Canonical Smiles : CC(=CCO)CCC=C(C)C(=O)OC1CC2C(C(OC=C2C(=O)O1)OC3C(C(C(C(O3)CO)O)O)O)C=C
Inchi Key : BGEODRYTLBLROB-HJXKKQCCSA-N
IUPAC : [(3S,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl] (2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoate
Pubchem ID : 101613236
Smiles : C=CC1C(OC2OC(CO)C(O)C(O)C2O)OC=C2C(=O)OC(OC(=O)C(C)=CCCC(C)=CCO)CC21
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 540.22
Volume : 522.247
Density : 1.034
nHA : 12
nHD : 5
nRot : 11
nRing : 3
Max Ring : 10
nHet: 12
fChar : 0
nRig : 22
Flexibility : 0.5
Stereo Centers : 9
TPSA : 181.44
logS : -1.814
logP: 0.516
logD7.4 : 1.543
ABSORPTION
Caco-2 Permeability : -5.589
MDCK Permeability : 0.000157292
Pgp-inhibitor : 0
Pgp-substrate : 0.107
HIA : 0.197
F20% : 0.021
F30% : 0.994
DISTRIBUTION
PPB : 0.500119
VD : 0.499
BBB Penetration : 0.362
Fu : 0.225096
METABOLISM
CYP 1A2 inhibitor : 0.01
CYP 1A2 substrate : 0.042
CYP 2C19 inhibitor : 0.008
CYP 2C19 substrate : 0.068
CYP 2C9 inhibitor : 0.002
CYP 2C9 substrate : 0.164
CYP 2D6 inhibitor : 0.007
CYP 2D6 substrate : 0.065
CYP 3A4 inhibitor : 0.431
CYP 3A4 substrate : 0.224
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MEDICINAL CHEMISTRY
QED : 0.142
SAscore : 5.244
Fsp : 0.615
MCE-18 : 56.952
NPscore : 3.206
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Rejected
PAINS : 0
ALARM NMR Rule : 2
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.012
H-HT : 0.31
DILI : 0.424
AMES Toxicity : 0.105
Rat Oral Acute Toxicity : 0.052
FDAMDD : 0.953
Skin Sensitization : 0.22
Carcinogencity : 0.958
Eye Corrosion : 0.003
Eye Irritation : 0.009
Respiratory Toxicity : 0.323
Bioconcentration Factor : 0.588
IGC50 : 2.403
LC50FM : 4.625
LC50DM : 4.837
NR-AR : 0.097
NR-AR-LBD: 0.409
NR-AhR : 0.009
NR-Aromatase : 0.013
NR-ER : 0.085
NR-ER-LBD : 0.019
NR-PPAR-gamma : 0.021
SR-ARE : 0.218
SR-ATAD5 : 0.098
SR-HSE : 0.072
SR-MMP : 0.358
SR-p53 : 0.117
Acute/Aquatic Toxicity Rule : 5
Genotoxic Carcinogenicity Rule : 2
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 3
Non Biodegradable Rule : 1
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 2
EXCRETION
CL : 1.564
t1/2 : 0.302
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