Cholic acid (BioCAD00000008432)

bile blood feces urine intestine kidney liver placenta platelet spleen

Metabolite Card

Formula: C24H40O5 (408.2876)
SMILES: C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C

Synonyms [en]

cholic acid; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid; cholate; Colalin; Cholsaeure; 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Cholic acid. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000008432). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Cholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487, 16037564, 12576301, 11907135). When present in sufficiently high levels, cholic acid can act as a hepatotoxin and a metabotoxin. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. Chronically high levels of cholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including cholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 10321-98-9
  • CAS Registry Number: 105227-32-5
  • CAS Registry Number: 129874-08-4
  • CAS Registry Number: 2955-27-3
  • CAS Registry Number: 361-09-1
  • CAS Registry Number: 72264-72-3
  • CAS Registry Number: 81-25-4
  • PubChem: 221493
  • PubChem: 303
  • ChEBI: ChEBI:16359
  • HMDB: HMDB0000505
  • HMDB: HMDB0000619
  • HMDB: HMDB00619
  • LipidMaps: LMST04010001
  • KEGG: C00695
  • KEGG: C00695 C01558
  • BioCyc: CHOLATE
  • NCBI MeSH: Cholic Acid
  • Wikipedia: Cholic_acid
  • DrugBank: DB02659
  • RefMet: RM0135798
  • MoNA: BAF_UVA_POS000938
  • MoNA: BML00963
  • MoNA: BML00972
  • MoNA: BML00989
  • MoNA: BML00997
  • MoNA: BML01005
  • MoNA: BML80930
  • MoNA: BML80931
  • MoNA: BML80933
  • MoNA: Bruker_HCD_library001891
  • MoNA: CCMSLIB00005435447
  • MoNA: CCMSLIB00005435448
  • MoNA: CCMSLIB00005435449
  • MoNA: CCMSLIB00005435506
  • MoNA: CCMSLIB00005435972
  • MoNA: CCMSLIB00005435973
  • MoNA: CCMSLIB00005435974
  • MoNA: CCMSLIB00005435975
  • MoNA: CCMSLIB00005435976
  • MoNA: CCMSLIB00005435977
  • MoNA: CCMSLIB00005435978
  • MoNA: CCMSLIB00005435979
  • MoNA: CCMSLIB00005435980
  • MoNA: CCMSLIB00005435981
  • MoNA: CCMSLIB00005435982
  • MoNA: CCMSLIB00005463904
  • MoNA: CCMSLIB00005463905
  • MoNA: CCMSLIB00005463906
  • MoNA: CCMSLIB00005720894
  • MoNA: EMBL_MCF_2_0_HRMS_Library000488
  • MoNA: EMBL_MCF_2_0_HRMS_Library000489
  • MoNA: FiehnHILIC001118
  • MoNA: FiehnHILIC002641
  • MoNA: FiehnLib000114
  • MoNA: HMDB0000619_c_ms_99586
  • MoNA: JP011901
  • MoNA: KO000461
  • MoNA: KO000462
  • MoNA: KO000463
  • MoNA: KO000464
  • MoNA: KO000465
  • MoNA: KO000495
  • MoNA: KO000496
  • MoNA: KO000497
  • MoNA: KO000498
  • MoNA: KO000499
  • MoNA: MoNA010095
  • MoNA: MoNA010096
  • MoNA: MoNA010097
  • MoNA: MoNA010098
  • MoNA: MoNA010099
  • MoNA: MoNA010100
  • MoNA: MoNA016598
  • MoNA: MoNA016849
  • MoNA: MoNA034685
  • MoNA: MoNA034686
  • MoNA: MoNA034687
  • MoNA: MoNA038101
  • MoNA: MT000010
  • MoNA: NU000191
  • MoNA: NU000192
  • MoNA: NU000193
  • MoNA: NU000194
  • MoNA: NU000195
  • MoNA: NUTRI-METAB-FEM-NEG000146
  • MoNA: PR100737
  • MoNA: PR100738
  • MoNA: PS066801
  • MoNA: PS066802
  • MoNA: PS066803
  • MoNA: PS066804
  • MoNA: PS066807
  • MoNA: PS066808
  • MoNA: PS066809
  • MoNA: PS066810
  • MoNA: PS066811
  • MoNA: TY000180
  • MoNA: UF415351
  • MoNA: UF415352
  • MoNA: UF415353
  • MoNA: UF415354
  • MoNA: UF422951
  • MoNA: UF422952
  • MoNA: UF422953
  • MoNA: UF422954
  • MoNA: VF-NPL-LTQ000250
  • MoNA: VF-NPL-LTQ000252
  • MoNA: VF-NPL-LTQ007113
  • MoNA: VF-NPL-LTQ007114
  • MoNA: VF-NPL-LTQ007116
  • MoNA: VF-NPL-QEHF000517
  • MoNA: VF-NPL-QEHF000518
  • MoNA: VF-NPL-QEHF000519
  • MoNA: VF-NPL-QEHF000520
  • MoNA: VF-NPL-QEHF000521
  • MoNA: VF-NPL-QEHF000522
  • MoNA: VF-NPL-QEHF000523
  • MoNA: VF-NPL-QEHF000524
  • MoNA: VF-NPL-QEHF000525
  • MoNA: VF-NPL-QEHF013867
  • MoNA: VF-NPL-QEHF013868
  • MoNA: VF-NPL-QEHF013869
  • MoNA: VF-NPL-QEHF013870
  • MoNA: VF-NPL-QEHF013871
  • MoNA: VF-NPL-QEHF013872
  • MoNA: VF-NPL-QEHF013873
  • MoNA: VF-NPL-QEHF013874
  • MoNA: VF-NPL-QEHF013875
  • MoNA: VF-NPL-QTOF007071
  • MoNA: VF-NPL-QTOF007072
  • MoNA: VF-NPL-QTOF007073
  • MoNA: VF-NPL-QTOF007074
  • MoNA: VF-NPL-QTOF007075
  • MoNA: VF-NPL-QTOF007076
  • MoNA: VF-NPL-QTOF007077
  • MoNA: VF-NPL-QTOF007078
  • MoNA: VF-NPL-QTOF007079
  • Metlin: METLIN_206
  • Coconut NaturalProduct: CNP0216438.2
  • Coconut NaturalProduct: CNP0256496.2
  • Coconut NaturalProduct: CNP0270280.1
  • Coconut NaturalProduct: CNP0347795.1
  • Coconut NaturalProduct: CNP0347795.11
  • Coconut NaturalProduct: CNP0347795.15
  • Coconut NaturalProduct: CNP0347795.2
  • Coconut NaturalProduct: CNP0507127.1
  • Coconut NaturalProduct: CNP0507127.2
  • Coconut NaturalProduct: CNP0507127.3
  • Coconut NaturalProduct: CNP0507127.4
  • Coconut NaturalProduct: CNP0576926.1
  • Coconut NaturalProduct: CNP0576926.2
  • Coconut NaturalProduct: CNP0576926.3
  • Coconut NaturalProduct: CNP0576926.4
  • Coconut NaturalProduct: CNP0581428.1
  • Coconut NaturalProduct: CNP0581428.2
  • Coconut NaturalProduct: CNP0581428.3
  • Coconut NaturalProduct: CNP0581428.4

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02792 1.1.1.159 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanate:NAD+ 7-oxidoreductase
KEGG:R02793 1.1.1.176 3alpha,7alpha,12alpha-trihydroxy-5beta-cholanate:NADP+ 12-oxidoreductase
KEGG:R02794 6.2.1.7 cholate:CoA ligase (AMP-forming)
KEGG:R02797 3.5.1.24 taurocholate amidohydrolase
KEGG:R02798 C00695<=>C11637 + C00001
KEGG:R05835 3.5.1.24 glycocholate amidohydrolase
KEGG:R07220 deoxycholate:FAD oxidoreductase (7alpha-dehydroxylating)
KEGG:R07295 2.8.3.25 deoxycholoyl-CoA:cholate CoA-transferase
KEGG:R07296 3.1.2.27 choloyl-CoA hydrolase
KEGG:R11539 2.8.3.25 lithocholoyl-CoA:cholate CoA-transferase
KEGG:R12550 1.14.14.139 chenodeoxycholate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (12alpha-hydroxylating)
BioCyc:RXN-17385 3.5.1.74 CPD-3743 + WATER --> CHOLATE + TAURINE
BioCyc:CHOLOYLGLYCINE-HYDROLASE-RXN 3.5.1.24 GLYCOCHOLIC_ACID + WATER --> CHOLATE + GLY
BioCyc:7-ALPHA-HYDROXYSTEROID-DEH-RXN 1.1.1.159 NAD + CHOLATE --> PROTON + NADH + CHOLANATE2
BioCyc:TRANS-RXN0-527 cholate diffusion
BioCyc:TRANS-RXN0-588 cholate:proton antiport
BioCyc:RXN-21344 2.8.3.25 CPD-18832 + CHOLATE --> CPD-202 + CPD-23245
BioCyc:RXN-17406 2.8.3.25 CPD-10557 + CHOLATE --> CPD-202 + CPD-7235
BioCyc:RXN-21338 CPD-18820 + CHOLATE --> CPD-23236 + CPD-202
BioCyc:RXN-21335 2.8.3.25 3-OXO-DELTA4-CHOLYL-COA + CHOLATE --> CPD-7273 + CPD-202
View More
Organism Source

Taxonomy Source

  1. Negombata magnifica [ncbi taxid: 344322]
  2. Hymenoxys insignis [ncbi taxid: ]
  3. Bos taurus [ncbi taxid: 9913]
  4. Bubalus bubalis [ncbi taxid: 89462]
  5. Calculus bovis artificiosus [ncbi taxid: ]
  6. Homo sapiens [ncbi taxid: 9606]
  7. Mus musculus [ncbi taxid: 10090]
  8. Ursus arctos [ncbi taxid: 9644]
  9. Ursus thibetanus [ncbi taxid: 9642]
  10. Homo sapiens [ncbi taxid: 9606]

Pathway Synthetic

pathway id name
WikiPathways:WP1 Statin pathway
WikiPathways:WP3604 Biochemical pathways: part I
WikiPathways:WP4545 Oxysterols derived from cholesterol
WikiPathways:WP145 Statin pathway
PathBank:SMP0120468 Congenital Bile Acid Synthesis Defect Type III
PathBank:SMP0000318 Congenital Bile Acid Synthesis Defect Type III
PathBank:SMP0086608 Bile Acid Direct Signalling Pathway (1)
PathBank:SMP0089751 Bile Acid Direct Signalling Pathway (2)
PathBank:SMP0120697 Familial Hypercholanemia (FHCA)
PathBank:SMP0120463 Cerebrotendinous Xanthomatosis (CTX)
PathBank:SMP0120467 Congenital Bile Acid Synthesis Defect Type II
PathBank:SMP0120495 Zellweger Syndrome
PathBank:SMP0000035 Bile Acid Biosynthesis
PathBank:SMP0000314 Congenital Bile Acid Synthesis Defect Type II
PathBank:SMP0000315 Cerebrotendinous Xanthomatosis (CTX)
PathBank:SMP0087329 Bile Acid Biosynthesis
PathBank:SMP0120652 27-Hydroxylase Deficiency
PathBank:SMP0120688 Congenital Bile Acid Synthesis Defect Type III
PathBank:SMP0120477 Familial Hypercholanemia (FHCA)
PathBank:SMP0000317 Familial Hypercholanemia (FHCA)
View All Pathways