5-[(2-hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

• ChemBase ID: 153970
• Molecular Formular: C21H16N2O2S
• Molecular Mass: 360.42894
• Monoisotopic Mass: 360.09324876
• SMILES: c1ccc(cc1)c1c(c(=O)[nH]c(=S)[nH]1)Cc1c2ccccc2ccc1O
• Canonical SMILES: S=c1[nH]c(=O)c(c([nH]1)c1ccccc1)Cc1c(O)ccc2c1cccc2
• InChI: InChI=1S/C21H16N2O2S/c24-18-11-10-13-6-4-5-9-15(13)16(18)12-17-19(14-7-2-1-3-8-14)22-21(26)23-20(17)25/h1-11,24H,12H2,(H2,22,23,25,26)
• InChIKey: RVNSQVIUFZVNAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2-hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one
• IUPAC Traditional name: 5-[(2-hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-sulfanylidene-1,3-dihydropyrimidin-4-one
• Synonyms: 5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one; 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone; NSC-1125476; Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone; Cambinol

Database IDs

• CAS Number: 14513-15-6
• MDL Number: MFCD09057543
• PubChem SID: 162248109
• PubChem CID: 3246390

CALCULATED PROPERTIES

• Acid pKa: 7.962518
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 3.9908392
• LogD (pH = 7.4): 3.8868742
• Log P: 3.9923177
• Molar Refractivity: 107.1275 cm^3
• Polarizability: 42.181488 Å^3
• Polar Surface Area: 61.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C21H16N2O2S

DETAILS

Sigma Aldrich - C0494

Biochem/physiol Actions
Cambinol is a Sirtuin (Human Silent Information Regulator) Type 1/2 Inhibitor. Sirtuins are structurally and mechanistically unrelated to HDACs Class 1 & 2 deacetylases but share many protein targets. HDAC is a large complex enzyme family involved in epigenetic-control of gene expression. Sirt2 has an IC50 equal to 59 μM.