Compound detail

SMILES: COC(=O)C1CCN(C(=O)c2ccc(N(CCCO)Cc3cnc4nc(N)nc(N)c4[nH+]3)cc2)CC1

Formula: C24H31N8O4+ | MW: 495.56400000000036

LogP: 0.4175000000000022 | TPSA: 174.92999999999998

HBA/HBD: 10/3 | RotB: 8

InChIKey: NKRKEQBTIYLTPA-UHFFFAOYSA-O

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.

Highlighted: 1 pattern Primary amine Clear highlight

Bio motif

ATP mimic pyrimidine N-Methyl amide ×2 H-bond acceptor N ×6 H-bond acceptor O ×3 H-bond donor ×4 Gatekeeper aromatic Ionizable base ×2 Metal chelator ×2 P-gp efflux flag ×2

Functional group

Carbonyl ×2 Amide Ester Primary amine ×2 Alcohol Tertiary amine ×2 Lactam Ether

Ring system

Benzene Pyrimidine Pyrazine Pipecolinyl ring

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.832875	-
DOCK_BASE_INTER_RANK	-1.139270	-
DOCK_BASE_INTER_RANK	-0.688959	-
DOCK_BASE_INTER_RANK	-1.029770	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_CLASH_COUNT	16.000000	-
DOCK_CLASH_COUNT	15.000000	-
DOCK_CLASH_COUNT	17.000000	-
DOCK_CLASH_COUNT	17.000000	-
DOCK_CONTACT_COUNT	23.000000	-
DOCK_CONTACT_COUNT	23.000000	-
DOCK_CONTACT_COUNT	24.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_EXPERIMENT	T08	-
DOCK_EXPERIMENT	T05	-
DOCK_EXPERIMENT	T07	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT_ID	5	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	7	-
DOCK_EXPERIMENT_ID	8	-
DOCK_FINAL_RANK	2.248832	-
DOCK_FINAL_RANK	5.159282	-
DOCK_FINAL_RANK	3.453882	-
DOCK_FINAL_RANK	1.464926	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_IFP::A:ALA170	1	-
DOCK_IFP::A:ALA170	1	-
DOCK_IFP::A:ALA34	1	-
DOCK_IFP::A:ALA96	1	-
DOCK_IFP::A:ARG100	1	-
DOCK_IFP::A:ARG14	1	-
DOCK_IFP::A:ARG14	1	-
DOCK_IFP::A:ARG17	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ASP161	1	-
DOCK_IFP::A:ASP161	1	-
DOCK_IFP::A:ASP181	1	-
DOCK_IFP::A:ASP54	1	-
DOCK_IFP::A:CYS168	1	-
DOCK_IFP::A:CYS168	1	-
DOCK_IFP::A:GLN56	1	-
DOCK_IFP::A:GLU217	1	-
DOCK_IFP::A:GLU217	1	-
DOCK_IFP::A:GLU50	1	-
DOCK_IFP::A:GLY161	1	-
DOCK_IFP::A:GLY205	1	-
DOCK_IFP::A:GLY205	1	-
DOCK_IFP::A:GLY225	1	-
DOCK_IFP::A:HIS182	1	-
DOCK_IFP::A:HIS241	1	-
DOCK_IFP::A:ILE160	1	-
DOCK_IFP::A:ILE47	1	-
DOCK_IFP::A:LEU188	1	-
DOCK_IFP::A:LEU208	1	-
DOCK_IFP::A:LEU208	1	-
DOCK_IFP::A:LEU209	1	-
DOCK_IFP::A:LEU209	1	-
DOCK_IFP::A:LEU226	1	-
DOCK_IFP::A:LEU229	1	-
DOCK_IFP::A:LEU263	1	-
DOCK_IFP::A:LEU263	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:LYS178	1	-
DOCK_IFP::A:LYS220	1	-
DOCK_IFP::A:LYS220	1	-
DOCK_IFP::A:MET163	1	-
DOCK_IFP::A:MET163	1	-
DOCK_IFP::A:MET169	1	-
DOCK_IFP::A:MET169	1	-
DOCK_IFP::A:MET183	1	-
DOCK_IFP::A:MET213	1	-
DOCK_IFP::A:MET213	1	-
DOCK_IFP::A:MET233	1	-
DOCK_IFP::A:MET55	1	-
DOCK_IFP::A:NAP301	1	-
DOCK_IFP::A:NAP301	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:NDP302	1	-
DOCK_IFP::A:PHE113	1	-
DOCK_IFP::A:PHE171	1	-
DOCK_IFP::A:PHE171	1	-
DOCK_IFP::A:PHE233	1	-
DOCK_IFP::A:PHE58	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PHE97	1	-
DOCK_IFP::A:PHE97	1	-
DOCK_IFP::A:PRO210	1	-
DOCK_IFP::A:PRO210	1	-
DOCK_IFP::A:PRO99	1	-
DOCK_IFP::A:PRO99	1	-
DOCK_IFP::A:SER111	1	-
DOCK_IFP::A:SER207	1	-
DOCK_IFP::A:SER95	1	-
DOCK_IFP::A:SER95	1	-
DOCK_IFP::A:THR184	1	-
DOCK_IFP::A:THR86	1	-
DOCK_IFP::A:TRP221	1	-
DOCK_IFP::A:TRP221	1	-
DOCK_IFP::A:TYR166	1	-
DOCK_IFP::A:TYR174	1	-
DOCK_IFP::A:TYR174	1	-
DOCK_IFP::A:TYR191	1	-
DOCK_IFP::A:TYR194	1	-
DOCK_IFP::A:TYR283	1	-
DOCK_IFP::A:TYR57	1	-
DOCK_IFP::A:VAL206	1	-
DOCK_IFP::A:VAL206	1	-
DOCK_IFP::A:VAL230	1	-
DOCK_IFP::A:VAL32	1	-
DOCK_IFP::A:VAL33	1	-
DOCK_IFP::D:ARG287	1	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_MAX_CLASH_OVERLAP	0.687765	-
DOCK_MAX_CLASH_OVERLAP	0.677235	-
DOCK_MAX_CLASH_OVERLAP	0.677357	-
DOCK_MAX_CLASH_OVERLAP	0.687820	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	3.317001	-
DOCK_PRE_RANK	1.373169	-
DOCK_PRE_RANK	5.056986	-
DOCK_PRE_RANK	2.155693	-
DOCK_PRIMARY_POSE_ID	4072	-
DOCK_PRIMARY_POSE_ID	4753	-
DOCK_PRIMARY_POSE_ID	3392	-
DOCK_PRIMARY_POSE_ID	2719	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_REPORT_ID	selection_import_t07	-
DOCK_REPORT_ID	selection_import_t08	-
DOCK_REPORT_ID	selection_import_t05	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_RESIDUE_CONTACTS	A:ARG17;A:ASP181;A:GLY225;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:MET183;A:MET233;A:NDP302;A:PHE113;A:SER111;A:TYR191;A:TYR194;A:TYR283;A:VAL230;D:ARG287	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG100;A:ARG59;A:ASP54;A:GLN56;A:GLU50;A:GLY161;A:HIS182;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE233;A:PHE58;A:PHE94;A:THR184;A:THR86;A:TYR166;A:TYR57;A:VAL32;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ALA170;A:ARG14;A:ASP161;A:CYS168;A:GLU217;A:GLY205;A:LEU208;A:LEU209;A:LEU263;A:LYS178;A:LYS220;A:MET163;A:MET169;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:PRO99;A:SER95;A:TRP221;A:TYR174;A:VAL206	-
DOCK_RESIDUE_CONTACTS	A:ALA170;A:ALA96;A:ARG14;A:ASP161;A:CYS168;A:GLU217;A:GLY205;A:LEU208;A:LEU209;A:LEU263;A:LYS220;A:MET163;A:MET169;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:PRO99;A:SER207;A:SER95;A:TRP221;A:TYR174;A:VAL206	-
DOCK_SCAFFOLD	O=C(c1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCCC1	-
DOCK_SCAFFOLD	O=C(c1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCCC1	-
DOCK_SCAFFOLD	O=C(c1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCCC1	-
DOCK_SCAFFOLD	O=C(c1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCCC1	-
DOCK_SCORE	-43.160900	-
DOCK_SCORE	-29.779300	-
DOCK_SCORE	-19.795700	-
DOCK_SCORE	-38.369300	-
DOCK_SCORE_INTER	-24.802500	-
DOCK_SCORE_INTER	-29.983500	-
DOCK_SCORE_INTER	-41.013700	-
DOCK_SCORE_INTER	-37.071600	-
DOCK_SCORE_INTER_KCAL	-8.854403	-
DOCK_SCORE_INTER_KCAL	-5.923978	-
DOCK_SCORE_INTER_KCAL	-9.795958	-
DOCK_SCORE_INTER_KCAL	-7.161439	-
DOCK_SCORE_INTER_NORM	-1.029770	-
DOCK_SCORE_INTER_NORM	-1.139270	-
DOCK_SCORE_INTER_NORM	-0.832875	-
DOCK_SCORE_INTER_NORM	-0.688959	-
DOCK_SCORE_INTRA	0.204152	-
DOCK_SCORE_INTRA	-2.147200	-
DOCK_SCORE_INTRA	-1.297690	-
DOCK_SCORE_INTRA	4.896020	-
DOCK_SCORE_INTRA_KCAL	1.169395	-
DOCK_SCORE_INTRA_KCAL	-0.309948	-
DOCK_SCORE_INTRA_KCAL	-0.512850	-
DOCK_SCORE_INTRA_KCAL	0.048761	-
DOCK_SCORE_INTRA_NORM	-0.059645	-
DOCK_SCORE_INTRA_NORM	0.005671	-
DOCK_SCORE_INTRA_NORM	-0.036047	-
DOCK_SCORE_INTRA_NORM	0.136000	-
DOCK_SCORE_KCAL	-7.112667	-
DOCK_SCORE_KCAL	-4.728124	-
DOCK_SCORE_KCAL	-9.164354	-
DOCK_SCORE_KCAL	-10.308808	-
DOCK_SCORE_NORM	-1.198910	-
DOCK_SCORE_NORM	-0.827204	-
DOCK_SCORE_NORM	-1.065810	-
DOCK_SCORE_NORM	-0.549881	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.110814	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.003078	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SOURCE_FILE	T07_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T08_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T05_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T06_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C24H31N8O4+	-
DOCK_SOURCE_FORMULA	C24H31N8O4+	-
DOCK_SOURCE_FORMULA	C24H31N8O4+	-
DOCK_SOURCE_FORMULA	C24H31N8O4+	-
DOCK_SOURCE_HBA	10.000000	-
DOCK_SOURCE_HBA	10.000000	-
DOCK_SOURCE_HBA	10.000000	-
DOCK_SOURCE_HBA	10.000000	-
DOCK_SOURCE_HBD	3.000000	-
DOCK_SOURCE_HBD	3.000000	-
DOCK_SOURCE_HBD	3.000000	-
DOCK_SOURCE_HBD	3.000000	-
DOCK_SOURCE_HEAVY_ATOMS	36.000000	-
DOCK_SOURCE_HEAVY_ATOMS	36.000000	-
DOCK_SOURCE_HEAVY_ATOMS	36.000000	-
DOCK_SOURCE_HEAVY_ATOMS	36.000000	-
DOCK_SOURCE_LOGP	0.417500	-
DOCK_SOURCE_LOGP	0.417500	-
DOCK_SOURCE_LOGP	0.417500	-
DOCK_SOURCE_LOGP	0.417500	-
DOCK_SOURCE_MW	495.564000	-
DOCK_SOURCE_MW	495.564000	-
DOCK_SOURCE_MW	495.564000	-
DOCK_SOURCE_MW	495.564000	-
DOCK_SOURCE_NAME	OHD_Leishmania_127	-
DOCK_SOURCE_NAME	OHD_Leishmania_127	-
DOCK_SOURCE_NAME	OHD_Leishmania_127	-
DOCK_SOURCE_NAME	OHD_Leishmania_127	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	174.930000	-
DOCK_SOURCE_TPSA	174.930000	-
DOCK_SOURCE_TPSA	174.930000	-
DOCK_SOURCE_TPSA	174.930000	-
DOCK_STRAIN_DELTA	56.674261	-
DOCK_STRAIN_DELTA	52.626555	-
DOCK_STRAIN_DELTA	69.443834	-
DOCK_STRAIN_DELTA	53.163180	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_TARGET	T06	-
DOCK_TARGET	T08	-
DOCK_TARGET	T05	-
DOCK_TARGET	T07	-
EXACT_MASS	495.24627789208995	Da
FORMULA	C24H31N8O4+	-
HBA	10	-
HBD	3	-
LOGP	0.4175000000000022	-
MOL_WEIGHT	495.56400000000036	g/mol
QED_SCORE	0.37130195176621167	-
ROTATABLE_BONDS	8	-
TPSA	174.92999999999998	A^2

Docking across targets

This compound is global in the current database. Below you can review all docking experiments and targets that contain imported poses for it, which is the basis for reverse docking analysis.

Open primary docking pose Docking experiments Reverse docking explorer Protein structures Docking IFP projection

Target	Experiment	Report	Poses	Best rank	Best score	Native overlap	Native recall	RMSD
T08	T08	selection_import_t08	1 native pose available	1.4649263562593215	-38.3693	17	0.89	-	Best pose
T07	T07	selection_import_t07	1 native pose available	2.2488318372352563	-43.1609	17	0.89	-	Best pose
T05	T05	selection_import_t05	1 native pose available	3.4538822767080197	-29.7793	14	0.82	-	Best pose
T06	T06	selection_import_t06	1 native pose available	5.159282173337576	-19.7957	18	0.86	-	Best pose

T08 — T08 1 poses · report selection_import_t08

Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
12	1.4649263562593215	-1.02977	-38.3693	9	23	17	0.89	0.67	0.80	0.80	-	no	geometry warning; 15 clashes; 4 protein contact clashes; 3 cofactor-context clashes; high strain Δ 52.6	Open pose

T07 — T07 1 poses · report selection_import_t07

Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
9	2.2488318372352563	-1.13927	-43.1609	9	24	17	0.89	0.83	0.80	0.80	-	no	geometry warning; 16 clashes; 1 protein clash; 1 severe cofactor-context clash; high strain Δ 53.2	Open pose

T05 — T05 1 poses · report selection_import_t05

Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
9	3.4538822767080197	-0.832875	-29.7793	9	17	14	0.82	0.71	0.67	0.80	-	no	geometry warning; 17 clashes; 1 protein clash; 3 cofactor-context clashes; high strain Δ 69.4	Open pose

T06 — T06 1 poses · report selection_import_t06

Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
6	5.159282173337576	-0.688959	-19.7957	10	23	18	0.86	0.60	0.75	0.75	-	no	geometry warning; 17 clashes; 2 protein clashes; high strain Δ 56.7	Open pose

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Structural Profile Fingerprint

Named-bit fingerprint from curated SMARTS patterns. Each bit = one chemical pattern.

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ADMET Profile

Computed from structure using RDKit. Indicative only — not a substitute for experimental data.

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3D Conformer

ETKDGv3 conformer generation with UFF minimisation. Rendered with 3Dmol.js.

Open receptor–ligand complex

This docking hit has a stored pose-level complex analysis page with clickable hydrogen bonds, π–π contacts, hydrophobic contacts, and clash inspection.

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Edit compound

OHD_Leishmania_127

Recognized patterns

Bio motif

Functional group

Ring system

Properties

Docking across targets

Similar compounds (PharmaFP-250 Tanimoto)

Drug Similarity

Structural Profile Fingerprint

ADMET Profile

3D Conformer