Compound information

Natural Products
ZC1301647
Molecular Formula
C21H24N2O6S
Molecular Weight
432.135507488 g/mol
Structure
IUPAC Name
(4-methylsulfanylphenyl) (2S)-2-[[(2R)-2-(benzyloxycarbonylamino)-3-hydroxy-propanoyl]amino]propanoate
InChI
InChI=1S/C21H24N2O6S/c1-14(20(26)29-16-8-10-17(30-2)11-9-16)22-19(25)18(12-24)23-21(27)28-13-15-6-4-3-5-7-15/h3-11,14,18,24H,12-13H2,1-2H3,(H,22,25)(H,23,27)/t14-,18+/m0/s1
InChI Key
UTPMZVGGVNZEHT-KBXCAEBGSA-N
SMILES
CSc1ccc(OC(=O)[C@H](C)NC(=O)[C@@H](CO)NC(=O)OCc2ccccc2)cc1
Source
ZINC000005201566

Warheads

Carbamate


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 30 Ring Count 2
Heteroatom Count 9 Rotatable Bond Count 9
Hydrogen Bond Acceptor Count 7 Hydrogen Bond Donor Count 3
Topological Polar Surface Area 113.96 Å2 LogP 2.543
LogS -4.646 LogD 3.272


Absorption

Property Value Property Value
Pgp inhibitor 0.002 Pgp substrate 0.016
HIA 0.955 F20 % 0.978
F30 % 0.372 Caco-2 -5.457
MDCK -5.291


Distribution

Property Value Property Value
BBB Penetration 0.26 PPB 94.509
VD 0.466 Fu 1.697


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.451 CYP1A2 substrate 0.703
CYP2A6 substrate 0.471 CYP2B6 substrate 0.505
CYP2C19 inhibitor 0.884 CYP2C19 substrate 0.935
CYP2C8 substrate 0.857 CYP2C9 inhibitor 0.084
CYP2C9 substrate 1.0 CYP2D6 inhibitor 0.013
CYP2D6 substrate 0.867 CYP2E1 substrate 0.205
CYP3A4 inhibitor 0.041 CYP3A4 substrate 0.986


Excretion

Property Value Property Value
T1/2 0.641 CL 5.799


Toxicity

Property Value Property Value
hERG Blockers 0.008 Hepatotoxicity 0.723
Mutagenicity 0.015 Rat Oral Acute Toxicity 0.092
FDAMDD 0.221 Skin Sensitization 0.806
Carcinogenicity 0.019 Eye Corrosion 0.005
Eye Irritation 0.0 Respiratory Toxicity 0.019


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -0.369 IGC50 3.252
LC50FM 4.208 LC50DM 6.078


Tox21 Pathway

Property Value Property Value
NR-AR 0.271 NR-AR-LBD 0.279
NR-AhR 0.008 NR-Aromatase 0.033
NR-ER 0.393 NR-ER-LBD 0.37
NR-PPAR-gamma 0.24 SR-ARE 0.463
SR-ATAD5 0.379 SR-HSE 0.097
SR-MMP 0.051 SR-p53 0.065


Similar covalent inhibitors

CI002990

Similarity Score: 0.58

CI003009

Similarity Score: 0.56

CI003025

Similarity Score: 0.54

CI002999

Similarity Score: 0.53

CI003037

Similarity Score: 0.52



Similar covalent drugs

No similar covalent drugs found for this compound.