Compound information

Natural Products
NACP154772
Molecular Formula
C13H19N5O10P2
Molecular Weight
467.060715068 g/mol
Structure
IUPAC Name
[[5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-(3-methyloxiran-2-yl)phosphinic acid
InChI
InChI=1S/C13H19N5O10P2/c1-5-13(26-5)29(21,22)28-30(23,24)25-2-6-8(19)9(20)12(27-6)18-4-17-7-10(14)15-3-16-11(7)18/h3-6,8-9,12-13,19-20H,2H2,1H3,(H,21,22)(H,23,24)(H2,14,15,16)
InChI Key
XLKKASKVRUMAHE-UHFFFAOYSA-N
SMILES
O=P(O)(OCC1OC(N2C=NC=3C(=NC=NC32)N)C(O)C1O)OP(=O)(O)C4OC4C
CAS
120909-50-4
SuperClass
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
SubClass
Purine ribonucleotides
Source
CNP0330710

Warheads

Epoxide


ADMET Property

Physicochemical Property

Property Value Property Value
Heavy Atom Count 30 Ring Count 4
Heteroatom Count 17 Rotatable Bond Count 7
Hydrogen Bond Acceptor Count 13 Hydrogen Bond Donor Count 5
Topological Polar Surface Area 224.9 Å2 LogP -3.915
LogS -0.786 LogD -1.602


Absorption

Property Value Property Value
Pgp inhibitor 0.997 Pgp substrate 0.444
HIA 0.922 F20 % 0.001
F30 % 0.004 Caco-2 -6.236
MDCK -5.999


Distribution

Property Value Property Value
BBB Penetration 0.448 PPB 33.859
VD 0.704 Fu 0.147


Metabolism

Property Value Property Value
CYP1A2 inhibitor 0.0 CYP1A2 substrate 0.359
CYP2A6 substrate 0.324 CYP2B6 substrate 0.271
CYP2C19 inhibitor 0.006 CYP2C19 substrate 0.228
CYP2C8 substrate 0.323 CYP2C9 inhibitor 0.004
CYP2C9 substrate 0.016 CYP2D6 inhibitor 0.072
CYP2D6 substrate 0.122 CYP2E1 substrate 0.57
CYP3A4 inhibitor 0.056 CYP3A4 substrate 0.011


Excretion

Property Value Property Value
T1/2 0.897 CL 0.942


Toxicity

Property Value Property Value
hERG Blockers 1.0 Hepatotoxicity 0.003
Mutagenicity 0.009 Rat Oral Acute Toxicity 0.586
FDAMDD 0.951 Skin Sensitization 0.0
Carcinogenicity 0.738 Eye Corrosion 0.001
Eye Irritation 0.005 Respiratory Toxicity 0.2


Environmental Toxicity

Property Value Property Value
Bioconcentration Factors 0.337 IGC50 2.368
LC50FM -3.465 LC50DM 4.53


Tox21 Pathway

Property Value Property Value
NR-AR 0.275 NR-AR-LBD 0.251
NR-AhR 0.003 NR-Aromatase 0.046
NR-ER 0.389 NR-ER-LBD 0.339
NR-PPAR-gamma 0.269 SR-ARE 0.013
SR-ATAD5 0.327 SR-HSE 0.0
SR-MMP 0.0 SR-p53 0.067


Similar covalent inhibitors

CI001039

Similarity Score: 0.58

CI001040

Similarity Score: 0.56

CI001038

Similarity Score: 0.55

CI001033

Similarity Score: 0.53

CI002680

Similarity Score: 0.52

CI001032

Similarity Score: 0.51



Similar covalent drugs

No similar covalent drugs found for this compound.