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114-25-0

114-25-0 | 3,18-Diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid

CAS No: 114-25-0 Catalog No: AG0038B8 MDL No:

Product Description

Catalog Number:
AG0038B8
Chemical Name:
3,18-Diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid
CAS Number:
114-25-0
Molecular Formula:
C33H34N4O6
Molecular Weight:
582.6463
IUPAC Name:
3-[(2Z,5Z)-2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid
InChI:
InChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)/b24-13-,27-14-,28-15-
InChI Key:
RCNSAJSGRJSBKK-NSQVQWHSSA-N
SMILES:
C=CC1=C(C)C(=CC2=NC(=Cc3[nH]c(c(c3CCC(=O)O)C)C=C3NC(=O)C(=C3C=C)C)C(=C2C)CCC(=O)O)NC1=O
EC Number:
204-042-2
UNII:
O9MIA842K9

Properties

Complexity:
1530  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
3  
Exact Mass:
582.248g/mol
Formal Charge:
0
Heavy Atom Count:
43  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
582.657g/mol
Monoisotopic Mass:
582.248g/mol
Rotatable Bond Count:
11  
Topological Polar Surface Area:
161A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5  

Literature

Title Journal
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Resistance to nitric oxide-induced necrosis in heme oxygenase-1 overexpressing pulmonary epithelial cells associated with decreased lipid peroxidation. The Journal of biological chemistry 20061201
The effect of perfusion prior to cold preservation and addition of biliverdin on the liver graft from non-heart-beating donors. Transplantation proceedings 20061201
Heme oxygenase-2 is a critical determinant for execution of an acute inflammatory and reparative response. The American journal of pathology 20061101
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Theoretical investigations of the reactivity of verdoheme analogues: opening of the planar macrocycle by amide, dimethyl amide, and hydroxide nucleophiles to form helical biliverdin type complexes. Journal of inorganic biochemistry 20060901
Biliverdin-induced brainstem auditory evoked potential abnormalities in the jaundiced Gunn rat. Brain research 20060830
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Parasites in a biodiversity hotspot: a survey of hematozoa and a molecular phylogenetic analysis of Plasmodium in New Guinea skinks. The Journal of parasitology 20060801
Induced-fitting and electrostatic potential change of PcyA upon substrate binding demonstrated by the crystal structure of the substrate-free form. FEBS letters 20060710
Heme oxygenase induction and biliverdin excretion: implications for the bile fluorescence biomarker. Marine environmental research 20060701
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Carbon monoxide and biliverdin prevent endothelial cell sloughing in rats with type I diabetes. Free radical biology & medicine 20060615
Heme oxygenase-1 protects tumor cells against photodynamic therapy-mediated cytotoxicity. Oncogene 20060608
Heme oxygenase-1 and transplantation tolerance. Human immunology 20060601
Ischemia/reperfusion injury in the monolayers of human intestinal epithelial cell line caco-2 and its recovery by antioxidants. Drug metabolism and pharmacokinetics 20060601
Bile fluorescence, heme oxygenase induction, and increased biliverdin excretion by mixtures of environmental toxicants. Aquatic toxicology (Amsterdam, Netherlands) 20060501
The effect of long-term depuration on phase I and phase II biotransformation in mullets (Mugil cephalus) chronically exposed to pollutants in River Douro Estuary, Portugal. Marine environmental research 20060401
Biliverdin protects against polymicrobial sepsis by modulating inflammatory mediators. American journal of physiology. Gastrointestinal and liver physiology 20060401
Reconstitution of blue-green reversible photoconversion of a cyanobacterial photoreceptor, PixJ1, in phycocyanobilin-producing Escherichia coli. Biochemistry 20060321
Excretion of fetal biliverdin by the rat placenta-maternal liver tandem. American journal of physiology. Regulatory, integrative and comparative physiology 20060301
Multiple heme oxygenase family members contribute to the biosynthesis of the phytochrome chromophore in Arabidopsis. Plant physiology 20060301
Products of heme oxygenase and their potential therapeutic applications. American journal of physiology. Renal physiology 20060301
A study on eggshell pigmentation: biliverdin in blue-shelled chickens. Poultry science 20060301
Metabolic engineering to produce phytochromes with phytochromobilin, phycocyanobilin, or phycoerythrobilin chromophore in Escherichia coli. FEBS letters 20060220
Synthesis and electrochemistry of undeca-substituted metallo-benzoylbiliverdins. Inorganic chemistry 20060220
Chronic CO levels have [corrected] a beneficial effect on vascular relaxation in diabetes. Biochemical and biophysical research communications 20060217
A conserved histidine-aspartate pair is required for exovinyl reduction of biliverdin by a cyanobacterial phycocyanobilin:ferredoxin oxidoreductase. The Journal of biological chemistry 20060210
Polypyrroles as antioxidants: kinetic studies on reactions of bilirubin and biliverdin dimethyl esters and synthetic model compounds with peroxyl radicals in solution. Chemical calculations on selected typical structures. The Journal of organic chemistry 20060106
Crystallization and preliminary X-ray crystallographic analysis of the N-terminal photosensory module of phytochrome Agp1, a biliverdin-binding photoreceptor from Agrobacterium tumefaciens. Journal of structural biology 20060101
Altered porphyrin excretion and histopathology of greylag geese (Anser anser) exposed to soil contaminated with lead and arsenic in the Guadalquivir Marshes, southwestern Spain. Environmental toxicology and chemistry 20060101
Role of carbon monoxide and biliverdin in renal ischemia/reperfusion injury. Nephron. Experimental nephrology 20060101
Biliverdin administration protects against endotoxin-induced acute lung injury in rats. American journal of physiology. Lung cellular and molecular physiology 20051201
Mechanisms of heme oxygenase-1-mediated cardiac and pulmonary vascular protection in chronic hypoxia: roles of carbon monoxide and bilirubin. Chest 20051201
A light-sensing knot revealed by the structure of the chromophore-binding domain of phytochrome. Nature 20051117
O(2)- and H(2)O(2)-dependent verdoheme degradation by heme oxygenase: reaction mechanisms and potential physiological roles of the dual pathway degradation. The Journal of biological chemistry 20051104
Carbon monoxide mediates protection against nitric oxide toxicity in HeLa cells. Free radical biology & medicine 20051015
Bilirubin: a natural inhibitor of vascular smooth muscle cell proliferation. Circulation 20050816
Regulation of tetrapyrrole biosynthesis in higher plants. Biochemical Society transactions 20050801
Heme oxygenase-1: a therapeutic amplification funnel. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050801
Biliverdin administration prevents the formation of intimal hyperplasia induced by vascular injury. Circulation 20050726
Sterically locked synthetic bilin derivatives and phytochrome Agp1 from Agrobacterium tumefaciens form photoinsensitive Pr- and Pfr-like adducts. The Journal of biological chemistry 20050701
[Structure and mechanism of heme oxygenase]. Seikagaku. The Journal of Japanese Biochemical Society 20050701
Agrobacterium phytochrome as an enzyme for the production of ZZE bilins. Biochemistry 20050614
Small interference RNA-mediated gene silencing of human biliverdin reductase, but not that of heme oxygenase-1, attenuates arsenite-mediated induction of the oxygenase and increases apoptosis in 293A kidney cells. The Journal of biological chemistry 20050429
HO in pregnancy. Free radical biology & medicine 20050415
Heme oxygenase-1-generated biliverdin ameliorates experimental murine colitis. Inflammatory bowel diseases 20050401
Biochemical and spectroscopic characterization of the bacterial phytochrome of Pseudomonas aeruginosa. The FEBS journal 20050401
Biliverdin, immune-mediated liver injury, and the Gigo effect. Hepatology (Baltimore, Md.) 20050301
Heme oxygenase-1-mediated partial cytoprotective effect by NO on cadmium-induced cytotoxicity in C6 rat glioma cells. Toxicology in vitro : an international journal published in association with BIBRA 20050201
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