Identification
- Generic Name
- Porphobilinogen
- DrugBank Accession Number
- DB02272
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Porphobilinogen (DB02272)
- Weight
- Average: 226.2292
Monoisotopic: 226.095356946 - Chemical Formula
- C10H14N2O4
- Synonyms
- 5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid
- Porphobilinogen
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDelta-aminolevulinic acid dehydratase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- Substituted pyrroles / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Amino acids / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives show 1 more
- Substituents
- Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Heteroaromatic compound show 10 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- dicarboxylic acid, pyrroles, aralkylamino compound (CHEBI:17381)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 74KHC72QXK
- CAS number
- 487-90-1
- InChI Key
- QSHWIQZFGQKFMA-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
- SMILES
- NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000245
- KEGG Compound
- C00931
- PubChem Compound
- 1021
- PubChem Substance
- 46505854
- ChemSpider
- 995
- ChEBI
- 17381
- ChEMBL
- CHEMBL1235151
- ZINC
- ZINC000000056609
- PDBe Ligand
- PBG
- Wikipedia
- Porphobilinogen
- PDB Entries
- 1e51 / 1ohl / 3obk / 5mhb
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2, 3 Completed Treatment Acute Intermittent Porphyria (AIP) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.72 mg/mL ALOGPS logP -2.4 ALOGPS logP -2.7 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 3.66 ChemAxon pKa (Strongest Basic) 8.99 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 116.41 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 56.38 m3·mol-1 ChemAxon Polarizability 22.53 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6694 Blood Brain Barrier + 0.53 Caco-2 permeable - 0.7613 P-glycoprotein substrate Substrate 0.6005 P-glycoprotein inhibitor I Non-inhibitor 0.9798 P-glycoprotein inhibitor II Non-inhibitor 0.9936 Renal organic cation transporter Non-inhibitor 0.8196 CYP450 2C9 substrate Non-substrate 0.904 CYP450 2D6 substrate Non-substrate 0.7938 CYP450 3A4 substrate Non-substrate 0.7691 CYP450 1A2 substrate Non-inhibitor 0.8127 CYP450 2C9 inhibitor Non-inhibitor 0.956 CYP450 2D6 inhibitor Non-inhibitor 0.9395 CYP450 2C19 inhibitor Non-inhibitor 0.939 CYP450 3A4 inhibitor Non-inhibitor 0.9709 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9959 Ames test Non AMES toxic 0.8901 Carcinogenicity Non-carcinogens 0.942 Biodegradation Not ready biodegradable 0.7077 Rat acute toxicity 2.0559 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9522 hERG inhibition (predictor II) Non-inhibitor 0.9012
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
- Gene Name
- ALAD
- Uniprot ID
- P13716
- Uniprot Name
- Delta-aminolevulinic acid dehydratase
- Molecular Weight
- 36294.485 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14