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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-10-09 20:57:18 UTC |
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HMDB ID | HMDB0000054 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Bilirubin |
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Description | Bilirubin is a bile pigment that is a degradation product of heme. In particular, bilirubin is a yellow breakdown product of normal heme catabolism. Its levels are elevated in certain diseases and it is responsible for the yellow colour of bruises. Bilirubin is an excretion product and the body does not control its levels. Bilirubin levels reflect the balance between production and excretion. Thus, there is no "normal" level of bilirubin. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole). In contrast, the heme molecule is a closed ring of four pyrroles, called porphyrin (Wikipedia ). Bilirubin is found to be associated with Crigler-Najjar syndrome type I, which is an inborn error of metabolism. |
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Structure | |
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Synonyms | Value | Source |
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1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid | ChEBI | 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid | ChEBI | 2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid | ChEBI | 8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione | ChEBI | Bilirubin(Z,Z) | ChEBI | Bilirubin-ixalpha | ChEBI | 1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate | Generator | 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate | Generator | 2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate | Generator | Bilirubin ixalpha | HMDB | (4Z,15Z)-Bilirubin ixa | HMDB | (Z,Z)-Bilirubin ixa | HMDB | 1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate | HMDB | 1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid | HMDB | 3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate | HMDB | 3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid | HMDB | 3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene | HMDB | 3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate | HMDB | 3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid | HMDB | 3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate | HMDB | 3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid | HMDB | Bilirubin IX-alpha | HMDB | Cholerythrin | HMDB | Hematoidin | HMDB | Bilirubin IX alpha | HMDB |
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Chemical Formula | C33H36N4O6 |
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Average Molecular Weight | 584.6621 |
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Monoisotopic Molecular Weight | 584.263484904 |
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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 |
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Traditional Name | bilirubin |
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CAS Registry Number | 635-65-4 |
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SMILES | CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1 |
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InChI Identifier | 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)/b26-13-,27-14- |
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InChI Key | BPYKTIZUTYGOLE-IFADSCNNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Tetrapyrroles and derivatives |
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Sub Class | Bilirubins |
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Direct Parent | Bilirubins |
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Alternative Parents | |
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Substituents | - Bilirubin skeleton
- Dicarboxylic acid or derivatives
- Substituted pyrrole
- Pyrrole
- Pyrroline
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Lactam
- Carboxamide group
- Azacycle
- Carboxylic acid
- Carboxylic acid derivative
- Organopnictogen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.009 mg/mL at 25 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00vr-0100090000-d19585e898437e8be1d5 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01vn-3100069000-c39a7113e7f8eb3fa22a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-000i-0090000000-50ff729317f07f6120b5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00ks-0000090000-ddf9acb7f968b9079764 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00g0-0110290000-ae6f323e9f5e9e26199c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uml-1102910000-df5146b3612e4fb4ce5e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0000090000-6deb1aed1a9c3839e2a9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-053i-1010190000-7435a4388bade8e83d10 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9010240000-cc90fff0581c6bcefd0d | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane (predicted from logP)
- Endoplasmic reticulum
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Biospecimen Locations | - Bile
- Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | - Bile
- Bone Marrow
- Brain
- Epidermis
- Erythrocyte
- Fibroblasts
- Intestine
- Kidney
- Liver
- Neuron
- Pancreas
- Placenta
- Platelet
- Skeletal Muscle
- Spleen
- Thyroid Gland
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 13.0 (5.0-21.0) uM | Adult (>18 years old) | Both | Normal | - McPherson, Richar...
- Louise M. Malark...
| details | Blood | Detected and Quantified | 15.2 +/- 2.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <12.828 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <12 uM | Newborn (0-30 days old) | Not Specified | Normal | | details | Blood | Detected and Quantified | <3.4 uM | Children (1-13 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 3-21 uM | Newborn (0-30 days old) | Not Specified | Normal | | details | Blood | Detected and Quantified | <20 uM | Children (1-13 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 8.0 +/- 0.9 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 310.265 +/- 65.850 uM | Newborn (0-30 days old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 6.842-20.525 uM | Children (1-13 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 5.131-17.104 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 5.10-18.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <17 uM | Children (1 - 13 years old) | Not Available | Normal | | details | Blood | Detected and Quantified | 8.500 +/- 4 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0 - 0.2 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | < 0.1 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.032 (0.0019-0.21) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | 0.51-5.13 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Bile | Detected and Quantified | 5000 (4300-5700) uM | Adult (>18 years old) | Both | Crohn's disease | | details | Bile | Detected and Quantified | 2600 (2400-2800) uM | Adult (>18 years old) | Both | Gallstone disease | | details | Bile | Detected and Quantified | 4600 (3900-5300) uM | Adult (>18 years old) | Both | Crohn's disease | | details | Bile | Detected and Quantified | 5900 (4300-7500) uM | Adult (>18 years old) | Both | Crohn's disease | | details | Blood | Detected and Quantified | 14.6 +/- 2.5 uM | Adult (>18 years old) | Both | Growth hormone deficiency | | details | Blood | Detected and Quantified | 650 uM | Adolescent (13-18 years old) | Male | Crigler-Najjar syndrome Type I | | details | Blood | Detected and Quantified | 25.656-78.678 uM | Adult (>18 years old) | Both | Anemia, congenital dyserythropoietic, type II | | details | Blood | Detected and Quantified | 28.7-170 uM | Children (1-13 years old) | Both | Infantile Liver Failure Syndrome 2 | | details | Blood | Detected and Quantified | 22-41 uM | Newborn (0-30 days old) | Both | Citrullinemia type II, neonatal-onset | | details | Blood | Detected and Quantified | 46.9-233 uM | Children (1-13 years old) | Both | Infantile Liver Failure Syndrome 2 | | details | Blood | Detected and Quantified | 41-101 uM | Newborn (0-30 days old) | Both | Citrullinemia type II, neonatal-onset | | details | Blood | Detected and Quantified | 73.1-85.0 uM | Infant (0-1 year old) | Female | Infantile Liver Failure Syndrome 2 | | details | Blood | Detected and Quantified | 41(6-381) uM | Children (1-13 years old) | Both | Cholestasis, progressive familial intrahepatic, 1 | | details | Blood | Detected and Quantified | 59.2 uM | Infant (0-1 year old) | Female | Wolcott-Rallison syndrome | | details | Blood | Detected and Quantified | 106 uM | Infant (0-1 year old) | Female | Bile Acid Synthesis Defect, Congenital, 1 | | details | Blood | Detected and Quantified | 24.5 uM | Adult (>18 years old) | Female | Lecithin:cholesterol Acyltransferase Deficiency | | details | Blood | Detected and Quantified | 8.80 +/- 1.22 uM | Adult (>18 years old) | Both | Growth hormone deficiency | | details | Blood | Detected and Quantified | 573.0 (291.0-855.0) uM | Children (1-13 years old) | Both | Crigler-Najjar syndrome Type I | | details | Blood | Detected and Quantified | 29.59 uM | Newborn (0-30 days old) | Male | Lathosterolosis | | details | Blood | Detected and Quantified | 380.733 +/- 142.989 uM | Newborn (0-30 days old) | Both | Glucose-6-phosphate dehydrogenase deficiency | | details | Blood | Detected and Quantified | 6.842-20.525 uM | Adult (>18 years old) | Male | Primary Hypomagnesemia | | details | Blood | Detected and Quantified | 18.814-518.248 uM | Adult (>18 years old) | Male | Cholestasis, progressive familial intrahepatic, 1 | | details | Blood | Detected and Quantified | 42.247 uM | Newborn (0-30 days old) | Male | Lathosterolosis | | details | Blood | Detected and Quantified | 42.760-141.962 uM | Children (1-13 years old) | Female | Cholestasis, progressive familial intrahepatic, 1 | | details | Blood | Detected and Quantified | 78.678 uM | Newborn (0-30 days old) | Male | Donohue Syndrome | | details | Blood | Detected and Quantified | 111.175 uM | Newborn (0-30 days old) | Male | Donohue Syndrome | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 17.3 +/- 12.4 uM | Adult (>18 years old) | Both | Cerebral Vasospasm | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Not Specified | Premature neonates | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Crohn's disease |
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- Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. [PubMed:16440420 ]
| Gallbladder disease |
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- Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. [PubMed:16440420 ]
| Growth hormone deficiency |
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- Darzy KH, Murray RD, Gleeson HK, Pezzoli SS, Thorner MO, Shalet SM: The impact of short-term fasting on the dynamics of 24-hour growth hormone (GH) secretion in patients with severe radiation-induced GH deficiency. J Clin Endocrinol Metab. 2006 Mar;91(3):987-94. Epub 2005 Dec 29. [PubMed:16384844 ]
| Crigler-Najjar syndrome type I |
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- Farrell GC, Gollan JL, Stevens SM, Grierson JM: Crigler-Najjar Type 1 syndrome: absence of hepatic bilirubin UDP-glucuronyl transferase activity and therapeutic responses to light. Aust N Z J Med. 1982 Aug;12(4):280-5. [PubMed:6814411 ]
- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
| Primary hypomagnesemia |
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- Jin-no Y, Kamiya Y, Okada M, Hirako M, Takada N, Kawaguchi M: Primary hypomagnesemia caused by isolated magnesium malabsorption: atypical case in adult. Intern Med. 1999 Mar;38(3):261-5. [PubMed:10337938 ]
| Anemia, congenital dyserythropoietic, type II |
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- Bianchi P, Fermo E, Vercellati C, Boschetti C, Barcellini W, Iurlo A, Marcello AP, Righetti PG, Zanella A: Congenital dyserythropoietic anemia type II (CDAII) is caused by mutations in the SEC23B gene. Hum Mutat. 2009 Sep;30(9):1292-8. doi: 10.1002/humu.21077. [PubMed:19621418 ]
| Lathosterolosis |
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- Brunetti-Pierri N, Corso G, Rossi M, Ferrari P, Balli F, Rivasi F, Annunziata I, Ballabio A, Russo AD, Andria G, Parenti G: Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase. Am J Hum Genet. 2002 Oct;71(4):952-8. Epub 2002 Aug 20. [PubMed:12189593 ]
| Glucose-6-phosphate dehydrogenase deficiency |
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- Iranpour R, Akbar MR, Haghshenas I: Glucose-6-phosphate dehydrogenase deficiency in neonates. Indian J Pediatr. 2003 Nov;70(11):855-7. [PubMed:14703221 ]
| Cholestasis, progressive familial intrahepatic, 1 |
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- Nagasaka H, Yorifuji T, Kosugiyama K, Egawa H, Kawai M, Murayama K, Hasegawa M, Sumazaki R, Tsubaki J, Kikuta H, Matsui A, Tanaka K, Matsuura N, Kobayashi K: Resistance to parathyroid hormone in two patients with familial intrahepatic cholestasis: possible involvement of the ATP8B1 gene in calcium regulation via parathyroid hormone. J Pediatr Gastroenterol Nutr. 2004 Oct;39(4):404-9. [PubMed:15448432 ]
- Schukfeh N, Metzelder ML, Petersen C, Reismann M, Pfister ED, Ure BM, Kuebler JF: Normalization of serum bile acids after partial external biliary diversion indicates an excellent long-term outcome in children with progressive familial intrahepatic cholestasis. J Pediatr Surg. 2012 Mar;47(3):501-5. doi: 10.1016/j.jpedsurg.2011.08.010. [PubMed:22424345 ]
| Donohue Syndrome |
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- Nijim Y, Awni Y, Adawi A, Bowirrat A: Classic Case Report of Donohue Syndrome (Leprechaunism; OMIM *246200): The Impact of Consanguineous Mating. Medicine (Baltimore). 2016 Feb;95(6):e2710. doi: 10.1097/MD.0000000000002710. [PubMed:26871809 ]
| Citrullinemia type II, neonatal-onset |
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- Ohura T, Kobayashi K, Tazawa Y, Nishi I, Abukawa D, Sakamoto O, Iinuma K, Saheki T: Neonatal presentation of adult-onset type II citrullinemia. Hum Genet. 2001 Feb;108(2):87-90. [PubMed:11281457 ]
| Infantile Liver Failure Syndrome 2 |
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- Staufner C, Haack TB, Kopke MG, Straub BK, Kolker S, Thiel C, Freisinger P, Baric I, McKiernan PJ, Dikow N, Harting I, Beisse F, Burgard P, Kotzaeridou U, Lenz D, Kuhr J, Himbert U, Taylor RW, Distelmaier F, Vockley J, Ghaloul-Gonzalez L, Ozolek JA, Zschocke J, Kuster A, Dick A, Das AM, Wieland T, Terrile C, Strom TM, Meitinger T, Prokisch H, Hoffmann GF: Recurrent acute liver failure due to NBAS deficiency: phenotypic spectrum, disease mechanisms, and therapeutic concepts. J Inherit Metab Dis. 2016 Jan;39(1):3-16. doi: 10.1007/s10545-015-9896-7. Epub 2015 Nov 5. [PubMed:26541327 ]
| Bile Acid Synthesis Defect, Congenital, 1 |
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- Huang HY, Zhou H, Wang H, Chen YX, Fang F: Novel Mutations in the 3beta-hydroxy-5-C27-steroid Dehydrogenase Gene (HSD3B7) in a Patient with Neonatal Cholestasis. Chin Med J (Engl). 2016 Jan 5;129(1):98-100. doi: 10.4103/0366-6999.172603. [PubMed:26712441 ]
| Lecithin:cholesterol Acyltransferase Deficiency |
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- Idzior-Walus B, Sieradzki J, Kostner G, Malecki MT, Klupa T, Wesolowska T, Rostworowski W, Hartwich J, Walus M, Kiec AD, Naruszewicz M: Familial lecithin-cholesterol acyltransferase deficiency: biochemical characteristics and molecular analysis of a new LCAT mutation in a Polish family. Atherosclerosis. 2006 Apr;185(2):413-20. Epub 2005 Jul 26. [PubMed:16051254 ]
| Wolcott-Rallison syndrome |
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- Can Thi Bich Ngoc, Vu Chi Dung, Sarah Flanagan and Sian Ellard (2013). Neonatal diabetes in Wolcott-Rallison syndrome: a case report. International Journal of Pediatric Endocrinology.
| Cerebral vasospasm |
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- Pyne-Geithman GJ, Morgan CJ, Wagner K, Dulaney EM, Carrozzella J, Kanter DS, Zuccarello M, Clark JF: Bilirubin production and oxidation in CSF of patients with cerebral vasospasm after subarachnoid hemorrhage. J Cereb Blood Flow Metab. 2005 Aug;25(8):1070-7. [PubMed:15789034 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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Associated OMIM IDs | - 266600 (Crohn's disease)
- 139250 (Growth hormone deficiency)
- 218800 (Crigler-Najjar syndrome type I)
- 248250 (Primary hypomagnesemia)
- 224100 (Anemia, congenital dyserythropoietic, type II)
- 607330 (Lathosterolosis)
- 300908 (Glucose-6-phosphate dehydrogenase deficiency)
- 211600 (Cholestasis, progressive familial intrahepatic, 1)
- 246200 (Donohue Syndrome)
- 605814 (Citrullinemia type II, neonatal-onset)
- 616483 (Infantile Liver Failure Syndrome 2)
- 607765 (Bile Acid Synthesis Defect, Congenital, 1)
- 245900 (Lecithin:cholesterol Acyltransferase Deficiency)
- 226980 (Wolcott-Rallison syndrome)
- 114500 (Colorectal cancer)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB021886 |
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KNApSAcK ID | C00029828 |
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Chemspider ID | 4444055 |
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KEGG Compound ID | C00486 |
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BioCyc ID | BILIRUBIN |
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BiGG ID | 35117 |
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Wikipedia Link | Bilirubin |
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METLIN ID | 81 |
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PubChem Compound | 5280352 |
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PDB ID | Not Available |
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ChEBI ID | 16990 |
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Food Biomarker Ontology | Not Available |
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VMH ID | BILIRUB |
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MarkerDB ID | MDB00000027 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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- Ochenashko OV, Volkova NA, Mazur SP, Somov AY, Fuller BJ, Petrenko AY: Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis. Cell Transplant. 2006;15(1):23-33. [PubMed:16700327 ]
- Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. [PubMed:16440420 ]
- Sikkel E, Pasman SA, Oepkes D, Kanhai HH, Vandenbussche FP: On the origin of amniotic fluid bilirubin. Placenta. 2004 May;25(5):463-8. [PubMed:15081641 ]
- Schmidt CM, Powell ES, Yiannoutsos CT, Howard TJ, Wiebke EA, Wiesenauer CA, Baumgardner JA, Cummings OW, Jacobson LE, Broadie TA, Canal DF, Goulet RJ Jr, Curie EA, Cardenes H, Watkins JM, Loehrer PJ, Lillemoe KD, Madura JA: Pancreaticoduodenectomy: a 20-year experience in 516 patients. Arch Surg. 2004 Jul;139(7):718-25; discussion 725-7. [PubMed:15249403 ]
- Nanjundaswamy S, Petrova A, Mehta R, Hegyi T: Transcutaneous bilirubinometry in preterm infants receiving phototherapy. Am J Perinatol. 2005 Apr;22(3):127-31. [PubMed:15838745 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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