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]
Affected Organisms
Humans and other mammals
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
UNII
9G2MP84A8W
DrugBank ID
DB08831
TTD ID
D0H3KI
VARIDT ID
DR00011
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]
Alpha-2-macroglobulin (A2M) OTFTX90K A2MG_HUMAN Regulation of Drug Effects [15]
AP-5 complex subunit sigma-1 (AP5S1) OTGS53SC AP5S1_HUMAN Gene/Protein Processing [14]
Collagenase 3 (MMP13) OTY8BZIE MMP13_HUMAN Gene/Protein Processing [16]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [17]
E3 ubiquitin-protein ligase Jade-2 (JADE2) OTVG2MYF JADE2_HUMAN Gene/Protein Processing [14]
ERBB receptor feedback inhibitor 1 (ERRFI1) OT7VZ2IZ ERRFI_HUMAN Gene/Protein Processing [14]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Gene/Protein Processing [18]
Inactive cell surface hyaluronidase CEMIP2 (CEMIP2) OT9I1XUO CEIP2_HUMAN Gene/Protein Processing [14]
Inhibitor of nuclear factor kappa-B kinase subunit alpha (CHUK) OTLF4ZB1 IKKA_HUMAN Protein Interaction/Cellular Processes [16]
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 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.
16 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.
17 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.
18 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.