paeonol

ID: ALA1079227

Cas Number: 552-41-0

PubChem CID: 11092

Product Number: H111081, Order Now?

Max Phase: Preclinical

Molecular Formula: C9H10O3

Molecular Weight: 166.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Paeonol | PAEONOL|552-41-0|2'-Hydroxy-4'-methoxyacetophenone|1-(2-Hydroxy-4-methoxyphenyl)ethanone|Peonol|2-Hydroxy-4-methoxyacetophenone|Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-|1-(2-hydroxy-4-methoxyphenyl)ethan-1-one|4-O-Methylresacetophenone|Resacetophenone-4-methyl ether|4'-Methoxy-2'-hydroxyacetophenone|MFCD00008730|Paeonal|Acetophenone, 2'-hydroxy-4'-methoxy-|2-acetyl-5-methoxyphenol|Resacetophenone, 4-O-methyl ester|EINECS 209-012-2|NSC 401442|UNII-3R834EPI82|BRN 1282794|1-(2-hydroxy-4-mShow More⌵

Canonical SMILES:  COc1ccc(C(C)=O)c(O)c1

Standard InChI:  InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3

Standard InChI Key:  UILPJVPSNHJFIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
   -5.3714  -28.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3727  -28.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6581  -29.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9418  -28.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451  -28.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6602  -27.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0855  -27.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848  -26.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2271  -29.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265  -30.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5129  -28.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6584  -30.2226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  2  0
  1  7  1  0
  3  4  2  0
  7  8  1  0
  4  9  1  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
  3 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079227

   Paeonol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 166.18

Molecular Weight (Monoisotopic): 166.0630

AlogP: 1.60

#Rotatable Bonds: 2

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 1.72

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.68

Np Likeness Score: 0.32

References

1. Ha do T, Ngoc TM, Lee I, Lee YM, Kim JS, Jung H, Lee S, Na M, Bae K..  (2009)  Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa).,  72  (8): [PMID:19670875] [10.1021/np9002004]

2. PubChem BioAssay data set, 

3. Mencherini T, Picerno P, Festa M, Russo P, Capasso A, Aquino R..  (2011)  Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.,  74  (10): [PMID:21954959] [10.1021/np200359v]

4. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

5. PubChem BioAssay data set, 

6. Wiśniowska B, Mendyk A, Fijorek K, Glinka A, Polak S..  (2012)  Predictive model for L-type channel inhibition: multichannel block in QT prolongation risk assessment.,  32  [PMID:22761000] [10.1002/jat.2784]

7. Huang L, Zhang B, Yang Y, Gong X, Chen Z, Wang Z, Zhang P, Zhang Q..  (2016)  Synthesis and anti-inflammatory activity of paeonol analogues in the murine model of complete Freund's adjuvant induced arthritis.,  26  (21): [PMID:27712938] [10.1016/j.bmcl.2016.09.060]

8. Sheng Z, Ge S, Xu X, Zhang Y, Wu P, Zhang K, Xu X, Li C, Zhao D, Tang X..  (2018)  Design, synthesis and evaluation of cinnamic acid ester derivatives as mushroom tyrosinase inhibitors.,  9  (5): [PMID:30108974] [10.1039/C8MD00099A]

9. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

10. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

11. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

12. Tomohara K, Hasegawa N, Adachi I, Horino Y, Nose T..  (2020)  Early identification of promiscuous attributes of aldose reductase inhibitors using a DMSO-perturbation assay.,  30  (2): [PMID:31744675] [10.1016/j.bmcl.2019.126815]

13. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

14. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

15. Lee H, Lee S, Baek JY, Seo CS, Yun H, Kim SN, Kang KS, Choi YK..  (2021)  Estrogenic activity of ethyl gallate and its potential use in hormone replacement therapy.,  40  [PMID:33711444] [10.1016/j.bmcl.2021.127919]

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6