Cholic acid (C24H40O5): structure, properties and hazards

Names and identifiers

IUPAC name: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Synonyms: bile acid, cholalic acid, Cholalic acid
+ 37 more
Colalin, Cholalin, Cholbam, Cholsaeure, cholicacid, NSC-6135, kolbam, orphacol, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oic acid, 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid, Cholic acid, 5beta-, 3,7,12-Trihydroxycholanic acid, (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid, G1JO7801AE, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3alpha,5beta,7alpha,12alpha)-, DTXSID6040660, CHEBI:16359, 3-alpha,7-alpha,12-alpha-Trihydroxycholansaeure, 17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3alpha,7alpha,12alpha-triol, 3,7,12-Trihydroxy-cholan-24-oic acid (3-alpha,5-beta,7-alpha,12-alpha), Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha,5-beta,7-alpha,12-alpha)-, (4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoic acid, RefChem:54816, DTXCID4020660, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-alpha, 5-beta, 7-alpha, 12-alpha)-, (4R)-4-((1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid, (4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-yl)pentanoic acid, 201-337-8, MFCD00003672, (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid, Cholic acid [USAN], C24H40O5, HSDB 982, Cholan-24-oic acid, 3,7,12-trihydroxy-, (3a,5b,7a,12a)-, Ursodeoxycholic Acid EP Impurity B, CHEMBL205596, NSC6135
Molecular formula: C₂₄H₄₀O₅
Empirical formula: C₂₄H₄₀O₅
Molecular weight: 408.6 g/mol
Exact mass: 408.28757
CAS number: 81-25-4
PubChem CID: 221493
Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

Appearance: Crystals[1]
Solubility in water: In water, 175 mg/L at 20 °C[1]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source
–shown In water, 175 mg/L at 20 °C [1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 1303
– Soluble in glacial acetic acid; practically insoluble in benzene [1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V2: 1115
log P: log Kow = 2.02[1]
pKa: pKa = 4.98 at 20 °C[1]

Value	As written	Source
–shown	In water, 175 mg/L at 20 °C	[1] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 1303
–	Soluble in glacial acetic acid; practically insoluble in benzene	[1] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V2: 1115

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms: 29
Rings: 4
Aromatic rings: 0
Fraction sp³ carbons (Fsp3): 0.96
H-bond donors: 4
H-bond acceptors: 4 computed here · PubChem 5
Rotatable bonds: 4
TPSA (Å²): 98
Formal charge: 0
XLogP3: 3.6 PubChem
Complexity: 637 PubChem
Stereocenters: 11 definedCIP: C2: R · C8: R · C11: S · C12: R · C13: R · C16: S · C18: R · C22: S · C24: S · C26: S · C28: R
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C70.55%
H9.87%
O19.58%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: 3.45 Crippen (Wildman and Crippen 1999)
log S (water solubility): -4.28 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 4.55 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 408.58
log P ≤ 5 (Crippen): 3.45
H-bond donors ≤ 5: 4
H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 15 company reports to ECHA. Source [2].

Harmful or irritant

H312Harmful in contact with skin (40% of reports)
H315Causes skin irritation (73.3% of reports)
H317May cause an allergic skin reaction (40% of reports)
H319Causes serious eye irritation (66.7% of reports)

Precautionary statements: P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P317, P321, P332+P317, P333+P317, P337+P317, P362+P364, P501

View all classifications (2)

[2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 26.7% (4 of 15) of reports.
[2] European Chemicals Agency (ECHA) · 15 reports · WarningH312, H315, H317, H319

Storage

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. Storage class (TRGS 510): Non Combustible Solids.[1]

Safety data sheets on the supplier’s page: Finetech Industry Limited, BOC Sciences, Alfa Chemistry.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
[2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
[6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[7]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.

Similar structures

Sodium deoxycholate 60%

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.