Compound information

Natural Products
ZC1258593
Molecular Formula
C21H25N5O6
Molecular Weight
443.18048352 g/mol
Structure
IUPAC Name
(4-nitrophenyl)methyl (2S)-2-(benzyloxycarbonylamino)-5-guanidino-pentanoate
InChI
InChI=1S/C21H25N5O6/c22-20(23)24-12-4-7-18(25-21(28)32-14-15-5-2-1-3-6-15)19(27)31-13-16-8-10-17(11-9-16)26(29)30/h1-3,5-6,8-11,18H,4,7,12-14H2,(H,25,28)(H4,22,23,24)/t18-/m0/s1
InChI Key
NTFJOKMRVLGBSN-SFHVURJKSA-N
SMILES
N=C(N)NCCC[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccc([N+](=O)[O-])cc1
Source
ZINC000013537014

Warheads

Carbamate


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 32 Ring Count 2
Heteroatom Count 11 Rotatable Bond Count 11
Hydrogen Bond Acceptor Count 7 Hydrogen Bond Donor Count 4
Topological Polar Surface Area 169.67 Å2 LogP 2.292
LogS -3.191 LogD 2.73


Absorption

Property Value Property Value
Pgp inhibitor 0.009 Pgp substrate 0.971
HIA 0.965 F20 % 0.907
F30 % 0.0 Caco-2 -5.37
MDCK -5.009


Distribution

Property Value Property Value
BBB Penetration 0.074 PPB 80.172
VD 1.19 Fu 0.631


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.771 CYP1A2 substrate 0.778
CYP2A6 substrate 0.431 CYP2B6 substrate 0.597
CYP2C19 inhibitor 0.358 CYP2C19 substrate 0.925
CYP2C8 substrate 0.874 CYP2C9 inhibitor 0.225
CYP2C9 substrate 0.877 CYP2D6 inhibitor 0.71
CYP2D6 substrate 0.969 CYP2E1 substrate 0.31
CYP3A4 inhibitor 0.134 CYP3A4 substrate 0.943


Excretion

Property Value Property Value
T1/2 0.444 CL 7.216


Toxicity

Property Value Property Value
hERG Blockers 0.887 Hepatotoxicity 0.83
Mutagenicity 0.617 Rat Oral Acute Toxicity 0.098
FDAMDD 0.492 Skin Sensitization 0.989
Carcinogenicity 0.142 Eye Corrosion 0.003
Eye Irritation 0.0 Respiratory Toxicity 0.26


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -0.494 IGC50 3.455
LC50FM 4.369 LC50DM 4.555


Tox21 Pathway

Property Value Property Value
NR-AR 0.168 NR-AR-LBD 0.223
NR-AhR 0.009 NR-Aromatase 0.023
NR-ER 0.319 NR-ER-LBD 0.466
NR-PPAR-gamma 0.272 SR-ARE 0.38
SR-ATAD5 0.451 SR-HSE 0.299
SR-MMP 0.077 SR-p53 0.19


Similar covalent inhibitors

CI002644

Similarity Score: 0.55

CI005325

Similarity Score: 0.51

CI004063

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.