Compound
(R)-lipoate
A lipoate that is the conjugate base of (R)-lipoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.
Definition from ChEBI (CHEBI:83088), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound, anion
- Formula
- C8H13O2S2
- Mass
- 205.324 g/mol
- Charge
- -1
- InChIKey
- AGBQKNBQESQNJD-SSDOTTSWSA-M
- SMILES
- O=C([O-])CCCC[C@@H]1CCSS1
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
5 entities
5 entities reached.
0 reported hops5 assembled from the scaffold
- DLDProteinUNIPROT:P09622substrate ofInferred only48 paths48 endpoints
- LIPAProteinUNIPROT:P38571substrate ofInferred only9 paths9 endpoints
- ACSM1ProteinUNIPROT:Q08AH1substrate ofInferred only8 paths8 endpoints
- SLC5A6ProteinUNIPROT:Q9Y289transported byInferred only8 paths4 endpoints
- CELProteinUNIPROT:P19835substrate ofInferred only8 paths8 endpoints
What the reference databases state
Statements
12 statements
12 statements · 3 reference databases · Subject: (R)-lipoate · Sources: Human-GEM, Rhea, UniProt
- (R)-lipoyl-5'-AMP is converted to (R)-lipoateCompoundRhea RHEA:12913Inferred only
- (R)-lipoate is converted to (R)-lipoyl-5'-AMPCompoundRhea RHEA:12913Inferred only
- DBT requires the cofactor (R)-lipoateProteinUniProt P11182Inferred only
- DLAT requires the cofactor (R)-lipoateProteinUniProt P10515Inferred only
- DLST requires the cofactor (R)-lipoateProteinUniProt P36957Inferred only
- GCSH requires the cofactor (R)-lipoateProteinUniProt P23434Inferred only
- (R)-lipoate is a substrate of ACSM1ProteinRhea RHEA:46700Inferred only
- (R)-lipoate is a substrate of CELProteinHuman-GEM MAR06405Inferred only
- (R)-lipoate is a substrate of DLDProteinHuman-GEM MAR06397Inferred only
- (R)-lipoate is a substrate of LIPAProteinHuman-GEM MAR06405Inferred only
- (R)-lipoate is transported by SLC5A6ProteinRhea RHEA:73379Inferred only
- (R)-lipoate is transported by SLC5A6ProteinHuman-GEM MAR09608Inferred only
Reactions
12 reactions
CHEBI:17208+(R)-lipoatedehydroascorbic acid+MAM01702c
Reaction pageReversibleBalancedEC 1.8.5.-cytosol
Human-GEM MAR06394CC BY 4.0Reference data
proton+(R)-lipoate+NADH(2-)MAM01702c+NAD(+)
Catalysed by DLD
Reaction pageReversibleBalancedEC 1.8.1.4cytosol
Human-GEM MAR06397CC BY 4.0Reference data
water+MAM02399c(R)-lipoate+CHEBI:18019
Reaction pageReversibleBalancedEC 3.1.1.13cytosol
Human-GEM MAR06405CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR09167CC BY 4.0Reference data
(R)-lipoate+2sodium(1+)(R)-lipoate+2sodium(1+)
Transported by SLC5A6
Reaction pageLeft to rightBalancedextracellular space, cytosol
Human-GEM MAR09608CC BY 4.0Reference data
0.034511-cis-retinol+0.0172all-trans-18-hydroxyretinoate+0.0172all-trans-18-hydroxyretinoate+0.0172MAM00611c+0.0172MAM00611m+0.0172MAM00622c+0.0172MAM00622m+0.0345MAM00766c+0.0172MAM01008c+0.0172MAM01008r+0.0172MAM01022c+0.0172MAM01022r+0.0172MAM01024c+0.0172MAM01024r+0.0345MAM01026r+0.0172MAM01028c+0.0172MAM01028r+0.0172MAM01030c+0.0172MAM01030r+0.0172all-trans-4-oxoretinoate+0.0172all-trans-4-oxoretinoate+0.0345all-trans-4-oxoretinol+0.0345MAM01060c+0.03459-cis-retinol+0.0345biotin+0.0345MAM01600m+0.0345FADH2+0.0345MAM01924c+0.0345heme b+0.0345(S)-carnitine+0.0345(R)-lipoate+0.0345MAM02624c+0.0345CHEBI:18405+0.0345riboflavin+0.03455,6,7,8-tetrahydrobiopterin+0.03455,6,7,8-tetrahydrofolic acid+0.0345thiamine(1+) diphosphate+0.0345ubiquinolMAM10012c
Reaction pageLeft to rightBalance undeterminablecytosol, endoplasmic reticulum, mitochondrial matrix
Human-GEM MAR10065CC BY 4.0Reference data
(R)-lipoate+ATP(4-)+hydron(R)-lipoyl-5'-AMP+diphosphate(3-)
Reaction pageDirection not assertedBalanced
Rhea RHEA:12913CC BY 4.0Reference data
Reaction pageDirection not assertedBalanced
Rhea RHEA:29755CC BY 4.0Reference data
(R)-lipoate+GTP+hydronCHEBI:86460+diphosphate(3-)
Catalysed by ACSM1
Reaction pageLeft to rightBalanced
Rhea RHEA:46700CC BY 4.0Reference data
L-lysyl-[lipoyl-carrier protein]+(R)-lipoate+ATP(4-)N(6)-[(R)-lipoyl]-L-lysyl-[lipoyl-carrier protein]+AMP+diphosphate(3-)+hydron
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:49288CC BY 4.0Reference data
(R)-lipoate+2sodium(1+)(R)-lipoate+2sodium(1+)
Transported by SLC5A6
Reaction pageDirection not assertedBalanced
Rhea RHEA:73379CC BY 4.0Reference data
N(6)-[(R)-lipoyl]-L-lysyl-[lipoyl-carrier protein]+waterL-lysyl-[lipoyl-carrier protein]+(R)-lipoate
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:76519CC BY 4.0Reference data
Where it reaches
2 systems, 2 regions, 3 tissues, 3 transporter routes — routes, not measurements: transporters known to carry (R)-lipoate are expressed there, and no source reports it arriving.
Loading the model…
Other names
1 name
Resolves to: (R)-lipoate
- Systematic name
- 5-[(3R)-1,2-dithiolan-3-yl]pentanoate