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
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
Diagnostic dilemmas in acute intermittent porphyria. A case report.	2002 Apr-Jun	12123102
5-Aminolaevulinic acid dehydratase: metals, mutants and mechanism.	2002 Aug	12196142
Delta-Aminolevulinic acid transport in murine mammary adenocarcinoma cells is mediated by beta transporters.	2002 Aug 12	12177786
Two course illuminating scheme improves aminolevulinic acid photodynamic therapy in cell cultures.	2002 Dec	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 Dec	12699244
Structure of porphobilinogen synthase from Pseudomonas aeruginosa in complex with 5-fluorolevulinic acid suggests a double Schiff base mechanism.	2002 Jul 5	12079382
[Nephrologists and porphyrias].	2002 Jul-Aug	12369042
Management of acute and cutaneous porphyrias.	2002 May	12074210
Metabolic characterization of tumor cell-specific protoporphyrin IX accumulation after exposure to 5-aminolevulinic acid in human colonic cells.	2002 Nov	12462647
Quantitative real-time RT-PCR using hybridization probes and imported standard curves for cytokine gene expression analysis.	2002 Nov	12449386
Adrenomedullin gene expression in human placental tIssue and leukocytes: a potential marker of severe tIssue hypoxia in neonates with birth asphyxia.	2002 Nov	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 Nov	12426626
Molecular and biochemical studies of acute intermittent porphyria in 196 patients and their families.	2002 Nov	12406973
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 Nov 29	12459049
Acute intermittent porphyria in Sweden. Molecular, functional and clinical consequences of some new mutations found in the porphobilinogen deaminase gene.	2002 Oct	12372055
Rat kidney porphobilinogen deaminase kinetics. Detection of enzyme-substrate complexes.	2002 Oct	12127573
Analysis of EF-hand-containing proteins in Arabidopsis.	2002 Sep 23	12372144
ALA and ALA hexyl ester induction of porphyrins after their systemic administration to tumour bearing mice.	2002 Sep 23	12232765
Quantification of human telomerase reverse transcriptase mRNA in testicular germ cell tumors by quantitative fluorescence real-time RT-PCR.	2002 Sep-Oct	12168080
Time-resolved and static-ensemble structural chemistry of hydroxymethylbilane synthase.	2003	12555854
Oesophageal squamous cell neoplasia in head and neck cancer patients: upregulation of COX-2 during carcinogenesis.	2003 Apr 22	12698187
Correction of the biochemical defect in porphobilinogen deaminase deficient cells by non-viral gene delivery.	2003 Aug	12962144
Leptospira spp. possess a complete haem biosynthetic pathway and are able to use exogenous haem sources.	2003 Aug	12864856
Necrotic cell death induced by delta-aminolevulinic acid in mouse astrocytes. Protective role of melatonin and other antioxidants.	2003 Aug	12823607
5-Aminolevulinic acid synthesis in epimastigotes of Trypanosoma cruzi.	2003 Aug	12757763
X-ray structure of a putative reaction intermediate of 5-aminolaevulinic acid dehydratase.	2003 Aug 1	12777167
A porphobilinogen deaminase (PBGD) Ran-binding protein interaction is implicated in nuclear trafficking of PBGD in differentiating glioma cells.	2003 Aug 14	12917623
Selective accumulation of ALA-induced PpIX and photodynamic effect in chemically induced hepatocellular carcinoma.	2003 Aug 18	12915887
The biology of the Ets1 proto-oncogene.	2003 Aug 20	12971829
Erythropoietin treatment in the neuropsychiatric porphyrias.	2003 Dec	14637267
Effects of continuous light exposure on antioxidant enzymes, porphyric enzymes and cellular damage in the Harderian gland of the Syrian hamster.	2003 Jan	12485373
A new synthesis of porphobilinogen analogues, inhibitors of hydroxymethylbilane synthase.	2003 Jan 7	12929382
Aminolaevulinic acid-induced protoporphyrin IX pharmacokinetics in central and peripheral arteries of the rat.	2003 Jul	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 Jul	12929745
Measurement of urinary porphyrins and porphyrin precursors in Dutch hospital laboratories: a review of quality control over 5 years.	2003 Jul	12880545
The porphyrias, appropriate test selection.	2003 Jul 15	12849906
Mechanistic studies on delta-aminolevulinic acid uptake and efflux in a mammary adenocarcinoma cell line.	2003 Jul 7	12838320
Acute porphyrias in the Argentinean population: a review.	2003 Jun	12899439
Human porphobilinogen deaminase mutations in the investigation of the mechanism of dipyrromethane cofactor assembly and tetrapyrrole formation.	2003 Jun	12773194
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 Mar 1	12408752
2,3-Dimercaptopropane-1-sulfonic acid and meso-2,3-dimercaptosuccinic acid increase mercury- and cadmium-induced inhibition of delta-aminolevulinate dehydratase.	2003 Mar 3	12499112
Acute intermittent porphyria in childhood: a population-based study.	2003 May	12839285
Stereochemistry and mechanism of the conversion of 5-aminolaevulinic acid into porphobilinogen catalysed by porphobilinogen synthase.	2003 May 7	12926268
[An acute attack of hereditary coproporphyria concomitant with severe generalized polyneuropathy and respiratory insufficiency].	2003 May-Jun	12918208
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 Nov	14506704
Renal transplantation in a case of acute intermittent porphyria.	2003 Oct	14517198
Identification of rate-limiting steps in yeast heme biosynthesis.	2003 Oct 31	14559249
Gene-specific monitoring of T7-based RNA amplification by real-time quantitative PCR.	2003 Sep	14513555

Substance Class	Chemical Created by `admin` on `Sat Dec 17 03:32:13 UTC 2022` Edited by `admin` on `Sat Dec 17 03:32:13 UTC 2022`
Record UNII	74KHC72QXK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PORPHOBILINOGEN

Common Name

English

PORPHOBILINOGEN [MI]

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