2-hydroxy-2-[4-hydroxy-3-methoxy(1,2,3,4,5,6-13C6)phenyl]acetic acid

• ChemBase ID: 170755
• Molecular Formular: C9H10O5
• Molecular Mass: 204.12862903
• Monoisotopic Mass: 204.07295245
• SMILES: [13cH]1[13cH][13c]([13c]([13cH][13c]1C(O)C(=O)O)OC)O
• Canonical SMILES: CO[13c]1[13cH][13c]([13cH][13cH][13c]1O)C(C(=O)O)O
• InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/i2+1,3+1,4+1,5+1,6+1,7+1
• InChIKey: CGQCWMIAEPEHNQ-WBJZHHNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-[4-hydroxy-3-methoxy(1,2,3,4,5,6-^1^3C₆)phenyl]acetic acid
• IUPAC Traditional name: hydroxy[4-hydroxy-3-methoxy(1,2,3,4,5,6-^1^3C₆)phenyl]acetic acid
• Synonyms: Levitra, Valdenafil; Vardenafil, Hydrochloride SaltDiscontinued See V098001; α,4-Dihydroxy-3-methoxybenzeneacetic Acid-13C6; (+/-)-Vanilmandelic Acid-13C6; (4-Hydroxy-3-methoxyphenyl)glycolic Acid-13C6; 3-Methoxy-4-hydroxyphenyl-hydroxyacetic Acid-13C6; HMMA-13C6; VMA-13C6; Vanilinmandelic Acid-13C6; dl-Vanillomandelic Acid-13C6; 4-Hydroxy-3-methoxymandelic Acid-13C6

Database IDs

• CAS Number: 224785-91-5
• PubChem SID: 164226665
• PubChem CID: 46783231

CALCULATED PROPERTIES

• Acid pKa: 3.1136312
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9234009
• LogD (pH = 7.4): -3.0261636
• Log P: 0.43459907
• Molar Refractivity: 47.1479 cm^3
• Polarizability: 18.376032 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White to Off-White Cyrstalline Solid
• Melting Point: 192°C

DETAILS

Toronto Research Chemicals - H946333

A labelled metabolite of catecholamines.

Toronto Research Chemicals - V098000

A phsphodiesterase 5 inhibitor.

REFERENCES

• Canfell, P., et al.: Clin. Chem., 32, 222 (1986)
• Nunez, C., et al.: Eur. J .Clin. Chem. Clin. Biochem., 32, 461 (1986)
• Weise, M., et al.: J. Clin. Endocrinol. Metab., 87, 1955 (1986)