Canonical Smiles : CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)C
Inchi Key : ARFRZOLTIRQFCI-NGQYDJQZSA-N
IUPAC : methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
Pubchem ID : 162823
Smiles : COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)C2C1C(O)CC2(C)OC(C)=O
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 448.16
Volume : 409.084
Density : 1.096
nHA : 12
nHD : 5
nRot : 7
nRing : 3
Max Ring : 9
nHet: 12
fChar : 0
nRig : 18
Flexibility : 0.389
Stereo Centers : 10
TPSA : 181.44
logS : -0.522
logP: -1.084
logD7.4 : 0.216
ABSORPTION
Caco-2 Permeability : -6.053
MDCK Permeability : 0.000249847
Pgp-inhibitor : 0
Pgp-substrate : 0.831
HIA : 0.989
F20% : 0.596
F30% : 0.997
DISTRIBUTION
PPB : 0.199594
VD : 0.273
BBB Penetration : 0.517
Fu : 0.586151
METABOLISM
CYP 1A2 inhibitor : 0.002
CYP 1A2 substrate : 0.084
CYP 2C19 inhibitor : 0.006
CYP 2C19 substrate : 0.413
CYP 2C9 inhibitor : 0.001
CYP 2C9 substrate : 0.061
CYP 2D6 inhibitor : 0.004
CYP 2D6 substrate : 0.093
CYP 3A4 inhibitor : 0.012
CYP 3A4 substrate : 0.074
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MEDICINAL CHEMISTRY
QED : 0.28
SAscore : 4.916
Fsp : 0.789
MCE-18 : 63.529
NPscore : 2.755
Lipinski Rule : Accepted
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Accepted
PAINS : 0
ALARM NMR Rule : 1
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.01
H-HT : 0.283
DILI : 0.936
AMES Toxicity : 0.06
Rat Oral Acute Toxicity : 0.774
FDAMDD : 0.101
Skin Sensitization : 0.013
Carcinogencity : 0.933
Eye Corrosion : 0.003
Eye Irritation : 0.007
Respiratory Toxicity : 0.301
Bioconcentration Factor : 0.383
IGC50 : 1.894
LC50FM : 2.637
LC50DM : 4.332
NR-AR : 0.008
NR-AR-LBD: 0.221
NR-AhR : 0.007
NR-Aromatase : 0.003
NR-ER : 0.064
NR-ER-LBD : 0.018
NR-PPAR-gamma : 0.005
SR-ARE : 0.027
SR-ATAD5 : 0.762
SR-HSE : 0.006
SR-MMP : 0.27
SR-p53 : 0.071
Acute/Aquatic Toxicity Rule : 5
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 2
Non Biodegradable Rule : 1
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 1
EXCRETION
CL : 1.622
t1/2 : 0.591
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