3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

• ChemBase ID: 2021
• Molecular Formular: C10H14N2O4
• Molecular Mass: 226.22916
• Monoisotopic Mass: 226.09535694
• SMILES: NCc1[nH]cc(CCC(=O)O)c1CC(=O)O
• Canonical SMILES: NCc1[nH]cc(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)
• InChIKey: QSHWIQZFGQKFMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
• IUPAC Traditional name: porphobilinogen
• Synonyms: 5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propanoic acid; Porphobilinogen; 2-aminomethylpyrrol-3-acetic acid 4-propionic acid; 5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid; PBG; Porphobilinogen; 5-[Aminomethyl]-4-[carboxymethyl]-1H-pyrrole-3-propanoic acid; 紫质胆素原

Database IDs

• CAS Number: 487-90-1
• EC Number: 207-666-3
• MDL Number: MFCD00005224
• Beilstein Number: 220051
• PubChem SID: 46505854; 24898159; 160965476
• PubChem CID: 1021
• DrugBank ID: DB02272
• MeSH Name: Porphobilinogen
• Wikipedia Title: Porphobilinogen

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -2.4
• LOG S: -1.92
• Solubility (Water): 2.72e+00 g/l

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C10H14N2O4

DETAILS

MP Biomedicals - 02156336

Pink crystals.

DrugBank - DB02272

• Drug Groups: experimental
• Description: Porphobilinogen is a pyrrole involved in porphyrin metabolism. It is generated by the enzyme ALA dehydratase, and converted into hydroxymethyl bilane by the enzyme porphobilinogen deaminase.
• External Links: Wikipedia

Sigma Aldrich - P1134

Biochem/physiol Actions
Intermediate in the biosynthesis of heme.
Preparation Note
Enzymatically prepared.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P1134.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 81480

Other Notes
Substrate for determining porphobilinogen deaminase activities in human erythrocytes, brain, liver etc.1

Toronto Research Chemicals - P689500

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)