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
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.
DBLinks
- CAS Registry Number: 81-25-4
- PubChem CID: 221493
- ChEBI: 16359
- HMDB: HMDB0000619
- LipidMaps: LMST04010001
- KEGG: C00695
- BioCyc: CHOLATE
- NCBI MeSH: Cholic Acid
- Wikipedia: Cholic_Acid
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
- WishartLab ClassyFire: [Bile acids, alcohols and derivatives] Bile acids, alcohols and derivatives
- RefMet: [C24 bile acids] C24 bile acids
- LipidMaps: [C24 bile acids, alcohols, and derivatives [ST0401]] C24 bile acids, alcohols, and derivatives [ST0401]
- ChEBI: [CHEBI:16359] cholic acid
- Coconut NaturalProduct: [Cholestane steroids] Cholestane steroids
- Coconut NaturalProduct: [Cholane steroids] Cholane steroids
- Coconut NaturalProduct: [Androstane steroids] Androstane steroids
- Coconut NaturalProduct: [Pseudoguaiane sesquiterpenoids] Pseudoguaiane sesquiterpenoids
| 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 |
Taxonomy Source
- Negombata magnifica [ncbi taxid: 344322]
- Hymenoxys insignis [ncbi taxid: ]
- Bos taurus [ncbi taxid: 9913]
- Bubalus bubalis [ncbi taxid: 89462]
- Calculus bovis artificiosus [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Ursus arctos [ncbi taxid: 9644]
- Ursus thibetanus [ncbi taxid: 9642]
- 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) |