Identification
NamePorphobilinogen
Accession NumberDB02272  (EXPT02507)
TypeSmall Molecule
GroupsExperimental
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.

Structure
Thumb
Synonyms
2-aminomethylpyrrol-3-acetic acid 4-propionic acid
5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid
PBG
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNII74KHC72QXK
CAS number487-90-1
WeightAverage: 226.2292
Monoisotopic: 226.095356946
Chemical FormulaC10H14N2O4
InChI KeyQSHWIQZFGQKFMA-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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Delta-aminolevulinic acid dehydrataseProteinunknownNot AvailableHumanP13716 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.72 mg/mLALOGPS
logP-2.4ALOGPS
logP-2.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.41 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.38 m3·mol-1ChemAxon
Polarizability22.53 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6694
Blood Brain Barrier+0.53
Caco-2 permeable-0.7613
P-glycoprotein substrateSubstrate0.6005
P-glycoprotein inhibitor INon-inhibitor0.9798
P-glycoprotein inhibitor IINon-inhibitor0.9936
Renal organic cation transporterNon-inhibitor0.8196
CYP450 2C9 substrateNon-substrate0.904
CYP450 2D6 substrateNon-substrate0.7938
CYP450 3A4 substrateNon-substrate0.7691
CYP450 1A2 substrateNon-inhibitor0.8127
CYP450 2C9 inhibitorNon-inhibitor0.956
CYP450 2D6 inhibitorNon-inhibitor0.9395
CYP450 2C19 inhibitorNon-inhibitor0.939
CYP450 3A4 inhibitorNon-inhibitor0.9709
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9959
Ames testNon AMES toxic0.8901
CarcinogenicityNon-carcinogens0.942
BiodegradationNot ready biodegradable0.7077
Rat acute toxicity2.0559 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9522
hERG inhibition (predictor II)Non-inhibitor0.9012
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001j-1923000000-70c31b91868484322655View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0090000000-912aa953bdd13d6d18caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-1900000000-8a87960bb63c4915db22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9500000000-c934217374e64d6edee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0980000000-423d28b762ba4c07586bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0910000000-31575764ba8bd8d50279View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074r-0900000000-9d96bd59f1a4371a8df4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0790000000-2cc911a67c1aa8e35d99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ur-0940000000-2c3da60da6ab9523fbf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-4900000000-cf52dffb4284f9eeaa5dView in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentAralkylamines
Alternative ParentsSubstituted pyrroles / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Amino acids / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
SubstituentsAralkylamine / Dicarboxylic acid or derivatives / Substituted pyrrole / Heteroaromatic compound / Pyrrole / Amino acid / Amino acid or derivatives / Carboxylic acid derivative / Azacycle / Carboxylic acid
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsdicarboxylic acid, pyrroles, aralkylamino compound (CHEBI:17381 )

Targets

Kind
Protein
Organism
Human
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
Molecular Weight:
36294.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 16:04