HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

D-Glucose, 2-deoxy-

HCID 225612
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
154-17-6
Standard SMILES
O=CCC(O)C(O)C(O)CO
InChIKey
VRYALKFFQXWPIH-UHFFFAOYSA-N
Molecular formula
C6H12O5
Average molar mass
164.16 g/mol
Monoisotopic mass
164.06847348

Overview

2-Deoxy-D-galactose has been reported in Triticum aestivum and Escherichia coli with data available.

Names & identifiers

Preferred name
D-Glucose, 2-deoxy-
IUPAC
3,4,5,6-tetrahydroxyhexanal
English name
2-Deoxy-D-glucose
Molecular formula
C6H12O5
Molecular weight
164.16

Names & synonyms

d-2-glucodesoseD-Glucose, 2-deoxy-2-Deoxy-3-Arabino-hexoseGlucose, 2-deoxy-72561-26-32-Deoxyhexose #2-Deoxyglucose-1-3H2-Deoxy-D-arabino-hexose;D-Arabino-2-deoxyhexose2-Deoxy-D-glucose 1-14CSCHEMBL2007142-DG (2-Deoxy-D-glucose)VRYALKFFQXWPIH-UHFFFAOYSA-N
Show more names
2-dg2-DEOXYGLUCOSEdeoxyglucose2-Dexoy-D-Glucose2-desoxy-d-glucoseD-Arabino-2-deoxyhexose2-deoxy-d-[UL-13C6]glucose(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal(4R,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triolba2758
WLN: VH1YQYQYQ1Q-D-ARABINOs4701AKOS024386266MD11720SB45112DB-013800ST510372272-Deoxy-D-arabino-hexose; D-Arabino-2-deoxyhexose

Database identifiers

CAS
154-17-6
PubChem CID

Properties

Computed structural properties

XLogP
-2.9
Topological polar surface area
98 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
5
Rotatable bonds
5
Heavy atoms
11
Formal charge
0
Complexity
116

Physicochemical properties

Melting point
146 · 146-147 °C(lit.)
alpha
45.5 · 45.5 º (c=2, H2O)
Boiling point
211.61 °C · 211.61°C (rough estimate)
Density
1.1738 · 1.1738 (rough estimate)
refractive index
46.5 ° · 46.5 ° (C=1, H2O)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: 50 mg/mL, clear, colorless to faintly yellow
form
crystalline
pka
1 · pK1:12.52 (25°C)
color
white
biological source
synthetic
optical activity
38.5 · +38.5 → +45.9
Water Solubility
Soluble in water.
Merck
14 · 14,2904
BRN
1723331 · 1723331
Stability
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
3-10
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
MQ3325000
hs_code
29400090
risk_code
20/21/22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
24/25-37/39-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazardous Substances Data
154-17-6(Hazardous Substances Data)

Chemistry & industry

Applications · 3 items

Description2-Deoxy-D-glucose (154-17-6) is a synthetic glucose analog with extensive biological effects. It is commonly thought of as an inhibitor of glycolysis, but its metabolic effects are wide-ranging. 2-Deoxy-D-glucose competitively inhibits glucose uptake via its metabolite 2-Deoxy-D-glucose-6-phosphate, which inhibits hexokinase and phosphoglucose-isomerase leading to decreased ATP production, cell cycle blockage, decreased cell growth and ultimately cell death.1,2

Uses2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical]

Uses2-Deoxy-D-glucose (2-DG) is used in glucoprivic feeding research to invoke and study the processes of counter-regulatory response (CRR). 2-Deoxy-D-glucose is used in the development of anti-cancer strategies that involve radio- and chemosensitization and oxidative stress.

Upstream & downstream products

Upstream raw materials

D-threo-Hexos-5-ulose, cyclic 1-(1,3-propanediyl acetal) (9CI)D-arabino-Hexose, 2-deoxy-, cyclic 1,3-propanediyl acetal (9CI)D-arabino-Heptose, 2,3-dideoxy-4,5:6,7-bis-O-(1-methylethylidene)-

Suppliers105 total

Related reactions

1 records
New reaction record
HRID 1555532 reaction equation
HRID 1555532As reactantTraining data from https://doi.org/10.1039/C8SC04228D (1/10)

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
225612
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
PMMURAAUARKVCB-CEZCPVKQSA-N
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
LogP
-1.46 · -1.460 (est)
CAS DataBase Reference
154 · 154-17-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
9 G2MP84A8W · 9G2MP84A8W
EPA Substance Registry System
2 · D-arabino-Hexose, 2-deoxy- (154-17-6)
UNSPSC Code
12352201 · 12352201
NACRES
79 · NA.79
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xn,Xi
Risk Statements
20 · 20/21/22-36/37/38
Safety Statements
24 · 24/25-37/39-36-26
WGK Germany
3 · 3
RTECS
3325000 · MQ3325000
F
3 · 3-10
TSCA
TSCA listed
HS Code
29400090 · 29400090
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
154 · 154-17-6(Hazardous Substances Data)
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
北京阿克曼科技有限公司18001219251 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
南京百芙利科技有限责任公司25-25-58740604 15951658055 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Carbone Scientific CO., LTD[email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海永增科技有限公司021-021-021-65281118 15921781258 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
南京奥生化学技术有限公司+86 (25) 82263158
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
怀化市冰峰化工有限公司0745-2866851 17711757908 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
上海攀鸿化工科技有限公司021-56491756 13512199871 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
杭州东帆化学有限公司86-0571-85151182
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
无锡中坤生化科技有限公司+86 0510-85629785
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
上海弘邦医药科技有限公司021-021-64975436 18917636693 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]