1-carbamimidamido-N-(3-chlorophenyl)methanimidamide

• ChemBase ID: 179887
• Molecular Formular: C8H10ClN5
• Molecular Mass: 211.6515
• Monoisotopic Mass: 211.06247303
• SMILES: C(=N)(NC(=N)N)Nc1cc(Cl)ccc1
• Canonical SMILES: NC(=N)NC(=N)Nc1cccc(c1)Cl
• InChI: InChI=1S/C8H10ClN5/c9-5-2-1-3-6(4-5)13-8(12)14-7(10)11/h1-4H,(H6,10,11,12,13,14)
• InChIKey: DIHXJZHAIHGSAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-carbamimidamido-N-(3-chlorophenyl)methanimidamide
• IUPAC Traditional name: 1-carbamimidamido-N-(3-chlorophenyl)methanimidamide
• Synonyms: 1-(3-Chlorophenyl)biguanide; m-Chlorophenylbiguanide

Database IDs

• CAS Number: 48144-44-1
• PubChem SID: 164235797
• PubChem CID: 1354

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -3.2587626
• LogD (pH = 7.4): -1.6481558
• Log P: 1.3301078
• Molar Refractivity: 77.7112 cm^3
• Polarizability: 20.776552 Å^3
• Polar Surface Area: 97.78 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Potent selective serotonin 5-HT3 receptor agonist

Product Information

• Application(s): Psychostimulant; Tranquilizer

REFERENCES

• 1. Parihar HS,Kirschbaum KS (2002)
• Electrostatic potential surfaces of 5-HT(3)R agonists suggest accessory cation-pi site adjacent to agonist binding domain.
• Bioorganic & medicinal chemistry letters 12, 2743-7
• 2. Dukat M,Abdel-Rahman AA,Ismaiel AM,Ingher S,Teitler M,Gyermek L,Glennon RA (1996)
• Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors.
• Journal of medicinal chemistry 39, 4017-26
• 3. Zhou Y,Peng H,Ji Q,Qi J,Zhu Z,Yang C (2006)
• Discovery of small molecule inhibitors of integrin alphavbeta3 through structure-based virtual screening.
• Bioorganic & medicinal chemistry letters 16, 5878-82
• 4. Rahman AA,Daoud MK,Dukat M,Herrick-Davis K,Purohit A,Teitler M,do Amaral AT,Malvezzi A,Glennon RA (2003) Conformationally-restricted analogues and partition coefficients of the 5-HT3 serotonin
• receptor ligands meta-chlorophenylbiguanide (mCPBG) and meta-chlorophenylguanidine (mCPG). Bioorganic & medicinal chemistry letters 13, 1119-23
• 5. Dukat M,Choi YN,Teitler M,Du Pre A,Herrick-Davis K,Smith C,Glennon RA (2001)
• The binding of arylguanidines at 5-HT(3) serotonin receptors: a structure-affinity investigation.
• Bioorganic & medicinal chemistry letters 11, 1599-603