Canonical Smiles : C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
Inchi Key : UFCLZKMFXSILNL-PSEXTPKNSA-N
IUPAC : (1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
Pubchem ID : 5281780
Smiles : O=C(C=Cc1ccc(O)c(O)c1)OC1CC(O)(C(=O)O)CC(O)C1OC(=O)C=Cc1ccc(O)c(O)c1
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 516.13
Volume : 491.768
Density : 1.05
nHA : 12
nHD : 7
nRot : 9
nRing : 3
Max Ring : 6
nHet: 12
fChar : 0
nRig : 23
Flexibility : 0.391
Stereo Centers : 4
TPSA : 211.28
logS : -2.6
logP: 1.773
logD7.4 : 1.084
ABSORPTION
Caco-2 Permeability : -6.273
MDCK Permeability : 0.00000875702
Pgp-inhibitor : 0
Pgp-substrate : 0.22
HIA : 0.901
F20% : 0.995
F30% : 0.999
DISTRIBUTION
PPB : 0.98144
VD : 0.325
BBB Penetration : 0.107
Fu : 0.0199995
METABOLISM
CYP 1A2 inhibitor : 0.154
CYP 1A2 substrate : 0.029
CYP 2C19 inhibitor : 0.079
CYP 2C19 substrate : 0.044
CYP 2C9 inhibitor : 0.378
CYP 2C9 substrate : 0.455
CYP 2D6 inhibitor : 0.051
CYP 2D6 substrate : 0.165
CYP 3A4 inhibitor : 0.078
CYP 3A4 substrate : 0.053
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MEDICINAL CHEMISTRY
QED : 0.156
SAscore : 4.141
Fsp : 0.24
MCE-18 : 81.29
NPscore : 1.642
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Rejected
PAINS : 1
ALARM NMR Rule : 3
BMS Rule : 0
Chelator Rule : 1
TOXICOLOGY
hERG Blockers : 0.025
H-HT : 0.125
DILI : 0.027
AMES Toxicity : 0.029
Rat Oral Acute Toxicity : 0.077
FDAMDD : 0.178
Skin Sensitization : 0.94
Carcinogencity : 0.127
Eye Corrosion : 0.003
Eye Irritation : 0.045
Respiratory Toxicity : 0.023
Bioconcentration Factor : 0.332
IGC50 : 3.902
LC50FM : 4.583
LC50DM : 5.213
NR-AR : 0.632
NR-AR-LBD: 0.919
NR-AhR : 0.405
NR-Aromatase : 0.77
NR-ER : 0.552
NR-ER-LBD : 0.833
NR-PPAR-gamma : 0.943
SR-ARE : 0.845
SR-ATAD5 : 0.472
SR-HSE : 0.917
SR-MMP : 0.947
SR-p53 : 0.884
Acute/Aquatic Toxicity Rule : 4
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 1
Skin Sensitization Rule : 8
Non Biodegradable Rule : 1
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 3
EXCRETION
CL : 5.195
t1/2 : 0.953
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