Canonical Smiles : CO[C@H]1C[C@H]2[C@@H](C=C([C@H]2[C@@H](O1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)COC(=O)c4ccc(cc4)O)O
Inchi Key : RPIYNUXBYSWXNA-TXNASDCWSA-N
IUPAC : [(1S,3R,4aR,5S,7aS)-1-(beta-D-Glucopyranosyloxy)-5-hydroxy-3-methoxy-1,3,4,4a,5,7a-hexahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
Pubchem ID :
Smiles : CO[C@H]1C[C@H]2[C@H](O)C=C(COC(=O)c3ccc(O)cc3)[C@H]2[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O1
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 498.17
Volume : 464.439
Density : 1.073
nHA : 12
nHD : 6
nRot : 8
nRing : 4
Max Ring : 9
nHet: 12
fChar : 0
nRig : 23
Flexibility : 0.348
Stereo Centers : 10
TPSA : 184.6
logS : -2.387
logP: 0.397
logD7.4 : 0.359
ABSORPTION
Caco-2 Permeability : -6.287
MDCK Permeability : 0.0000583762
Pgp-inhibitor : 0.053
Pgp-substrate : 0.97
HIA : 0.913
F20% : 0.024
F30% : 0.996
DISTRIBUTION
PPB : 0.317801
VD : 0.45
BBB Penetration : 0.234
Fu : 0.461066
METABOLISM
CYP 1A2 inhibitor : 0.011
CYP 1A2 substrate : 0.061
CYP 2C19 inhibitor : 0.013
CYP 2C19 substrate : 0.125
CYP 2C9 inhibitor : 0.006
CYP 2C9 substrate : 0.091
CYP 2D6 inhibitor : 0.005
CYP 2D6 substrate : 0.101
CYP 3A4 inhibitor : 0.014
CYP 3A4 substrate : 0.074
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MEDICINAL CHEMISTRY
QED : 0.191
SAscore : 4.77
Fsp : 0.609
MCE-18 : 93.459
NPscore : 2.175
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Accepted
PAINS : 0
ALARM NMR Rule : 2
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.025
H-HT : 0.096
DILI : 0.971
AMES Toxicity : 0.519
Rat Oral Acute Toxicity : 0.164
FDAMDD : 0.012
Skin Sensitization : 0.084
Carcinogencity : 0.756
Eye Corrosion : 0.003
Eye Irritation : 0.042
Respiratory Toxicity : 0.106
Bioconcentration Factor : 0.568
IGC50 : 3.506
LC50FM : 4.526
LC50DM : 4.611
NR-AR : 0.057
NR-AR-LBD: 0.835
NR-AhR : 0.007
NR-Aromatase : 0.057
NR-ER : 0.56
NR-ER-LBD : 0.262
NR-PPAR-gamma : 0.017
SR-ARE : 0.094
SR-ATAD5 : 0.098
SR-HSE : 0.009
SR-MMP : 0.42
SR-p53 : 0.752
Acute/Aquatic Toxicity Rule : 2
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 : 1.531
t1/2 : 0.887
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