Compound information

Natural Products
ZC1044027
Molecular Formula
C33H44N10O5
Molecular Weight
660.349614508 g/mol
Structure
IUPAC Name
benzyl N-[(1S)-2-[[(1R)-4-guanidino-1-[[(1R)-4-guanidino-1-(2-naphthylcarbamoyl)butyl]carbamoyl]butyl]amino]-1-methyl-2-oxo-ethyl]carbamate
InChI
InChI=1S/C33H44N10O5/c1-21(40-33(47)48-20-22-9-3-2-4-10-22)28(44)42-27(14-8-18-39-32(36)37)30(46)43-26(13-7-17-38-31(34)35)29(45)41-25-16-15-23-11-5-6-12-24(23)19-25/h2-6,9-12,15-16,19,21,26-27H,7-8,13-14,17-18,20H2,1H3,(H,40,47)(H,41,45)(H,42,44)(H,43,46)(H4,34,35,38)(H4,36,37,39)/t21-,26+,27+/m0/s1
InChI Key
VGQZQSPQIKXUFM-GCCWUPBUSA-N
SMILES
C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCNC(=N)N)C(=O)Nc1ccc2ccccc2c1
Source
ZINC000257373311

Warheads

Carbamate


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 48 Ring Count 3
Heteroatom Count 15 Rotatable Bond Count 17
Hydrogen Bond Acceptor Count 7 Hydrogen Bond Donor Count 10
Topological Polar Surface Area 249.43 Å2 LogP 1.082
LogS -3.064 LogD 1.992


Absorption

Property Value Property Value
Pgp inhibitor 0.003 Pgp substrate 1.0
HIA 0.0 F20 % 0.001
F30 % 0.0 Caco-2 -6.496
MDCK -5.84


Distribution

Property Value Property Value
BBB Penetration 0.404 PPB 54.767
VD 0.665 Fu 0.792


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.001 CYP1A2 substrate 0.675
CYP2A6 substrate 0.423 CYP2B6 substrate 0.48
CYP2C19 inhibitor 0.189 CYP2C19 substrate 0.808
CYP2C8 substrate 0.709 CYP2C9 inhibitor 0.012
CYP2C9 substrate 0.992 CYP2D6 inhibitor 0.4
CYP2D6 substrate 0.943 CYP2E1 substrate 0.207
CYP3A4 inhibitor 0.083 CYP3A4 substrate 0.952


Excretion

Property Value Property Value
T1/2 0.39 CL 2.859


Toxicity

Property Value Property Value
hERG Blockers 0.396 Hepatotoxicity 0.094
Mutagenicity 0.01 Rat Oral Acute Toxicity 0.11
FDAMDD 0.301 Skin Sensitization 0.333
Carcinogenicity 0.001 Eye Corrosion 0.002
Eye Irritation 0.0 Respiratory Toxicity 0.705


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -3.401 IGC50 3.149
LC50FM -1.263 LC50DM -5.841


Tox21 Pathway

Property Value Property Value
NR-AR 0.315 NR-AR-LBD 0.305
NR-AhR 0.108 NR-Aromatase 0.012
NR-ER 0.268 NR-ER-LBD 0.298
NR-PPAR-gamma 0.321 SR-ARE 0.726
SR-ATAD5 0.468 SR-HSE 0.053
SR-MMP 0.042 SR-p53 0.272


Similar covalent inhibitors

CI005325

Similarity Score: 0.55

CI002644

Similarity Score: 0.53

CI002212

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.