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Biliverdin

CAT: 0804-HY-135005A-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-135005A-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Biliverdin, a tetrapyrrolic pigment, is a product of heme catabolism. Heme is broken down into Biliverdin and carbon monoxide and iron by heme oxidase. Biliverdin is then quickly broken down to bilirubin by Biliverdin reductase. Biliverdin can mediate the protective effects of HO-1 in many disease models including IRI and organ transplantation. Biliverdin exhibits anti-mutagenic, an antioxidant, anti-inflammatory, and immunosuppressant properties[1][2][3].
CAS Number
114-25-0
UNSPSC
12352005
Hazard Statement
H315, H319
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/biliverdin.html
Purity
99.0
Solubility
DMSO : 3 mg/mL (ultrasonic; warming)
Smiles
OC(CCC(C(C)=C(N1)/C=C2C(C=C)=C(C(N/2)=O)C)=C1/C=C3C(CCC(O)=O)=C(C(/C=C4C(C)=C(C(N/4)=O)C=C)=N/3)C)=O
Molecular Formula
C33H34N4O6
Molecular Weight
582.65
Precautions
H315, H319
References & Citations
[1]McDonnell MC, et al. Biochemistry, Biliverdin. 2023 May 1. In: StatPearls [Internet]. Treasure Island (FL) : StatPearls Publishing; 2025 Jan. |[2]Jansen, T., & Daiber, A. (2012) . Direct Antioxidant Properties of Bilirubin and Biliverdin. Is there a Role for Biliverdin Reductase?. Frontiers in pharmacology, 3, 30.|[3]Ollinger, R., et al., (2007) . Therapeutic applications of bilirubin and biliverdin in transplantation. Antioxidants & redox signaling, 9 (12), 2175–2185.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

Chemical Information

Biliverdine Ix Alpha

Biliverdin is a linear tetrapyrrole produced in the reticuloendothelial system by the first step of heme degradation, catalysed by heme oxygenase. It has a role as a mouse metabolite and a human metabolite. It is a conjugate acid of a biliverdin(2-).

CAS Number114-25-0
PubChem CID5280353
IUPAC Name3-[(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
Molecular FormulaC33H34N4O6
Molecular Weight582.6
XLogP2.5
Topological Polar Surface Area161
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Heavy Atom Count43
Formal Charge0
Complexity1530
SMILES
CC\1=C(/C(=C/C2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/N/C1=C\C4=NC(=O)C(=C4C)C=C)CCC(=O)O
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-
InChIKey
RCNSAJSGRJSBKK-NSQVQWHSSA-N
Chemical Structure
2D Structure
2D structure of Biliverdine Ix Alpha
CAS: 114-25-0
CID: 5280353
Formula: C33H34N4O6
MW: 582.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight582.6
XLogP32.5
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count11
Exact Mass582.24783482
Monoisotopic Mass582.24783482
Topological Polar Surface Area161 Ų
Heavy Atom Count43
Formal Charge0
Complexity1530
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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