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ONTOLOGY REPORT - ANNOTATIONS
Term:(R)-lipoic acid
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Accession:CHEBI:30314 term browser browse the term
Definition:The (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties.
Synonyms:exact_synonym: 5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
 related_synonym: (R)-(+)-Lipoate;   (R)-1,2-Dithiolane-3-pentanoic acid;   (R)-1,2-dithiolane-3-valeric acid;   (R)-6,8-thioctic acid;   Formula=C8H14O2S2;   InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1;   InChIKey=AGBQKNBQESQNJD-SSDOTTSWSA-N;   Lipoic acid;   R-LA;   RLA;   SMILES=OC(=O)CCCC[C@@H]1CCSS1;   Thioctic acid;   Thioctic acid d-form;   alpha-Lipoic acid
 xref: Beilstein:81851 "Beilstein";   CAS:1200-22-2 "ChemIDplus";   CAS:1200-22-2 "KEGG COMPOUND";   CAS:62-46-4 "KEGG COMPOUND";   COMe:MOL000161;   HMDB:HMDB0001451;   KEGG:C00725;   KEGG:C16241;   KNApSAcK:C00000754;   LIPID_MAPS_instance:LMFA01130001 "LIPID MAPS"
 xref_mesh: MESH:D008063
 xref: MetaCyc:LIPOIC-ACID;   PMID:10218658 "Europe PMC";   PMID:14991456 "Europe PMC";   PMID:15157071 "Europe PMC";   PMID:9252495 "Europe PMC";   Wikipedia:Lipoic_acid
 cyclic_relationship: is_conjugate_acid_of CHEBI:83088;   is_enantiomer_of CHEBI:43796

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(R)-lipoic acid term browser
Symbol Object Name JBrowse Chr Start Stop Reference
G Abcb1a ATP binding cassette subfamily B member 1A JBrowse link 4 22,339,829 22,517,642 RGD:6480464
G Acadl acyl-CoA dehydrogenase, long chain JBrowse link 9 73,833,368 73,871,857 RGD:6480464
G Ace angiotensin I converting enzyme JBrowse link 10 94,170,766 94,213,831 RGD:6480464
G Ache acetylcholinesterase JBrowse link 12 22,472,358 22,477,052 RGD:6480464
G Acox1 acyl-CoA oxidase 1 JBrowse link 10 104,724,534 104,748,003 RGD:6480464
G Acta2 actin alpha 2, smooth muscle JBrowse link 1 252,537,614 252,550,394 RGD:6480464
G Adipoq adiponectin, C1Q and collagen domain containing JBrowse link 11 81,330,845 81,344,488 RGD:6480464
G Agt angiotensinogen JBrowse link 19 57,321,594 57,333,460 RGD:6480464
G Agtr1a angiotensin II receptor, type 1a JBrowse link 17 35,907,102 35,958,136 RGD:6480464
G Akt1 AKT serine/threonine kinase 1 JBrowse link 6 137,218,398 137,239,970 RGD:6480464
G Alad aminolevulinate dehydratase JBrowse link 5 78,368,867 78,379,206 RGD:6480464
G Alb albumin JBrowse link 14 19,176,275 19,191,793 RGD:6480464
G Apln apelin JBrowse link X 134,856,719 134,866,210 RGD:6480464
G Atf4 activating transcription factor 4 JBrowse link 7 121,480,723 121,482,781 RGD:6480464
G Atf6 activating transcription factor 6 JBrowse link 13 89,053,457 89,242,531 RGD:6480464
G Atp1b1 ATPase Na+/K+ transporting subunit beta 1 JBrowse link 13 82,737,161 82,757,681 RGD:6480464
G Atp2a2 ATPase sarcoplasmic/endoplasmic reticulum Ca2+ transporting 2 JBrowse link 12 39,553,903 39,603,326 RGD:6480464
G Bax BCL2 associated X, apoptosis regulator JBrowse link 1 101,451,801 101,457,207 RGD:6480464
G Bbc3 Bcl-2 binding component 3 JBrowse link 1 78,261,491 78,267,802 RGD:6480464
G Bche butyrylcholinesterase JBrowse link 2 171,104,476 171,196,186 RGD:6480464
G Bcl2 BCL2, apoptosis regulator JBrowse link 13 26,605,426 26,769,374 RGD:6480464
G Bcl2l1 Bcl2-like 1 JBrowse link 3 148,259,594 148,314,191 RGD:6480464
G Brca2 BRCA2, DNA repair associated JBrowse link 12 503,660 544,754 RGD:6480464
G C1qa complement C1q A chain JBrowse link 5 155,261,254 155,264,101 RGD:6480464
G C4b complement C4B (Chido blood group) JBrowse link 20 4,302,344 4,316,752 RGD:6480464
G Calb2 calbindin 2 JBrowse link 19 41,482,743 41,509,617 RGD:6480464
G Calm1 calmodulin 1 JBrowse link 6 124,217,241 124,225,292 RGD:6480464
G Casp3 caspase 3 JBrowse link 16 48,845,011 48,863,249 RGD:6480464
G Casp8 caspase 8 JBrowse link 9 65,614,142 65,662,624 RGD:6480464
G Casp9 caspase 9 JBrowse link 5 160,356,211 160,373,774 RGD:6480464
G Cat catalase JBrowse link 3 93,379,872 93,412,058 RGD:6480464
G Ccl2 C-C motif chemokine ligand 2 JBrowse link 10 69,412,065 69,413,863 RGD:6480464
G Ccnd1 cyclin D1 JBrowse link 1 218,090,750 218,100,447 RGD:6480464
G Cd36 CD36 molecule JBrowse link 4 14,150,309 14,191,498 RGD:6480464
G Cd86 CD86 molecule JBrowse link 11 67,060,305 67,117,990 RGD:6480464
G Cd8a CD8a molecule JBrowse link 4 99,217,640 99,243,352 RGD:6480464
G Cdx4 caudal type homeo box 4 JBrowse link X 74,165,172 74,173,758 RGD:6480464
G Chat choline O-acetyltransferase JBrowse link 16 8,576,858 8,686,131 RGD:6480464
G Cntf ciliary neurotrophic factor JBrowse link 1 229,599,009 229,601,032 RGD:6480464
G Col1a1 collagen type I alpha 1 chain JBrowse link 10 82,745,801 82,762,790 RGD:6480464
G Cpt1a carnitine palmitoyltransferase 1A JBrowse link 1 218,568,157 218,629,679 RGD:6480464
G Crp C-reactive protein JBrowse link 13 91,080,448 91,081,358 RGD:6480464
G Cryaa crystallin, alpha A JBrowse link 20 10,438,444 10,442,189 RGD:6480464
G Ctsd cathepsin D JBrowse link 1 215,541,570 215,553,446 RGD:6480464
G Ctss cathepsin S JBrowse link 2 197,655,780 197,679,768 RGD:6480464
G Cybb cytochrome b-245 beta chain JBrowse link X 14,578,330 14,610,049 RGD:6480464
G Cycs cytochrome c, somatic JBrowse link 4 80,331,226 80,333,326 RGD:6480464
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 JBrowse link 8 62,472,087 62,478,122 RGD:6480464
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 JBrowse link 8 62,451,360 62,458,244 RGD:6480464
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 JBrowse link 1 147,713,879 147,814,410 RGD:6480464
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 JBrowse link 1 147,236,480 147,307,988 RGD:6480464
G Cyp2d4 cytochrome P450, family 2, subfamily d, polypeptide 4 JBrowse link 7 123,599,264 123,608,436 RGD:6480464
G Dab1 DAB adaptor protein 1 JBrowse link 5 123,154,360 124,279,170 RGD:6480464
G Ddit3 DNA-damage inducible transcript 3 JBrowse link 7 70,578,564 70,585,074 RGD:6480464
G Dgat2 diacylglycerol O-acyltransferase 2 JBrowse link 1 164,113,459 164,143,818 RGD:6480464
G Dio1 iodothyronine deiodinase 1 JBrowse link 5 126,894,837 126,911,532 RGD:6480464
G Dld dihydrolipoamide dehydrogenase JBrowse link 6 50,597,677 50,618,694 RGD:6480464
G Drd2 dopamine receptor D2 JBrowse link 8 53,678,777 53,743,643 RGD:6480464
G Eif2a eukaryotic translation initiation factor 2A JBrowse link 2 148,722,343 148,755,781 RGD:6480464
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha JBrowse link 6 102,048,372 102,073,041 RGD:6480464
G Fas Fas cell surface death receptor JBrowse link 1 252,589,785 252,624,790 RGD:6480464
G Flt1 Fms related receptor tyrosine kinase 1 JBrowse link 12 9,033,993 9,205,886 RGD:6480464
G Fos Fos proto-oncogene, AP-1 transcription factor subunit JBrowse link 6 109,300,433 109,303,299 RGD:6480464
G Foxo3 forkhead box O3 JBrowse link 20 46,428,078 46,519,156 RGD:6480464
G Fras1 Fraser extracellular matrix complex subunit 1 JBrowse link 14 14,438,392 14,853,016 RGD:6480464
G Fshb follicle stimulating hormone subunit beta JBrowse link 3 98,088,321 98,092,131 RGD:6480464
G Gad1 glutamate decarboxylase 1 JBrowse link 3 56,861,440 56,902,139 RGD:6480464
G Gclc glutamate-cysteine ligase, catalytic subunit JBrowse link 8 85,059,051 85,097,471 RGD:6480464
G Gclm glutamate cysteine ligase, modifier subunit JBrowse link 2 225,827,504 225,847,876 RGD:6480464
G Gfap glial fibrillary acidic protein JBrowse link 10 90,990,762 90,999,435 RGD:6480464
G Ggt1 gamma-glutamyltransferase 1 JBrowse link 20 14,019,723 14,045,781 RGD:6480464
G Gja1 gap junction protein, alpha 1 JBrowse link 20 37,876,650 37,889,097 RGD:6480464
G Gnrhr gonadotropin releasing hormone receptor JBrowse link 14 23,480,462 23,498,450 RGD:6480464
G Gpt glutamic--pyruvic transaminase JBrowse link 7 117,759,083 117,761,932 RGD:6480464
G Gpx1 glutathione peroxidase 1 JBrowse link 8 117,117,430 117,118,528 RGD:6480464
G Gpx2 glutathione peroxidase 2 JBrowse link 6 99,839,960 99,843,245 RGD:6480464
G Gpx3 glutathione peroxidase 3 JBrowse link 10 40,247,436 40,255,423 RGD:6480464
G Gpx5 glutathione peroxidase 5 JBrowse link 17 45,508,657 45,518,686 RGD:6480464
G Grin2a glutamate ionotropic receptor NMDA type subunit 2A JBrowse link 10 5,707,806 6,123,568 RGD:6480464
G Gsk3b glycogen synthase kinase 3 beta JBrowse link 11 65,060,884 65,208,842 RGD:6480464
G Gsr glutathione-disulfide reductase JBrowse link 16 62,197,617 62,239,987 RGD:6480464
G Gstm1 glutathione S-transferase mu 1 JBrowse link 2 210,803,869 210,809,461 RGD:6480464
G Gstm7 glutathione S-transferase, mu 7 JBrowse link 2 210,720,719 210,726,179 RGD:6480464
G Gstp1 glutathione S-transferase pi 1 JBrowse link 1 219,291,679 219,294,147 RGD:6480464
G Gusb glucuronidase, beta JBrowse link 12 30,202,066 30,215,583 RGD:6480464
G Havcr1 hepatitis A virus cellular receptor 1 JBrowse link 10 31,813,819 31,860,934 RGD:6480464
G Hmox1 heme oxygenase 1 JBrowse link 19 14,508,634 14,515,455 RGD:6480464
G Hs1bp3 HCLS1 binding protein 3 JBrowse link 6 33,517,711 33,548,015 RGD:6480464
G Hspa1a heat shock protein family A (Hsp70) member 1A JBrowse link 20 4,875,834 4,881,751 RGD:6480464
G Hspa5 heat shock protein family A (Hsp70) member 5 JBrowse link 3 13,838,304 13,842,763 RGD:6480464
G Igfbp3 insulin-like growth factor binding protein 3 JBrowse link 14 87,457,647 87,465,374 RGD:6480464
G Il10 interleukin 10 JBrowse link 13 47,738,933 47,743,392 RGD:6480464
G Il1a interleukin 1 alpha JBrowse link 3 121,824,712 121,836,122 RGD:6480464
G Il1b interleukin 1 beta JBrowse link 3 121,876,256 121,882,637 RGD:6480464
G Il2 interleukin 2 JBrowse link 2 123,847,150 123,851,854 RGD:6480464
G Il22ra2 interleukin 22 receptor subunit alpha 2 JBrowse link 1 15,084,136 15,107,423 RGD:6480464
G Il4 interleukin 4 JBrowse link 10 38,963,979 38,969,531 RGD:6480464
G Il6 interleukin 6 JBrowse link 4 3,043,231 3,047,807 RGD:6480464
G Ins2 insulin 2 JBrowse link 1 215,856,967 215,858,034 RGD:6480464
G Irf1 interferon regulatory factor 1 JBrowse link 10 39,109,530 39,116,532 RGD:6480464
G Jun Jun proto-oncogene, AP-1 transcription factor subunit JBrowse link 5 114,011,184 114,014,277 RGD:6480464
G Keap1 Kelch-like ECH-associated protein 1 JBrowse link 8 22,250,518 22,259,868 RGD:6480464
G Ldhc lactate dehydrogenase C JBrowse link 1 102,914,875 102,931,843 RGD:6480464
G Lep leptin JBrowse link 4 56,337,695 56,351,818 RGD:6480464
G Lhb luteinizing hormone subunit beta JBrowse link 1 101,409,992 101,413,725 RGD:6480464
G Lipe lipase E, hormone sensitive type JBrowse link 1 82,248,031 82,266,727 RGD:6480464
G LOC108348233 protocadherin beta-6-like JBrowse link 18 30,512,507 30,518,524 RGD:6480464
G Mapk1 mitogen activated protein kinase 1 JBrowse link 11 88,203,863 88,273,301 RGD:6480464
G Mapk14 mitogen activated protein kinase 14 JBrowse link 20 5,933,290 5,995,137 RGD:6480464
G Mapk3 mitogen activated protein kinase 3 JBrowse link 1 198,192,773 198,198,975 RGD:6480464
G Mapk8 mitogen-activated protein kinase 8 JBrowse link 16 9,620,854 9,709,342 RGD:6480464
G Mir21 microRNA 21 JBrowse link 10 73,902,210 73,902,301 RGD:6480464
G Mir210 microRNA 210 JBrowse link 1 214,208,355 214,208,464 RGD:6480464
G Mmp12 matrix metallopeptidase 12 JBrowse link 8 5,594,717 5,616,494 RGD:6480464
G Mmp13 matrix metallopeptidase 13 JBrowse link 8 5,522,739 5,533,018 RGD:6480464
G Mmp2 matrix metallopeptidase 2 JBrowse link 19 15,542,771 15,570,589 RGD:6480464
G Mmp3 matrix metallopeptidase 3 JBrowse link 8 5,676,608 5,698,579 RGD:6480464
G Msr1 macrophage scavenger receptor 1 JBrowse link 16 56,817,714 56,900,025 RGD:6480464
G Mt1 metallothionein 1 JBrowse link 19 11,301,991 11,303,007 RGD:6480464
G Mvd mevalonate diphosphate decarboxylase JBrowse link 19 55,258,910 55,268,933 RGD:6480464
G Myc MYC proto-oncogene, bHLH transcription factor JBrowse link 7 102,586,313 102,591,240 RGD:6480464
G Ncf1 neutrophil cytosolic factor 1 JBrowse link 12 25,497,104 25,506,300 RGD:6480464
G Nfe2l2 nuclear factor, erythroid 2-like 2 JBrowse link 3 62,497,568 62,525,146 RGD:6480464
G Nfkb1 nuclear factor kappa B subunit 1 JBrowse link 2 240,773,520 240,890,053 RGD:6480464
G Ngfr nerve growth factor receptor JBrowse link 10 83,389,828 83,408,061 RGD:6480464
G Nos2 nitric oxide synthase 2 JBrowse link 10 66,188,290 66,221,621 RGD:6480464
G Nos3 nitric oxide synthase 3 JBrowse link 4 7,321,908 7,342,404 RGD:6480464
G Nox1 NADPH oxidase 1 JBrowse link X 104,909,328 104,932,508 RGD:6480464
G Nox4 NADPH oxidase 4 JBrowse link 1 150,796,359 150,976,186 RGD:6480464
G Nqo1 NAD(P)H quinone dehydrogenase 1 JBrowse link 19 38,422,210 38,437,103 RGD:6480464
G Otx2 orthodenticle homeobox 2 JBrowse link 15 25,500,037 25,511,619 RGD:6480464
G Pah phenylalanine hydroxylase JBrowse link 7 28,066,639 28,129,772 RGD:6480464
G Pcna proliferating cell nuclear antigen JBrowse link 3 124,880,698 124,884,570 RGD:6480464
G Plaat3 phospholipase A and acyltransferase 3 JBrowse link 1 222,844,238 222,877,180 RGD:6480464
G Plin1 perilipin 1 JBrowse link 1 141,458,907 141,470,927 RGD:6480464
G Por cytochrome p450 oxidoreductase JBrowse link 12 23,998,411 24,017,063 RGD:6480464
G Ppara peroxisome proliferator activated receptor alpha JBrowse link 7 126,618,872 126,687,282 RGD:6480464
G Pparg peroxisome proliferator-activated receptor gamma JBrowse link 4 147,274,055 147,399,383 RGD:6480464
G Ppargc1a PPARG coactivator 1 alpha JBrowse link 14 63,095,291 63,190,688 RGD:6480464
G Ppargc1b PPARG coactivator 1 beta JBrowse link 18 56,626,725 56,650,524 RGD:6480464
G Ptgs2 prostaglandin-endoperoxide synthase 2 JBrowse link 13 67,351,230 67,356,920 RGD:6480464
G Rela RELA proto-oncogene, NF-kB subunit JBrowse link 1 220,992,770 221,003,249 RGD:6480464
G Reln reelin JBrowse link 4 9,347,533 9,774,257 RGD:6480464
G S100b S100 calcium binding protein B JBrowse link 20 13,130,633 13,142,856 RGD:6480464
G Sema5a semaphorin 5A JBrowse link 2 85,377,318 85,808,970 RGD:6480464
G Serpinh1 serpin family H member 1 JBrowse link 1 164,301,010 164,308,306 RGD:6480464
G Sirt1 sirtuin 1 JBrowse link 20 26,831,971 26,851,587 RGD:6480464
G Sirt3 sirtuin 3 JBrowse link 1 213,613,502 213,636,061 RGD:6480464
G Slc12a2 solute carrier family 12 member 2 JBrowse link 18 52,917,124 52,985,281 RGD:6480464
G Slc38a2 solute carrier family 38, member 2 JBrowse link 7 138,088,654 138,100,869 RGD:6480464
G Slc5a6 solute carrier family 5 member 6 JBrowse link 6 26,685,823 26,697,110 RGD:6480464
G Snca synuclein alpha JBrowse link 4 90,782,412 90,883,236 RGD:6480464
G Sod1 superoxide dismutase 1 JBrowse link 11 30,363,282 30,368,858 RGD:6480464
G Sod2 superoxide dismutase 2 JBrowse link 1 47,914,757 47,921,587 RGD:6480464
G Sp1 Sp1 transcription factor JBrowse link 7 144,014,173 144,044,635 RGD:6480464
G Srebf1 sterol regulatory element binding transcription factor 1 JBrowse link 10 46,570,996 46,593,021 RGD:6480464
G Star steroidogenic acute regulatory protein JBrowse link 16 71,036,204 71,040,847 RGD:6480464
G Stat1 signal transducer and activator of transcription 1 JBrowse link 9 54,287,540 54,327,958 RGD:6480464
G Stat3 signal transducer and activator of transcription 3 JBrowse link 10 88,790,401 88,842,263 RGD:6480464
G Sumo1 small ubiquitin-like modifier 1 JBrowse link 9 66,453,428 66,483,614 RGD:6480464
G Tgfb1 transforming growth factor, beta 1 JBrowse link 1 82,480,875 82,497,196 RGD:6480464
G Tgfb1i1 transforming growth factor beta 1 induced transcript 1 JBrowse link 1 199,664,039 199,670,970 RGD:6480464
G Tgfb2 transforming growth factor, beta 2 JBrowse link 13 105,039,639 105,142,010 RGD:6480464
G Thra thyroid hormone receptor alpha JBrowse link 10 86,657,285 86,684,935 RGD:6480464
G Tnf tumor necrosis factor JBrowse link 20 5,189,382 5,192,000 RGD:6480464
G Tnfrsf26 tumor necrosis factor receptor superfamily, member 26 JBrowse link 1 216,808,642 216,829,361 RGD:6480464
G Tnfsf10 TNF superfamily member 10 JBrowse link 2 113,008,008 113,026,899 RGD:6480464
G Tnni3 troponin I3, cardiac type JBrowse link 1 72,882,806 72,886,490 RGD:6480464
G Tp53 tumor protein p53 JBrowse link 10 56,186,299 56,198,449 RGD:6480464
G Trib3 tribbles pseudokinase 3 JBrowse link 3 147,814,056 147,819,650 RGD:6480464
G Txn1 thioredoxin 1 JBrowse link 5 75,049,735 75,057,731 RGD:6480464
G Txnrd1 thioredoxin reductase 1 JBrowse link 7 26,946,124 26,984,400 RGD:6480464
G Ucp2 uncoupling protein 2 JBrowse link 1 165,506,375 165,512,744 RGD:6480464
G Vegfa vascular endothelial growth factor A JBrowse link 9 17,340,341 17,355,681 RGD:6480464
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19734
    role 19680
      biological role 19678
        biochemical role 19177
          cofactor 15390
            (R)-lipoic acid 173
              (R)-lipoamide 0
              (R)-lipoyl group 0
              (R)-lipoyl-AMP 0
              (R)-lipoyl-GMP 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19734
    subatomic particle 19730
      composite particle 19730
        hadron 19730
          baryon 19730
            nucleon 19730
              atomic nucleus 19730
                atom 19730
                  main group element atom 19614
                    p-block element atom 19614
                      carbon group element atom 19506
                        carbon atom 19500
                          organic molecular entity 19500
                            organic group 18414
                              organic divalent group 18406
                                organodiyl group 18406
                                  carbonyl group 18295
                                    carbonyl compound 18295
                                      carboxylic acid 17963
                                        monocarboxylic acid 17265
                                          fatty acid 15819
                                            saturated fatty acid 15786
                                              straight-chain saturated fatty acid 15183
                                                octanoic acid 2175
                                                  lipoic acid 174
                                                    (R)-lipoic acid 173
                                                      (R)-lipoamide 0
                                                      (R)-lipoyl group 0
                                                      (R)-lipoyl-AMP 0
                                                      (R)-lipoyl-GMP 0
paths to the root

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.