(2E)-2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]-N-(3-phenylpropyl)prop-2-enamide

• ChemBase ID: 131280
• Molecular Formular: C25H30N2O2
• Molecular Mass: 390.5179
• Monoisotopic Mass: 390.23072821
• SMILES: CC(C)c1cc(cc(c1O)C(C)C)/C=C(\C#N)/C(=O)NCCCc1ccccc1
• Canonical SMILES: CC(c1cc(/C=C(/C(=O)NCCCc2ccccc2)\C#N)cc(c1O)C(C)C)C
• InChI: InChI=1S/C25H30N2O2/c1-17(2)22-14-20(15-23(18(3)4)24(22)28)13-21(16-26)25(29)27-12-8-11-19-9-6-5-7-10-19/h5-7,9-10,13-15,17-18,28H,8,11-12H2,1-4H3,(H,27,29)/b21-13+
• InChIKey: JANPYFTYAGTSIN-FYJGNVAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-cyano-3-[4-hydroxy-3,5-bis(propan-2-yl)phenyl]-N-(3-phenylpropyl)prop-2-enamide
• IUPAC Traditional name: (2E)-2-cyano-3-(4-hydroxy-3,5-diisopropylphenyl)-N-(3-phenylpropyl)prop-2-enamide
• Synonyms: (E)-N-(3″-Phenylpropyl)-α-cyano-3′,5′-diisopropyl-4′-hydroxycinnamamide; Tyrphostin SU 1498

Database IDs

• MDL Number: MFCD03453026
• PubChem SID: 162225558; 24900199
• PubChem CID: 5941539

CALCULATED PROPERTIES

• Acid pKa: 9.291619
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.008765
• LogD (pH = 7.4): 6.0034394
• Log P: 6.0088344
• Molar Refractivity: 119.1635 cm^3
• Polarizability: 45.206646 Å^3
• Polar Surface Area: 73.12 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%
• Potency: 700 nM IC50

DETAILS

Sigma Aldrich - T4192

Biochem/physiol Actions
Potent and selective inhibitor of the VEGF receptor kinase, Flk-1. Very weak inhibitor of PDGFR-kinase, EGFR-kinase and HER-2 kinase.