Compound information

Natural Products
ZC3127726
Molecular Formula
C25H24O5
Molecular Weight
404.162373868 g/mol
Structure
IUPAC Name
(2E,5E)-2,5-bis[(Z)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enylidene]cyclopentanone
InChI
InChI=1S/C25H24O5/c1-29-23-15-17(9-13-21(23)26)5-3-7-19-11-12-20(25(19)28)8-4-6-18-10-14-22(27)24(16-18)30-2/h3-10,13-16,26-27H,11-12H2,1-2H3/b5-3-,6-4-,19-7+,20-8+
InChI Key
GYYPECSETJYYJN-IFVXQAMFSA-N
SMILES
COc1cc(/C=C\C=C2/CC/C(=C\C=C/c3ccc(O)c(OC)c3)C2=O)ccc1O
Source
ZINC000017255117

Warheads

Michael Acceptor
Michael Acceptor


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 30 Ring Count 3
Heteroatom Count 5 Rotatable Bond Count 6
Hydrogen Bond Acceptor Count 5 Hydrogen Bond Donor Count 2
Topological Polar Surface Area 75.99 Å2 LogP 3.677
LogS -5.195 LogD 3.355


Absorption

Property Value Property Value
Pgp inhibitor 0.171 Pgp substrate 0.001
HIA 0.975 F20 % 0.972
F30 % 0.392 Caco-2 -5.039
MDCK -5.033


Distribution

Property Value Property Value
BBB Penetration 0.003 PPB 95.547
VD 0.894 Fu 1.099


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.551 CYP1A2 substrate 0.765
CYP2A6 substrate 0.546 CYP2B6 substrate 0.603
CYP2C19 inhibitor 0.431 CYP2C19 substrate 0.698
CYP2C8 substrate 0.729 CYP2C9 inhibitor 0.913
CYP2C9 substrate 0.34 CYP2D6 inhibitor 0.144
CYP2D6 substrate 0.553 CYP2E1 substrate 0.276
CYP3A4 inhibitor 0.948 CYP3A4 substrate 0.281


Excretion

Property Value Property Value
T1/2 0.901 CL 7.53


Toxicity

Property Value Property Value
hERG Blockers 0.017 Hepatotoxicity 0.781
Mutagenicity 0.001 Rat Oral Acute Toxicity 0.071
FDAMDD 0.787 Skin Sensitization 0.998
Carcinogenicity 0.229 Eye Corrosion 0.001
Eye Irritation 0.458 Respiratory Toxicity 0.163


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors 1.116 IGC50 5.325
LC50FM 6.391 LC50DM 6.176


Tox21 Pathway

Property Value Property Value
NR-AR 0.074 NR-AR-LBD 0.445
NR-AhR 0.013 NR-Aromatase 0.014
NR-ER 0.137 NR-ER-LBD 0.656
NR-PPAR-gamma 0.736 SR-ARE 0.992
SR-ATAD5 0.753 SR-HSE 0.0
SR-MMP 0.391 SR-p53 0.964


Similar covalent inhibitors

CI006125

Similarity Score: 0.53

CI000144

Similarity Score: 0.52

CI006752

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.