General Information of Drug (ID: DM5LFYN)

Drug Name
alpha-ketoglutaric acid Drug Info
Synonyms 2-ketoglutarate; 2-oxoglutarate; alpha-ketoglutarate; 2-ketoglutaric acid; oxoglutarate
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
51
ChEBI ID
CHEMBL1686
CAS Number
CAS 328-50-7
TTD Drug ID
DM5LFYN
VARIDT Drug ID
DR00139
INTEDE Drug ID
DR2059

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Investigative Drug(s)
Preclinical Drug(s)
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
LTE4 DMCPB0Q Discovery agent N.A. Investigative [14]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dicarboxylate DML3HEM N. A. N. A. Investigative [5]
Succinate DMPY09A N. A. N. A. Investigative [5]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Citrate DM37NYK N. A. N. A. Preclinical [6]
Succinate DMPY09A N. A. N. A. Investigative [6]
Drug Name Drug ID Indication ICD 11 Highest Status REF
alpha-oxoadipic acid DM0KXN4 Discovery agent N.A. Investigative [3]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Vitamin C DMXJ7O8 Adenocarcinoma 2D40 Approved [7]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Vitamin C DMXJ7O8 Adenocarcinoma 2D40 Approved [7]
Drug(s) Metabolized By HIF-prolyl hydroxylase 2 (EGLN1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Vitamin C DMXJ7O8 Adenocarcinoma 2D40 Approved [8]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Vitamin C DMXJ7O8 Adenocarcinoma 2D40 Approved [11]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Penicillamine DM40EF6 Cystinuria 5C60.2 Approved [15]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [16]
Diazepam DM08E9O Alcohol withdrawal Approved [17]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [18]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [19]
Methotrexate DM2TEOL Anterior urethra cancer Approved [20]
Ceruletide DM2WE5K Caerulein stimulated gastric and pancreatic secretion 5A4Y Approved [21]
Dactinomycin DM2YGNW Adult kidney Wilms tumor Approved [22]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [23]
Quercetin DM3NC4M Obesity 5B81 Approved [24]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Osteocalcin (BGLAP)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [25]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [26]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [19]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [27]
Quercetin DM3NC4M Obesity 5B81 Approved [28]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [29]
Pamidronate DMB4AVP Bone Paget disease Approved [30]
Falecalcitrol DMBI9ZJ Hyperparathyroidism 5A51 Approved [31]
Atorvastatin DMF28YC Acute coronary syndrome BA41 Approved [32]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [33]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [34]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [35]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [36]
Calcidiol DMN4CV5 Hypophosphatemia Approved [35]
Magnesium DMU4ORS Ischemic stroke 8B11.5Z Approved [37]
Vitamin C DMXJ7O8 Adenocarcinoma 2D40 Approved [38]
Camptothecin DM6CHNJ Solid tumour/cancer 2A00-2F9Z Phase 3 [39]
GSK2816126 DMJDVW4 Solid tumour/cancer 2A00-2F9Z Phase 1 [40]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [41]
EUGENOL DM7US1H Discovery agent N.A. Patented [42]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [43]
Methotrexate DM2TEOL Anterior urethra cancer Approved [44]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [45]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [46]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [47]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [48]
Testosterone DM7HUNW Hot flushes GA30 Approved [49]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [50]
Capivasertib DM9SKW8 Breast cancer 2C60-2C65 Approved [51]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [52]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Transcription factor Sp7 (SP7)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [26]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [53]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [54]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [55]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [56]
Berberine DMC5Q8X N. A. N. A. Phase 4 [57]
Resveratrol DM3RWXL Giant cell arteritis 4A44.2 Phase 3 [56]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [41]
bisphenol A DM2ZLD7 Discovery agent N.A. Investigative [58]
PD98059 DMZC90M Cardiac arrest MC82 Investigative [56]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [55]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [59]
Arsenic DMTL2Y1 N. A. N. A. Approved [60]
(+)-JQ1 DM1CZSJ Testicular cancer 2C80 Phase 1 [61]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [41]
PMID28460551-Compound-2 DM4DOUB N. A. N. A. Patented [62]
bisphenol A DM2ZLD7 Discovery agent N.A. Investigative [63]
⏷ Show the Full List of 7 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Oxoglutarate receptor (OXGR1) TTAS1QK OXGR1_HUMAN Agonist [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Mitochondrial 2-oxodicarboxylate carrier (SLC25A21) DT2UQYR ODC_HUMAN Substrate [3]
Mitochondrial 2-oxoglutarate/malate carrier (SLC25A11) DT0YAUQ M2OM_HUMAN Substrate [4]
Sodium/dicarboxylate cotransporter 3 (SLC13A3) DTKXTPW S13A3_HUMAN Substrate [5]
Sodium-coupled citrate transporter (SLC13A5) DTFPWJ9 S13A5_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Prolyl 4-hydroxylase alpha-1 (P4HA1) DESO5ZY P4HA1_HUMAN Substrate [7]
Prolyl 4-hydroxylase alpha-2 (P4HA2) DE5EGK0 P4HA2_HUMAN Substrate [7]
HIF-prolyl hydroxylase 3 (EGLN3) DEMQTKH EGLN3_HUMAN Substrate [8]
HIF-prolyl hydroxylase 2 (EGLN1) DEWO724 EGLN1_HUMAN Substrate [8]
Factor inhibiting HIF-1 (HIF1AN) DEY1CBW HIF1N_HUMAN Substrate [9]
Prolyl 3-hydroxylase 1 (P3H1) DEW527E P3H1_HUMAN Substrate [10]
Prolyl 3-hydroxylase 2 (P3H2) DELB5PA P3H2_HUMAN Substrate [10]
Prolyl 4-hydroxylase alpha-3 (P4HA3) DE2L4RX P4HA3_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [12]
D-2-hydroxyglutarate dehydrogenase, mitochondrial (D2HGDH) OTLHXW69 D2HDH_HUMAN Biotransformations [13]
Integrin-binding sialoprotein (IBSP) OT29944Y SIAL_HUMAN Gene/Protein Processing [12]
Osteocalcin (BGLAP) OTK1YLWQ OSTCN_HUMAN Gene/Protein Processing [12]
Small ribosomal subunit protein eS6 (RPS6) OTT4D1LN RS6_HUMAN Post-Translational Modifications [12]
Transcription factor Sp7 (SP7) OT07ETZT SP7_HUMAN Gene/Protein Processing [12]

References

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3 Mitochondrial oxodicarboxylate carrier deficiency is associated with mitochondrial DNA depletion and spinal muscular atrophy-like disease. Genet Med. 2018 Oct;20(10):1224-1235.
4 The mitochondrial dicarboxylate and 2-oxoglutarate carriers do not transport glutathione. FEBS Lett. 2015 Feb 27;589(5):621-8.
5 SLC13A3 variants cause acute reversible leukoencephalopathy and -ketoglutarate accumulation. Ann Neurol. 2019 Mar;85(3):385-395.
6 SLC13 family of Na+ coupled di- and tri-carboxylate/sulfate transporters. Mol Aspects Med. 2013 Apr-Jun;34(2-3):299-312.
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8 Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor. J Biol Chem. 2003 Aug 15;278(33):30772-80.
9 The facial triad in the alpha-ketoglutarate dependent oxygenase FIH: a role for sterics in linking substrate binding to O2 activation. J Inorg Biochem. 2017 Jan;166:26-33.
10 Characterization of recombinant human prolyl 3-hydroxylase isoenzyme 2, an enzyme modifying the basement membrane collagen IV. J Biol Chem. 2008 Jul 11;283(28):19432-9.
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24 Antifibrotic effects of quercetin in primary orbital fibroblasts and orbital fat tissue cultures of Graves' orbitopathy. Invest Ophthalmol Vis Sci. 2012 Aug 31;53(9):5921-9. doi: 10.1167/iovs.12-9646.
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26 Cannabidiol induces osteoblast differentiation via angiopoietin1 and p38 MAPK. Environ Toxicol. 2020 Dec;35(12):1318-1325. doi: 10.1002/tox.22996. Epub 2020 Jul 13.
27 The effect of simvastatin on the proliferation and differentiation of human bone marrow stromal cells. J Korean Med Sci. 2005 Jun;20(3):438-44. doi: 10.3346/jkms.2005.20.3.438.
28 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
29 Glucosamine promotes osteogenic differentiation of dental pulp stem cells through modulating the level of the transforming growth factor-beta type I receptor. J Cell Physiol. 2010 Oct;225(1):140-51.
30 Pamidronate increases markers of bone formation in patients with multiple myeloma in plateau phase under interferon-alpha treatment. Calcif Tissue Int. 2001 May;68(5):285-90.
31 A highly potent 26,27-Hexafluoro-1a,25-dihydroxyvitamin D3 on calcification in SV40-transformed human fetal osteoblastic cells. Calcif Tissue Int. 2002 Jun;70(6):488-95.
32 Simvastatin and atorvastatin enhance gene expression of collagen type 1 and osteocalcin in primary human osteoblasts and MG-63 cultures. J Cell Biochem. 2007 Aug 15;101(6):1430-8. doi: 10.1002/jcb.21259.
33 Design principles of concentration-dependent transcriptome deviations in drug-exposed differentiating stem cells. Chem Res Toxicol. 2014 Mar 17;27(3):408-20.
34 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
35 Effects of 25-hydroxyvitamin D(3) on proliferation and osteoblast differentiation of human marrow stromal cells require CYP27B1/1alpha-hydroxylase. J Bone Miner Res. 2011 May;26(5):1145-53.
36 Zoledronic acid up-regulates bone sialoprotein expression in osteoblastic cells through Rho GTPase inhibition. Biochem J. 2004 Dec 15;384(Pt 3):591-8. doi: 10.1042/BJ20040380.
37 Effect of surface chemical modification of bioceramic on phenotype of human bone-derived cells. J Biomed Mater Res. 1999 Mar 15;44(4):389-96. doi: 10.1002/(sici)1097-4636(19990315)44:4<389::aid-jbm4>3.0.co;2-o.
38 Potential osteoinductive effects of calcitriol on the m-RNA of mesenchymal stem cells derived from human alveolar periosteum. Biomed Res Int. 2016;2016:3529561.
39 ATR inhibitors VE-821 and VX-970 sensitize cancer cells to topoisomerase i inhibitors by disabling DNA replication initiation and fork elongation responses. Cancer Res. 2014 Dec 1;74(23):6968-79.
40 Epigenetic control of skeletal development by the histone methyltransferase Ezh2. J Biol Chem. 2015 Nov 13;290(46):27604-17.
41 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
42 Cytotoxic effect of eugenol on the expression of molecular markers related to the osteogenic differentiation of human dental pulp cells. Odontology. 2011 Jul;99(2):188-92. doi: 10.1007/s10266-011-0009-2. Epub 2011 Jun 26.
43 Cannabidiol Reduces Leukemic Cell Size - But Is It Important?. Front Pharmacol. 2017 Mar 24;8:144. doi: 10.3389/fphar.2017.00144. eCollection 2017.
44 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
45 Crizotinib-resistant mutants of EML4-ALK identified through an accelerated mutagenesis screen. Chem Biol Drug Des. 2011 Dec;78(6):999-1005. doi: 10.1111/j.1747-0285.2011.01239.x. Epub 2011 Oct 31.
46 D-glucosamine down-regulates HIF-1alpha through inhibition of protein translation in DU145 prostate cancer cells. Biochem Biophys Res Commun. 2009 Apr 24;382(1):96-101. doi: 10.1016/j.bbrc.2009.02.129. Epub 2009 Feb 28.
47 Proteomics-based identification of differentially abundant proteins from human keratinocytes exposed to arsenic trioxide. J Proteomics Bioinform. 2014 Jul;7(7):166-178.
48 Potential anti-aging agents suppress the level of constitutive mTOR- and DNA damage- signaling. Aging (Albany NY). 2012 Dec;4(12):952-65. doi: 10.18632/aging.100521.
49 Androgen receptor-mTOR crosstalk is regulated by testosterone availability: implication for prostate cancer cell survival. Anticancer Res. 2010 Oct;30(10):3895-901.
50 Imatinib disturbs lysosomal function and morphology and impairs the activity of mTORC1 in human hepatocyte cell lines. Food Chem Toxicol. 2022 Apr;162:112869. doi: 10.1016/j.fct.2022.112869. Epub 2022 Feb 16.
51 Inhibition of cholesterol metabolism underlies synergy between mTOR pathway inhibition and chloroquine in bladder cancer cells. Oncogene. 2016 Aug 25;35(34):4518-28. doi: 10.1038/onc.2015.511. Epub 2016 Feb 8.
52 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
53 Naringin protects human adipose-derived mesenchymal stem cells against hydrogen peroxide-induced inhibition of osteogenic differentiation. Chem Biol Interact. 2015 Dec 5;242:255-61. doi: 10.1016/j.cbi.2015.10.010. Epub 2015 Oct 19.
54 Small ubiquitin-related modifier-1 modification regulates all-trans-retinoic acid-induced differentiation via stabilization of retinoic acid receptor . FEBS J. 2014 Jul;281(13):3032-47. doi: 10.1111/febs.12840. Epub 2014 Jun 2.
55 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
56 Resveratrol enhances proliferation and osteoblastic differentiation in human mesenchymal stem cells via ER-dependent ERK1/2 activation. Phytomedicine. 2007 Dec;14(12):806-14. doi: 10.1016/j.phymed.2007.04.003. Epub 2007 Aug 8.
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58 Repercussions of Bisphenol A on the Physiology of Human Osteoblasts. Int J Mol Sci. 2022 May 11;23(10):5349. doi: 10.3390/ijms23105349.
59 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
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61 Targeting MYCN in neuroblastoma by BET bromodomain inhibition. Cancer Discov. 2013 Mar;3(3):308-23.
62 Cell-based two-dimensional morphological assessment system to predict cancer drug-induced cardiotoxicity using human induced pluripotent stem cell-derived cardiomyocytes. Toxicol Appl Pharmacol. 2019 Nov 15;383:114761. doi: 10.1016/j.taap.2019.114761. Epub 2019 Sep 15.
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