DT-Web

DB00166 - Lipoic Acid


Identification
Name Lipoic Acid
Accession Number DB00166 (NUTR00035)
Type small molecule
Description A vitamin-like antioxidant. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 206.326
Groups approved
Monoisotopic Weight 206.043521072
Pharmacology
Indication For nutritional supplementation, also for treating dietary shortage or imbalance.
Mechanism of action Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Lipoyltransferase 1, mitochondrial
Name Lipoyltransferase 1, mitochondrial
Gene Name LIPT1
Pharmacological action unknown
Actions Not Available
References
  • Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. - Pubmed
  • Fujiwara K, Toma S, Okamura-Ikeda K, Motokawa Y, Nakagawa A, Taniguchi H: Crystal structure of lipoate-protein ligase A from Escherichia coli. Determination of the lipoic acid-binding site. J Biol Chem. 2005 Sep 30;280(39):33645-51. Epub 2005 Jul 25. - Pubmed
  • Gueguen V, Macherel D, Neuburger M, Pierre CS, Jaquinod M, Gans P, Douce R, Bourguignon J: Structural and functional characterization of H protein mutants of the glycine decarboxylase complex. J Biol Chem. 1999 Sep 10;274(37):26344-52. - Pubmed
  • Macherel D, Bourguignon J, Forest E, Faure M, Cohen-Addad C, Douce R: Expression, lipoylation and structure determination of recombinant pea H-protein in Escherichia coli. Eur J Biochem. 1996 Feb 15;236(1):27-33. - Pubmed
  • Fujiwara K, Hosaka H, Matsuda M, Okamura-Ikeda K, Motokawa Y, Suzuki M, Nakagawa A, Taniguchi H: Crystal structure of bovine lipoyltransferase in complex with lipoyl-AMP. J Mol Biol. 2007 Aug 3;371(1):222-34. Epub 2007 May 26. - Pubmed
DTHybrid score 1.1303
Lipoic acid synthetase, mitochondrial
Name Lipoic acid synthetase, mitochondrial
Gene Name LIAS
Pharmacological action unknown
Actions Not Available
References
  • Morikawa T, Yasuno R, Wada H: Do mammalian cells synthesize lipoic acid? Identification of a mouse cDNA encoding a lipoic acid synthase located in mitochondria. FEBS Lett. 2001 Jun 1;498(1):16-21. - Pubmed
  • Yasuno R, Wada H: Biosynthesis of lipoic acid in Arabidopsis: cloning and characterization of the cDNA for lipoic acid synthase. Plant Physiol. 1998 Nov;118(3):935-43. - Pubmed
  • Ollagnier-de Choudens S, Fontecave M: The lipoate synthase from Escherichia coli is an iron-sulfur protein. FEBS Lett. 1999 Jun 18;453(1-2):25-8. - Pubmed
  • Wrenger C, Muller S: The human malaria parasite Plasmodium falciparum has distinct organelle-specific lipoylation pathways. Mol Microbiol. 2004 Jul;53(1):103-13. - Pubmed
  • Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. - Pubmed
DTHybrid score 1.1302
Sodium-dependent multivitamin transporter
Name Sodium-dependent multivitamin transporter
Gene Name SLC5A6
Pharmacological action unknown
Actions Not Available
References
  • Prasad PD, Wang H, Huang W, Fei YJ, Leibach FH, Devoe LD, Ganapathy V: Molecular and functional characterization of the intestinal Na+-dependent multivitamin transporter. Arch Biochem Biophys. 1999 Jun 1;366(1):95-106. - Pubmed
  • Dey S, Subramanian VS, Chatterjee NS, Rubin SA, Said HM: Characterization of the 5' regulatory region of the human sodium-dependent multivitamin transporter, hSMVT. Biochim Biophys Acta. 2002 Mar 19;1574(2):187-92. - Pubmed
  • Griffin JB, Stanley JS, Zempleni J: Synthesis of a rabbit polyclonal antibody to the human sodium-dependent multivitamin transporter. Int J Vitam Nutr Res. 2002 Jul;72(4):195-8. - Pubmed
DTHybrid score 1.5401

Enzymes


NADPH--cytochrome P450 reductase
Name NADPH--cytochrome P450 reductase
Gene Name POR
Actions inhibitor
References
  • Dudka J: Decrease in NADPH-cytochrome P450 reductase activity of the human heart, Liver and lungs in the presence of alpha-lipoic acid. Ann Nutr Metab. 2006;50(2):121-5. Epub 2006 Jan 2. - Pubmed
  • Wen B, Coe KJ, Rademacher P, Fitch WL, Monshouwer M, Nelson SD: Comparison of in vitro bioactivation of flutamide and its cyano analogue: evidence for reductive activation by human NADPH:cytochrome P450 reductase. Chem Res Toxicol. 2008 Dec;21(12):2393-406. - Pubmed
  • Gan L, von Moltke LL, Trepanier LA, Harmatz JS, Greenblatt DJ, Court MH: Role of NADPH-cytochrome P450 reductase and cytochrome-b5/NADH-b5 reductase in variability of CYP3A activity in human liver microsomes. Drug Metab Dispos. 2009 Jan;37(1):90-6. Epub 2008 Oct 6. - Pubmed
DTHybrid score 0.6298

Predictions


Id Partner name Gene Name Score
81 Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial MCCC2 0.0659
547 Propionyl-CoA carboxylase alpha chain, mitochondrial PCCA 0.0658
495 Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial MCCC1 0.0658
177 Biotin--protein ligase HLCS 0.0658
690 Acetyl-CoA carboxylase 1 ACACA 0.0658
601 Propionyl-CoA carboxylase beta chain, mitochondrial PCCB 0.0534
771 Pyruvate carboxylase, mitochondrial PC 0.0484
775 Acetyl-CoA carboxylase 2 ACACB 0.04
1898 Cytochrome P450 1B1 CYP1B1 0.0345
685 Oxygen-insensitive NADPH nitroreductase nfsA 0.0327
6945 Oxygen-insensitive NADPH nitroreductase rdxA 0.0327
176 30S ribosomal protein S10 rpsJ 0.0325
6175 30S ribosomal protein S10 rpsJ 0.0325
4117 Probable pyruvate-flavodoxin oxidoreductase ydbK 0.0324
1588 Multidrug resistance protein 1 ABCB1 0.0312
6030 Cytochrome P450 2B6 CYP2B6 0.0215
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0199
4512 Cytochrome P450 3A4 CYP3A4 0.0187
146 Androgen receptor AR 0.0164
131 Synaptic vesicular amine transporter SLC18A2 0.0148
847 Mu-type opioid receptor OPRM1 0.013
713 Sodium-dependent dopamine transporter SLC6A3 0.0115
4924 Cytochrome P450 2C8 CYP2C8 0.0114
6016 Cytochrome P450 2C19 CYP2C19 0.011
4119 Cytochrome P450 2D6 CYP2D6 0.0105
4757 Cytochrome P450 2C9 CYP2C9 0.0105
318 Alpha-2A adrenergic receptor ADRA2A 0.0103
6107 Cytochrome P450 3A7 CYP3A7 0.0101
556 Alpha-1A adrenergic receptor ADRA1A 0.0097
6137 Multidrug resistance-associated protein 6 ABCC6 0.0096
3947 Xanthine dehydrogenase/oxidase XDH 0.0095
6148 Multidrug resistance-associated protein 7 ABCC10 0.0089
817 DNA topoisomerase 2-alpha TOP2A 0.0084
76 Nitric-oxide synthase, brain NOS1 0.0082
776 Bile salt export pump ABCB11 0.0076
6861 Alcohol dehydrogenase [NADP+] AKR1A1 0.0075
4192 DNA topoisomerase 2-beta TOP2B 0.0072
862 Multidrug resistance-associated protein 1 ABCC1 0.007
3573 2,4-dienoyl-CoA reductase [NADPH] fadH 0.0066
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0065
6172 ATP-binding cassette sub-family B member 8, mitochondrial ABCB8 0.0064
650 Aldo-keto reductase family 1 member C3 AKR1C3 0.0061
214 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial NDUFS3 0.0054
337 NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial NDUFS7 0.0054
803 NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NDUFS2 0.0054
6168 Solute carrier family 22 member 16 SLC22A16 0.0052
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.0049
5075 Sulfite reductase [NADPH] flavoprotein alpha-component cysJ 0.0047
5073 Ferredoxin--NADP reductase petH 0.0046
5076 Ferredoxin--NADP reductase fpr 0.0046
5119 Ferredoxin--NADP reductase petH 0.0046
5121 Ferredoxin--NADP reductase fpr 0.0046
654 Flavin reductase BLVRB 0.0043
5251 Carbonyl reductase [NADPH] 1 CBR1 0.0043
6144 Solute carrier family 22 member 2 SLC22A2 0.0042
6024 Cytochrome P450 1A1 CYP1A1 0.0038
4503 NADPH-flavin oxidoreductase frp 0.0035
5189 Trimethylamine dehydrogenase tmd 0.0035
4836 Ferredoxin-dependent glutamate synthase 2 gltS 0.0035
1302 Dihydropyrimidine dehydrogenase [NADP+] DPYD 0.0035
5201 FMN-binding protein DvMF_2023 0.0034
5178 Protein nrdI nrdI 0.0034
3293 Flavodoxin Not Available 0.0034
4614 Flavodoxin DVU_2680 0.0034
5172 Flavodoxin isiB 0.0034
5173 Flavodoxin isiB 0.0034
5182 Flavodoxin fldA 0.0034
5198 Flavodoxin-1 fldA 0.0034
5170 Epidermin decarboxylase epiD 0.0034
5179 Probable aromatic acid decarboxylase pad1 0.0034
5175 Hypothetical protein SMU.260 SMU_260 0.0034
5202 Nitroreductase family protein BC_1844 0.0034
5197 Trp repressor binding protein WrbA, putative DR_A0214 0.0034
2586 Isopentenyl-diphosphate Delta-isomerase idi 0.0034
5187 Isopentenyl-diphosphate delta-isomerase fni 0.0034
5199 Isopentenyl-diphosphate delta-isomerase fni 0.0034
5131 PhzG phzG 0.0034
5181 Hypothetical protein yhdA azr 0.0034
5190 Rubredoxin-oxygen oxidoreductase roo 0.0034
4037 Hypothetical protein GPX1 0.0034
4297 Hypothetical protein SP_1951 0.0034
4521 Hypothetical protein BC_2969 0.0034
4540 Hypothetical protein TM_1070 0.0034
4555 Hypothetical protein MT1739 0.0034
4569 Hypothetical protein mshD 0.0034
4578 Hypothetical protein PA3270 0.0034
4747 Hypothetical protein PA3967 0.0034
5177 Hypothetical protein TM_0096 0.0034
5194 Hypothetical protein PA1204 0.0034
5240 Hypothetical protein Rv2991 0.0034
5370 Hypothetical protein TM_1158 0.0034
5710 Hypothetical protein Tb927.5.1360 0.0034
5200 NADH dehydrogenase nox 0.0034
5191 Morphinone reductase morB 0.0034
5193 Phenazine biosynthesis protein phzG phzG 0.0034
4405 Nitric oxide reductase fprA 0.0034
4118 Cytochrome P450 3A5 CYP3A5 0.0034
4484 2,5-diketo-D-gluconic acid reductase A dkgA 0.0032
7 Nitric oxide synthase, inducible NOS2 0.0032
4200 Cytochrome P450 1A2 CYP1A2 0.0032
291 Nitric-oxide synthase, endothelial NOS3 0.0031
3772 3-oxoacyl-[acyl-carrier-protein] reductase fabG 0.0031
5326 Oxidoreductase, short chain dehydrogenase/reductase family TM_0441 0.0031
5157 Dehydrogenase/reductase SDR family member 11 DHRS11 0.0031
5346 Oxidoreductase, aldo/keto reductase family TM_1009 0.0031
5332 MtdA bifunctional protein mtdA 0.0031
5322 Oxidoreductase ydhF ydhF 0.0031
4403 Protein iolS iolS 0.0031
5343 NADP-dependent fatty aldehyde dehydrogenase aldH 0.0031
5330 General stress protein 69 yhdN 0.0031
5333 Alcohol dehydrogenase, iron-containing TM_0920 0.0031
5342 NADH-dependent butanol dehydrogenase, putative TM_0820 0.0031
3778 NAD(P) transhydrogenase subunit beta pntB 0.0031
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0031
408 Riboflavin kinase RFK 0.003
4407 FMN-dependent NADH-azoreductase azoR 0.003
5169 FMN-dependent NADH-azoreductase azoR 0.003
5176 YtnJ moxC 0.003
3680 Dihydroorotate dehydrogenase A pyrDA 0.003
5206 Phosphopantothenoylcysteine decarboxylase PPCDC 0.0029
3766 Pyridoxamine 5'-phosphate oxidase pdxH 0.0029
3507 Chorismate synthase aroC 0.0029
5171 Chorismate synthase aroC 0.0029
4366 Riboflavin kinase/FMN adenylyltransferase TM_0857 0.0028
6608 Serine/threonine-protein kinase Sgk1 SGK1 0.0027
646 Malate dehydrogenase, cytoplasmic MDH1 0.0027
4582 Putative pteridine reductase 2 ptr2 0.0027
2775 Dihydroorotate dehydrogenase pyrD 0.0027
2375 ADP-L-glycero-D-manno-heptose-6-epimerase hldD 0.0027
2305 Isocitrate dehydrogenase [NADP] cytoplasmic IDH1 0.0027
2286 Isocitrate dehydrogenase [NADP] icd 0.0027
2302 Isocitrate dehydrogenase [NADP] icd 0.0027
2771 Isocitrate dehydrogenase [NADP] icd 0.0027
5328 Prostaglandin F synthase Tb11.02.2310 0.0027
1799 Glucose-6-phosphate 1-dehydrogenase G6PD 0.0027
2630 Glucose-6-phosphate 1-dehydrogenase zwf 0.0027
3446 NADP-dependent alcohol dehydrogenase adh 0.0027
2636 Shikimate dehydrogenase aroE 0.0027
3515 Shikimate dehydrogenase aroE 0.0027
729 GDP-L-fucose synthetase TSTA3 0.0027
3463 GDP-L-fucose synthetase fcl 0.0027
4628 NADP-dependent glyceraldehyde-3-phosphate dehydrogenase gapN 0.0027
989 L-xylulose reductase DCXR 0.0027
2261 Major NAD(P)H-flavin oxidoreductase Not Available 0.0027
5325 2,4-dienoyl-CoA reductase, mitochondrial DECR1 0.0026
635 Estradiol 17-beta-dehydrogenase 8 HSD17B8 0.0026
666 NADP-dependent malic enzyme ME1 0.0026
5180 L(+)-mandelate dehydrogenase mdlB 0.0026
4531 Putative ketoacyl reductase actIII 0.0025
6297 Prostaglandin reductase 1 PTGR1 0.0025
6862 Aldo-keto reductase family 1 member B10 AKR1B10 0.0025
2159 Quinone oxidoreductase CRYZ 0.0025
203 Pyridoxine-5'-phosphate oxidase PNPO 0.0025
3062 Aspartate-semialdehyde dehydrogenase asd 0.0025
11 NAD(P) transhydrogenase, mitochondrial NNT 0.0024
2936 Oxygen-insensitive NAD(P)H nitroreductase nfnB 0.0024
5184 Oxygen-insensitive NAD(P)H nitroreductase nfnB 0.0024
1124 Sepiapterin reductase SPR 0.0024
2675 Pteridine reductase 1 PTR1 0.0023
4486 Phenol 2-hydroxylase component B pheA2 0.0023
4477 Dihydrolipoyl dehydrogenase lpdV 0.0023
5077 Dihydrolipoyl dehydrogenase Not Available 0.0023
5117 Dihydrolipoyl dehydrogenase lpd 0.0023
4439 Ferredoxin reductase bphA4 0.0023
4284 Pentaerythritol tetranitrate reductase onr 0.0023
5078 Amine oxidase, flavin-containing PSPTO1126 0.0022
5122 Mersacidin decarboxylase mrsD 0.0022
5114 Putative acyl-CoA dehydrogenase TT_C0779 0.0022
5112 Benzoate 1,2-dioxygenase electron transfer component benC 0.0022
3763 5,10-methylenetetrahydrofolate reductase metF 0.0022
3918 5,10-methylenetetrahydrofolate reductase MTHFR 0.0022
5094 5,10-methylenetetrahydrofolate reductase metF 0.0022
5083 Cryptochrome DASH cry 0.0022
5100 Gamma-aminobutyrate metabolism dehydratase/isomerase abfD 0.0022
526 Thioredoxin reductase trxB 0.0022
3767 Thioredoxin reductase trxB 0.0022
5115 FkbI fkbI 0.0022
3133 UDP-galactopyranose mutase glf 0.0022
5099 UDP-galactopyranose mutase glf 0.0022
1329 Apoptosis-inducing factor 1, mitochondrial AIFM1 0.0022
5095 Putidaredoxin reductase camA 0.0022
5097 PROBABLE DIHYDROLIPOAMIDE DEHYDROGENASE LPDA lpdA 0.0022
5102 4-cresol dehydrogenase [hydroxylating] flavoprotein subunit pchF 0.0022
5107 Alkyl hydroperoxide reductase subunit F ahpF 0.0022
5118 Alkyl hydroperoxide reductase subunit F ahpF 0.0022
1410 Oxidoreductase HSD17B6 0.0022
4725 Oxidoreductase Not Available 0.0022
5124 Oxidoreductase Not Available 0.0022
5081 L-aspartate oxidase nadB 0.0022
5111 Phenylacetone monooxygenase pamO 0.0022
5109 Outer membrane protein p64k or PM-6 m-6 0.0022
6268 Hydroxyacid oxidase 1 HAO1 0.0022
686 Aldo-keto reductase family 1 member C2 AKR1C2 0.0022
679 C-1-tetrahydrofolate synthase, cytoplasmic MTHFD1 0.0022
3102 Flavohemoprotein hmp 0.002
4969 Flavohemoprotein hmp 0.002
4440 NADH peroxidase npr 0.002
139 Aldo-keto reductase family 1 member C1 AKR1C1 0.002
217 Estradiol 17-beta-dehydrogenase 1 HSD17B1 0.002
178 NADH-cytochrome b5 reductase 3 CYB5R3 0.002
812 Dihydrolipoyl dehydrogenase, mitochondrial DLD 0.002
327 Glutathione reductase gor 0.002
5110 Glutathione reductase GR2 0.002
5072 N,N-dimethylglycine oxidase dmg 0.002
5091 UDP-N-acetylenolpyruvoylglucosamine reductase murB 0.002
5093 UDP-N-acetylenolpyruvoylglucosamine reductase murB 0.002
2268 Cholesterol oxidase choB 0.002
2822 Cholesterol oxidase choA 0.002
444 Alcohol dehydrogenase 1B ADH1B 0.002
3594 Deoxyribodipyrimidine photo-lyase phr 0.002
5079 Deoxyribodipyrimidine photo-lyase phrB 0.002
5080 Deoxyribodipyrimidine photo-lyase phr 0.002
2470 Pyruvate oxidase pox5 0.0019
2526 NADPH-ferredoxin reductase fprA fprA 0.0019
440 Isovaleryl-CoA dehydrogenase, mitochondrial IVD 0.0019
6639 Peroxisomal acyl-coenzyme A oxidase 1 ACOX1 0.0019
3506 Glutaryl-CoA dehydrogenase, mitochondrial GCDH 0.0019
667 Acyl-CoA dehydrogenase family member 8, mitochondrial ACAD8 0.0019
5003 Acyl-CoA dehydrogenase, short-chain specific Not Available 0.0019
3247 2-oxopropyl-CoM reductase, carboxylating xecC 0.0019
126 D-lactate dehydrogenase dld 0.0018
3545 D-lactate dehydrogenase Not Available 0.0018
4510 D-lactate dehydrogenase ldhA 0.0018
605 Fumarate reductase flavoprotein subunit frdA 0.0018
2709 Fumarate reductase flavoprotein subunit SO_0970 0.0018
3673 Fumarate reductase flavoprotein subunit fccA 0.0018
4912 Fumarate reductase flavoprotein subunit ifcA 0.0018
6549 Fumarate reductase flavoprotein subunit frdA 0.0018
424 Dihydroorotate dehydrogenase, mitochondrial DHODH 0.0018
3254 Bifunctional protein putA [Includes: Proline dehydrogenase putA 0.0018
3185 Medium-chain specific acyl-CoA dehydrogenase, mitochondrial ACADM 0.0018
2893 Glycine oxidase thiO 0.0018
839 Short-chain specific acyl-CoA dehydrogenase, mitochondrial ACADS 0.0017
364 Corticosteroid 11-beta-dehydrogenase isozyme 1 HSD11B1 0.0017
631 3-hydroxy-3-methylglutaryl-coenzyme A reductase HMGCR 0.0017
3387 3-hydroxy-3-methylglutaryl-coenzyme A reductase mvaA 0.0017
2567 Thymidylate synthase thyX thyX 0.0017
2823 Trypanothione reductase TPR 0.0017
2769 P-hydroxybenzoate hydroxylase pobA 0.0017
2809 P-hydroxybenzoate hydroxylase pobA 0.0017
822 Aldose reductase AKR1B1 0.0016
2380 Monomeric sarcosine oxidase soxA 0.0016
3610 Thioredoxin reductase 1, cytoplasmic TXNRD1 0.0016
365 Dihydrofolate reductase DHFR 0.0016
2381 Dihydrofolate reductase DFR1 0.0016
2833 Dihydrofolate reductase Not Available 0.0016
2931 Dihydrofolate reductase folA 0.0016
3544 Dihydrofolate reductase folA 0.0016
3682 Dihydrofolate reductase folA 0.0016
6642 Dihydrofolate reductase folA 0.0016
6756 Dihydrofolate reductase dfrA 0.0016
6645 D-amino-acid oxidase DAO 0.0015
714 Glutathione reductase, mitochondrial GSR 0.0013
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.0013
3939 Amine oxidase [flavin-containing] B MAOB 0.001
3941 Amine oxidase [flavin-containing] A MAOA 0.001
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