cycloheximide

Identification (Source:EPA,EU)

ID 456
Name cycloheximide
CAS 66-81-9
IUPAC
Inchi InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1
CIPAC
EPA Code 043401
Formula C15H23NO4
SMILES O([H])[C@]([H])(C([H])([H])C([H])(C([H])([H])C(N1[H])=O)C([H])([H])C1=O)[C@@]2([H])C([C@@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C2([H])[H])=O
Status Not Available

Classification

Mode of Action A protein biosynthesis inhibitor
Pesticide Type Fungicide, Plant Growth Regulator
Chemical Group Unclassified
Classification unclassified plant growth regulators
antibiotic fungicides

Properties (Source:PubChem)

Molecular Weight 281.16
Physical State Colourless crystalline solid
AlogP 0.933
H-Bond Donor 2
H-Bond Acceptor 4
Surface Area 279.19
Polar Surface Area 83.47

Structure



ChemMapper Search Option (Docunmentation of ChemMapper)

3D similarity method

2D similarity method

Compound Database



Bioactivity Database

KEGG (5,928)

PDB (7,072)


Similarity Threshold

Ecotoxicology (Source:PPDB,IPM)

Species Method Study Time Dose Type Value
Birds Acute LD50 82.5 mg kg-1

Related targets

Target Name RScore (About this table)
caspase 3 949(7,14,16,169) Details
vascular endothelial growth factor 736(7,9,9,116) Details
FLIP 664(7,9,9,44) Details
caspase 8 689(5,11,12,104) Details
p38 744(5,10,13,179) Details
IL 1 beta 705(5,9,12,170) Details
heme oxygenase 1 664(5,8,10,164) Details
caspase (protein family or complex) 858(4,16,17,173) Details
mitogen activated protein kinase (protein family or complex) 786(4,12,12,226) Details
mcl 1 472(4,7,8,57) Details
CYP1A1 463(4,7,8,48) Details
peroxisome proliferator activated receptor 367(4,4,5,42) Details
tumor necrosis factor alpha 1123(3,23,40,198) Details
TRAIL 644(3,11,15,144) Details
interleukin 8 456(3,7,7,96) Details
PPAR gamma 450(3,6,9,105) Details
ERK1 384(3,5,5,84) Details
calpain (protein family or complex) 273(3,3,3,33) Details
estrogen receptor 446(2,8,9,101) Details
CD95 325(2,6,6,45) Details
PI3K 341(2,5,7,81) Details
bcl 2 336(2,5,5,86) Details
alkaline phosphatase 286(2,5,5,36) Details
signal transducer and activator of transcription 3 248(2,4,4,28) Details
STAT1 240(2,4,4,20) Details
STAT5 230(2,4,4,10) Details
cytochrome c 255(2,3,4,60) Details
P27 250(2,3,4,55) Details
catalase 228(2,3,3,38) Details
NHE3 216(2,3,3,26) Details
FKBP38 195(2,3,3,5) Details
epidermal growth factor receptor 217(2,2,2,57) Details
Aa nat 187(2,2,2,27) Details
elastin 187(2,2,3,22) Details
CA1 185(2,2,3,20) Details
PIN1 182(2,2,3,17) Details
arginase 177(2,2,2,17) Details
kinase suppressor of Ras 1 176(2,2,2,16) Details
V2R 171(2,2,2,11) Details
myosin light chain kinase 169(2,2,2,9) Details
factor VIIa 163(2,2,2,3) Details
E2F1 245(1,5,5,45) Details
Protein S 217(1,5,5,17) Details
activator protein 1 176(1,3,3,36) Details
DR5 174(1,3,3,34) Details
chemokine 161(1,2,2,51) Details
IL 4 160(1,2,2,50) Details
thrombin 155(1,2,3,40) Details
Bcl xL 151(1,2,3,36) Details
Toll like receptor 4 140(1,2,2,30) Details
c Myc 134(1,2,3,19) Details
Cx43 134(1,2,2,24) Details
glucocorticoid receptor 133(1,2,2,23) Details
aquaporin 4 132(1,2,2,22) Details
PUMA 131(1,2,2,21) Details
Hsp90 126(1,2,2,16) Details
Ghrelin 126(1,2,2,16) Details
UGT1A6 124(1,2,3,9) Details
cytochrome P450 3A4 122(1,2,2,12) Details
IgE 120(1,2,2,10) Details
DR4 119(1,2,2,9) Details
TIMP3 116(1,2,2,6) Details
Fas Ligand 129(1,1,4,34) Details
c Jun N terminal kinase (protein family or complex) 107(1,1,1,27) Details
gelsolin 106(1,1,1,26) Details
IL 13 106(1,1,1,26) Details
TNFR1 105(1,1,1,25) Details
reelin 104(1,1,1,24) Details
GATA 2 103(1,1,2,18) Details
interleukin 7 100(1,1,2,15) Details
casein 100(1,1,3,10) Details
CDK11 p58 99(1,1,2,14) Details
calmodulin 98(1,1,1,18) Details
phosphoenolpyruvate carboxylase 96(1,1,1,16) Details
cholesterol sulfotransferase 95(1,1,1,15) Details
TNFR 2 94(1,1,1,14) Details
Cited2 93(1,1,1,13) Details
Sphingosine kinase 1 93(1,1,1,13) Details
PGDS 93(1,1,1,13) Details
Amylin 92(1,1,1,12) Details
plasminogen 91(1,1,1,11) Details
K ras 91(1,1,1,11) Details
ADAM9 91(1,1,1,11) Details
CYP24A1 91(1,1,1,11) Details
CCL1 91(1,1,1,11) Details
FOXO1 91(1,1,1,11) Details
NHE1 90(1,1,1,10) Details
beta adrenoceptors (protein family or complex) 90(1,1,1,10) Details
hCTR1 90(1,1,1,10) Details
p42 90(1,1,1,10) Details
syndecan 4 90(1,1,1,10) Details
5 lipoxygenase 89(1,1,1,9) Details
caspase 6 89(1,1,1,9) Details
aquaporins (protein family or complex) 89(1,1,1,9) Details
IL 21 89(1,1,1,9) Details
NFIL3 89(1,1,1,9) Details
upstream stimulatory factor 2 89(1,1,1,9) Details
TR3 89(1,1,1,9) Details
CFTR 88(1,1,1,8) Details
Glut 4 88(1,1,1,8) Details
ATF5 88(1,1,1,8) Details
NESK 88(1,1,1,8) Details
FIP1L1 88(1,1,1,8) Details
CA3 87(1,1,1,7) Details
CKIP 1 87(1,1,1,7) Details
eIF 4E 87(1,1,1,7) Details
K18 87(1,1,1,7) Details
CCAAT enhancer binding protein beta 87(1,1,1,7) Details
PDE4B 87(1,1,1,7) Details
mitochondrial uncoupling protein 3 87(1,1,1,7) Details
hemoglobin (protein family or complex) 86(1,1,1,6) Details
caspase 1 86(1,1,1,6) Details
SNF5 86(1,1,1,6) Details
calnexin 86(1,1,1,6) Details
Nm23 H1 86(1,1,1,6) Details
IkappaB kinase 86(1,1,1,6) Details
glutathione S transferase 85(1,1,1,5) Details
beta glucosidase 85(1,1,1,5) Details
Myocilin 85(1,1,1,5) Details
glyoxalase I 85(1,1,1,5) Details
peripherin 85(1,1,1,5) Details
CHRM1 85(1,1,1,5) Details
FUT5 85(1,1,1,5) Details
CCR1 85(1,1,1,5) Details
HERP 85(1,1,1,5) Details
Sumo 2 85(1,1,1,5) Details
HSD11B 85(1,1,1,5) Details
MUC5AC 84(1,1,1,4) Details
IRP2 84(1,1,1,4) Details
novel protein 84(1,1,1,4) Details
endozepine 84(1,1,1,4) Details
PGIS 83(1,1,1,3) Details
EP1 82(1,1,1,2) Details
cyclin D2 82(1,1,1,2) Details
serine threonine protein kinases 81(1,1,1,1) Details
microsomal triglyceride transfer protein 81(1,1,1,1) Details
LPA3 81(1,1,1,1) Details
Nle 81(1,1,1,1) Details
CD47 81(1,1,1,1) Details
protein kinase C (protein family or complex) 216(0,5,5,66) Details
phosphatidylinositol 3 kinase (protein family or complex) 181(0,4,4,61) Details
caspase 9 132(0,3,3,42) Details
protein kinase A (protein family or complex) 129(0,3,3,39) Details
androgen receptor 117(0,3,3,27) Details
JNK1 109(0,3,4,14) Details
26S proteasome (protein family or complex) 105(0,3,3,15) Details
STAT5A 94(0,3,3,4) Details
IL 6 136(0,2,2,76) Details
integrins 122(0,2,3,57) Details
ATPase 109(0,2,2,49) Details
histone deacetylase (protein family or complex) 107(0,2,2,47) Details
aryl hydrocarbon receptor 102(0,2,2,42) Details
Resistin 95(0,2,3,30) Details
superoxide dismutase 91(0,2,2,31) Details
fibronectin 90(0,2,2,30) Details
adiponectin 89(0,2,2,29) Details
albumin 86(0,2,2,26) Details
RANTES 83(0,2,2,23) Details
GTPase 82(0,2,2,22) Details
bradykinin 78(0,2,2,18) Details
hTERT 76(0,2,2,16) Details
NMDA receptors (protein family or complex) 76(0,2,2,16) Details
SOCS3 76(0,2,2,16) Details
FADD 69(0,2,2,9) Details
calpain inhibitors 65(0,2,2,5) Details
glutamate receptor 64(0,2,2,4) Details
receptor interacting protein 64(0,2,2,4) Details
serotonin receptor 62(0,2,2,2) Details
cyclin D1 116(0,1,3,76) Details
interleukin 10 80(0,1,2,45) Details
protein is 78(0,1,1,48) Details
angiotensin II 77(0,1,1,47) Details
mammalian target of rapamycin 65(0,1,1,35) Details
cyclin 59(0,1,1,29) Details
TIMP 1 57(0,1,2,22) Details
c fos 57(0,1,1,27) Details
XIAP 56(0,1,1,26) Details
Jak 2 56(0,1,1,26) Details
P glycoprotein 56(0,1,2,21) Details
E cadherin 55(0,1,2,20) Details
fibroblast growth factor 2 54(0,1,1,24) Details
Regucalcin 54(0,1,1,24) Details
Hsp70 54(0,1,1,24) Details
interleukin (protein family or complex) 53(0,1,1,23) Details
MEK1 52(0,1,1,22) Details
MSPL 51(0,1,4,6) Details
SOX9 50(0,1,2,15) Details
KLF5 50(0,1,1,20) Details
cyclin dependent kinase (protein family or complex) 49(0,1,1,19) Details
CHOP 49(0,1,2,14) Details
calcineurin (protein family or complex) 48(0,1,1,18) Details
activin A 48(0,1,1,18) Details
glucose transporter 1 47(0,1,1,17) Details
Monad 47(0,1,2,12) Details
HC11 47(0,1,3,7) Details
elongation factor 2 46(0,1,1,16) Details
adipose differentiation related protein 46(0,1,1,16) Details
Gc globulin 45(0,1,1,15) Details
human ether a go go related gene 45(0,1,1,15) Details
PARP 45(0,1,1,15) Details
osteocalcin 44(0,1,1,14) Details
TLR3 44(0,1,2,9) Details
CXCR4 44(0,1,1,14) Details
c kit 44(0,1,2,9) Details
TRPC1 44(0,1,1,14) Details
SF 1 43(0,1,1,13) Details
Nerve growth factor 43(0,1,2,8) Details
BTG2 43(0,1,1,13) Details
NDRG1 43(0,1,1,13) Details
S1P 42(0,1,1,12) Details
NF E2 related factor 2 42(0,1,1,12) Details
adenylyl cyclase 41(0,1,1,11) Details
p65 41(0,1,1,11) Details
galectin 1 41(0,1,1,11) Details
HDAC4 41(0,1,1,11) Details
TN C 41(0,1,1,11) Details
osteopontin 41(0,1,1,11) Details
RNase A 41(0,1,2,6) Details
G0S2 41(0,1,1,11) Details
gelatinase B 40(0,1,1,10) Details
TRPV6 40(0,1,1,10) Details
lactate dehydrogenase (protein family or complex) 40(0,1,1,10) Details
B cell activating factor 40(0,1,1,10) Details
apolipoprotein A I 40(0,1,1,10) Details
RhoBTB2 40(0,1,1,10) Details
Pigment epithelium derived factor 40(0,1,1,10) Details
cytosolic phospholipase A2 40(0,1,1,10) Details
Mimitin 40(0,1,1,10) Details
Matriptase 40(0,1,1,10) Details
PHGPx 40(0,1,2,5) Details
lipocalin 2 39(0,1,1,9) Details
FGF23 39(0,1,1,9) Details
AT1 39(0,1,1,9) Details
GAL1 39(0,1,1,9) Details
entactin 39(0,1,1,9) Details
chemokine receptor (protein family or complex) 39(0,1,1,9) Details
S100A4 39(0,1,1,9) Details
galectin 8 39(0,1,1,9) Details
Tis11B 39(0,1,1,9) Details
N myc 38(0,1,1,8) Details
PAX3 38(0,1,1,8) Details
IFI16 38(0,1,1,8) Details
Rho kinase 38(0,1,1,8) Details
p50 38(0,1,1,8) Details
c IAP2 38(0,1,1,8) Details
EP4 receptors 37(0,1,1,7) Details
GRIK1 37(0,1,1,7) Details
OX40 ligand 37(0,1,1,7) Details
HDAC2 37(0,1,1,7) Details
galactosyltransferase I 37(0,1,2,2) Details
inhibitor of differentiation 1 37(0,1,1,7) Details
cIAP1 37(0,1,1,7) Details
class II transactivator 36(0,1,1,6) Details
XBP1 36(0,1,1,6) Details
BMP2 36(0,1,1,6) Details
IGF2 36(0,1,1,6) Details
GRIK2 36(0,1,1,6) Details
CD40 36(0,1,1,6) Details
thioredoxin reductase 36(0,1,1,6) Details
DIABLO 36(0,1,1,6) Details
apelin 36(0,1,1,6) Details
serglycin 36(0,1,1,6) Details
EP2 35(0,1,1,5) Details
beta endorphin 35(0,1,1,5) Details
CD11b 35(0,1,1,5) Details
NSP1 35(0,1,1,5) Details
ATF4 35(0,1,1,5) Details
DNMT 1 35(0,1,1,5) Details
P46 35(0,1,1,5) Details
GLUT 2 34(0,1,1,4) Details
ARNT 34(0,1,1,4) Details
TR1 34(0,1,1,4) Details
psoriasin 34(0,1,1,4) Details
lipoxygenase 12 34(0,1,1,4) Details
HSS1 34(0,1,1,4) Details
acetylcholine receptors (protein family or complex) 34(0,1,1,4) Details
prostate specific antigen 34(0,1,1,4) Details
Interleukin 5 34(0,1,1,4) Details
VEGF C 34(0,1,1,4) Details
cingulin 34(0,1,1,4) Details
polymerases 34(0,1,1,4) Details
caspase 4 33(0,1,1,3) Details
CD59 33(0,1,1,3) Details
SET7 33(0,1,1,3) Details
PABP 33(0,1,1,3) Details
RPD3 33(0,1,1,3) Details
corticotropin releasing factor 33(0,1,1,3) Details
MRP2 33(0,1,1,3) Details
SR a 33(0,1,1,3) Details
galactosyltransferase 1 33(0,1,1,3) Details
CTCF 33(0,1,1,3) Details
CCCTC binding factor 32(0,1,1,2) Details
histone acetyltransferase 32(0,1,1,2) Details
HAS3 32(0,1,1,2) Details
caspase 10 32(0,1,1,2) Details
FKBP5 32(0,1,1,2) Details
voltage dependent anion channel 1 32(0,1,1,2) Details
CYP1A2 32(0,1,1,2) Details
MRP4 32(0,1,1,2) Details
cytochrome P450 1B1 32(0,1,1,2) Details
heparan sulfate proteoglycans 32(0,1,1,2) Details
cysLT1 32(0,1,1,2) Details
S100beta 32(0,1,1,2) Details
anaphase promoting complex (protein family or complex) 31(0,1,1,1) Details
AdipoR1 31(0,1,1,1) Details
acid phosphatase 31(0,1,1,1) Details
sulfotransferase 31(0,1,1,1) Details
FKBP12 31(0,1,1,1) Details
far 2 31(0,1,1,1) Details
CD35 31(0,1,1,1) Details
voltage dependent anion channel 31(0,1,1,1) Details
apical sodium dependent bile acid transporter 31(0,1,1,1) Details
PU.1 31(0,1,1,1) Details
multidrug resistance associated protein 3 31(0,1,1,1) Details
stem cell factor 31(0,1,1,1) Details
ubiquitin 117(0,0,1,112) Details
annexin V 81(0,0,5,56) Details
leptin 48(0,0,0,48) Details
beta catenin 38(0,0,2,28) Details
brain derived neurotrophic factor 35(0,0,1,30) Details
interferon gamma 33(0,0,0,33) Details
thioredoxin 31(0,0,1,26) Details
CCL26 30(0,0,0,30) Details
PACAP 27(0,0,3,12) Details
eIF4E binding protein 1 27(0,0,1,22) Details
CREB 27(0,0,0,27) Details
connective tissue growth factor 27(0,0,0,27) Details
cyclin E 26(0,0,2,16) Details
protein as 25(0,0,1,20) Details
HDAC 24(0,0,0,24) Details
cyclooxygenase 2 24(0,0,0,24) Details
TORC1 23(0,0,0,23) Details
laminin (protein family or complex) 23(0,0,0,23) Details
Eotaxins 23(0,0,1,18) Details
T bet 23(0,0,1,18) Details
endothelin 1 23(0,0,1,18) Details
HCAM 22(0,0,0,22) Details
serum glucocorticoid regulated kinase 22(0,0,0,22) Details
N cadherin 22(0,0,1,17) Details
Vascular endothelial growth factor D 21(0,0,1,16) Details
GRP78 21(0,0,1,16) Details
IkappaBalpha 21(0,0,0,21) Details
CD4 20(0,0,0,20) Details
insulin like growth factor binding protein 1 20(0,0,1,15) Details
RANKL 20(0,0,0,20) Details
glucagon like peptide 2 19(0,0,0,19) Details
caveolin 1 19(0,0,1,14) Details
aldose reductase 19(0,0,0,19) Details
ATPases 19(0,0,0,19) Details
WAF1 19(0,0,0,19) Details
suppressor of cytokine signaling 1 18(0,0,1,13) Details
NFkappaB (protein family or complex) 18(0,0,0,18) Details
cyclin B1 18(0,0,0,18) Details
epidermal growth factor 18(0,0,0,18) Details
PERK 18(0,0,0,18) Details
interferon (protein family or complex) 18(0,0,0,18) Details
H:quinone oxidoreductase 18(0,0,0,18) Details
NK 1 17(0,0,1,12) Details
SSAT 17(0,0,0,17) Details
GPCR 17(0,0,1,12) Details
glycogen synthase kinase 3 17(0,0,0,17) Details
cytokeratin 19 16(0,0,1,11) Details
ALAS 16(0,0,1,11) Details
REDD1 16(0,0,1,11) Details
NUPR1 16(0,0,1,11) Details
AP 1 (protein family or complex) 15(0,0,0,15) Details
glyceraldehyde 3 phosphate dehydrogenase 15(0,0,0,15) Details
adipose triglyceride lipase 15(0,0,0,15) Details
TSP1 15(0,0,1,10) Details
TSC2 15(0,0,0,15) Details
cyclin dependent kinase inhibitor p27 15(0,0,0,15) Details
IL 17 15(0,0,1,10) Details
G protein coupled receptor 15(0,0,0,15) Details
insulin like growth factor I 15(0,0,0,15) Details
ISG15 15(0,0,0,15) Details
CXCR2 15(0,0,0,15) Details
mitogen activated protein kinase 1 15(0,0,0,15) Details
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