Details of the Drug

General Information of Drug (ID: DMIAHVU)

Drug Name
2-deoxyglucose
Synonyms
154-17-6; Deoxyglucose; 2-Deoxy-D-mannose; 2-Deoxy-D-arabinohexose; UNII-9G2MP84A8W; D-Arabino-hexose, 2-deoxy-; HSDB 5484; arabino-Hexose, 2-deoxy-; D-Glucose, 2-deoxy-; 9G2MP84A8W; (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal; AK-44445; 2 Deoxyglucose; 2 Deoxy D glucose; 2 Desoxy D glucose; D-arabino-2-desoxyhexose; d-2-glucodesose; D-2dGlc; deoxy-d-glucose, 2-; 2-DEOXYLGLUCOSE; 2-INNo-D-AEIIC; SCHEMBL7670; AC1L33KH; KSC175S5P; 4-01-00-04282 (Beilstein Handbook Reference); Jsp003004; CHEMBL2074932; CTK0H5957; MolPort-002-317-302; 2-deoxy-D-glucose
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 164.16
Logarithm of the Partition Coefficient (xlogp) -2.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C6H12O5
IUPAC Name
(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Canonical SMILES
C(C=O)[C@H]([C@@H]([C@@H](CO)O)O)O
InChI
InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1
InChIKey
VRYALKFFQXWPIH-PBXRRBTRSA-N
Cross-matching ID
PubChem CID
108223
CAS Number
154-17-6
DrugBank ID
DB08831
TTD ID
D0H3KI
VARIDT ID
DR00011

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Sodium/glucose cotransporter 4 (SLC5A9) DT1CP40 SC5A9_HUMAN Substrate [2]
Sodium/glucose cotransporter 3 (SLC5A4) DTO4FLB SC5A4_HUMAN Substrate [3]
Sodium/glucose cotransporter 5 (SLC5A10) DTQNIG7 SC5AA_HUMAN Substrate [3]
Glucose transporter type 12 (SLC2A12) DTA5QI0 GTR12_HUMAN Substrate [4]
Proton-associated sugar transporter A (SLC45A1) DTMSNOU S45A1_HUMAN Substrate [5]
Glucose transporter type 6 (SLC2A6) DTS4MKQ GTR6_HUMAN Substrate [6]
Glucose transporter type 4, insulin-responsive (SLC2A4) DT4827A GLUT4_HUMAN Substrate [7]
Glucose transporter type 3, brain (SLC2A3) DT9SQ3L GTR3_HUMAN Substrate [8]
Glucose transporter type 14 (SLC2A14) DT18YD9 GTR14_HUMAN Substrate [9]
Sodium/glucose cotransporter 1 (SLC5A1) DTOKC04 SC5A1_HUMAN Substrate [10]
Glucose transporter type 8 (SLC2A8) DT2I7BM GTR8_HUMAN Substrate [6]
Glucose transporter type 7 (SLC2A7) DT8SQBG GTR7_HUMAN Substrate [6]
Glucose transporter type 2, liver (SLC2A2) DTUJPOL GTR2_HUMAN Substrate [11]
Glucose transporter type 10 (SLC2A10) DT3BI6S GTR10_HUMAN Substrate [12]
Glucose transporter type 1, erythrocyte/brain (SLC2A1) DTG3T6X GTR1_HUMAN Substrate [13]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
7SK snRNA methylphosphate capping enzyme (MEPCE) OTRBQEYP MEPCE_HUMAN Gene/Protein Processing [14]
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Regulation of Drug Effects [15]
Alpha-2-macroglobulin (A2M) OTFTX90K A2MG_HUMAN Regulation of Drug Effects [16]
AP-5 complex subunit sigma-1 (AP5S1) OTGS53SC AP5S1_HUMAN Gene/Protein Processing [14]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [17]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [18]
Collagenase 3 (MMP13) OTY8BZIE MMP13_HUMAN Gene/Protein Processing [19]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [18]
E3 ubiquitin-protein ligase Jade-2 (JADE2) OTVG2MYF JADE2_HUMAN Gene/Protein Processing [14]
Endoplasmic reticulum chaperone BiP (HSPA5) OTFUIRAO BIP_HUMAN Gene/Protein Processing [20]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00633087) A Phase I/II Trial of 2-Deoxyglucose (2DG) for the Treatment of Advanced Cancer and Hormone Refractory Prostate Cancer. U.S. National Institutes of Health.
2 SLC5A9/SGLT4, a new Na+-dependent glucose transporter, is an essential transporter for mannose, 1,5-anhydro-D-glucitol, and fructose. Life Sci. 2005 Jan 14;76(9):1039-50.
3 The sodium/glucose cotransport family SLC5. Pflugers Arch. 2004 Feb;447(5):510-8.
4 The human facilitative glucose transporter GLUT12: Expression and regulation in Caco-2 and 3T3-L1cells.
5 Dysfunction of the Cerebral Glucose Transporter SLC45A1 in Individuals with Intellectual Disability and Epilepsy. Am J Hum Genet. 2017 May 4;100(5):824-830.
6 Functional Properties and Genomics of Glucose Transporters. Curr Genomics. 2007 Apr; 8(2): 113128.
7 Need for GLUT4 activation to reach maximum effect of insulin-mediated glucose uptake in brown adipocytes isolated from GLUT4myc-expressing mice. Diabetes. 2002 Sep;51(9):2719-26.
8 Ascorbic acid-dependent GLUT3 inhibition is a critical step for switching neuronal metabolism. J Cell Physiol. 2011 Dec;226(12):3286-94.
9 The SLC2A14 gene, encoding the novel glucose/dehydroascorbate transporter GLUT14, is associated with inflammatory bowel disease. Am J Clin Nutr. 2017 Dec;106(6):1508-1513.
10 The role of SGLT1 and GLUT2 in intestinal glucose transport and sensing. PLoS One. 2014 Feb 26;9(2):e89977.
11 GLUT2 (SLC2A2) is not the principal glucose transporter in human pancreatic beta cells: implications for understanding genetic association signals at this locus. Mol Genet Metab. 2011 Dec;104(4):648-53.
12 Sequence and functional analysis of GLUT10: a glucose transporter in the Type 2 diabetes-linked region of chromosome 20q12-13.1. Mol Genet Metab. 2001 Sep-Oct;74(1-2):186-99.
13 Glutamine 161 of Glut1 glucose transporter is critical for transport activity and exofacial ligand binding. J Biol Chem. 1994 Aug 12;269(32):20533-8.
14 Development and validation of the TGx-HDACi transcriptomic biomarker to detect histone deacetylase inhibitors in human TK6 cells. Arch Toxicol. 2021 May;95(5):1631-1645. doi: 10.1007/s00204-021-03014-2. Epub 2021 Mar 26.
15 A collagen domain-derived short adiponectin peptide activates APPL1 and AMPK signaling pathways and improves glucose and fatty acid metabolisms. J Biol Chem. 2018 Aug 31;293(35):13509-13523. doi: 10.1074/jbc.RA118.001801. Epub 2018 Jul 10.
16 Activated 2-macroglobulin binding to human prostate cancer cells triggers insulin-like responses. J Biol Chem. 2015 Apr 10;290(15):9571-87. doi: 10.1074/jbc.M114.617837. Epub 2015 Feb 26.
17 Cytotoxic effects of mithramycin DIG-MSK can depend on the rise of autophagy. Toxicol In Vitro. 2015 Oct;29(7):1537-44. doi: 10.1016/j.tiv.2015.06.008. Epub 2015 Jun 13.
18 2-Deoxy-D-glucose activates autophagy via endoplasmic reticulum stress rather than ATP depletion. Cancer Chemother Pharmacol. 2011 Apr;67(4):899-910. doi: 10.1007/s00280-010-1391-0. Epub 2010 Jul 1.
19 IKK inibition by a glucosamine derivative enhances Maspin expression in osteosarcoma cell line. Chem Biol Interact. 2017 Jan 25;262:19-28. doi: 10.1016/j.cbi.2016.12.005. Epub 2016 Dec 6.
20 HHQ-4, a quinoline derivate, preferentially inhibits proliferation of glucose-deprived breast cancer cells as a GRP78 down-regulator. Toxicol Appl Pharmacol. 2019 Jun 15;373:10-25. doi: 10.1016/j.taap.2019.04.017. Epub 2019 Apr 22.