Compound information

Natural Products
ZC1580442
Molecular Formula
C20H22NO8P
Molecular Weight
435.108303294 g/mol
Structure
IUPAC Name
2-[[[(1S)-1-(benzyloxycarbonylamino)-2-phenyl-ethyl]-hydroxy-phosphoryl]methyl]propanedioic acid
InChI
InChI=1S/C20H22NO8P/c22-18(23)16(19(24)25)13-30(27,28)17(11-14-7-3-1-4-8-14)21-20(26)29-12-15-9-5-2-6-10-15/h1-10,16-17H,11-13H2,(H,21,26)(H,22,23)(H,24,25)(H,27,28)/t17-/m0/s1
InChI Key
HMYUTAVMRPOHIX-KRWDZBQOSA-N
SMILES
O=C(N[C@H](Cc1ccccc1)[P@](=O)(O)CC(C(=O)O)C(=O)O)OCc1ccccc1
Source
ZINC000137558218

Warheads

Carbamate


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 30 Ring Count 2
Heteroatom Count 10 Rotatable Bond Count 10
Hydrogen Bond Acceptor Count 5 Hydrogen Bond Donor Count 4
Topological Polar Surface Area 150.23 Å2 LogP 1.382
LogS -2.844 LogD -0.088


Absorption

Property Value Property Value
Pgp inhibitor 0.0 Pgp substrate 0.419
HIA 0.815 F20 % 0.46
F30 % 0.008 Caco-2 -6.666
MDCK -5.89


Distribution

Property Value Property Value
BBB Penetration 0.067 PPB 95.697
VD 0.37 Fu 1.36


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.001 CYP1A2 substrate 0.429
CYP2A6 substrate 0.227 CYP2B6 substrate 0.397
CYP2C19 inhibitor 0.071 CYP2C19 substrate 0.591
CYP2C8 substrate 0.521 CYP2C9 inhibitor 0.008
CYP2C9 substrate 0.999 CYP2D6 inhibitor 0.133
CYP2D6 substrate 0.197 CYP2E1 substrate 0.192
CYP3A4 inhibitor 0.007 CYP3A4 substrate 0.272


Excretion

Property Value Property Value
T1/2 0.896 CL 0.72


Toxicity

Property Value Property Value
hERG Blockers 0.665 Hepatotoxicity 0.924
Mutagenicity 0.17 Rat Oral Acute Toxicity 0.052
FDAMDD 0.153 Skin Sensitization 0.225
Carcinogenicity 0.008 Eye Corrosion 0.006
Eye Irritation 0.441 Respiratory Toxicity 0.164


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors -0.083 IGC50 2.288
LC50FM 3.533 LC50DM 4.826


Tox21 Pathway

Property Value Property Value
NR-AR 0.597 NR-AR-LBD 0.51
NR-AhR 0.004 NR-Aromatase 0.026
NR-ER 0.434 NR-ER-LBD 0.244
NR-PPAR-gamma 0.122 SR-ARE 0.002
SR-ATAD5 0.219 SR-HSE 0.001
SR-MMP 0.0 SR-p53 0.073


Similar covalent inhibitors

CI002645

Similarity Score: 0.54

CI002656

Similarity Score: 0.54

CI002992

Similarity Score: 0.54

CI003332

Similarity Score: 0.53

CI003014

Similarity Score: 0.52

CI003032

Similarity Score: 0.52



Similar covalent drugs

No similar covalent drugs found for this compound.