Porphobilinogen

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
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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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDelta-aminolevulinic acid dehydrataseNot AvailableHumans
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
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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
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 / 5mhb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)8.78Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area116.41 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity56.38 m3·mol-1Chemaxon
Polarizability22.56 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-MSsplash10-001i-3920000000-d4006159f28f6672d3a5
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/MSsplash10-0bvi-0590000000-e96003e7e657db632bea
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0910000000-c9f54afea5e0339772fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0iki-0910000000-746da51b39890d8b87cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k9i-2900000000-b8cd039bfdd1db9a521e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9800000000-679e47cb2fbb05f7e884
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6900000000-30d2e49d849d5674c7bb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-155.8382426
predicted
DarkChem Lite v0.1.0
[M-H]-148.1749477
predicted
DarkChem Standard v0.1.0
[M-H]-158.4703426
predicted
DarkChem Lite v0.1.0
[M-H]-159.7364426
predicted
DarkChem Lite v0.1.0
[M-H]-145.77887
predicted
DeepCCS 1.0 (2019)
[M+H]+156.5662426
predicted
DarkChem Lite v0.1.0
[M+H]+157.8938426
predicted
DarkChem Lite v0.1.0
[M+H]+159.8443426
predicted
DarkChem Lite v0.1.0
[M+H]+160.6117426
predicted
DarkChem Lite v0.1.0
[M+H]+148.13689
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.0742426
predicted
DarkChem Lite v0.1.0
[M+Na]+157.1680894
predicted
DarkChem Standard v0.1.0
[M+Na]+159.0503426
predicted
DarkChem Lite v0.1.0
[M+Na]+160.2821426
predicted
DarkChem Lite v0.1.0
[M+Na]+155.1462
predicted
DeepCCS 1.0 (2019)

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14