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C10H14N5O7P 3'-AMP 347.06308 389566 ChemSpider HMDB00138 HMDB 20380-11-4 CAS C27H46O4 3a,7a,12a-Trihydroxy-5b-cholestan-26-al 434.3396 CHEBI:16496 ChEBI CHEBI:18431 ChEBI 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 HMDB01231 HMDB 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 53477686 PubChem-compound BTO:0000759 BRENDA TISSUE ONTOLOGY HMDB00359 HMDB 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 HMDB00123 HMDB HMDB03873 HMDB 389556 ChemSpider HMDB01457 HMDB 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(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 HMDB01423 HMDB A 3a,7a,12a-Trihydroxy-5b-cholestanoic acid 9914991 ChemSpider Adenosine triphosphate C03990 KEGG Compound HMDB01419 HMDB 1.0 1.0 AH2 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 C13550 KEGG 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 53-84-9 CAS 1.0 11740284 PubChem-compound C15519 KEGG Compound 317-66-8 CAS 7 alpha,26-Dihydroxy-4-cholesten-3-one NADP 1.0 CL:0000000 CELL TYPE ONTOLOGY 3862-25-7 CAS C00037 KEGG Compound C01367 KEGG Compound BiologicalState29 BiologicalState31 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 HMDB00538 HMDB Propionyl-CoA 193196 ChemSpider CE(22:2(13Z,16Z)) 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 HMDB06292 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])CC[C@]12C)[C@H](C)CCC(O)=O 1.0 57-10-3 CAS HMDB00761 HMDB C10H16N5O13P3 Adenosine triphosphate 506.99576 C27H46O5 3a,7a,12a-Trihydroxy-5b-cholestanoic acid 450.33453 BiologicalState18 3a,7a-Dihydroxy-5b-cholestanoyl-CoA HMDB11644 HMDB 41211 PubChem-compound HMDB00518 HMDB P38571 UniProt C15557 KEGG Compound 962 PubChem-compound 25-hydroxycholesterol 7-alpha-hydroxylase 1.0 3a,7a-Dihydroxycoprostanic acid 110306 ChemSpider 1.0 SMILES O=O C03594 KEGG Compound Chenodeoxycholic acid glycine conjugate SubPathwayInput CHENODEOXYCHOLOYLTAURINE BioCyc BiologicalState5 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 BiologicalState2 7a-Hydroxy-cholestene-3-one CHEBI:34310 ChEBI Deoxycholic acid SubPathwayOutput HMDB06280 HMDB Cholic acid SubPathwayInput CHEBI:76591 ChEBI HMDB06281 HMDB C24H40O4 Deoxycholic acid 392.29266 Aldo-keto reductase family 1 member C4 C24H40O5 Cholic acid 408.28757 1.0 985 PubChem-compound 3a,7a-Dihydroxy-5b-cholestane 23657849 PubChem-compound 644102 PubChem-compound HMDB00951 HMDB 27-HYDROXYCHOLESTEROL BioCyc 1.0 3-oxo-5-beta-steroid 4-dehydrogenase 1.0 1.0 Bile acid-CoA:amino acid N-acyltransferase 123976 PubChem-compound NADH BioCyc 53477807 PubChem-compound 977 PubChem-compound HMDB00722 HMDB 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 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 5-b-Cholestane-3a ,7a ,12a-triol 17974-66-2 CAS 1.0 1.0 C26H43NO5 Chenodeoxycholic acid glycine conjugate 449.31412 1.0 C26H43NO5 Deoxycholic acid glycine conjugate 449.31412 C27H46O4 3a,7a-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 HMDB02197 HMDB 440985 PubChem-compound 58-68-4 CAS 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])C3[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 21865494 ChemSpider 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@@]12C[C@H](O)CCC1(C)C1C[C@H](O)C3(C)C(CCC3C1[C@H](O)C2)C(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 5957 PubChem-compound 640-79-9 CAS CPD-202 BioCyc 1.0 CHEBI:15756 ChEBI 25-hydroxycholesterol 7-alpha-hydroxylase C27H46O2 7a-Hydroxycholesterol 402.3498 11025495 PubChem-compound GO:0005737 GENE ONTOLOGY SMILES [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C 7a-Hydroxycholesterol SMILES [H][C@@](C)(CCC(O)=O)[C@@]1([H])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 1.0 SMILES [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@H](O)CC[C@]12C HMDB02159 HMDB CHEBI:17500 ChEBI 53481407 PubChem-compound 1.0 ReactionCatalysis1280 ACTIVATION 53481408 PubChem-compound 53481409 PubChem-compound 5682 ChemSpider C27H42O4 7 alpha-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 Aldo-keto reductase family 1 member C4 ReactionCatalysis1282 ACTIVATION ReactionCatalysis1285 ACTIVATION ReactionCatalysis1284 ACTIVATION ReactionCatalysis1287 ACTIVATION C27H44O4 3 beta,7 alpha-Dihydroxy-5-cholestenoate 432.32397 ReactionCatalysis1286 ACTIVATION GLYCOCHOLIC_ACID BioCyc CPD-1836 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 ReactionCatalysis1295 ACTIVATION ReactionCatalysis1298 ACTIVATION ReactionCatalysis1297 ACTIVATION Cell 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 HMDB06737 HMDB 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 440567 PubChem-compound 7 alpha-Hydroxy-3-oxo-4-cholestenoate CHEBI:28865 ChEBI 3 beta,7 alpha-Dihydroxy-5-cholestenoate 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane 439573 PubChem-compound CHEBI:15539 ChEBI 3 beta-Hydroxy-5-cholestenoate GO:0005783 GENE ONTOLOGY 53481411 PubChem-compound 1.0 107-35-7 CAS 53481412 PubChem-compound 1.0 1.0 7782-44-7 CAS CHEBI:48043 ChEBI 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 HMDB02111 HMDB 3.0 CHEBI:15377 ChEBI CHEBI:16466 ChEBI 1.0 30776546 ChemSpider CHEBI:15379 ChEBI 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@@]12CC[C@H]([C@H](C)CCC[C@@H](C)C(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C CHEBI:13193 ChEBI HMDB01275 HMDB 9200676 ChemSpider Cholesterol-esters BioCyc Lithocholyltaurine SubPathwayOutput HMDB01487 HMDB 389467 ChemSpider 1.0 25-Hydroxycholesterol 1.0 3 beta-hydroxysteroid dehydrogenase type 7 Cholesterol 24-hydroxylase TAUROLITHOCHOLATE-SULFATE BioCyc 13628315 ChemSpider CHEBI:1307929 ChEBI HMDB02103 HMDB HMDB01496 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 HMDB00250 HMDB HMDB00251 HMDB HMDB01341 HMDB CHOLESTEROL BioCyc 1.0 1.0 SMP00023 SMPDB 2338356 ChemSpider C26H45NO6S Taurodeoxycholic acid 499.29675 HMDB03533 HMDB 1.0 C27H48O4 27-Deoxy-5b-cyprinol 436.35526 NAD CE(22:2(13Z,16Z)) ATP BioCyc 1.0 PW000050 PathWhiz 360-65-6 CAS 24-hydroxycholesterol 7-alpha-hydroxylase SMP00035 SMPDB 388578 ChemSpider Lithocholic acid glycine conjugate SubPathwayOutput CHEBI:16359 ChEBI 1.0 Reduced acceptor O75881 UniProt 27-Deoxy-5b-cyprinol CHEBI:15022 ChEBI 952 ChemSpider 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase 474-74-8 CAS SMILES C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C 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 SMILES C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C SMILES CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C SMILES C[C@H](CCCC(C)C(O)=O)C1CCC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C 7-a,27-Dihydroxycholesterol C02528 KEGG Compound C00100 KEGG Compound Cholesterol 4.0 1.0 PPI BioCyc HMDB12459 HMDB HMDB12458 HMDB HMDB12456 HMDB HMDB12455 HMDB 81-24-3 CAS HMDB12454 HMDB HMDB12453 HMDB 11954197 PubChem-compound 7a-Hydroxy-5b-cholestan-3-one C24H40N7O17P3S Propionyl-CoA 823.1414 HMDB00698 HMDB Water HMDB00217 HMDB Cytosol 388310 ChemSpider 4675-38-1 CAS C02530 KEGG Compound Lysosomal acid lipase/cholesteryl ester hydrolase 221493 PubChem-compound ReactionCatalysis2058 ACTIVATION HMDB00221 HMDB 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 HMDB00220 HMDB 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 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 HMDB00896 HMDB 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 HMDB01993 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 Q9UHK6 UniProt 1.0 C45H74N7O19P3S Chenodeoxycholoyl-CoA 1141.3973 ALPHA-N-DIACETYLNEURAMINYL-23-BETA-D-ETC BioCyc HMDB00631 HMDB 3.0 33964-75-9 CAS 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 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 HMDB00626 HMDB 516-35-8 CAS NAD 23617285 PubChem-compound 56-40-6 CAS C00187 KEGG Compound Peroxisomal multifunctional enzyme type 2 Cholesterol 25-hydroxylase P51659 UniProt SMILES [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C 53477716 PubChem-compound HMDB00637 HMDB 22833540 PubChem-compound Q9UNU6 UniProt 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 24747221 ChemSpider Q99424 UniProt 960 ChemSpider C48H80N7O19P3S 3a,7a-Dihydroxy-5b-cholestanoyl-CoA 1183.4442 Q9Y2P5 UniProt Choloyl-CoA HMDB00619 HMDB 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@@]12CC[C@H]([C@H](C)CCC[C@@H](C)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C 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 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 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 HMDB06247 HMDB C05457 KEGG Compound 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 HMDB00902 HMDB 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 Steroid Biosynthesis SubPathway 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 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 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 53-57-6 CAS HMDB06893 HMDB 24-hydroxycholesterol 7-alpha-hydroxylase HMDB06892 HMDB HMDB06891 HMDB HMDB06890 HMDB HMDB06895 HMDB HMDB06894 HMDB 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 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 HMDB06889 HMDB HMDB06888 HMDB HMDB06887 HMDB 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 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 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 1.14.13.15 false 1.14.13.15 3a,7a-Dihydroxy-5b-cholestan-26-al → 3a,7a-Dihydroxycoprostanic acid LEFT_TO_RIGHT CHEBI:15428 ChEBI 6.2.1.7 false 6.2.1.7 3a,7a-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 PW000145 PathWhiz Coenzyme A 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 HMDB00067 HMDB 5886 PubChem-compound CHEBI:15494 ChEBI 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 → 3a,7a,12a-Trihydroxy-5b-cholestanoic acid LEFT_TO_RIGHT 6.2.1.7 false 6.2.1.7 3a,7a,12a-Trihydroxy-5b-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 HMDB00036 HMDB Bile Acid Biosynthesis 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 Cholesterol 1.0 222528 PubChem-compound HMDB03540 HMDB 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 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 3 beta,7 alpha-Dihydroxy-5-cholestenoate + NAD → 7 alpha-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 → 3 beta,7 alpha-Dihydroxy-5-cholestenoate + NADP + Water LEFT_TO_RIGHT HMDB01377 HMDB CHEBI:16325 ChEBI CHEBI:17899 ChEBI 3836-01-9 CAS 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 HMDB01374 HMDB 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