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C10H14N5O7P 3'-AMP 347.06308 389566 ChemSpider 20380-11-4 CAS C27H46O4 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 434.3396 CHEBI:16496 ChEBI CHEBI:18431 ChEBI HMDB0002159 HMDB 1.0 439153 PubChem-compound 474-73-7 CAS CHEBI:27393 ChEBI 1.0 CPD-3743 BioCyc Peroxisomal acyl-coenzyme A oxidase 2 53477893 PubChem-compound 3.0 CHEBI:28477 ChEBI 559142 ChemSpider (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol Transport125 false CE(22:2(13Z,16Z)) (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Liver, Cell LEFT_TO_RIGHT Transport124 false Cholesterol (→) Transport: Homo sapiens, Extracellular Space to Homo sapiens, Liver, Cell LEFT_TO_RIGHT NAD C27H46O3 (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol 418.3447 BTO:0000759 BRENDA TISSUE ONTOLOGY Alpha-methylacyl-CoA racemase Choloyl-CoA Taurocholic acid 5742 ChemSpider C01301 KEGG Compound CHEBI:16474 ChEBI C00695 KEGG Compound 1.0 CHEBI:27379 ChEBI 3'-AMP SMP0000317 SMPDB 389556 ChemSpider C01794 KEGG Compound 3a,7a,12a-Trihydroxy-5b-cholestan-26-al Q9Y6A2 UniProt 389554 ChemSpider SMILES CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS 1.0 439164 PubChem-compound 37610 ChemSpider 1.0 SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C 1.0 A 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid Adenosine triphosphate C03990 KEGG Compound 1.0 1.0 AH2 HMDB0002197 HMDB 2733768 PubChem-compound CHEBI:28047 ChEBI C00008 KEGG Compound C00007 KEGG Compound C00249 KEGG Compound C00006 KEGG Compound CHEBI:18009 ChEBI C00001 KEGG Compound NADP 1.0 C00005 KEGG Compound C00004 KEGG Compound C00003 KEGG Compound C00245 KEGG Compound C00002 KEGG Compound CHEBI:83036 ChEBI C13550 KEGG Compound 5284239 PubChem-compound 388658 ChemSpider C00010 KEGG Compound C24H40O3 Lithocholic acid 376.29776 C00013 KEGG Compound 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 1.0 Peroxisomal multifunctional enzyme type 2 1.0 56-65-5 CAS 5775 ChemSpider 53-84-9 CAS PW000194 PathWhiz 1.0 C15519 KEGG Compound 317-66-8 CAS 7 alpha,26-Dihydroxy-4-cholesten-3-one NADP 1.0 3862-25-7 CAS C00037 KEGG Compound C01367 KEGG Compound BiologicalState29 Homo sapiens, Liver HMDB0000138 HMDB C15520 KEGG Compound SMILES NCCS(O)(=O)=O SMILES [O-]P([O-])(=O)OP([O-])([O-])=O SubPathwayInteraction423 SubPathway423Reaction SubPathwayReaction SubPathwayInteraction424 SubPathway424Reaction SubPathwayReaction SubPathwayInteraction425 SubPathwayReaction SubPathway425Reaction C04644 KEGG Compound Q9H2F3 UniProt SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O CHEBI:9410 ChEBI 3081084 PubChem-compound 3081085 PubChem-compound HMDB0001231 HMDB Propionyl-CoA 193196 ChemSpider CE(22:2(13Z,16Z)) HMDB0001487 HMDB SMILES [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O 1.0 57-10-3 CAS C10H16N5O13P3 Adenosine triphosphate 506.99576 C27H46O5 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid 450.33453 3a,7a-Dihydroxy-5b-cholestanoyl-CoA HMDB0002103 HMDB 41211 PubChem-compound HMDB0001496 HMDB P38571 UniProt C15557 KEGG Compound 962 PubChem-compound 25-hydroxycholesterol 7-alpha-hydroxylase 1.0 3alpha,7alpha-Dihydroxycoprostanic acid 110306 ChemSpider 1.0 SMILES O=O C03594 KEGG Compound Chenodeoxycholic acid glycine conjugate SubPathwayInput CHENODEOXYCHOLOYLTAURINE BioCyc HMDB0002111 HMDB SMILES [H][C@@]12CCC(C(C)CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)CC2C[C@H](O)CCC12C 7a-Hydroxy-cholestene-3-one CHEBI:34310 ChEBI Deoxycholic acid SubPathwayOutput Cholic acid SubPathwayInput CHEBI:76591 ChEBI C24H40O4 Deoxycholic acid 392.29266 Aldo-keto reductase family 1 member C4 HMDB0001275 HMDB C24H40O5 Cholic acid 408.28757 1.0 985 PubChem-compound 3a,7a-Dihydroxy-5b-cholestane 644102 PubChem-compound 27-HYDROXYCHOLESTEROL BioCyc 1.0 3-oxo-5-beta-steroid 4-dehydrogenase 1.0 HMDB0006737 HMDB 1.0 Bile acid-CoA:amino acid N-acyltransferase 123976 PubChem-compound NADH BioCyc 53477807 PubChem-compound 977 PubChem-compound 123743 PubChem-compound 17215925 ChemSpider CHEBI:37998 ChEBI 1.0 CHEBI:2290 ChEBI C04483 KEGG Compound 1.0 NADH C27H48O3 5-b-Cholestane-3a ,7a ,12a-triol 420.36035 64907-22-8 CAS HMDB0000538 HMDB 1123 PubChem-compound C05337 KEGG Compound Cholesterol SubPathwayOutput 6816 PubChem-compound C27H46O Cholesterol 386.35486 C17333 KEGG Compound 1.0 C27H44O2 7a-Hydroxy-cholestene-3-one 400.33414 5997 PubChem-compound 5-b-Cholestane-3a ,7a ,12a-triol 17974-66-2 CAS 1.0 1.0 C26H43NO5 Chenodeoxycholic acid glycine conjugate 449.31412 1.0 547-98-8 CAS C26H43NO5 Deoxycholic acid glycine conjugate 449.31412 C27H46O4 3alpha,7alpha-Dihydroxycoprostanic acid 434.3396 1.0 2461-62-3 CAS 167758 ChemSpider Taurocholic acid SubPathwayInput 25-Hydroxycholesterol 1.0 1.0 C05122 KEGG Compound 1.0 CHEBI:2288 ChEBI C27H46O2 25-Hydroxycholesterol 402.3498 C26H45NO7S Taurocholic acid 515.2917 Peroxisomal acyl-coenzyme A oxidase 2 C17335 KEGG Compound C17336 KEGG Compound 53481010 PubChem-compound C17337 KEGG Compound NADPH BioCyc 1.0 1.0 SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C CPD-6641 BioCyc HMDB0001419 HMDB 440985 PubChem-compound 58-68-4 CAS HMDB0001423 HMDB SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O C2H5NO2 Glycine 75.03203 CHEBI:15519 ChEBI SMILES [H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O NADPH Liver SMILES [H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C Glycocholic acid SubPathwayInput SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O CHEBI:28834 ChEBI CHEBI:27505 ChEBI C26H43NO6 Glycocholic acid 465.30905 516-90-5 CAS C21H29N7O14P2 NADH 665.12476 Glycine HMDB0000359 HMDB 5957 PubChem-compound 640-79-9 CAS CPD-202 BioCyc 1.0 CHEBI:15756 ChEBI 25-hydroxycholesterol 7-alpha-hydroxylase HMDB0000123 HMDB C27H46O2 7a-Hydroxycholesterol 402.3498 HMDB0001457 HMDB GO:0005737 GENE ONTOLOGY SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O 7a-Hydroxycholesterol SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O 1.0 SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O CHEBI:17500 ChEBI 53481407 PubChem-compound 1.0 ReactionCatalysis1280 ACTIVATION 53481409 PubChem-compound 5682 ChemSpider C27H42O4 7alpha-Hydroxy-3-oxo-4-cholestenoate 430.30832 343282 ChemSpider C48H80N7O20P3S 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 1199.4392 C27H48O3 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 420.36035 1091 ChemSpider C27H44O3 7 alpha,26-Dihydroxy-4-cholesten-3-one 416.32904 Familial Hypercholanemia (FHCA) Aldo-keto reductase family 1 member C4 ReactionCatalysis1282 ACTIVATION ReactionCatalysis1285 ACTIVATION ReactionCatalysis1284 ACTIVATION ReactionCatalysis1287 ACTIVATION C27H44O4 3beta,7alpha-Dihydroxy-5-cholestenoate 432.32397 ReactionCatalysis1286 ACTIVATION GLYCOCHOLIC_ACID BioCyc C27H44O3 3 beta-Hydroxy-5-cholestenoate 416.32904 ReactionCatalysis1289 ACTIVATION 14000-31-8 CAS ReactionCatalysis1288 ACTIVATION ReactionCatalysis1290 ACTIVATION CO-A BioCyc ReactionCatalysis1292 ACTIVATION CHEBI:15339 ChEBI ReactionCatalysis1291 ACTIVATION CPD-8475 BioCyc 5675 ChemSpider CHEBI:36259 ChEBI 160520 PubChem-compound Water 862-53-3 CAS ReactionCatalysis1294 ACTIVATION 1.0 ReactionCatalysis1293 ACTIVATION ReactionCatalysis1296 ACTIVATION HMDB0006247 HMDB ReactionCatalysis1295 ACTIVATION ReactionCatalysis1298 ACTIVATION ReactionCatalysis1297 ACTIVATION ReactionCatalysis1299 ACTIVATION SMILES NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H]3O)C2=NC=N1 10128492 ChemSpider 516-50-7 CAS 1.0 6557 ChemSpider 103116 ChemSpider P22680 UniProt Q02318 UniProt SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C=O 7alpha-Hydroxy-3-oxo-4-cholestenoate CHEBI:28865 ChEBI HMDB0000951 HMDB 3beta,7alpha-Dihydroxy-5-cholestenoate 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 439573 PubChem-compound CHEBI:15539 ChEBI 3 beta-Hydroxy-5-cholestenoate SMP0000023 SMPDB GO:0005783 GENE ONTOLOGY 1.0 107-35-7 CAS 53481412 PubChem-compound 1.0 1.0 7782-44-7 CAS 6675 PubChem-compound HMDB0000722 HMDB GO:0005777 GENE ONTOLOGY SMILES [H][C@@]12CCC([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C 9606 TAXONOMY 4444355 ChemSpider Q9NYL5 UniProt 4444354 ChemSpider 1.0 1.0 Non-specific lipid-transfer protein 115538-84-6 CAS 3.0 CHEBI:15377 ChEBI CHEBI:16466 ChEBI 1.0 HMDB0006281 HMDB 30776546 ChemSpider CHEBI:15379 ChEBI CHEBI:18402 ChEBI HMDB0006280 HMDB C05464 KEGG Compound SMILES NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O CHEBI:13193 ChEBI Cholesterol-esters BioCyc Lithocholyltaurine SubPathwayOutput CHEBI:81015 ChEBI HMDB0006292 HMDB 1.0 25-Hydroxycholesterol HMDB0011644 HMDB 1.0 3 beta-hydroxysteroid dehydrogenase type 7 Cholesterol 24-hydroxylase TAUROLITHOCHOLATE-SULFATE BioCyc 13628315 ChemSpider 9903 PubChem-compound HMDB0000518 HMDB HMDB0000761 HMDB ReactionCatalysis1279 ACTIVATION CHEBI:29746 ChEBI 11966205 PubChem-compound 85-61-0 CAS 434-13-9 CAS ReactionCatalysis1278 ACTIVATION ReactionCatalysis1277 ACTIVATION 6022 PubChem-compound 937 ChemSpider Bile acyl-CoA synthetase CHOLESTEROL BioCyc 1.0 1.0 2338356 ChemSpider C26H45NO6S Taurodeoxycholic acid 499.29675 1.0 C27H48O4 27-Deoxy-5b-cyprinol 436.35526 NAD CE(22:2(13Z,16Z)) 122312 PubChem-compound ATP BioCyc 1.0 PW000050 PathWhiz HMDB0006887 HMDB 360-65-6 CAS HMDB0006888 HMDB HMDB0006889 HMDB 24-hydroxycholesterol 7-alpha-hydroxylase 388578 ChemSpider CHEBI:16113 ChEBI Lithocholic acid glycine conjugate SubPathwayOutput CHEBI:16359 ChEBI 1.0 Reduced acceptor O75881 UniProt 109066 ChemSpider 27-Deoxy-5b-cyprinol CHEBI:15022 ChEBI 952 ChemSpider 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase 474-74-8 CAS SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O 6561-58-6 CAS SMILES CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N HMDB0006894 HMDB SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O SMILES CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C HMDB0006895 HMDB SMILES C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C HMDB0006890 HMDB HMDB0006891 HMDB HMDB0006892 HMDB HMDB0006893 HMDB 7-a,27-Dihydroxycholesterol C02528 KEGG Compound C00100 KEGG Compound Cholesterol 4.0 1.0 PPI BioCyc 81-24-3 CAS 11954197 PubChem-compound 7a-Hydroxy-5b-cholestan-3-one C24H40N7O17P3S Propionyl-CoA 823.1414 Water Cytosol 388310 ChemSpider 4675-38-1 CAS C02530 KEGG Compound Lysosomal acid lipase/cholesteryl ester hydrolase 221493 PubChem-compound ReactionCatalysis2058 ACTIVATION C26H45NO6S Taurochenodesoxycholic acid 499.29675 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA 53477732 PubChem-compound 5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL BioCyc Chenodeoxycholoyl-CoA C04722 KEGG Compound 7-a,25-Dihydroxycholesterol 7-a,27-Dihydroxycholesterol PROPIONYL-COA BioCyc CHEBI:18361 ChEBI CHEBI:17278 ChEBI Oxygen 57-88-5 CAS 110495 ChemSpider 3 beta-hydroxysteroid dehydrogenase type 7 Taurochenodesoxycholic acid SubPathwayInput C21H28N7O14P2 NAD 664.11694 5-BETA-CHOLESTANE-3-ALPHA7-TETRAOL BioCyc Taurine HMDB0000902 HMDB C49H84O2 CE(22:2(13Z,16Z)) 704.64716 Extracellular Space 60731-52-4 CAS NAD(P) BioCyc Cholesterol 7-alpha-monooxygenase 192176 ChemSpider 10133 PubChem-compound CHEBI:17499 ChEBI 1.0 1.0 1.0 1.0 3a,7a-Dihydroxy-5b-cholestane 3a,7a-Dihydroxy-5b-cholestan-26-al SMILES NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O Water Peroxisome 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA 7a-Hydroxy-5b-cholestan-3-one 22833539 PubChem-compound 5b-Cyprinol sulfate C26H43NO4 Lithocholic acid glycine conjugate 433.3192 HMDB0000251 HMDB HMDB0000250 HMDB HMDB0001341 HMDB 1.0 CPD-266 BioCyc P17516 UniProt NADH 7a,12a-Dihydroxy-5b-cholestan-3-one 27-Hydroxycholesterol Non-specific lipid-transfer protein SMILES CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C C02592 KEGG Compound 1.0 HMDB0003533 HMDB 2338764 ChemSpider 2338765 ChemSpider Q9UHK6 UniProt 1.0 C45H74N7O19P3S Chenodeoxycholoyl-CoA 1141.3973 ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC BioCyc 3.0 C27H46O3 7-a,25-Dihydroxycholesterol 418.3447 7732-18-5 CAS C27H46O3 7-a,27-Dihydroxycholesterol 418.3447 3862-26-8 CAS 3-oxo-5-beta-steroid 4-dehydrogenase Bile acid-CoA:amino acid N-acyltransferase HMDB0000036 HMDB SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C 1.0 516-35-8 CAS HMDB0003540 HMDB NAD 23617285 PubChem-compound 56-40-6 CAS C00187 KEGG Compound Peroxisomal multifunctional enzyme type 2 HMDB0001377 HMDB Cholesterol 25-hydroxylase P51659 UniProt SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C 53477716 PubChem-compound 22833540 PubChem-compound Q9UNU6 UniProt HMDB0001374 HMDB 1.0 5800 ChemSpider 730 ChemSpider 387316 PubChem-compound Lithocholic acid SubPathwayOutput 1.0 53477903 PubChem-compound 53477905 PubChem-compound 53477904 PubChem-compound 53477906 PubChem-compound 389810 ChemSpider 58-64-0 CAS 3a,7a-Dihydroxy-5b-cholestanoyl-CoA HMDB0000067 HMDB 24747221 ChemSpider Q99424 UniProt 960 ChemSpider C48H80N7O19P3S 3a,7a-Dihydroxy-5b-cholestanoyl-CoA 1183.4442 Q9Y2P5 UniProt Choloyl-CoA 1.0 C27H46O2 27-Hydroxycholesterol 402.3498 C27H46O3 7a,12a-Dihydroxy-5b-cholestan-3-one 418.3447 2140-46-7 CAS 22833512 PubChem-compound C27H48O8S 5b-Cyprinol sulfate 532.307 C48H78N7O20P3S 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 1197.4235 C48H80N7O21P3S 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA 1215.4341 83-44-3 CAS H2O Water 18.010565 C48H78N7O21P3S 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA 1213.4185 C27H46O2 7a-Hydroxy-5b-cholestan-3-one 402.3498 C27H48O2 3a,7a-Dihydroxy-5b-cholestane 404.36542 SMILES NCC(O)=O 1.0 C26H45NO5S Lithocholyltaurine 483.30185 17215983 ChemSpider 17215984 ChemSpider 547-96-6 CAS NAD BioCyc 1.0 C27H46O3 3a,7a-Dihydroxy-5b-cholestan-26-al 418.3447 C48H78N7O19P3S 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA 1181.4286 P51857 UniProt SMILES [H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C Sterol 26-hydroxylase, mitochondrial Deoxycholic acid glycine conjugate SubPathwayOutput C05448 KEGG Compound 3080603 PubChem-compound C05447 KEGG Compound SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO C05444 KEGG Compound 108790 ChemSpider Taurodeoxycholic acid SubPathwayOutput C05446 KEGG Compound C05445 KEGG Compound SMILES [H][C@]12CCC(C(C)CCCC(C)C)[C@@]1(C)C([H])(O)C[C@@]1([H])C2[C@H](O)CC2CC(=O)CC[C@]12C C05451 KEGG Compound SMILES [H][C@@]12CCC(C(C)CCC(=O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)C[C@]2([H])C[C@H](O)CCC12C SMILES CC(C)CCCC(C)C1CCC2C3[C@@H](O)CC4CC(=O)CC[C@]4(C)C3CC[C@]12C C27H44O3 7a,12a-Dihydroxy-cholestene-3-one 416.32904 Acceptor C05450 KEGG Compound SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C C05453 KEGG Compound ReactionCatalysis1326 ACTIVATION C05452 KEGG Compound SMILES CC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O Taurine ReactionCatalysis1325 ACTIVATION 1.0 SMILES CC(CCCC(CO)COS(O)(=O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3C[C@@H](O)[C@]12C HMDB0000896 HMDB 475-31-0 CAS Lysosomal acid lipase/cholesteryl ester hydrolase SMILES CC(CC\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C1CCC2C3[C@H](O)C[C@]4([H])C[C@H](O)CCC4(C)C3C[C@H](O)C12C SMILES O SMILES [H][C@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(C)CCC(O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N SMILES C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C 1.0 C24H40O4 Chenodeoxycholic acid 392.29266 Pyrophosphate 1.0 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA 9519 ChemSpider 1.0 CHEBI:37623 ChEBI C05455 KEGG Compound SMILES CC(CC\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C1CCC2C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)C3CC[C@]12C C05454 KEGG Compound C05457 KEGG Compound HMDB0001993 HMDB ReactionCatalysis1335 ACTIVATION ReactionCatalysis1334 ACTIVATION 1.0 ReactionCatalysis1337 ACTIVATION ReactionCatalysis1336 ACTIVATION C05463 KEGG Compound ReactionCatalysis1339 ACTIVATION ReactionCatalysis1338 ACTIVATION C05460 KEGG Compound CHEBI:37616 ChEBI CHEBI:15846 ChEBI 1.0 ADP BioCyc Chenodeoxycholoyl-CoA 53-59-8 CAS C05466 KEGG Compound C05465 KEGG Compound C05468 KEGG Compound C05467 KEGG Compound SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O GO:0005829 GENE ONTOLOGY Cholesterol 7-alpha-monooxygenase Chenodeoxycholic acid SubPathwayInput 7a,12a-Dihydroxy-cholestene-3-one CHEBI:16908 ChEBI 3 beta-hydroxysteroid dehydrogenase type 7 NADPH 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA Cholesterol 24-hydroxylase Sterol 26-hydroxylase, mitochondrial Palmitic acid NADP C21H30N7O17P3 NADPH 745.0911 C16H32O2 Palmitic acid 256.24023 C21H29N7O17P3 NADP 744.08325 Intestinal Microflora SubPathway 474-25-9 CAS Intestinal Microflora SubPathway 10128154 ChemSpider GLY BioCyc 141053 ChemSpider 1.0 C06341 KEGG Compound 1.0 Choloyl-CoA C06340 KEGG Compound HMDB0000698 HMDB HMDB0000217 HMDB Oxygen Bile acyl-CoA synthetase Cholesterol 25-hydroxylase 1.0 CHEBI:15891 ChEBI SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O HMDB0000221 HMDB 5280796 PubChem-compound 5257127 PubChem-compound 5280797 PubChem-compound SMILES NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O SMILES CCCCCCCCCCCCCCCC(O)=O CHEBI:2149 ChEBI 121948 PubChem-compound HMDB0000220 HMDB 53-57-6 CAS HMDB0012453 HMDB HMDB0012454 HMDB HMDB0012455 HMDB 4447327 ChemSpider HMDB0012456 HMDB HMDB0012458 HMDB HMDB0012459 HMDB 24-hydroxycholesterol 7-alpha-hydroxylase C2H7NO3S Taurine 125.01466 ReactionCatalysis1302 ACTIVATION O7P2 Pyrophosphate 173.91193 ReactionCatalysis1301 ACTIVATION ReactionCatalysis1304 ACTIVATION ReactionCatalysis1303 ACTIVATION 1.0 CHEBI:28701 ChEBI ReactionCatalysis1306 ACTIVATION ReactionCatalysis1308 ACTIVATION ReactionCatalysis1307 ACTIVATION ReactionCatalysis1300 ACTIVATION Q14032 UniProt ReactionCatalysis1309 ACTIVATION 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase SMILES [H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)C(C)CCCC(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12 ReactionCatalysis1313 ACTIVATION Steroid Biosynthesis SubPathway Adenosine diphosphate ReactionCatalysis1312 ACTIVATION CHEBI:28931 ChEBI GO:0005615 GENE ONTOLOGY C10H15N5O10P2 Adenosine diphosphate 427.02942 1.0 Coenzyme A 1.0 ReactionCatalysis1311 ACTIVATION ReactionCatalysis1310 ACTIVATION O95992 UniProt C01921 KEGG Compound 1.0 3.0 Endoplasmic Reticulum SMILES NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O 1.0 15313-69-6 CAS SMILES CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C CHEBI:1146900 ChEBI 440420 PubChem-compound P22307 UniProt Bile acid-CoA:amino acid N-acyltransferase A AH2 Coenzyme A C21H36N7O16P3S Coenzyme A 767.11523 24-Hydroxycholesterol CHEBI:27428 ChEBI Cytoplasm 84-21-9 CAS 21252277 PubChem-compound C27H46O2 24-Hydroxycholesterol 402.3498 CHEBI:15422 ChEBI CHEBI:16755 ChEBI Homo sapiens 115538-85-7 CAS 388299 ChemSpider Acceptor Reduced acceptor 1.17.99.3 false 1.17.99.3 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Water → 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA LEFT_TO_RIGHT Reaction1551 false 3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA + Water → 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA LEFT_TO_RIGHT O2 Oxygen 31.98983 1.14.13.95 false 1.14.13.95 7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Water LEFT_TO_RIGHT 1.14.13.17 false 1.14.13.17 Cholesterol + NADPH + Oxygen → 7a-Hydroxycholesterol + NADP + Water LEFT_TO_RIGHT 6.2.1.7 false 6.2.1.7 Adenosine triphosphate + Chenodeoxycholoyl-CoA + Cholic acid → 3'-AMP + Chenodeoxycholic acid + Pyrophosphate LEFT_TO_RIGHT Reaction1557 false 7a-Hydroxycholesterol + NAD → 7a-Hydroxy-cholestene-3-one + NADH LEFT_TO_RIGHT 193321 PubChem-compound Reaction1554 false Chenodeoxycholoyl-CoA + Taurine → Taurochenodesoxycholic acid LEFT_TO_RIGHT 1.0 Reaction1555 false Chenodeoxycholoyl-CoA + Glycine → Chenodeoxycholic acid glycine conjugate + Glycocholic acid LEFT_TO_RIGHT Reaction1552 false 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA → Chenodeoxycholoyl-CoA + Water LEFT_TO_RIGHT 2.3.1.176 false 2.3.1.176 Chenodeoxycholoyl-CoA + Coenzyme A → Chenodeoxycholoyl-CoA + Propionyl-CoA LEFT_TO_RIGHT C45H74N7O20P3S Choloyl-CoA 1157.3922 CHEBI:16525 ChEBI 5.1.99.4 false 5.1.99.4 3a,7a-Dihydroxy-5b-cholestanoyl-CoA → 3a,7a-Dihydroxy-5b-cholestanoyl-CoA LEFT_TO_RIGHT 6423 ChemSpider SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O CHEBI:16761 ChEBI 440677 PubChem-compound 440675 PubChem-compound CHEBI:27403 ChEBI HMDB0000601 HMDB 1.14.13.15 false 1.14.13.15 3a,7a-Dihydroxy-5b-cholestan-26-al → 3alpha,7alpha-Dihydroxycoprostanic acid LEFT_TO_RIGHT CHEBI:15428 ChEBI 6.2.1.7 false 6.2.1.7 3alpha,7alpha-Dihydroxycoprostanic acid + Adenosine triphosphate + Coenzyme A → 3'-AMP + 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Pyrophosphate LEFT_TO_RIGHT 1.14.13.15 false 1.14.13.15 3a,7a-Dihydroxy-5b-cholestane + 3 NADPH + 3 Oxygen → 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane + 3 NADP + 3 Water LEFT_TO_RIGHT 1.14.13.15 false 1.14.13.15 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane → 3a,7a-Dihydroxy-5b-cholestan-26-al LEFT_TO_RIGHT Reaction1541 false 7a-Hydroxy-5b-cholestan-3-one + NAD → 3a,7a-Dihydroxy-5b-cholestane + NADP LEFT_TO_RIGHT 1.3.1.3 false 1.3.1.3 7a-Hydroxy-cholestene-3-one + NADPH ← 7a-Hydroxy-5b-cholestan-3-one + NADP RIGHT_TO_LEFT Coenzyme A CHEBI:16577 ChEBI 9728 ChemSpider SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N 389367 ChemSpider 5893 PubChem-compound SMILES [H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CO 115245 PubChem-compound 439479 PubChem-compound 1.17.99.3 false 1.17.99.3 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Acceptor + Water → 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Reduced acceptor LEFT_TO_RIGHT 1.0 1.0 Reaction1578 false Choloyl-CoA + Glycine → Coenzyme A + Glycocholic acid LEFT_TO_RIGHT 6.2.1.7 false 6.2.1.7 3'-AMP + Choloyl-CoA + Pyrophosphate → Adenosine triphosphate + Cholic acid + Coenzyme A LEFT_TO_RIGHT CHEBI:27471 ChEBI 2.3.1.176 false 2.3.1.176 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Coenzyme A → Choloyl-CoA + Propionyl-CoA LEFT_TO_RIGHT Reaction1577 false Choloyl-CoA + Taurine → Coenzyme A + Taurocholic acid LEFT_TO_RIGHT Reaction1575 false 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA + NAD → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + NADH LEFT_TO_RIGHT 5886 PubChem-compound CHEBI:15494 ChEBI HMDB0000619 HMDB Alpha-methylacyl-CoA racemase 1.3.1.3 false 1.3.1.3 7a,12a-Dihydroxy-cholestene-3-one + NADPH → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADP LEFT_TO_RIGHT 2015539 ChemSpider 1.14.13.15 false 1.14.13.15 5-b-Cholestane-3a ,7a ,12a-triol + 3 NADPH + 3 Oxygen → 27-Deoxy-5b-cyprinol + 3 NADP + 4 Water LEFT_TO_RIGHT Aldo-keto reductase family 1 member C4 1.0 3.1.1.13 false 3.1.1.13 CE(22:2(13Z,16Z)) + Water → Cholesterol + Palmitic acid LEFT_TO_RIGHT 440690 PubChem-compound 5.1.99.4 false 5.1.99.4 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA LEFT_TO_RIGHT 1.14.13.15 false 1.14.13.15 3a,7a,12a-Trihydroxy-5b-cholestan-26-al → 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid LEFT_TO_RIGHT 6.2.1.7 false 6.2.1.7 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoic acid + Adenosine triphosphate + Coenzyme A → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + Adenosine diphosphate + Pyrophosphate LEFT_TO_RIGHT 81-25-4 CAS 1.14.13.15 false 1.14.13.15 27-Deoxy-5b-cyprinol + 3 NADPH + 3 Oxygen → 3a,7a,12a-Trihydroxy-5b-cholestan-26-al + 3 NADP + 4 Water LEFT_TO_RIGHT Reaction1563 false 7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 5-b-Cholestane-3a ,7a ,12a-triol + NADPH LEFT_TO_RIGHT Reaction1564 false 27-Deoxy-5b-cyprinol → 5b-Cyprinol sulfate LEFT_TO_RIGHT Reaction2209 false 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Water → 3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA LEFT_TO_RIGHT CPD-7239 BioCyc HMDB0000626 HMDB Cholesterol 1.0 222528 PubChem-compound SMILES CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N Reaction1594 false 7-a,27-Dihydroxycholesterol + NADP → 7 alpha,26-Dihydroxy-4-cholesten-3-one + NADPH LEFT_TO_RIGHT 4725-24-0 CAS 1.14.13.100 false 1.14.13.100 27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water LEFT_TO_RIGHT HMDB0000631 HMDB 1.14.13.17 false 1.14.13.17 27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water LEFT_TO_RIGHT CHEBI:27458 ChEBI 1.14.13.100 false 1.14.13.100 Cholesterol + 3 NADPH + 3 Oxygen → 27-Hydroxycholesterol + 3 NADP + 4 Water LEFT_TO_RIGHT Reaction1598 false 3beta,7alpha-Dihydroxy-5-cholestenoate + NAD → 7alpha-Hydroxy-3-oxo-4-cholestenoate + NADH LEFT_TO_RIGHT CHEBI:28540 ChEBI 1.14.13.15 false 1.14.13.15 27-Hydroxycholesterol + 3 NADPH + 3 Oxygen → 3 beta-Hydroxy-5-cholestenoate + 3 NADP + 4 Water LEFT_TO_RIGHT 1.14.13.100 false 1.14.13.100 3 beta-Hydroxy-5-cholestenoate + NADPH + Oxygen → 3beta,7alpha-Dihydroxy-5-cholestenoate + NADP + Water LEFT_TO_RIGHT CHEBI:16325 ChEBI CHEBI:17899 ChEBI 3836-01-9 CAS HMDB0000637 HMDB CPD-7243 BioCyc SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O CPD-7241 BioCyc 1.14.13.99 false 1.14.13.99 24-Hydroxycholesterol + NADPH + Oxygen → (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol + NADP + Water LEFT_TO_RIGHT 1.14.99.38 false 1.14.99.38 AH2 + Cholesterol + Oxygen → 25-Hydroxycholesterol + A + Water LEFT_TO_RIGHT 1.14.13.98 false 1.14.13.98 Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Water LEFT_TO_RIGHT 1.14.13.100 false 1.14.13.100 25-Hydroxycholesterol + NADPH + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Water LEFT_TO_RIGHT