Canonical Smiles : C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O
Inchi Key : DBOVHQOUSDWAPQ-WTONXPSSSA-N
IUPAC : [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
Pubchem ID : 115149
Smiles : C=CC1C(OC2OC(CO)C(O)C(O)C2OC(=O)c2c(O)cc(O)cc2-c2cccc(O)c2)OC=C2C(=O)OCCC21
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 586.17
Volume : 555.266
Density : 1.056
nHA : 13
nHD : 6
nRot : 8
nRing : 5
Max Ring : 10
nHet: 13
fChar : 0
nRig : 32
Flexibility : 0.25
Stereo Centers : 8
TPSA : 201.67
logS : -3.182
logP: 2.099
logD7.4 : 2.226
ABSORPTION
Caco-2 Permeability : -6.191
MDCK Permeability : 0.0000315909
Pgp-inhibitor : 0
Pgp-substrate : 0.001
HIA : 0.933
F20% : 0.329
F30% : 0.998
DISTRIBUTION
PPB : 0.910745
VD : 0.681
BBB Penetration : 0.071
Fu : 0.0675749
METABOLISM
CYP 1A2 inhibitor : 0.041
CYP 1A2 substrate : 0.047
CYP 2C19 inhibitor : 0.028
CYP 2C19 substrate : 0.056
CYP 2C9 inhibitor : 0.087
CYP 2C9 substrate : 0.81
CYP 2D6 inhibitor : 0.723
CYP 2D6 substrate : 0.139
CYP 3A4 inhibitor : 0.757
CYP 3A4 substrate : 0.155
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MEDICINAL CHEMISTRY
QED : 0.199
SAscore : 4.908
Fsp : 0.379
MCE-18 : 112
NPscore : 2.344
Lipinski Rule : Rejected
Pfizer Rule : Accepted
GSK Rule : Rejected
Golden Triangle : Rejected
PAINS : 0
ALARM NMR Rule : 4
BMS Rule : 0
Chelator Rule : 0
TOXICOLOGY
hERG Blockers : 0.138
H-HT : 0.204
DILI : 0.917
AMES Toxicity : 0.139
Rat Oral Acute Toxicity : 0.347
FDAMDD : 0.877
Skin Sensitization : 0.044
Carcinogencity : 0.752
Eye Corrosion : 0.003
Eye Irritation : 0.014
Respiratory Toxicity : 0.069
Bioconcentration Factor : 0.698
IGC50 : 4.393
LC50FM : 5.506
LC50DM : 5.855
NR-AR : 0.02
NR-AR-LBD: 0.329
NR-AhR : 0.766
NR-Aromatase : 0.017
NR-ER : 0.61
NR-ER-LBD : 0.848
NR-PPAR-gamma : 0.406
SR-ARE : 0.399
SR-ATAD5 : 0.523
SR-HSE : 0.84
SR-MMP : 0.951
SR-p53 : 0.82
Acute/Aquatic Toxicity Rule : 5
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 0
Skin Sensitization Rule : 5
Non Biodegradable Rule : 2
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 3
EXCRETION
CL : 2.823
t1/2 : 0.538
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