PORPHOBILINOGEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H14N2O4
Molecular Weight	226.2292
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1

InChI

InChIKey=QSHWIQZFGQKFMA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C10H14N2O4
Molecular Weight	226.2292
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.echelon-inc.com/index.php?module=Products&func=detail&id=665 | https://emedicine.medscape.com/article/2088383-overview | Turgeon, M.L. (2014) Linne & Ringsrud's Clinical Laboratory Science, page 395, retrieved from: https://books.google.ru/books?id=Y7fwAwAAQBAJ

An acute attack may be precipitated by drugs affecting the liver, by infection and by diet. The discovery of porphobilinogen in urine is a critical value that can eliminate or reduce adverse effects from drugs or anesthetics.

Approval Year

PubMed

Title	Date	PubMed
Erythropoietin treatment in the neuropsychiatric porphyrias.	2003-12	14637267
Development of a real-time RT-PCR assay for the quantification of the most frequent MLL/AF9 fusion types resulting from translocation t(9;11)(p22;q23) in acute myeloid leukemia.	2003-11	14506704
Identification of rate-limiting steps in yeast heme biosynthesis.	2003-10-31	14559249
Renal transplantation in a case of acute intermittent porphyria.	2003-10	14517198
Gene-specific monitoring of T7-based RNA amplification by real-time quantitative PCR.	2003-09	14513555
The biology of the Ets1 proto-oncogene.	2003-08-20	12971829
Selective accumulation of ALA-induced PpIX and photodynamic effect in chemically induced hepatocellular carcinoma.	2003-08-18	12915887
[An acute attack of hereditary coproporphyria concomitant with severe generalized polyneuropathy and respiratory insufficiency].	2003-08-16	12918208
A porphobilinogen deaminase (PBGD) Ran-binding protein interaction is implicated in nuclear trafficking of PBGD in differentiating glioma cells.	2003-08-14	12917623
X-ray structure of a putative reaction intermediate of 5-aminolaevulinic acid dehydratase.	2003-08-01	12777167
Correction of the biochemical defect in porphobilinogen deaminase deficient cells by non-viral gene delivery.	2003-08	12962144
Leptospira spp. possess a complete haem biosynthetic pathway and are able to use exogenous haem sources.	2003-08	12864856
Necrotic cell death induced by delta-aminolevulinic acid in mouse astrocytes. Protective role of melatonin and other antioxidants.	2003-08	12823607
5-Aminolevulinic acid synthesis in epimastigotes of Trypanosoma cruzi.	2003-08	12757763
The porphyrias, appropriate test selection.	2003-07-15	12849906
Mechanistic studies on delta-aminolevulinic acid uptake and efflux in a mammary adenocarcinoma cell line.	2003-07-07	12838320
Aminolaevulinic acid-induced protoporphyrin IX pharmacokinetics in central and peripheral arteries of the rat.	2003-07	12929753
Photophysical and lasing properties of new analogs of the boron-dipyrromethene laser dye pyrromethene 567 incorporated into or covalently bounded to solid matrices of poly(methyl methacrylate).	2003-07	12929745
Measurement of urinary porphyrins and porphyrin precursors in Dutch hospital laboratories: a review of quality control over 5 years.	2003-07	12880545
Acute porphyrias in the Argentinean population: a review.	2003-06	12899439
Human porphobilinogen deaminase mutations in the investigation of the mechanism of dipyrromethane cofactor assembly and tetrapyrrole formation.	2003-06	12773194
Stereochemistry and mechanism of the conversion of 5-aminolaevulinic acid into porphobilinogen catalysed by porphobilinogen synthase.	2003-05-07	12926268
Acute intermittent porphyria in childhood: a population-based study.	2003-05	12839285
Oesophageal squamous cell neoplasia in head and neck cancer patients: upregulation of COX-2 during carcinogenesis.	2003-04-22	12698187
2,3-Dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid increase mercury- and cadmium-induced inhibition of delta-aminolevulinate dehydratase.	2003-03-03	12499112
Identification and functional analysis of enzymes required for precorrin-2 dehydrogenation and metal ion insertion in the biosynthesis of sirohaem and cobalamin in Bacillus megaterium.	2003-03-01	12408752
A new synthesis of porphobilinogen analogues, inhibitors of hydroxymethylbilane synthase.	2003-01-07	12929382
Effects of continuous light exposure on antioxidant enzymes, porphyric enzymes and cellular damage in the Harderian gland of the Syrian hamster.	2003-01	12485373
Time-resolved and static-ensemble structural chemistry of hydroxymethylbilane synthase.	2003	12555854
Two course illuminating scheme improves aminolevulinic acid photodynamic therapy in cell cultures.	2002-12	12699249
Residual activity of human porphobilinogen deaminase with R167Q or R167W mutations: an explanation for survival of homozygous and compound heterozygous acute intermittent porphyrics.	2002-12	12699244
The differentiation status of primary gonadal germ cell tumors correlates inversely with telomerase activity and the expression level of the gene encoding the catalytic subunit of telomerase.	2002-11-29	12459049
Metabolic characterization of tumor cell-specific protoporphyrin IX accumulation after exposure to 5-aminolevulinic acid in human colonic cells.	2002-11	12462647
Quantitative real-time RT-PCR using hybridization probes and imported standard curves for cytokine gene expression analysis.	2002-11	12449386
Adrenomedullin gene expression in human placental tIssue and leukocytes: a potential marker of severe tIssue hypoxia in neonates with birth asphyxia.	2002-11	12444904
The decrease in uroporphyrinogen decarboxylase activity induced by ethanol predisposes rats to the development of porphyria and accelerates xenobiotic-triggered porphyria, regardless of hepatic damage.	2002-11	12426626
Molecular and biochemical studies of acute intermittent porphyria in 196 patients and their families.	2002-11	12406973
[Nephrologists and porphyrias].	2002-10-09	12369042
Acute intermittent porphyria in Sweden. Molecular, functional and clinical consequences of some new mutations found in the porphobilinogen deaminase gene.	2002-10	12372055
Rat kidney porphobilinogen deaminase kinetics. Detection of enzyme-substrate complexes.	2002-10	12127573
Analysis of EF-hand-containing proteins in Arabidopsis.	2002-09-23	12372144
ALA and ALA hexyl ester induction of porphyrins after their systemic administration to tumour bearing mice.	2002-09-23	12232765
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters.	2002-08-12	12177786
Quantification of human telomerase reverse transcriptase mRNA in testicular germ cell tumors by quantitative fluorescence real-time RT-PCR.	2002-08-09	12168080
5-Aminolaevulinic acid dehydratase: metals, mutants and mechanism.	2002-08	12196142
Diagnostic dilemmas in acute intermittent porphyria. A case report.	2002-07-19	12123102
Structure of porphobilinogen synthase from Pseudomonas aeruginosa in complex with 5-fluorolevulinic acid suggests a double Schiff base mechanism.	2002-07-05	12079382
Management of acute and cutaneous porphyrias.	2002-05	12074210
Ancestral founder of mutation W283X in the porphobilinogen deaminase gene among acute intermittent porphyria patients.	2002	12566739
Porphobilinogen deaminase: accumulation and detection of tetrapyrrole intermediates using enzyme immobilization.	2002	12418240

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:55:24 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:24 GMT 2025`
Record UNII	74KHC72QXK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PORPHOBILINOGEN [MI]

Preferred Name

English

PORPHOBILINOGEN

Common Name

English

1H-PYRROLE-3-PROPANOIC ACID, 5-(AMINOMETHYL)-4-(CARBOXYMETHYL)-

Systematic Name

English

3-(5-(AMINOMETHYL)-4-(CARBOXYMETHYL)-1H-PYRROL-3-YL)PROPANOIC ACID

Systematic Name

English

Classification Tree Code System Code

LOINC

34356-6