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Bilirubin

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Also known as: 635-65-4, Hematoidin, Hemetoidin, Bilirubin ix-alpha, Cholerythrin, Principal bile pigment

Molecular Formula

C₃₃H₃₆N₄O₆

Molecular Weight

584.7 g/mol

InChI Key

BPYKTIZUTYGOLE-IFADSCNNSA-N

FDA UNII

RFM9X3LJ49

A bile pigment that is a degradation product of HEME.

1 2D Structure

Bilirubin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid

2.1.2 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)/b26-13-,27-14-

2.1.3 InChI Key

BPYKTIZUTYGOLE-IFADSCNNSA-N

2.1.4 Canonical SMILES

CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)C=C4C(=C(C(=O)N4)C=C)C

2.1.5 Isomeric SMILES

CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\4/C(=C(C(=O)N4)C=C)C

2.2 Other Identifiers

2.2.1 UNII

RFM9X3LJ49

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bilirubin Ix Alpha

2. Bilirubin, (15e)-isomer

3. Bilirubin, (4e)-isomer

4. Bilirubin, (4e,15e)-isomer

5. Bilirubin, Calcium Salt

6. Bilirubin, Disodium Salt

7. Bilirubin, Monosodium Salt

8. Bilirubinate, Calcium

9. Calcium Bilirubinate

10. Calcium Salt Bilirubin

11. Delta Bilirubin

12. Delta-bilirubin

13. Disodium Salt Bilirubin

14. Hematoidin

15. Monosodium Salt Bilirubin

16. Salt Bilirubin, Calcium

2.3.2 Depositor-Supplied Synonyms

1. 635-65-4

2. Hematoidin

3. Hemetoidin

4. Bilirubin Ix-alpha

5. Cholerythrin

6. Principal Bile Pigment

7. Bilibubin

8. Bilirubin Ix.alpha.

9. 3-[2-[[3-(2-carboxyethyl)-5-[(z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1h-pyrrol-2-yl]methyl]-5-[(z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1h-pyrrol-3-yl]propanoic Acid

10. Bilirubin Ixalpha

11. Disodium Bilirubinate Ixalpha

12. Rfm9x3lj49

13. 21h-biline-8,12-dipropanoic Acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-

14. (4z,15z)-bilirubin Ix.alpha.

15. Chebi:16990

16. Nsc-26685

17. Pheophytin

18. Biline-8,12-dipropionic Acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-

19. 93891-87-3

20. 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic Acid

21. 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21h-biline-8,12-dipropanoic Acid

22. 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((z)-(3-methyl-5-oxo-4-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-2-yl)methyl)-4-methyl-5-((z)-(4-methyl-5-oxo-3-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-3-yl)propanoic Acid

23. Calcium Bilirubinate

24. Basinite

25. Einecs 211-239-7

26. Bilirubin Ix Alpha

27. 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-ox

28. Mfcd00005499

29. Nsc 26685

30. Unii-rfm9x3lj49

31. Brn 0074376

32. Bilirubin Test

33. Ai3-23078

34. Ccris 9347

35. Bilirubin-ixalpha

36. Bilirubin(z,z)

37. Bilirubin,(s)

38. 3-[5-[(z)-(4-ethenyl-3-methyl-5-oxidanylidene-pyrrol-2-ylidene)methyl]-2-[[5-[(z)-(3-ethenyl-4-methyl-5-oxidanylidene-pyrrol-2-ylidene)methyl]-3-(3-hydroxy-3-oxopropyl)-4-methyl-1h-pyrrol-2-yl]methyl]-4-methyl-1h-pyrrol-3-yl]propanoic Acid

39. Einecs 299-468-9

40. Bilirubin, 98%

41. (z,z)-bilirubin Ixa

42. Bilirubin [mi]

43. Spectrum5_000410

44. Bmse000627

45. Bilirubin [who-dd]

46. Schembl19065

47. (4z,15z)-bilirubin Ixa

48. Bspbio_002531

49. 5-26-15-00523 (beilstein Handbook Reference)

50. Spectrum1500857

51. Bilirubin Test [vandf]

52. Chembl501680

53. Gtpl4577

54. Schembl5086205

55. Dtxsid8060905

56. S00334a

57. Albb-030171

58. Bcp13520

59. Hy-n0323

60. Bdbm50442897

61. Ccg-38548

62. Hsci1_000394

63. S5116

64. Stl564421

65. Zinc18007499

66. Akos015895627

67. Bilirubin, Purum, >=95.0% (uv)

68. Sdccgmls-0066651.p001

69. Ncgc00095645-01

70. 18422-02-1

71. Ac-20194

72. Ac-34137

73. Disodium 1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-2,17-divinyl-21h-biline-8,12-dipropionate

74. Cs-0008888

75. B-2500

76. B-2501

77. C00486

78. Methyl-5-((z)-(4-methyl-5-oxo-3-vinyl-1h-

79. 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((z)

80. 635b654

81. Bilirubin, >=98% (emm/453 = 60), Powder

82. Q104219

83. Sr-05000002757

84. Sr-05000002757-1

85. Pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-3-yl)propanoic Acid

86. 1,3,6,7-tetramethyl-4,5-dicarboxyethyl-2,8-divinyl-(b-13)-dihydrobilenone

87. 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate

88. 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic Acid

89. 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21h-biline-8,12-dipropanoate

90. 2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21h-biline-8,12-dipropanoic Acid

91. 21h-biline-8,12-dipropanoic Acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-, Calcium Salt

92. 21h-biline-8,12-dipropanoic Acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-, Disodium Salt

93. 21h-biline-8,12-dipropanoic Acid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-

94. 3,18-diethenyl-2,7,13,17-tetramethyl-1,19-dioxo-1,10,19,22,23,24-hexahydro-21h-biline-8,12-dipropanoic Acid

95. 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

96. 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

97. 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((z)-(3-methyl-5-oxo-4-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-2-yl)methyl)-4-methyl-5-((z)-(4-methyl-5-oxo-3-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrr

98. 3-(2-((3-(2-carboxyethyl)-4-methyl-5-((z)-(3-methyl-5-oxo-4-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-2-yl)methyl)-4-methyl-5-((z)-(4-methyl-5-oxo-3-vinyl-1h-pyrrol-2(5h)-ylidene)methyl)-1h-pyrrol-3-yl)propanoicacid

99. 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

100. 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 #

101. 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

102. 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

103. 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

104. 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

105. 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

106. 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

107. 3-[2-[3-(2-carboxy-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-pyrrol-2-ylidenemethyl)-1h-pyrrol-2-ylmethyl]-4-methyl-5-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-pyrrol-2-ylidenemethyl)-1h-pyrrol-

108. 3q9

109. 8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21h,24h)-dione

110. Bilirubin: 21h-biline-8,12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-,

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₃₆N₄O₆
Molecular Weight	584.7 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	12
Exact Mass	584.26348488 g/mol
Monoisotopic Mass	584.26348488 g/mol
Topological Polar Surface Area	164 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1340
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

4.2 Metabolism/Metabolites

Bilirubin has known human metabolites that include 6-[3-[2-[[3-(2-carboxyethyl)-5-[(Z)-(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and Bilirubin acyl-b-D-glucuronide (mixture).

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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