Canonical Smiles : C(C1C(C(C(C(O1)OC(=C(CC(=O)O)C=CC(=O)O)C#N)O)O)O)O
Inchi Key : LABCALMTQNDOAI-PKNBYVPASA-N
IUPAC : (Z,4E)-4-[cyano-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylidene]hex-2-enedioic acid
Pubchem ID : 5281124
Smiles : C(C1C(C(C(C(O1)OC(=C(CC(=O)O)C=CC(=O)O)C#N)O)O)O)O
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 359.09
Volume : 325.224
Density : 1.104
nHA : 11
nHD : 6
nRot : 7
nRing : 1
Max Ring : 6
nHet: 11
fChar : 0
nRig : 11
Flexibility : 0.636
Stereo Centers : 5
TPSA : 197.77
logS : -0.596
logP: -1.594
logD7.4 : -0.833
ABSORPTION
Caco-2 Permeability : -6.215
MDCK Permeability : 0.000248811
Pgp-inhibitor : 0
Pgp-substrate : 0.811
HIA : 0.973
F20% : 0.259
F30% : 0.995
DISTRIBUTION
PPB : 0.362175
VD : 0.247
BBB Penetration : 0.662
Fu : 0.410906
METABOLISM
CYP 1A2 inhibitor : 0.007
CYP 1A2 substrate : 0.01
CYP 2C19 inhibitor : 0.024
CYP 2C19 substrate : 0.039
CYP 2C9 inhibitor : 0.003
CYP 2C9 substrate : 0.385
CYP 2D6 inhibitor : 0.013
CYP 2D6 substrate : 0.08
CYP 3A4 inhibitor : 0.022
CYP 3A4 substrate : 0.004
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MEDICINAL CHEMISTRY
QED : 0.124
SAscore : 4.457
Fsp : 0.5
MCE-18 : 29.714
NPscore : 1.591
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Accepted
Golden Triangle : Accepted
PAINS : 0
ALARM NMR Rule : 0
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.004
H-HT : 0.434
DILI : 0.971
AMES Toxicity : 0.081
Rat Oral Acute Toxicity : 0.608
FDAMDD : 0.008
Skin Sensitization : 0.806
Carcinogencity : 0.141
Eye Corrosion : 0.003
Eye Irritation : 0.015
Respiratory Toxicity : 0.488
Bioconcentration Factor : 0.17
IGC50 : 2.517
LC50FM : 3.651
LC50DM : 3.75
NR-AR : 0.488
NR-AR-LBD: 0.562
NR-AhR : 0.006
NR-Aromatase : 0.078
NR-ER : 0.146
NR-ER-LBD : 0.22
NR-PPAR-gamma : 0.403
SR-ARE : 0.584
SR-ATAD5 : 0.049
SR-HSE : 0.019
SR-MMP : 0.056
SR-p53 : 0.034
Acute/Aquatic Toxicity Rule : 3
Genotoxic Carcinogenicity Rule : 0
Non Genotoxic Carcinogenicity Rule : 1
Skin Sensitization Rule : 4
Non Biodegradable Rule : 1
SureChEMBL Rule : 1
FAF-Drugs4 Rule : 3
EXCRETION
CL : 1.796
t1/2 : 0.933
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