Porphobilinogen

Identification

Name
Porphobilinogen
Accession Number
DB02272  (EXPT02507)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • 2-aminomethylpyrrol-3-acetic acid 4-propionic acid
  • 5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrole-3-propionic acid
  • PBG
Categories
Not Available
UNII
74KHC72QXK
CAS number
487-90-1
Weight
Average: 226.2292
Monoisotopic: 226.095356946
Chemical Formula
C10H14N2O4
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDelta-aminolevulinic acid dehydrataseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB00245
KEGG Compound
C00931
ChemSpider
995
ChEBI
17381
HET
PBG
Wikipedia
Porphobilinogen
PDB Entries
1e51 / 1ohl / 3obk / 5mhb

Clinical Trials

Clinical Trials
Not Available

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
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-001j-1923000000-70c31b91868484322655
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-001j-1923000000-70c31b91868484322655
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0a4i-0090000000-912aa953bdd13d6d18ca
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00dl-1900000000-8a87960bb63c4915db22
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-006x-9500000000-c934217374e64d6edee3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-0980000000-423d28b762ba4c07586b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0910000000-31575764ba8bd8d50279
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-074r-0900000000-9d96bd59f1a4371a8df4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-0790000000-2cc911a67c1aa8e35d99
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06ur-0940000000-2c3da60da6ab9523fbf3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-4900000000-cf52dffb4284f9eeaa5d

Taxonomy

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
Aralkylamine / Dicarboxylic acid or derivatives / Substituted pyrrole / Heteroaromatic compound / Pyrrole / Amino acid / Amino acid or derivatives / Carboxylic acid derivative / Azacycle / Carboxylic acid
show 10 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
dicarboxylic 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
Uniprot Name
Delta-aminolevulinic acid dehydratase
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 October 02, 2017 05:08