(R)-2-cyano-3-(3,4-dihydroxyphenyl)-N-(1-phenylethyl)acrylamide

ID: ALA258767

Chembl Id: CHEMBL258767

Cas Number: 133550-32-0

PubChem CID: 5328772

Max Phase: Preclinical

Molecular Formula: C18H16N2O3

Molecular Weight: 308.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: AG-527 | Tyrphostin B44, (-) enantiomer|Tyrphostin B44|133550-32-0|Tyrphostin AG 527|(E)-2-cyano-3-(3,4-dihydroxyphenyl)-N-[(1R)-1-phenylethyl]prop-2-enamide|AG-527|AG 527|SR-01000076158|Tocris-0578|Tyrphostin deriv. 44|ag527|Lopac0_001177|MLS002153178|BDBM4302|CHEMBL258767|cid_5328772|DTXSID90416171|HMS2235B13|HSCI1_000018|AKOS024458568|CCG-205251|NCGC00024662-01|NCGC00024662-02|NCGC00024662-03|NCGC00024662-04|NCGC00024662-05|SMR001230670|EU-0101177|M01337|T 4443|A806631|SR-01000597717|J-006401Show More⌵

Canonical SMILES:  C[C@@H](NC(=O)/C(C#N)=C/c1ccc(O)c(O)c1)c1ccccc1

Standard InChI:  InChI=1S/C18H16N2O3/c1-12(14-5-3-2-4-6-14)20-18(23)15(11-19)9-13-7-8-16(21)17(22)10-13/h2-10,12,21-22H,1H3,(H,20,23)/b15-9+/t12-/m1/s1

Standard InChI Key:  UMGQVUWXNOJOSJ-KMHUVPDISA-N

Alternative Forms

1. Parent:

   

   ALA258767

   Tyrphostin B44, (-) enantiomer

Molecule Features

Natural Product: No

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: 308.34

Molecular Weight (Monoisotopic): 308.1161

AlogP: 2.88

#Rotatable Bonds: 4

Polar Surface Area: 93.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.43

CX Basic pKa: ┄

CX LogP: 2.90

CX LogD: 2.86

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.46

Np Likeness Score: -0.52

References

1. Lipson RS, Clarke SG..  (2007)  S-adenosylmethionine-dependent protein methylation in mammalian cytosol via tyrphostin modification by catechol-O-methyltransferase.,  282  (42): [PMID:17724020] [10.1074/jbc.m705456200]

2. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays