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Details of : naphthalene-1,4-dione (Lapachol)
Canonical Smiles : CC(=CCC1=C(C(=O)C2=CC=CC=C2C1=O)OC)C
Inchi Key : NHTTYMNGELRKMP-UHFFFAOYSA-N
IUPAC : 2-methoxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
Pubchem ID : 96950
Smiles : CC(=CCC1=C(C(=O)C2=CC=CC=C2C1=O)OC)C
Click here to download sdf file
PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 256.11
Volume : 276.095
Density : 0.928
nHA : 3
nHD : 2
nRot : 3
nRing : 2
Max Ring : 10
nHet: 3
fChar : 0
nRig : 13
Flexibility : 0.231
Stereo Centers : 0
TPSA : 49.69
logS : -4.268
logP: 4.406
logD7.4 : 3.404
ABSORPTION
Caco-2 Permeability : -4.89
MDCK Permeability : 0.0000240578
Pgp-inhibitor : 0.002
Pgp-substrate : 0.001
HIA : 0.006
F20% : 0.003
F30% : 0.002
DISTRIBUTION
PPB : 0.990428
VD : 0.406
BBB Penetration : 0.095
Fu : 0.0274653
METABOLISM
CYP 1A2 inhibitor : 0.967
CYP 1A2 substrate : 0.922
CYP 2C19 inhibitor : 0.216
CYP 2C19 substrate : 0.768
CYP 2C9 inhibitor : 0.251
CYP 2C9 substrate : 0.794
CYP 2D6 inhibitor : 0.381
CYP 2D6 substrate : 0.884
CYP 3A4 inhibitor : 0.196
CYP 3A4 substrate : 0.241
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MEDICINAL CHEMISTRY
QED : 0.647
SAscore : 2.592
Fsp : 0.125
MCE-18 : 13
NPscore : 1.193
Lipinski Rule : Accepted
Pfizer Rule : Rejected
GSK Rule : Rejected
Golden Triangle : Accepted
PAINS : 0
ALARM NMR Rule : 3
BMS Rule : 0
Chelator Rule : 1
TOXICOLOGY
hERG Blockers : 0.025
H-HT : 0.235
DILI : 0.346
AMES Toxicity : 0.336
Rat Oral Acute Toxicity : 0.909
FDAMDD : 0.58
Skin Sensitization : 0.954
Carcinogencity : 0.752
Eye Corrosion : 0.004
Eye Irritation : 0.918
Respiratory Toxicity : 0.889
Bioconcentration Factor : 1.352
IGC50 : 4.07
LC50FM : 4.427
LC50DM : 6.016
NR-AR : 0.007
NR-AR-LBD: 0.426
NR-AhR : 0.956
NR-Aromatase : 0.849
NR-ER : 0.292
NR-ER-LBD : 0.607
NR-PPAR-gamma : 0.962
SR-ARE : 0.932
SR-ATAD5 : 0.906
SR-HSE : 0.954
SR-MMP : 0.928
SR-p53 : 0.973
Acute/Aquatic Toxicity Rule : 0
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 11
Non Biodegradable Rule : 1
SureChEMBL Rule : 1
FAF-Drugs4 Rule : 3
EXCRETION
CL : 5.567
t1/2 : 0.697
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