Canonical Smiles : CC(=O)OCC1=CC(C2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)O
Inchi Key : DGDWCRWJRNMRKX-DILZHRMZSA-N
IUPAC : (1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Pubchem ID : 11968867
Smiles : CC(=O)OCC1=CC(O)C2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O)C3O)C12
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 432.13
Volume : 389.152
Density : 1.11
nHA : 12
nHD : 6
nRot : 7
nRing : 3
Max Ring : 9
nHet: 12
fChar : 0
nRig : 18
Flexibility : 0.389
Stereo Centers : 9
TPSA : 192.44
logS : -0.346
logP: -1.546
logD7.4 : -0.153
ABSORPTION
Caco-2 Permeability : -6.238
MDCK Permeability : 0.000305772
Pgp-inhibitor : 0
Pgp-substrate : 0.731
HIA : 0.992
F20% : 0.768
F30% : 0.999
DISTRIBUTION
PPB : 0.185048
VD : 0.248
BBB Penetration : 0.584
Fu : 0.65751
METABOLISM
CYP 1A2 inhibitor : 0.003
CYP 1A2 substrate : 0.014
CYP 2C19 inhibitor : 0.01
CYP 2C19 substrate : 0.051
CYP 2C9 inhibitor : 0.001
CYP 2C9 substrate : 0.061
CYP 2D6 inhibitor : 0.015
CYP 2D6 substrate : 0.098
CYP 3A4 inhibitor : 0.012
CYP 3A4 substrate : 0.022
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MEDICINAL CHEMISTRY
QED : 0.187
SAscore : 4.79
Fsp : 0.667
MCE-18 : 57.2
NPscore : 2.661
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Accepted
PAINS : 0
ALARM NMR Rule : 0
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.007
H-HT : 0.09
DILI : 0.983
AMES Toxicity : 0.083
Rat Oral Acute Toxicity : 0.745
FDAMDD : 0.031
Skin Sensitization : 0.018
Carcinogencity : 0.962
Eye Corrosion : 0.003
Eye Irritation : 0.007
Respiratory Toxicity : 0.164
Bioconcentration Factor : 0.176
IGC50 : 2.139
LC50FM : 3.613
LC50DM : 3.538
NR-AR : 0.003
NR-AR-LBD: 0.109
NR-AhR : 0.005
NR-Aromatase : 0.002
NR-ER : 0.06
NR-ER-LBD : 0.008
NR-PPAR-gamma : 0.008
SR-ARE : 0.026
SR-ATAD5 : 0.894
SR-HSE : 0.01
SR-MMP : 0.145
SR-p53 : 0.084
Acute/Aquatic Toxicity Rule : 4
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 3
Non Biodegradable Rule : 1
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 1
EXCRETION
CL : 1.702
t1/2 : 0.694
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