3-{5-[amino(13C)methyl]-4-(carboxymethyl)(2,5-13C2)-1H-pyrrol-3-yl}propanoic acid

• ChemBase ID: 176839
• Molecular Formular: C10H14N2O4
• Molecular Mass: 229.20712451
• Monoisotopic Mass: 229.10542145
• SMILES: c1(c([13cH][nH][13c]1[13CH2]N)CCC(=O)O)CC(=O)O
• Canonical SMILES: N[13CH2][13c]1[nH][13cH]c(c1CC(=O)O)CCC(=O)O
• InChI: InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)/i4+1,5+1,8+1
• InChIKey: QSHWIQZFGQKFMA-LGMPQVEQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{5-[amino(^1^3C)methyl]-4-(carboxymethyl)(2,5-^1^3C₂)-1H-pyrrol-3-yl}propanoic acid
• IUPAC Traditional name: 3-{5-[amino(^1^3C)methyl]-4-(carboxymethyl)(2,5-^1^3C₂)-1H-pyrrol-3-yl}propanoic acid
• Synonyms: 5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propanoic Acid-13C3; PBG-13C3; Porphobilinogen-13C3

Database IDs

• PubChem SID: 164232749
• PubChem CID: 71751727

CALCULATED PROPERTIES

• Acid pKa: 3.6647267
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.5743368
• LogD (pH = 7.4): -5.3416476
• Log P: -2.6799998
• Molar Refractivity: 56.3839 cm^3
• Polarizability: 21.7231 Å^3
• Polar Surface Area: 116.41 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P689502

Labelled Porphobilinogen. An intermediate in the biosynthesis of Heme, found in the urine of patients with acute porphyria.

REFERENCES

• Westall, et al.: Nature, 170, 614 (1952)
• Cookson, R., et al.: Biochem, J., 57, 476 (1952)
• MacDonald, J., Can. J. Chem., 35, 715 (1952)