Compound information

Natural Products
ZC2130458
Molecular Formula
C21H23N3O2
Molecular Weight
349.179026976 g/mol
Structure
IUPAC Name
(3S)-3-(benzyloxymethyl)-N-[4-(cyanomethyl)phenyl]pyrrolidine-1-carboxamide
InChI
InChI=1S/C21H23N3O2/c22-12-10-17-6-8-20(9-7-17)23-21(25)24-13-11-19(14-24)16-26-15-18-4-2-1-3-5-18/h1-9,19H,10-11,13-16H2,(H,23,25)/t19-/m0/s1
InChI Key
MMSMVWGVBZWVIM-IBGZPJMESA-N
SMILES
N#CCc1ccc(NC(=O)N2CC[C@H](COCc3ccccc3)C2)cc1
Source
ZINC000096433898

Warheads

Nitrile
Urea carbonyl


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 26 Ring Count 3
Heteroatom Count 5 Rotatable Bond Count 6
Hydrogen Bond Acceptor Count 3 Hydrogen Bond Donor Count 1
Topological Polar Surface Area 65.36 Å2 LogP 3.029
LogS -4.62 LogD 2.979


Absorption

Property Value Property Value
Pgp inhibitor 0.981 Pgp substrate 0.984
HIA 0.97 F20 % 0.992
F30 % 0.82 Caco-2 -4.678
MDCK -5.421


Distribution

Property Value Property Value
BBB Penetration 0.398 PPB 88.863
VD 0.692 Fu 1.138


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.924 CYP1A2 substrate 0.752
CYP2A6 substrate 0.723 CYP2B6 substrate 0.7
CYP2C19 inhibitor 0.633 CYP2C19 substrate 0.794
CYP2C8 substrate 0.875 CYP2C9 inhibitor 0.401
CYP2C9 substrate 0.999 CYP2D6 inhibitor 0.279
CYP2D6 substrate 0.997 CYP2E1 substrate 0.297
CYP3A4 inhibitor 0.589 CYP3A4 substrate 1.0


Excretion

Property Value Property Value
T1/2 0.507 CL 11.361


Toxicity

Property Value Property Value
hERG Blockers 0.48 Hepatotoxicity 0.996
Mutagenicity 0.493 Rat Oral Acute Toxicity 0.015
FDAMDD 0.618 Skin Sensitization 0.981
Carcinogenicity 0.05 Eye Corrosion 0.006
Eye Irritation 0.806 Respiratory Toxicity 0.892


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -0.105 IGC50 3.394
LC50FM 1.764 LC50DM 1.114


Tox21 Pathway

Property Value Property Value
NR-AR 0.194 NR-AR-LBD 0.159
NR-AhR 0.73 NR-Aromatase 0.066
NR-ER 0.376 NR-ER-LBD 0.333
NR-PPAR-gamma 0.271 SR-ARE 0.67
SR-ATAD5 0.697 SR-HSE 0.258
SR-MMP 0.389 SR-p53 0.167


Similar covalent inhibitors

CI000305

Similarity Score: 0.52



Similar covalent drugs

No similar covalent drugs found for this compound.