Canonical Smiles : C1C(C(C(CC1(C(=O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)O)O
Inchi Key : LDPLFHGGZNSKDS-FTBFGRRBSA-N
IUPAC : (1S,3R,4R,5R)-1,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxycyclohexane-1-carboxylic acid
Pubchem ID : 442988
Smiles : C1C(C(C(CC1(C(=O)O)O)OC(=O)C2=CC(=C(C(=C2)O)O)O)O)O
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 344.07
Volume : 308.307
Density : 1.116
nHA : 10
nHD : 7
nRot : 4
nRing : 2
Max Ring : 6
nHet: 10
fChar : 0
nRig : 14
Flexibility : 0.286
Stereo Centers : 4
TPSA : 184.98
logS : -1.075
logP: -0.546
logD7.4 : 0.056
ABSORPTION
Caco-2 Permeability : -6.308
MDCK Permeability : 0.000143731
Pgp-inhibitor : 0
Pgp-substrate : 0.255
HIA : 0.898
F20% : 0.995
F30% : 0.999
DISTRIBUTION
PPB : 0.630005
VD : 0.469
BBB Penetration : 0.322
Fu : 0.369934
METABOLISM
CYP 1A2 inhibitor : 0.031
CYP 1A2 substrate : 0.039
CYP 2C19 inhibitor : 0.012
CYP 2C19 substrate : 0.045
CYP 2C9 inhibitor : 0.01
CYP 2C9 substrate : 0.108
CYP 2D6 inhibitor : 0.001
CYP 2D6 substrate : 0.129
CYP 3A4 inhibitor : 0.022
CYP 3A4 substrate : 0.008
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MEDICINAL CHEMISTRY
QED : 0.256
SAscore : 3.902
Fsp : 0.429
MCE-18 : 64.8
NPscore : 2.119
Lipinski Rule : Accepted
Pfizer Rule : Accepted
GSK Rule : Accepted
Golden Triangle : Accepted
PAINS : 1
ALARM NMR Rule : 3
BMS Rule : 0
Chelator Rule : 1
TOXICOLOGY
hERG Blockers : 0.014
H-HT : 0.053
DILI : 0.371
AMES Toxicity : 0.024
Rat Oral Acute Toxicity : 0.001
FDAMDD : 0.005
Skin Sensitization : 0.066
Carcinogencity : 0.003
Eye Corrosion : 0.003
Eye Irritation : 0.056
Respiratory Toxicity : 0.018
Bioconcentration Factor : 0.203
IGC50 : 2.568
LC50FM : 2.997
LC50DM : 4.77
NR-AR : 0.012
NR-AR-LBD: 0.163
NR-AhR : 0.111
NR-Aromatase : 0.019
NR-ER : 0.239
NR-ER-LBD : 0.021
NR-PPAR-gamma : 0.24
SR-ARE : 0.061
SR-ATAD5 : 0.017
SR-HSE : 0.102
SR-MMP : 0.176
SR-p53 : 0.269
Acute/Aquatic Toxicity Rule : 1
Genotoxic Carcinogenicity Rule : 0
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 7
Non Biodegradable Rule : 1
SureChEMBL Rule : 1
FAF-Drugs4 Rule : 2
EXCRETION
CL : 3.605
t1/2 : 0.953
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