

C₃₀H₃₂O₁₃

Average Mass

600.5730 Da

Monoisotopic Mass

600.18429 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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-HRCYFWENSA-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
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032759

Chemspider ID

10260966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21631107

PDB ID

Not Available

ChEBI ID

132791

Good Scents ID

Not Available

References

General References

Wu SH, Chen YW, Yang LY, Li SL, Li ZY: Monoterpene glycosides from Paeonia delavayi. Fitoterapia. 2007 Jan;78(1):76-8. doi: 10.1016/j.fitote.2006.09.014. Epub 2006 Sep 23. [PubMed:17067761 ]
Ding HY, Lin HC, Chang TS: Tyrosinase inhibitors isolated from the roots of Paeonia suffruticosa. J Cosmet Sci. 2009 May-Jun;60(3):347-52. [PubMed:19586602 ]
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 ]
Chen G, Zhang L, Yang P: Determination of three bioactive constituents in moutan cortex by capillary electrophoresis with electrochemical detection. Anal Sci. 2005 Oct;21(10):1161-5. doi: 10.2116/analsci.21.1161. [PubMed:16270571 ]
Koo YK, Kim JM, Koo JY, Kang SS, Bae K, Kim YS, Chung JH, Yun-Choi HS: Platelet anti-aggregatory and blood anti-coagulant effects of compounds isolated from Paeonia lactiflora and Paeonia suffruticosa. Pharmazie. 2010 Aug;65(8):624-8. [PubMed:20824965 ]

Showing NP-Card for Benzoyloxypeoniflorin (NP0141226)

MOL for NP0141226 (Benzoyloxypeoniflorin)

3D MOL for NP0141226 (Benzoyloxypeoniflorin)

3D SDF for NP0141226 (Benzoyloxypeoniflorin)

3D-SDF for NP0141226 (Benzoyloxypeoniflorin)

PDB for NP0141226 (Benzoyloxypeoniflorin)

3D PDB for NP0141226 (Benzoyloxypeoniflorin)

SMILES for NP0141226 (Benzoyloxypeoniflorin)

INCHI for NP0141226 (Benzoyloxypeoniflorin)

Structure for NP0141226 (Benzoyloxypeoniflorin)

3D Structure for NP0141226 (Benzoyloxypeoniflorin)