Canonical Smiles : C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
Inchi Key : YDDUMTOHNYZQPO-PSEXTPKNSA-N
IUPAC : (1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
Pubchem ID : 6474640
Smiles : O=C(C=Cc1ccc(O)c(O)c1)OC1CC(OC(=O)C=Cc2ccc(O)c(O)c2)(C(=O)O)CC(O)C1O
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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 : -2.026
logP: 1.426
logD7.4 : 0.876
ABSORPTION
Caco-2 Permeability : -6.212
MDCK Permeability : 0.00000962
Pgp-inhibitor : 0
Pgp-substrate : 0.582
HIA : 0.916
F20% : 0.996
F30% : 0.999
DISTRIBUTION
PPB : 0.986005
VD : 0.275
BBB Penetration : 0.078
Fu : 0.0193048
METABOLISM
CYP 1A2 inhibitor : 0.074
CYP 1A2 substrate : 0.026
CYP 2C19 inhibitor : 0.063
CYP 2C19 substrate : 0.045
CYP 2C9 inhibitor : 0.401
CYP 2C9 substrate : 0.653
CYP 2D6 inhibitor : 0.019
CYP 2D6 substrate : 0.164
CYP 3A4 inhibitor : 0.095
CYP 3A4 substrate : 0.042
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MEDICINAL CHEMISTRY
QED : 0.156
SAscore : 4.164
Fsp : 0.24
MCE-18 : 81.29
NPscore : 1.67
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 : 0.018
H-HT : 0.111
DILI : 0.045
AMES Toxicity : 0.043
Rat Oral Acute Toxicity : 0.076
FDAMDD : 0.063
Skin Sensitization : 0.908
Carcinogencity : 0.13
Eye Corrosion : 0.003
Eye Irritation : 0.024
Respiratory Toxicity : 0.021
Bioconcentration Factor : 0.364
IGC50 : 3.881
LC50FM : 4.484
LC50DM : 5.238
NR-AR : 0.685
NR-AR-LBD: 0.921
NR-AhR : 0.385
NR-Aromatase : 0.508
NR-ER : 0.612
NR-ER-LBD : 0.848
NR-PPAR-gamma : 0.966
SR-ARE : 0.867
SR-ATAD5 : 0.311
SR-HSE : 0.93
SR-MMP : 0.942
SR-p53 : 0.857
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 : 4.548
t1/2 : 0.957
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