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Human Metabolome Database Version 3.5

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Showing metabocard for Bilirubin (HMDB00054)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:49 -0700
HMDB ID HMDB00054
Secondary Accession Numbers None
Metabolite Identification
Common Name Bilirubin
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 color of bruises. Bilirubin is an excretion product, and the body does not control 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); by contrast, the heme molecule is a closed ring of four pyrroles, called porphyrin. -- Wikipedia.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (4Z,15Z)-Bilirubin IXa
  2. (Z,Z)-Bilirubin IXa
  3. 1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionate
  4. 1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionic acid
  5. 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoate
  6. 2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoic acid
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. Bilirubin
  15. Bilirubin IX-alpha
  16. Cholerythrin
  17. Hematoidin
Chemical Formula C33H36N4O6
Average Molecular Weight 584.6621
Monoisotopic Molecular Weight 584.263484904
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
Traditional IUPAC Name bilirubin
CAS Registry Number 635-65-4
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
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-
InChI Key BPYKTIZUTYGOLE-IFADSCNNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Bilirubins
Other Descriptors
  • Organic Compounds
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Dipyrrin
  • Pyrrole
Direct Parent Bilirubins
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
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
Predicted Properties
Property Value Source
Water Solubility 0.0096 g/L ALOGPS
LogP 3.22 ALOGPS
LogP 3.12 ChemAxon
LogS -4.78 ALOGPS
pKa (strongest acidic) 4.03 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 164.38 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 168.9 ChemAxon
Polarizability 66.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid Locations
  • Bile
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Bone Marrow
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Erythrocyte
  • Kidney
  • Liver
  • Thyroid Gland
  • Brain
  • Myelin
  • Skin
  • Nerve Cells
  • Platelet
  • Spleen
  • Bile Duct
  • Lymph Node
  • Reticulocyte
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
13.0 (5.0-21.0) uM Adult (>18 years old) Both Normal Age >5 days-60 years
Blood Detected and Quantified
Article_icon
15.2 +/- 2.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
8.0 +/- 0.9 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0 - 0.2 uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
< 0.1 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.032 (0.0019-0.21) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.51-5.13 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Bile Detected and Quantified
Article_icon
5000 (4300-5700) uM Adult (>18 years old) Both Crohn's disease Not Available
Bile Detected and Quantified
Article_icon
2600 (2400-2800) uM Adult (>18 years old) Both Gallstone disease Not Available
Bile Detected and Quantified
Article_icon
4600 (3900-5300) uM Adult (>18 years old) Both Crohn's disease in patients with ileitis or ileocolitis.
Bile Detected and Quantified
Article_icon
5900 (4300-7500) uM Adult (>18 years old) Both Crohn's disease In patients with colitis.
Blood Detected and Quantified
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14.6 +/- 2.5 uM Adult (>18 years old) Both Growth hormone deficiency Severe radiation-induced GH deficiency,...
Blood Detected and Quantified
Article_icon
8.80 +/- 1.22 uM Adult (>18 years old) Both Growth hormone deficiency Severe radiation-induced GH deficiency,...
Blood Detected and Quantified
Article_icon
573.0 (291.0-855.0) uM Adult (>18 years old) Both Crigler-Najjar syndrome Type I Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
17.3 +/- 12.4 uM Adult (>18 years old) Both Cerebral Vasospasm Cerebral vasospasm after subarachnoid hemorrhage
Associated Disorders and Diseases
Disease References
Crohn's disease
  • 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 Link_out
    Gallbladder disease
    • 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 Link_out
      Cerebral vasospasm
      • 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 Link_out
        Growth hormone deficiency
        • 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 Link_out
          Crigler-Najjar syndrome type I
            • http://www.metagene.de/program/d.prg?mp=CRIGLER-NAJJAR%20SYNDROME%20TYPE%20I
            Associated OMIM IDs
            DrugBank ID Not Available
            Phenol Explorer Compound ID Not Available
            Phenol Explorer Metabolite ID Not Available
            FoodDB ID FDB021886
            KNApSAcK ID Not Available
            Chemspider ID 4444055 Link_out
            KEGG Compound ID C00486 Link_out
            BioCyc ID BILIRUBIN Link_out
            BiGG ID 35117 Link_out
            Wikipedia Link Bilirubin Link_out
            NuGOwiki Link HMDB00054 Link_out
            Metagene Link HMDB00054 Link_out
            METLIN ID 81 Link_out
            PubChem Compound 5280352 Link_out
            PDB ID Not Available
            ChEBI ID 16990 Link_out
            References
            Synthesis Reference Not Available
            Material Safety Data Sheet (MSDS) Download (PDF)
            General References
            1. Randeberg LL, Roll EB, Nilsen LT, Christensen T, Svaasand LO: In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. Acta Paediatr. 2005 Jan;94(1):65-71. Pubmed: 15858963 Link_out
            2. Bayes Garcia R, Maldonado Lozano J, Molina Font JA: [Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions] An Esp Pediatr. 1989 Jan;30(1):27-31. Pubmed: 2648917 Link_out
            3. Yamamoto S, Kubo S, Hai S, Uenishi T, Yamamoto T, Shuto T, Takemura S, Tanaka H, Yamazaki O, Hirohashi K, Tanaka T: Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. Cancer Sci. 2004 Jul;95(7):592-5. Pubmed: 15245596 Link_out
            4. Kabicek P: Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia. Cent Eur J Public Health. 2004 Jun;12(2):102-9. Pubmed: 15242029 Link_out
            5. Tiribelli C, Ostrow JD: New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. Hepatology. 1996 Nov;24(5):1296-311. Pubmed: 8903413 Link_out
            6. Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome] Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. Pubmed: 15189696 Link_out
            7. Deja M, Hildebrandt B, Ahlers O, Riess H, Wust P, Gerlach H, Kerner T: Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. Chest. 2005 Aug;128(2):580-6. Pubmed: 16100141 Link_out
            8. Kikuchi S, Hata M, Fukumoto K, Yamane Y, Matsui T, Tamura A, Yonemura S, Yamagishi H, Keppler D, Tsukita S, Tsukita S: Radixin deficiency causes conjugated hyperbilirubinemia with loss of Mrp2 from bile canalicular membranes. Nat Genet. 2002 Jul;31(3):320-5. Epub 2002 Jun 17. Pubmed: 12068294 Link_out
            9. Lin JM, Jiang CQ: [Clinical manifestation and ultrasonic characteristics of five patients with acute arsenic poisoning] Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2003 Dec;21(6):420-2. Pubmed: 14761351 Link_out
            10. Azer SA: A multimedia CD-ROM tool to improve student understanding of bile salts and bilirubin metabolism: evaluation of its use in a medical hybrid PBL course. Adv Physiol Educ. 2005 Mar;29(1):40-50. Pubmed: 15718382 Link_out
            11. Slusher TM, Angyo IA, Bode-Thomas F, Akor F, Pam SD, Adetunji AA, McLaren DW, Wong RJ, Vreman HJ, Stevenson DK: Transcutaneous bilirubin measurements and serum total bilirubin levels in indigenous African infants. Pediatrics. 2004 Jun;113(6):1636-41. Pubmed: 15173484 Link_out
            12. Ciszowski K, Gomolka E, Jenner B: [The influence of the dose, time since ingestion and concentration of the xenobiotic on the clinical state and severity of liver damage with patients intoxicated with paracetamol] Przegl Lek. 2005;62(6):456-61. Pubmed: 16225094 Link_out
            13. Sando M, Sato Y, Iwata S, Akita H, Sunakawa K: In vitro protein binding of teicoplanin to neonatal serum. J Infect Chemother. 2004 Oct;10(5):280-3. Pubmed: 16163462 Link_out
            14. Danko I, Jia Z, Zhang G: Nonviral gene transfer into liver and muscle for treatment of hyperbilirubinemia in the gunn rat. Hum Gene Ther. 2004 Dec;15(12):1279-86. Pubmed: 15684703 Link_out
            15. Kotal P, Van der Veere CN, Sinaasappel M, Elferink RO, Vitek L, Brodanova M, Jansen PL, Fevery J: Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. Pediatr Res. 1997 Aug;42(2):195-200. Pubmed: 9262222 Link_out
            16. 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 Link_out
            17. 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 Link_out
            18. 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 Link_out
            19. 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 Link_out
            20. 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 Link_out
            Enzymes
            Name: Heme oxygenase 1
            Reactions:
            • heme + 3 AH2 + 3 O2 = biliverdin + Fe2+ + CO + 3 A + 3 H2O [RN:R00311]
            Gene Name: HMOX1
            Uniprot ID: P09601 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B28
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B28
            Uniprot ID: Q9BY64 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B4
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B4
            Uniprot ID: P06133 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-4
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A4
            Uniprot ID: P22310 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B7
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B7
            Uniprot ID: P16662 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B15
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B15
            Uniprot ID: P54855 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2A1
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2A1
            Uniprot ID: Q9Y4X1 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-1
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A1
            Uniprot ID: P22309 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-9
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A9
            Uniprot ID: O60656 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-3
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A3
            Uniprot ID: P35503 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B17
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B17
            Uniprot ID: O75795 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-6
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A6
            Uniprot ID: P19224 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 1-5
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT1A5
            Uniprot ID: P35504 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: UDP-glucuronosyltransferase 2B11
            Reactions:
            • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
            Gene Name: UGT2B11
            Uniprot ID: O75310 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Biliverdin reductase A
            Reactions:
            • bilirubin + NAD(P)+ = biliverdin + NAD(P)H + H+ [RN:R02391 R02393]
            Gene Name: BLVRA
            Uniprot ID: P53004 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Flavin reductase
            Reactions:
            • reduced riboflavin + NADP+ = riboflavin + NADPH + H+ [RN:R05707]
            Gene Name: BLVRB
            Uniprot ID: P30043 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Serum albumin
            Reactions:
              Gene Name: ALB
              Uniprot ID: P02768 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Alpha-fetoprotein
              Reactions:
                Gene Name: AFP
                Uniprot ID: P02771 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: UDP-glucuronosyltransferase 2A3
                Reactions:
                • UDP-glucuronate + acceptor = UDP + acceptor beta-D-glucuronoside [RN:R01383]
                Gene Name: UGT2A3
                Uniprot ID: Q6UWM9 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: HCG2039726, isoform CRA_f
                Reactions:
                  Gene Name: UGT1A10
                  Uniprot ID: Q5DT02 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: HCG2039726, isoform CRA_e
                  Reactions:
                    Gene Name: UGT1A8
                    Uniprot ID: Q5DSZ6 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: UDP glycosyltransferase 1 family polypeptide A7
                    Reactions:
                      Gene Name: UGT1A7
                      Uniprot ID: Q5DSZ7 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Transporters
                      Name: Solute carrier organic anion transporter family member 1B1
                      Reactions:
                      • --- []
                      Gene Name: SLCO1B1
                      Uniprot ID: Q9Y6L6 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Canalicular multispecific organic anion transporter 1
                      Reactions:
                        Gene Name: ABCC2
                        Uniprot ID: Q92887 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA