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phycocyanobilin

CAS No.:
20298-86-6
Catalog Number:
AG00C2LE
Molecular Formula:
C33H38N4O6
Molecular Weight:
586.6780
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Product Description
Catalog Number:
AG00C2LE
Chemical Name:
phycocyanobilin
CAS Number:
20298-86-6
Molecular Formula:
C33H38N4O6
Molecular Weight:
586.6780
MDL Number:
MFCD22684686
IUPAC Name:
3-[(2Z,5E)-2-[[3-(2-carboxyethyl)-5-[(Z)-[(3E,4R)-3-ethylidene-4-methyl-5-oxopyrrolidin-2-ylidene]methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[(4-ethyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid
InChI:
InChI=1S/C33H38N4O6/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/h7,13-15,19,34-35H,8-12H2,1-6H3,(H,37,42)(H,38,39)(H,40,41)/b20-7+,24-13+,27-14-,28-15-/t19-/m1/s1
InChI Key:
NNMALANKTSRILL-LXENMSTPSA-N
SMILES:
CCC1=C(C)/C(=C\C2=N/C(=C/c3[nH]c(c(c3CCC(=O)O)C)/C=C\3/NC(=O)C(/C3=C\C)C)/C(=C2C)CCC(=O)O)/NC1=O
Properties
Complexity:
1460  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
4  
Exact Mass:
586.279g/mol
Formal Charge:
0
Heavy Atom Count:
43  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
586.689g/mol
Monoisotopic Mass:
586.279g/mol
Rotatable Bond Count:
10  
Topological Polar Surface Area:
161A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5  
Literature
Title Journal
Identification of amino acid residues essential to the activity of lyase CpcT1 from Nostoc sp. PCC7120. Gene 20121210
Assembly of synthetic locked phycocyanobilin derivatives with phytochrome in vitro and in vivo in Ceratodon purpureus and Arabidopsis. The Plant cell 20120501
Marinobufagenin and cyclic strain may activate endothelial NADPH oxidase, contributing to the adverse impact of salty diets on vascular and cerebral health. Medical hypotheses 20120201
Clinical potential of phycocyanobilin for induction of T regulatory cells in the management of inflammatory disorders. Medical hypotheses 20111201
Novel photosensory two-component system (PixA-NixB-NixC) involved in the regulation of positive and negative phototaxis of cyanobacterium Synechocystis sp. PCC 6803. Plant & cell physiology 20111201
Initial excited-state relaxation of the bilin chromophores of phytochromes: a computational study. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20110401
Structure of the chromophore binding pocket in the Pr state of plant phytochrome phyA. The journal of physical chemistry. B 20110210
Structural basis for hydration dynamics in radical stabilization of bilin reductase mutants. Biochemistry 20100727
Oral phycocyanobilin may diminish the pathogenicity of activated brain microglia in neurodegenerative disorders. Medical hypotheses 20100301
Oxygen radical absorbance capacity of phycocyanin and phycocyanobilin from the food supplement Aphanizomenon flos-aquae. Journal of medicinal food 20100201
Structural insights into vinyl reduction regiospecificity of phycocyanobilin:ferredoxin oxidoreductase (PcyA). The Journal of biological chemistry 20100108
Practical strategies for targeting NF-kappaB and NADPH oxidase may improve survival during lethal influenza epidemics. Medical hypotheses 20100101
Role of the protein cavity in phytochrome chromoprotein assembly and double-bond isomerization: a comparison with model compounds. Photochemistry and photobiology 20100101
Catalytic mechanism of S-type phycobiliprotein lyase: chaperone-like action and functional amino acid residues. The Journal of biological chemistry 20091225
Cyanochromes are blue/green light photoreversible photoreceptors defined by a stable double cysteine linkage to a phycoviolobilin-type chromophore. The Journal of biological chemistry 20091023
Characterization of the covalent and noncovalent adducts of Agp1 phytochrome assembled with biliverdin and phycocyanobilin by circular dichroism and flash photolysis. Biochemistry 20090714
Toward a mechanism for biliprotein lyases: revisiting nucleophilic addition to phycocyanobilin. Journal of the American Chemical Society 20090422
Genistein and phycocyanobilin may prevent hepatic fibrosis by suppressing proliferation and activation of hepatic stellate cells. Medical hypotheses 20090301
Biosynthesis of fluorescent allophycocyanin alpha-subunits by autocatalysis in Escherichia coli. Biotechnology and applied biochemistry 20090201
Solution structure of a cyanobacterial phytochrome GAF domain in the red-light-absorbing ground state. Journal of molecular biology 20081107
A novel photoactive GAF domain of cyanobacteriochrome AnPixJ that shows reversible green/red photoconversion. Journal of molecular biology 20080725
Intermediate binding of phycocyanobilin to the lyase, CpeS1, and transfer to apoprotein. Photosynthesis research 20080101
Clinical potential of Spirulina as a source of phycocyanobilin. Journal of medicinal food 20071201
The chromophore structures of the Pr States in plant and bacterial phytochromes. Biophysical journal 20071001
Domain interaction in cyanobacterial phytochromes as a prerequisite for spectral integrity. European biophysics journal : EBJ 20070901
A time-dependent density functional theory investigation of the spectroscopic properties of the beta-subunit in C-phycocyanin. The journal of physical chemistry. B 20060921
Identification and characterization of a new class of bilin lyase: the cpcT gene encodes a bilin lyase responsible for attachment of phycocyanobilin to Cys-153 on the beta-subunit of phycocyanin in Synechococcus sp. PCC 7002. The Journal of biological chemistry 20060630
Chromophore attachment to phycobiliprotein beta-subunits: phycocyanobilin:cysteine-beta84 phycobiliprotein lyase activity of CpeS-like protein from Anabaena Sp. PCC7120. The Journal of biological chemistry 20060331
Reconstitution of blue-green reversible photoconversion of a cyanobacterial photoreceptor, PixJ1, in phycocyanobilin-producing Escherichia coli. Biochemistry 20060321
Chromophore attachment in phycocyanin. Functional amino acids of phycocyanobilin--alpha-phycocyanin lyase and evidence for chromophore binding. The FEBS journal 20060301
Metabolic engineering to produce phytochromes with phytochromobilin, phycocyanobilin, or phycoerythrobilin chromophore in Escherichia coli. FEBS letters 20060220
Assignments of the Pfr-Pr FTIR difference spectrum of cyanobacterial phytochrome Cph1 using 15N and 13C isotopically labeled phycocyanobilin chromophore. The journal of physical chemistry. B 20051103
Agrobacterium phytochrome as an enzyme for the production of ZZE bilins. Biochemistry 20050614
A time dependent density functional theory study of alpha-84 phycocyanobilin chromophore in C-phycocyanin. The journal of physical chemistry. B 20050609
Amino acid residues associated with enzymatic activities of the isomerizing phycoviolobilin-lyase PecE/F. Biochemistry 20050607
Reconstitution of phycobilisome core-membrane linker, LCM, by autocatalytic chromophore binding to ApcE. Biochimica et biophysica acta 20050107
Photochromic biliproteins from the cyanobacterium Anabaena sp. PCC 7120: lyase activities, chromophore exchange, and photochromism in phytochrome AphA. Biochemistry 20040914
Biliverdin reduction by cyanobacterial phycocyanobilin:ferredoxin oxidoreductase (PcyA) proceeds via linear tetrapyrrole radical intermediates. Journal of the American Chemical Society 20040721
Chromophore selectivity in bacterial phytochromes: dissecting the process of chromophore attachment. European journal of biochemistry 20040301
Differing involvement of sulfoquinovosyl diacylglycerol in photosystem II in two species of unicellular cyanobacteria. European journal of biochemistry 20040201
Mechanism of Cph1 phytochrome assembly from stopped-flow kinetics and circular dichroism. Biochemistry 20031125
Biochemical properties of CikA, an unusual phytochrome-like histidine protein kinase that resets the circadian clock in Synechococcus elongatus PCC 7942. The Journal of biological chemistry 20030523
Dimerization and inter-chromophore distance of Cph1 phytochrome from Synechocystis, as monitored by fluorescence homo and hetero energy transfer. Biochemistry 20030520
Expression and characterization of cyanobacterium heme oxygenase, a key enzyme in the phycobilin synthesis. Properties of the heme complex of recombinant active enzyme. European journal of biochemistry 20030201
Ultrafast dynamics of phytochrome from the cyanobacterium synechocystis, reconstituted with phycocyanobilin and phycoerythrobilin. Biophysical journal 20020201
Recombinant holophytochrome in Escherichia coli. FEBS letters 20011123
Scavenging of peroxynitrite by phycocyanin and phycocyanobilin from Spirulina platensis: protection against oxidative damage to DNA. Biochemical and biophysical research communications 20010713
Characterization of the Cph1 holo-phytochrome from Synechocystis sp. PCC 6803. European journal of biochemistry 20010401
Properties