Compound

lithocholate

A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.

Definition from MeSH (D008095), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:29744ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of lithocholate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C24H39O3
Mass: 375.573 g/mol
Charge: -1
InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-M
SMILES: [H][C@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCC(=O)[O-])[C@@]1(C)CC[C@@H](O)C2
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

6 entities

6 entities reached.

0 reported hops6 assembled from the scaffold

What the reference databases state

Chemical structure

beta-D-glucosyl-(1->3)-O-lithocholate has the functional parent lithocholateCompoundChEBI CHEBI:142611Inferred only

Statements

17 statements

17 statements · 1 reference database · Subject: lithocholate · Sources: Rhea

Order

3-oxo-5beta-cholan-24-oate is converted to lithocholateCompoundRhea RHEA:47496Inferred only
lithocholate is converted to 3-oxo-5beta-cholan-24-oateCompoundRhea RHEA:19585Inferred only
3-oxo-5beta-cholan-24-oate is converted to lithocholateCompoundRhea RHEA:19585Inferred only
chenodeoxycholate is converted to lithocholateCompoundRhea RHEA:11572Inferred only
lithocholate is converted to chenodeoxycholateCompoundRhea RHEA:11572Inferred only
lithocholate is converted to lithocholate 3-sulfateCompoundRhea RHEA:51064Inferred only
lithocholate is converted to lithocholoyl-24-O-(beta-D-glucuronate)CompoundRhea RHEA:52952Inferred only
lithocholate is converted to lithocholoyl-3-O-(beta-D-glucuronate)CompoundRhea RHEA:53028Inferred only
lithocholate is converted to lithocholoyl-CoACompoundRhea RHEA:47136Inferred only
lithocholate is metabolised by SULT1C3ProteinRhea RHEA:51064Inferred only
lithocholate is metabolised by SULT2A1ProteinRhea RHEA:51064Inferred only
lithocholate is metabolised by UGT1A3ProteinRhea RHEA:52952Inferred only

Show the remaining 5

lithocholate is metabolised by UGT2A1ProteinRhea RHEA:52952Inferred only
lithocholate is metabolised by UGT2A1ProteinRhea RHEA:53028Inferred only
lithocholate is metabolised by UGT2A2ProteinRhea RHEA:52952Inferred only
lithocholate is a substrate of SLC27A5ProteinRhea RHEA:47136Inferred only
lithocholate is transported by SLCO1B3-SLCO1B7ProteinRhea RHEA:73139Inferred only

Reactions

16 reactions

lithocholate+FAD(3-)+water+hydronchenodeoxycholate+FADH2(2-)
Reaction pageDirection not assertedBalanced
Rhea RHEA:11572CC BY 4.0Reference data
lithocholate+reduced [NADPH--hemoprotein reductase]+dioxygenCHEBI:58876+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:18857CC BY 4.0Reference data
lithocholate+NAD(1-)3-oxo-5beta-cholan-24-oate+NADH(2-)+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:19585CC BY 4.0Reference data
lithocholate+reduced [NADPH--hemoprotein reductase]+dioxygenhyodeoxycholate+oxidized [NADPH--hemoprotein reductase]+water+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:23644CC BY 4.0Reference data
lithocholate+ATP(4-)+coenzyme A(4-)lithocholoyl-CoA+AMP+diphosphate(3-)
Catalysed by SLC27A5
Reaction pageLeft to rightBalanced
Rhea RHEA:47136CC BY 4.0Reference data
lithocholate+NADP(3-)3-oxo-5beta-cholan-24-oate+NADPH(4-)+hydron
Catalysed by DHRS4
Reaction pageRight to leftBalanced
Rhea RHEA:47496CC BY 4.0Reference data
lithocholoyl-CoA+cholatecholoyl-CoA+lithocholate
Reaction pageDirection not assertedBalanced
Rhea RHEA:49432CC BY 4.0Reference data
lithocholate+3'-phosphoadenylyl sulfatelithocholate 3-sulfate+adenosine 3',5'-bisphosphate+hydron
Catalysed by SULT2A1 or SULT1C3
Reaction pageLeft to rightBalanced
Rhea RHEA:51064CC BY 4.0Reference data
lithocholate+UDP-alpha-D-glucuronatelithocholoyl-24-O-(beta-D-glucuronate)+UDP
Catalysed by UGT2A1 or UGT2A2 or UGT1A3
Reaction pageLeft to rightBalanced
Rhea RHEA:52952CC BY 4.0Reference data
lithocholate+UDP-alpha-D-glucuronatelithocholoyl-3-O-(beta-D-glucuronate)+UDP+hydron
Catalysed by UGT2A1
Reaction pageLeft to rightBalanced
Rhea RHEA:53028CC BY 4.0Reference data
CHEBI:137661+lithocholoyl-CoACHEBI:137663+lithocholate
Reaction pageDirection not assertedBalanced
Rhea RHEA:53764CC BY 4.0Reference data
lithocholoyl-CoA+chenodeoxycholatechenodeoxycholoyl-CoA+lithocholate
Reaction pageDirection not assertedBalanced
Rhea RHEA:53772CC BY 4.0Reference data

Show the remaining 4

Other names

2 names

Resolves to: lithocholate

Systematic name: 3alpha-hydroxy-5beta-cholan-24-oate3α-hydroxy-5β-cholan-24-oate