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Compound Detail

CHEMBL296435

(+)-EHNA
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CCCCCC[C@H]([C@H](C)O)n1cnc2c(N)ncnc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL296435
Name (+)-EHNA
Phase Preclinical
Structure Type MOL
InChI Key IOSAAWHGJUZBOG-WDEREUQCSA-N
5
Targets
19
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

277.4
MW (Da)
2.30
ALogP
6
HBA
2
HBD
89.8
PSA (Ų)
0.76
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C14H23N5O
MW 277.37
Aromatic Rings 2
Heavy Atoms 20

Activity Summary

Ki 10 meas. best 9.09
IC50 9 meas. best 6.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine deaminase
CHEMBL2966
 Ki 9.09 8.8557 0.8 7
Adenosine deaminase
CHEMBL1910
 Ki 9.0 8.85 1.0 2
Unchecked
CHEMBL612545
 Ki 8.94 8.94 1.1 1
cGMP-dependent 3',5'-cyclic phosphodiesterase
CHEMBL2652
 IC50 6.2 5.918 635.0 5
Unchecked
CHEMBL612545
 IC50 6.16 5.9867 700.0 3
Phosphodiesterase 4
CHEMBL2093863
 IC50 5.77 5.77 1700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 97.08 ng.hr.mL-1 Rattus norvegicus
CL - - Rattus norvegicus
T1/2 0.5167 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine deaminase Ki = 0.82 nM 9.09 Tested for binding affinity against calf intestinal Adenosine Deaminase (ADA) 7966142
Adenosine deaminase Ki = 1.0 nM 9.0 Binding affinity to ADA (unknown origin) assessed as inhibition constant 34624823
Adenosine deaminase Ki = 1.13 nM 8.95 Inhibition of Adenosine deaminase (ADA) of calf intestine 11101360
Adenosine deaminase Ki = 1.13 nM 8.95 Inhibitory activity against adenosine deaminase in calf intestinal mucosa. -
Unchecked Ki = 1.14 nM 8.94 Inhibition of bovine spleen adenosine deaminase type 9 by spectrophotometry 19226143
Adenosine deaminase Ki = 1.14 nM 8.94 Inhibitory constant against bovine spleen Adenosine deaminase 16078836
Adenosine deaminase Ki = 2.0 nM 8.7 Compound was evaluated for inhibition of calf intestinal mucosa adenosine deamin... 9873405
Adenosine deaminase Ki = 2.0 nM 8.7 Compound was evaluated for the inhibition of adenosine deaminase 7310814
Adenosine deaminase Ki = 2.0 nM 8.7 Binding affinity (Ki) at calf intestinal Adenosine deaminase 1433220
Adenosine deaminase Ki = 2.2 nM 8.66 Inhibition of bovine adenosine deaminase pre-incubated for 5 mins before adenosi... 28951094
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 635.0 nM 6.2 Inhibitory activity against PDE2 by scintillation proximity assay 16275071
Unchecked IC50 = 700.0 nM 6.16 Inhibition of cGMP activated PDE2 (unknown origin) -
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 800.0 nM 6.1 Inhibition of human PDE2 using c[8-3H]cAMP or c[8-3H]cGMP as substrate measured ... 30554955
Unchecked IC50 = 800.0 nM 6.1 Inhibition of PDE2 (unknown origin) 29174506
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 800.0 nM 6.1 Inhibition of cGMP stimulated human PDE2A -
Phosphodiesterase 4 IC50 = 1700.0 nM 5.77 Inhibition of PDE4 (unknown origin) -
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of cGMP stimulated pig PDE2A -
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 2460.0 nM 5.61 Inhibition of recombinant human PDE2A catalytic domain (580 to 919 residues) exp... 29174506
cGMP-dependent 3',5'-cyclic phosphodiesterase IC50 = 2620.0 nM 5.58 Inhibition of human recombinant PDE2A using cGMP as substrate incubated for 20 m... 33022582

Literature References

PubMed DOI Target Context # Activities
28951094 10.1016/j.bmc.2017.09.015 Rattus norvegicus 3
16275071 10.1016/j.bmcl.2005.10.005 Caco-2 2
16275071 10.1016/j.bmcl.2005.10.005 MDCK 2
- 10.1039/C5MD00419E Unchecked 2
16275071 10.1016/j.bmcl.2005.10.005 cGMP-dependent 3',5'-cyclic phosphodiesterase 2
29174506 10.1016/j.bmc.2017.11.022 cGMP-dependent 3',5'-cyclic phosphodiesterase 2
16275071 10.1016/j.bmcl.2005.10.005 Phosphodiesterase 3 1
16275071 10.1016/j.bmcl.2005.10.005 High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A 1
16275071 10.1016/j.bmcl.2005.10.005 High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B 1
16275071 10.1016/j.bmcl.2005.10.005 cGMP-specific 3',5'-cyclic phosphodiesterase 1
16275071 10.1016/j.bmcl.2005.10.005 3',5'-cyclic-AMP phosphodiesterase 4D 1
16275071 10.1016/j.bmcl.2005.10.005 3',5'-cyclic-AMP phosphodiesterase 4C 1
16275071 10.1016/j.bmcl.2005.10.005 3',5'-cyclic-AMP phosphodiesterase 4B 1
16275071 10.1016/j.bmcl.2005.10.005 3',5'-cyclic-AMP phosphodiesterase 4A 1
16078836 10.1021/jm050136d Adenosine deaminase 1
34624823 10.1016/j.ejmech.2021.113877 Adenosine deaminase 1
11101360 10.1021/jm0002533 Adenosine deaminase 1
9873405 10.1016/s0960-894x(98)00291-1 Adenosine deaminase 1
9406591 10.1021/jm960729b No relevant target 1
7310814 10.1021/jm00144a002 Adenosine deaminase 1

Data from ChEMBL 36 via Core Engine