cholic acid (CHEBI:16359)

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CHEBI:16359 - cholic acid

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ChEBI Name	cholic acid

ChEBI ID	CHEBI:16359

Definition	A bile acid that is 5β-cholan-24-oic acid bearing three α-hydroxy substituents at position 3, 7 and 12.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:1694, CHEBI:20223, CHEBI:41494, CHEBI:23210, CHEBI:29077

Supplier Information	ChemicalBook:CB9263222, ChemicalBook:CB52741764, eMolecules:29504030, eMolecules:30512922, eMolecules:29541145, ZINC000006858022

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69 72 0 0 1 0 999 V2000

-0.8933 -0.1532 -1.3445 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.3283 0.9495 -0.3903 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.8294 -1.5781 -0.6685 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.3205 0.1677 -1.8816 C 0 0 1 0 0 0 0 0 0 0 0 0

1.1440 0.7035 0.0893 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.3713 2.4306 -0.8230 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3267 -2.7599 -1.6064 C 0 0 2 0 0 0 0 0 0 0 0 0

0.5304 -1.8387 0.0637 C 0 0 0 0 0 0 0 0 0 0 0 0

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-3.2259 0.4457 -0.8124 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3755 2.0112 0.9346 C 0 0 2 0 0 0 0 0 0 0 0 0

1.1078 -0.6562 0.8837 C 0 0 2 0 0 0 0 0 0 0 0 0

2.1971 0.6124 -1.0782 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6397 3.1177 0.1170 C 0 0 0 0 0 0 0 0 0 0 0 0

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2.8082 2.4195 1.4487 C 0 0 1 0 0 0 0 0 0 0 0 0

0.3970 -0.5573 2.1207 O 0 0 0 0 0 0 0 0 0 0 0 0

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2.7652 3.7590 2.2528 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4852 1.3005 2.2920 C 0 0 0 0 0 0 0 0 0 0 0 0

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4.1178 4.3265 2.7615 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.9814 -4.0779 0.4637 O 0 0 0 0 0 0 0 0 0 0 0 0

3.9696 5.5574 3.5022 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2928 5.5704 4.5253 O 0 0 0 0 0 0 0 0 0 0 0 0

4.5092 6.5912 3.1366 O 0 0 0 0 0 0 0 0 0 0 0 0

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2.1072 -0.9791 1.1675 H 0 0 0 0 0 0 0 0 0 0 0 0

2.2450 1.5248 -1.6741 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2015 0.4277 -0.6968 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0001 -0.1955 -1.7812 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1197 3.8102 0.7873 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3369 3.7113 -0.4810 H 0 0 0 0 0 0 0 0 0 0 0 0

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3.4442 2.5948 0.5759 H 0 0 0 0 0 0 0 0 0 0 0 0

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2.0840 3.6268 3.0993 H 0 0 0 0 0 0 0 0 0 0 0 0

2.3370 4.5469 1.6270 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4833 1.5648 2.6331 H 0 0 0 0 0 0 0 0 0 0 0 0

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1 2 1 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

2 5 1 0 0 0 0

2 6 1 0 0 0 0

3 7 1 0 0 0 0

3 8 1 0 0 0 0

4 9 1 0 0 0 0

4 10 1 0 0 0 0

5 11 1 0 0 0 0

5 12 1 0 0 0 0

5 13 1 0 0 0 0

6 14 1 0 0 0 0

7 15 1 0 0 0 0

7 16 1 0 0 0 0

7 17 1 0 0 0 0

11 18 1 0 0 0 0

12 19 1 0 0 0 0

15 20 1 0 0 0 0

16 21 1 0 0 0 0

18 22 1 0 0 0 0

18 23 1 0 0 0 0

20 24 1 0 0 0 0

22 25 1 0 0 0 0

24 26 1 0 0 0 0

25 27 1 0 0 0 0

27 28 1 0 0 0 0

27 29 2 0 0 0 0

8 12 1 0 0 0 0

9 15 1 0 0 0 0

11 14 1 0 0 0 0

21 24 1 0 0 0 0

1 30 1 0 0 0 0

2 31 1 0 0 0 0

3 32 1 0 0 0 0

11 33 1 0 0 0 0

15 34 1 0 0 0 0

4 35 1 0 0 0 0

6 36 1 0 0 0 0

6 37 1 0 0 0 0

8 38 1 0 0 0 0

8 39 1 0 0 0 0

9 40 1 0 0 0 0

9 41 1 0 0 0 0

10 42 1 0 0 0 0

12 43 1 0 0 0 0

13 44 1 0 0 0 0

13 45 1 0 0 0 0

13 46 1 0 0 0 0

14 47 1 0 0 0 0

14 48 1 0 0 0 0

16 49 1 0 0 0 0

16 50 1 0 0 0 0

17 51 1 0 0 0 0

17 52 1 0 0 0 0

17 53 1 0 0 0 0

18 54 1 0 0 0 0

19 55 1 0 0 0 0

20 56 1 0 0 0 0

20 57 1 0 0 0 0

21 58 1 0 0 0 0

21 59 1 0 0 0 0

22 60 1 0 0 0 0

22 61 1 0 0 0 0

23 62 1 0 0 0 0

23 63 1 0 0 0 0

23 64 1 0 0 0 0

24 65 1 0 0 0 0

25 66 1 0 0 0 0

25 67 1 0 0 0 0

26 68 1 0 0 0 0

28 69 1 0 0 0 0

M END): 17 ms

reading 69 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

69 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
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Formula

C24H40O5

Net Charge

Average Mass

408.57140

Monoisotopic Mass

408.28757

InChI

InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

InChIKey

BHQCQFFYRZLCQQ-OELDTZBJSA-N

SMILES

[H][C@@]12C[C@H](O)CC[C@]1(C)[C@@]1([H])C[C@H](O)[C@]3(C)[C@]([H])(CC[C@@]3([H])[C@]1([H])[C@H](O)C2)[C@H](C)CCC(O)=O

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	See: DOI
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	cholic acid (CHEBI:16359) has role human metabolite (CHEBI:77746) cholic acid (CHEBI:16359) has role mouse metabolite (CHEBI:75771) cholic acid (CHEBI:16359) is a 12α-hydroxy steroid (CHEBI:36846) cholic acid (CHEBI:16359) is a 3α-hydroxy steroid (CHEBI:36835) cholic acid (CHEBI:16359) is a 7α-hydroxy steroid (CHEBI:36843) cholic acid (CHEBI:16359) is a bile acid (CHEBI:3098) cholic acid (CHEBI:16359) is a C₂₄-steroid (CHEBI:131620) cholic acid (CHEBI:16359) is a trihydroxy-5β-cholanic acid (CHEBI:27114) cholic acid (CHEBI:16359) is conjugate acid of cholate (CHEBI:29747)

Incoming	(23S)-methyl-3α,7α,12α-trihydroxy-5β-cholan-24-oic acid (CHEBI:488147) has functional parent cholic acid (CHEBI:16359) 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate (CHEBI:1418) has functional parent cholic acid (CHEBI:16359) N-(2-phosphonoethyl)cholamide (CHEBI:1019) has functional parent cholic acid (CHEBI:16359) S-choloyl-4ʼ-phosphopantetheine (CHEBI:132321) has functional parent cholic acid (CHEBI:16359) cholate salt (CHEBI:23169) has functional parent cholic acid (CHEBI:16359) cholic acid 24-O-(β-D-glucuronide) (CHEBI:137791) has functional parent cholic acid (CHEBI:16359) Cholic acid sulfate (CHEBI:233476) has functional parent cholic acid (CHEBI:16359) choloyl-CoA (CHEBI:15519) has functional parent cholic acid (CHEBI:16359) glycochenodeoxycholic acid 7-sulfate (CHEBI:52031) has functional parent cholic acid (CHEBI:16359) glycocholic acid (CHEBI:17687) has functional parent cholic acid (CHEBI:16359) hyodeoxycholic acid (CHEBI:52023) has functional parent cholic acid (CHEBI:16359) murideoxycholic acid (CHEBI:52030) has functional parent cholic acid (CHEBI:16359) taurocholic acid (CHEBI:28865) has functional parent cholic acid (CHEBI:16359) taurohyocholic acid (CHEBI:52022) has functional parent cholic acid (CHEBI:16359) cholate (CHEBI:29747) is conjugate base of cholic acid (CHEBI:16359)

IUPAC Name

3α,7α,12α-trihydroxy-5β-cholan-24-oic acid

Synonyms	Sources
(3α,5β,7α,12α)-3,7,12-trihydroxycholan-24-oic acid	NIST Chemistry WebBook
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate	KEGG COMPOUND
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid	KEGG COMPOUND
3α,7α,12α-trihydroxy-5β-cholanic acid	NIST Chemistry WebBook
CHOLIC ACID	PDBeChem
Cholic acid	KEGG COMPOUND
Cholsäure	ChEBI

Manual Xrefs	Databases
3096	DrugCentral
C00695	KEGG COMPOUND
CHD	PDBeChem
CHOLATE	MetaCyc
Cholic_Acid	Wikipedia
DB02659	DrugBank
HMDB0000619	HMDB
LMST04010001	LIPID MAPS
LSM-5541	LINCS
View more database links

Registry Numbers	Types	Sources
2822009	Reaxys Registry Number	Reaxys
81-25-4	CAS Registry Number	ChemIDplus
81-25-4	CAS Registry Number	NIST Chemistry WebBook

Citation

Last Modified

01 September 2017

CHEBI:16359 - cholic acid

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