1-{[(5Z)-3-hydroxy-1-methyl-6-oxo-2,3,5,6-tetrahydro-1H-inden-5-ylidene]amino}guanidine; methanesulfonic acid

• ChemBase ID: 159579
• Molecular Formular: C12H18N4O5S
• Molecular Mass: 330.36012
• Monoisotopic Mass: 330.0997907
• SMILES: C1(=O)/C(=N\NC(=N)N)/C=C2C(=C1)C(CC2O)C.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.NC(=N)N/N=C\1/C=C2C(O)CC(C2=CC1=O)C
• InChI: InChI=1S/C11H14N4O2.CH4O3S/c1-5-2-9(16)7-3-8(14-15-11(12)13)10(17)4-6(5)7;1-5(2,3)4/h3-5,9,16H,2H2,1H3,(H4,12,13,15);1H3,(H,2,3,4)/b14-8-
• InChIKey: OJCWHPWCBHHEBM-ZXDBEMHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(5Z)-3-hydroxy-1-methyl-6-oxo-2,3,5,6-tetrahydro-1H-inden-5-ylidene]amino}guanidine; methanesulfonic acid
• IUPAC Traditional name: 1-{[(5Z)-3-hydroxy-1-methyl-6-oxo-2,3-dihydro-1H-inden-5-ylidene]amino}guanidine; methanesulfonic acid
• Synonyms: 2-(1,2,3,6-Tetrahydro-3-hydroxy-1-methyl-6-oxo-5H-indol-5-ylidene)-hydrazinecarboximidamide Monomethanesulfonate Salt; A-Peest; AMM; Adchnon S; S-Adchnon; S-Adchnone; Adrenochrome Monoaminoguanidine Mesilate

Database IDs

• CAS Number: 4009-68-1
• PubChem SID: 162253714
• PubChem CID: 45038089

CALCULATED PROPERTIES

• Acid pKa: 14.501176
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.225357
• LogD (pH = 7.4): -1.2187136
• Log P: 0.13376038
• Molar Refractivity: 85.4146 cm^3
• Polarizability: 23.512646 Å^3
• Polar Surface Area: 111.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A305240

An Adrenochrome derivative; used as hemostatic agent.

REFERENCES

• Iozumi, K., et al.: J. Invest. Dermatol., 100, 806 (1993)
• Cabanes, J., et al.: J. Pharm. Pharmacol., 46, 982 (1993)
• Nihei, K., et al.: Bioorg. Med. Chem. Lett., 13, 2409 (1993)