Compound information

Natural Products
NACP84391
Molecular Formula
C21H22O6
Molecular Weight
370.141638424 g/mol
Structure
IUPAC Name
1,7-bis(4-hydroxy-3-methoxy-phenyl)hept-1-ene-3,5-dione
InChI
InChI=1S/C21H22O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3,5-7,9-12,24-25H,4,8,13H2,1-2H3
InChI Key
MUYJSOCNDLUHPJ-UHFFFAOYSA-N
SMILES
O=C(C=CC1=CC=C(O)C(OC)=C1)CC(=O)CCC2=CC=C(O)C(OC)=C2
CAS
76474-56-1
SuperClass
Phenylpropanoids and polyketides
Class
Diarylheptanoids
SubClass
Linear diarylheptanoids
Source
CNP0188467

Warheads

Carbonyl


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 27 Ring Count 2
Heteroatom Count 6 Rotatable Bond Count 9
Hydrogen Bond Acceptor Count 6 Hydrogen Bond Donor Count 2
Topological Polar Surface Area 93.06 Å2 LogP 2.372
LogS -5.606 LogD 2.796


Absorption

Property Value Property Value
Pgp inhibitor 0.818 Pgp substrate 0.003
HIA 0.963 F20 % 0.955
F30 % 0.893 Caco-2 -4.858
MDCK -4.914


Distribution

Property Value Property Value
BBB Penetration 0.021 PPB 73.077
VD 1.539 Fu 1.037


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.837 CYP1A2 substrate 0.588
CYP2A6 substrate 0.434 CYP2B6 substrate 0.675
CYP2C19 inhibitor 0.721 CYP2C19 substrate 0.773
CYP2C8 substrate 0.807 CYP2C9 inhibitor 0.909
CYP2C9 substrate 0.065 CYP2D6 inhibitor 0.297
CYP2D6 substrate 0.54 CYP2E1 substrate 0.202
CYP3A4 inhibitor 0.815 CYP3A4 substrate 0.073


Excretion

Property Value Property Value
T1/2 0.987 CL 14.846


Toxicity

Property Value Property Value
hERG Blockers 0.246 Hepatotoxicity 0.037
Mutagenicity 0.007 Rat Oral Acute Toxicity 0.092
FDAMDD 0.708 Skin Sensitization 0.998
Carcinogenicity 0.265 Eye Corrosion 0.001
Eye Irritation 0.698 Respiratory Toxicity 0.445


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors 1.077 IGC50 5.428
LC50FM 5.956 LC50DM 4.601


Tox21 Pathway

Property Value Property Value
NR-AR 0.505 NR-AR-LBD 0.869
NR-AhR 0.573 NR-Aromatase 0.202
NR-ER 0.832 NR-ER-LBD 0.64
NR-PPAR-gamma 0.913 SR-ARE 0.479
SR-ATAD5 0.817 SR-HSE 0.839
SR-MMP 0.771 SR-p53 0.647


Similar covalent inhibitors

CI000144

Similarity Score: 0.74

CI000955

Similarity Score: 0.58

CI006125

Similarity Score: 0.57

CI001839

Similarity Score: 0.54

CI001827

Similarity Score: 0.53

CI001053

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.