Standard Compound Records

Database Entry: cq_00341

2D-Structure

3D-Structure

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Basic Information

Name:Bilirubin
Synonyms:Bilirubin;11053-42-2;114-24-9;18422-02-1;19245-52-4;21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-;39372-61-7;493-86-7;5-26-15-00523 (Beilstein Handbook Reference);55527-40-7;635-65-4;917-01-1;93891-87-3;AI3-23078;BILIRUBIN;BRN 0074376;Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-;Bilirubin IX-alpha;EINECS 211-239-7;Hematoidin;Hemetoidin;Principal bile pigment;3-[2-[[3-(2-carboxyethyl)-4-methyl-5-[(4-methyl-5-oxo-3-vinyl-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl]methyl]-4-methyl-5-[(3-methyl-5-oxo-4-vinyl-pyrrol-2-ylidene)methyl]-1H-pyrrol-3-yl]propanoic acid;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;HMDB00054;;(4Z,15Z)-Bilirubin IXa;(Z,Z)-Bilirubin;(Z,Z)-Bilirubin IXa;1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionate;1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionic acid;2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoate;2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoic acid;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;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;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;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;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;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;Bilirubin IXa;Bilirubin IXalpha;Cholerythrin;PHEOPHYTIN
Molecular Weight:584.66214
Formula:C33H36N4O6
CAS:11053-42-2;114-24-9;18422-02-1;19245-52-4;39372-61-7;493-86-7;55527-40-7;635-65-4;917-01-1;93891-87-3
Isomeric 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
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
InChI:InChI=1/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-
Experimental Water Solubility:0.009 mg/mL at 25 oC [BEILSTEIN]
Predicted Water Solubility:0.00974 mg/mL [Predicted by ALOGPS]
Experimental LogP(octanol-water):
Predicted LogP(octanol-water):3.23 [Predicted by ALOGPS]; 1.945 [Predicted by PubChem via XLOGP]; 5.04 [MEYLAN,WM & HOWARD,PH (1995)]

Biology and Chemistry related

KEGG Compound ID:C00486
PubChem SID:155796
PubChem CID:250
ChemIDplus:000635654
CHEBI:16990
HMDB:|HMDB00054|
PDB Component ID:
MetaCyc ID:|BILIRUBIN|
UM-BBD ID:
BMRB ID:|bilirubin|

NMR related

MMCD Experimental_NMR: expnmr_00645 ||

HMDB_PREDICTED_HNMR: HMDB00054 ||

HMDB_PREDICTED_CNMR: HMDB00054 ||

Atom IDAtom TypeSMILES Canonical IDSMILES Symmetry ClassNeighborsInChI Canonical IDInChI Symmetry ClassEmpirical Chemical ShiftTheoretical Chemical ShiftExperimental Chemical ShiftLiterature NMR Data
1H211573N_AN_A2.05N_AN_AN_A
2H221573N_AN_A2.05N_AN_AN_A
3H231573N_AN_A2.05N_AN_AN_A
4H241674N_AN_A2.05N_AN_AN_A
5H251674N_AN_A2.05N_AN_AN_A
6H261674N_AN_A2.05N_AN_AN_A
7H151371N_AN_A1.93N_AN_AN_A
8H161371N_AN_A1.93N_AN_AN_A
9H171371N_AN_A1.93N_AN_AN_A
10H181472N_AN_A1.71N_AN_AN_A
11H191472N_AN_A1.71N_AN_AN_A
12H201472N_AN_A1.71N_AN_AN_A
13H332078N_AN_A2.7N_AN_AN_A
14H342078N_AN_A2.7N_AN_AN_A
15H352179N_AN_A2.7N_AN_AN_A
16H362179N_AN_A2.7N_AN_AN_A
17H271775N_AN_A3.89N_AN_AN_A
18H281775N_AN_A3.89N_AN_AN_A
19H291876N_AN_A2.5N_AN_AN_A
20H301876N_AN_A2.5N_AN_AN_A
21H311977N_AN_A2.5N_AN_AN_A
22H321977N_AN_A2.5N_AN_AN_A
23C4675269,59,731818120.5N_AN_AN_A
24C4685370,60,741717120.5N_AN_AN_A
25C4695467,61,782323122.0N_AN_AN_A
26C4705568,62,792222122.0N_AN_AN_A
27C4594467,55,452525127.5N_AN_AN_A
28C4604568,56,462424127.5N_AN_AN_A
29C4614669,75,452929131.0N_AN_AN_A
30C4624770,75,462828131.0N_AN_AN_A
31C4644965,57,542020151.5N_AN_AN_A
32C4634866,51,532121122.5N_AN_AN_A
33C4655064,52,711919123.5N_AN_AN_A
34C4665163,58,721616142.0N_AN_AN_A
35C4574264,55,442727127.5N_AN_AN_A
36C4584366,56,432626133.5N_AN_AN_A
37C4513663,43,393333167.5N_AN_AN_A
38C4523765,44,403232172.5N_AN_AN_A
39C2483354,9,1011116.0N_AN_AN_A
40C2473253,7,822116.0N_AN_AN_A
41C3554059,57,13141498.8N_AN_AN_A
42C3564160,58,14131398.8N_AN_AN_A
43C3543964,48,1277130.5N_AN_AN_A
44C3533863,47,1188130.5N_AN_AN_A
45C4493476,37,413131177.5N_AN_AN_A
46C4503577,38,423030177.5N_AN_AN_A
47C1735821,22,23,675514.3N_AN_AN_A
48C1745924,25,26,684414.3N_AN_AN_A
49C1715615,16,17,656612.0N_AN_AN_A
50C1725718,19,20,663315.5N_AN_AN_A
51C2786333,34,69,76101024.6N_AN_AN_A
52C2796435,36,70,779924.6N_AN_AN_A
53C2756027,28,61,62151531.6N_AN_AN_A
54C2766129,30,49,78121237.6N_AN_AN_A
55C2776231,32,50,79111137.6N_AN_AN_A
56N453059,61,53535N_AN_AN_AN_A
57N463160,62,63434N_AN_AN_AN_A
58N442957,52,43737N_AN_AN_AN_A
59N432858,51,33636N_AN_AN_AN_A
60O3924514343N_AN_AN_AN_A
61O4025524242N_AN_AN_AN_A
62O3722494040N_AN_AN_AN_A
63O3823503838N_AN_AN_AN_A
64O412649,14140N_AN_AN_AN_A
65O422750,23938N_AN_AN_AN_A
66H9848N_AN_A5.27N_AN_AN_A
67H10848N_AN_A5.2N_AN_AN_A
68H7747N_AN_A5.27N_AN_AN_A
69H8747N_AN_A5.2N_AN_AN_A
70H131155N_AN_A5.93N_AN_AN_A
71H141256N_AN_A5.93N_AN_AN_A
72H121054N_AN_A6.49N_AN_AN_A
73H11953N_AN_A6.49N_AN_AN_A
74H5545N_AN_A12.0N_AN_AN_A
75H6646N_AN_A12.0N_AN_AN_A
76H4444N_AN_A8.0N_AN_AN_A
77H3343N_AN_A8.0N_AN_AN_A
78H1141N_AN_A12.35N_AN_AN_A
79H2242N_AN_A12.35N_AN_AN_A

Mass Spectra related

C12N14 Mass data:584.263484909
C13N14 Mass data:617.374194556
C12N15 Mass data:588.251624482
C13N15 Mass data:621.362334129

Miscellanea

Order_Status:DONE
Organism:ana; ava; bcz; bur; cel; daga; dame; dbmo; dcbr; ddpo; dfru; dme; dmgr; dncr; dtni; eath; ecsi; egar; egma; egra; ehvu; elco; eles; elsa; emtr; eosa; epba; epta; esbi; esof; estu; etae; evvi; ezma; gvi; hsa; map; mmu; rno; syn; bma; bpm; bps; bta; bte; dre; emte; espu; fal; ko; net; nmu; pna; ptr; rma; tcx; xtr; afw; bam; bbt; cfa; dcin; gga; mjl; rde; sen; spu; stp; vok; xau
Location:Fridge C UW Box 1 D3
Isomer:
Salt:
Data Source:kegg;hmdb;biocyc
Similar Structure:|cq_10647||cq_10630|
Comments: