Canonical Smiles : COC1=C(C=CC(=C1)C=CC(=O)OC2CC(CC(C2O)O)(C(=O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O
Inchi Key : DJXURFUTIYZESV-BQYLRUKMSA-N
IUPAC : (1R,3R,4S,5R)-1-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
Pubchem ID : 121225501
Smiles : COc1cc(C=CC(=O)OC2CC(OC(=O)C=Cc3ccc(O)c(O)c3)(C(=O)O)CC(O)C2O)ccc1O
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 530.14
Volume : 509.064
Density : 1.041
nHA : 12
nHD : 6
nRot : 10
nRing : 3
Max Ring : 6
nHet: 12
fChar : 0
nRig : 23
Flexibility : 0.435
Stereo Centers : 4
TPSA : 200.28
logS : -2.279
logP: 1.647
logD7.4 : 1.284
ABSORPTION
Caco-2 Permeability : -6.095
MDCK Permeability : 0.0000116052
Pgp-inhibitor : 0
Pgp-substrate : 0.634
HIA : 0.95
F20% : 0.998
F30% : 0.998
DISTRIBUTION
PPB : 0.991626
VD : 0.216
BBB Penetration : 0.145
Fu : 0.0166382
METABOLISM
CYP 1A2 inhibitor : 0.049
CYP 1A2 substrate : 0.063
CYP 2C19 inhibitor : 0.065
CYP 2C19 substrate : 0.055
CYP 2C9 inhibitor : 0.354
CYP 2C9 substrate : 0.828
CYP 2D6 inhibitor : 0.023
CYP 2D6 substrate : 0.192
CYP 3A4 inhibitor : 0.11
CYP 3A4 substrate : 0.067
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MEDICINAL CHEMISTRY
QED : 0.163
SAscore : 4.113
Fsp : 0.269
MCE-18 : 80.727
NPscore : 1.724
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Rejected
PAINS : 1
ALARM NMR Rule : 3
BMS Rule : 0
Chelator Rule : 2
TOXICOLOGY
hERG Blockers : 0.028
H-HT : 0.154
DILI : 0.052
AMES Toxicity : 0.018
Rat Oral Acute Toxicity : 0.07
FDAMDD : 0.149
Skin Sensitization : 0.59
Carcinogencity : 0.142
Eye Corrosion : 0.003
Eye Irritation : 0.014
Respiratory Toxicity : 0.029
Bioconcentration Factor : 0.396
IGC50 : 3.886
LC50FM : 4.493
LC50DM : 5.181
NR-AR : 0.751
NR-AR-LBD: 0.922
NR-AhR : 0.375
NR-Aromatase : 0.525
NR-ER : 0.567
NR-ER-LBD : 0.665
NR-PPAR-gamma : 0.976
SR-ARE : 0.882
SR-ATAD5 : 0.549
SR-HSE : 0.913
SR-MMP : 0.929
SR-p53 : 0.891
Acute/Aquatic Toxicity Rule : 4
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 1
Skin Sensitization Rule : 11
Non Biodegradable Rule : 1
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 3
EXCRETION
CL : 4.505
t1/2 : 0.958
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