NP-MRD: Showing NP-Card for Paeoniflorigenone (NP0141221)

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Record Information

Version

1.0

Created at

2022-06-29 22:18:19 UTC

Updated at

2022-06-29 22:18:19 UTC

NP-MRD ID

NP0141221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paeoniflorigenone

Description

Paeoniflorigenone belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Paeoniflorigenone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Paeoniflorigenone is found in Paeonia suffruticosa. It was first documented in 2017 (PMID: 28317437). Based on a literature review a significant number of articles have been published on paeoniflorigenone (PMID: 35496313) (PMID: 35051602) (PMID: 34665368) (PMID: 30836860).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -2.7365   -1.8828   -1.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -0.8201   -0.7634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4671   -1.4913    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045   -0.4069    1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1392   -0.5925    1.7963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6681    0.8578    1.3067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1586    0.5306    1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920    0.1054   -0.3309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5639   -0.4274   -0.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.2002   -1.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7139    1.3155   -1.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2979    0.0282   -1.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    1.8437    0.2071 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0886    2.3118    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0180    1.2572    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3777    1.4169    0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8083    2.5929    0.3186 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3349    0.3271    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540   -0.9836   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -2.0052   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2461   -1.7253   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6433   -0.4047   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6870    0.5825    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7519   -1.5628   -2.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7772   -2.1145   -1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -2.8210   -1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1949   -2.0694    0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735   -2.1104   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    1.3441    2.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7002    1.4841    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4829   -0.2648    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865   -0.7601    0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    2.0385   -1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9942    2.7276    0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491    3.1324   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2451    2.7474    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -1.2515   -0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040   -3.0334   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802   -2.4964   -0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085   -0.2154   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0408    1.5954    0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 23 18  1  0
 12  2  1  0
 13  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  1
  7 30  1  0
  7 31  1  0
  9 32  1  0
 11 33  1  6
 13 34  1  1
 14 35  1  0
 14 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
M  END


  Mrv1652306302200182D          

 23 26  0  0  1  0            999 V2000
    0.5502    1.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536    1.1494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6221    1.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9947    0.7197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7906   -0.1907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2626   -0.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    0.4251    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1893    0.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1447   -0.2332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9480   -0.8026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9527   -1.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.0442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -2.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622   -3.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4620   -4.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -4.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8909   -4.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8957   -3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836   -2.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847    0.8492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.6609    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  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
 10 22  1  0  0  0  0
  2 22  1  0  0  0  0
  8 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0141221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC(=O)[C@@H]3C[C@@]1(O)O[C@H](O2)[C@@H]3COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12-,15+,16+,17-/m1/s1

> <INCHI_KEY>
BANPEMKDTXIFRE-LQPBRMSDSA-N

> <FORMULA>
C17H18O6

> <MOLECULAR_WEIGHT>
318.325

> <EXACT_MASS>
318.1103383

$$$$

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       1.027   3.638   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.407   2.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.028   2.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.062   1.153   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.590   1.344   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.342  -0.356   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.357  -0.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.374   0.794   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.353   0.496   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.270  -0.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.770  -1.498   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.778  -3.038   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.449  -3.816   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.458  -5.356   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.796  -6.118   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.871  -6.133   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.862  -7.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.192  -8.451   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.530  -7.689   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.539  -6.149   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.209  -5.371   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.158   1.585   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.850   1.234   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9   23                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   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                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   10    2                                                       
CONECT   23    8                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
(+)-Paeoniflorigenone	ChEBI

Chemical Formula

C₁₇H₁₈O₆

Average Mass

318.3250 Da

Monoisotopic Mass

318.11034 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]12CC(=O)[C@@H]3C[C@@]1(O)O[C@H](O2)[C@@H]3COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12-,15+,16+,17-/m1/s1

InChI Key

BANPEMKDTXIFRE-LQPBRMSDSA-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 benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Oxepane
Oxane
Meta-dioxolane
Cyclic alcohol
Carboxylic acid ester
Hemiacetal
Ketone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzoate ester (CHEBI:69582 )

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

C00010954

Chemspider ID

30790852

KEGG Compound ID

C17453

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698143

PDB ID

Not Available

ChEBI ID

132788

Good Scents ID

Not Available

References

General References

Li T, Wu F, Zhang A, Dong H, Ullah I, Lin H, Miao J, Sun H, Han Y, He Y, Wang X: High-Throughput Chinmedomics Strategy Discovers the Quality Markers and Mechanisms of Wutou Decoction Therapeutic for Rheumatoid Arthritis. Front Pharmacol. 2022 Apr 12;13:854087. doi: 10.3389/fphar.2022.854087. eCollection 2022. [PubMed:35496313 ]
Park KR, Lee H, Kim SH, Yun HM: Paeoniflorigenone regulates apoptosis, autophagy, and necroptosis to induce anti-cancer bioactivities in human head and neck squamous cell carcinomas. J Ethnopharmacol. 2022 Apr 24;288:115000. doi: 10.1016/j.jep.2022.115000. Epub 2022 Jan 17. [PubMed:35051602 ]
Zhang J, Zhuge Y, Rong X, Ni C, Niu C, Wen Z, Lin H, Chu M, Jia C: Protective Roles of Xijiao Dihuang Tang on Coronary Artery Injury in Kawasaki Disease. Cardiovasc Drugs Ther. 2023 Apr;37(2):257-270. doi: 10.1007/s10557-021-07277-w. Epub 2021 Oct 19. [PubMed:34665368 ]
Huang Y, Ohno O, Miyamoto K: PFG acted as an inducer of premature senescence in TIG-1 normal diploid fibroblast and an inhibitor of mitosis in the HeLa cells. Biosci Biotechnol Biochem. 2019 Jun;83(6):986-995. doi: 10.1080/09168451.2019.1585744. Epub 2019 Mar 5. [PubMed:30836860 ]
Huang Y, Ohno O, Suenaga K, Miyamoto K: Apoptosis-inducing activity and antiproliferative effect of Paeoniflorigenone from moutan cortex. Biosci Biotechnol Biochem. 2017 Jun;81(6):1106-1113. doi: 10.1080/09168451.2017.1300517. Epub 2017 Mar 20. [PubMed:28317437 ]

Showing NP-Card for Paeoniflorigenone (NP0141221)

MOL for NP0141221 (Paeoniflorigenone)

3D MOL for NP0141221 (Paeoniflorigenone)

3D SDF for NP0141221 (Paeoniflorigenone)

3D-SDF for NP0141221 (Paeoniflorigenone)

PDB for NP0141221 (Paeoniflorigenone)

3D PDB for NP0141221 (Paeoniflorigenone)

SMILES for NP0141221 (Paeoniflorigenone)

INCHI for NP0141221 (Paeoniflorigenone)

Structure for NP0141221 (Paeoniflorigenone)

3D Structure for NP0141221 (Paeoniflorigenone)