Compound information

Natural Products
ZC1043343
Molecular Formula
C33H44N10O5
Molecular Weight
660.349614508 g/mol
Structure
IUPAC Name
benzyl N-[(1S)-2-[[(1R)-4-guanidino-1-[[(1S)-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-NJTBCWBZSA-N
SMILES
C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)Nc1ccc2ccccc2c1
Source
ZINC000150359843

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 8
Topological Polar Surface Area 254.43 Å2 LogP 1.762
LogS -3.755 LogD 0.851


Absorption

Property Value Property Value
Pgp inhibitor 0.009 Pgp substrate 1.0
HIA 0.015 F20 % 0.361
F30 % 0.001 Caco-2 -6.183
MDCK -5.7


Distribution

Property Value Property Value
BBB Penetration 0.036 PPB 97.068
VD 0.599 Fu 0.869


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.003 CYP1A2 substrate 0.614
CYP2A6 substrate 0.478 CYP2B6 substrate 0.546
CYP2C19 inhibitor 0.055 CYP2C19 substrate 0.944
CYP2C8 substrate 0.862 CYP2C9 inhibitor 0.005
CYP2C9 substrate 0.347 CYP2D6 inhibitor 0.022
CYP2D6 substrate 0.869 CYP2E1 substrate 0.128
CYP3A4 inhibitor 0.008 CYP3A4 substrate 0.979


Excretion

Property Value Property Value
T1/2 0.057 CL 1.105


Toxicity

Property Value Property Value
hERG Blockers 0.981 Hepatotoxicity 0.505
Mutagenicity 0.041 Rat Oral Acute Toxicity 0.115
FDAMDD 0.559 Skin Sensitization 0.697
Carcinogenicity 0.0 Eye Corrosion 0.001
Eye Irritation 0.0 Respiratory Toxicity 0.908


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -2.387 IGC50 3.084
LC50FM -5.397 LC50DM 2.056


Tox21 Pathway

Property Value Property Value
NR-AR 0.317 NR-AR-LBD 0.254
NR-AhR 0.189 NR-Aromatase 0.016
NR-ER 0.422 NR-ER-LBD 0.398
NR-PPAR-gamma 0.508 SR-ARE 0.474
SR-ATAD5 0.554 SR-HSE 0.186
SR-MMP 0.034 SR-p53 0.576


Similar covalent inhibitors

CI002211

Similarity Score: 0.58

CI002210

Similarity Score: 0.56

CI002208

Similarity Score: 0.54



Similar covalent drugs

No similar covalent drugs found for this compound.