3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

• ChemBase ID: 130443
• Molecular Formular: C33H36N4O6
• Molecular Mass: 584.66214
• Monoisotopic Mass: 584.26348489
• SMILES: Cc1c(c([nH]c1/C=C\1/C(=C(C(=O)N1)C=C)C)Cc1c(c(c([nH]1)/C=C\1/C(=C(C(=O)N1)C)C=C)C)CCC(=O)O)CCC(=O)O
• Canonical SMILES: C=CC1=C(C)/C(=C/c2[nH]c(c(c2C)CCC(=O)O)Cc2[nH]c(c(c2CCC(=O)O)C)/C=C/2\NC(=O)C(=C2C=C)C)/NC1=O
• InChI: InChI=1S/C33H36N4O6/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/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
• InChIKey: BPYKTIZUTYGOLE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• IUPAC Traditional name: bilirubin; 3-(2-{[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid; 3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
• Synonyms: Pheophytin; Bilirubin; Bilirubin; 胆红素

Database IDs

• CAS Number: 635-65-4
• EC Number: 211-239-7
• MDL Number: MFCD00005499
• Beilstein Number: 74376
• Merck Index: 141218
• PubChem SID: 162224722; 24891751; 24848604
• PubChem CID: 5280352
• CHEBI ID: 16990
• CHEMBL: 501680
• Chemspider ID: 4444055
• Unique Ingredient Identifier: RFM9X3LJ49
• Wikipedia Title: Bilirubin

CALCULATED PROPERTIES

• Acid pKa: 4.0274906
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 0.72434396
• LogD (pH = 7.4): -2.7640595
• Log P: 3.1191065
• Molar Refractivity: 168.896 cm^3
• Polarizability: 61.830246 Å^3
• Polar Surface Area: 164.38 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: aqueous acid: soluble; aqueous base: soluble; benzene: soluble; chloroform: soluble
• Apperance: orange-brown powder

Safety Information

• RTECS: DU3038000
• German water hazard class: 2
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (UV); ≥98% (EmM/453 = 60); 97%
• Grade: purum
• Ignition Residue: ≤0.5%
• Description: Isomers; mixed isomers
• Empirical Formula (Hill Notation): C33H36N4O6
• Classification: Rare Genuine Natural Compounds

DETAILS

Sigma Aldrich - B4126

Biochem/physiol Actions
It appears to function as an antioxidant and efficient peroxyl radical scavenger, protecting membrane lipids from oxidation by these radicals. At nanomolar concentrations it has been shown to protect neurons from oxidative damage.
Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.
Caution
Protect from light.
Other Notes
A major component of hemoglobin decomposition. The principal pigment of bile, and the yellow color in jaundice.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. B4126.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
包装
1, 5 g in glass bottle

Sigma Aldrich - 14370

Analysis Note
λmax. ～453 nm, mol. absorption >56100 (chloroform)
Application
Bilirubin can be used to study cell biology, bioactive small molecules, biochemicals and reagents, plasma and blood proteins, and proteins and derivatives. Bilirubin-reducing enzymes effectively dispose of electrons produced by fermentolytic processes in the anaerobic bacteria, Pseudomonas dacunhae. Bilirubin has been used in a study to indicate a cytokine link between acute pancreatitis and fibromyalgia, as well as to study hematological abnormalities in hepatitis C virus infection.
Biochem/physiol Actions
Well over 99% of total bilirubin is transported as a conjugate with albumin. Abnormally high levels of bilirubin can cause severe neurological damage, but mildly elevated levels are linked to protection from oxidative stress.