Compound detail

SMILES: O=C(CCc1ccc(-c2ccccc2)o1)N1CCN(c2ccc(O)cc2)CC1

Formula: C23H24N2O3 | MW: 376.45600000000013

LogP: 3.933600000000003 | TPSA: 56.92

HBA/HBD: 4/1 | RotB: 5

InChIKey: WYAUNISRHUZLPM-UHFFFAOYSA-N

Recognized patterns

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

Bio motif

N-Methyl amide ×2 H-bond acceptor N ×2 H-bond acceptor O ×2 H-bond donor Gatekeeper aromatic ×2 β-Turn mimetic ×2 Metal chelator P-gp efflux flag ×2

Functional group

Carbonyl Amide Phenol Tertiary amine ×2 Lactam

Ring system

Benzene ×2 Furan

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.886636	-
DOCK_BASE_INTER_RANK	-0.892848	-
DOCK_BASE_INTER_RANK	-1.145090	-
DOCK_BASE_INTER_RANK	-0.876783	-
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	13.000000	-
DOCK_CLASH_COUNT	10.000000	-
DOCK_CLASH_COUNT	13.000000	-
DOCK_CLASH_COUNT	13.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_CONTACT_COUNT	13.000000	-
DOCK_CONTACT_COUNT	20.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT	T04	-
DOCK_EXPERIMENT	T08	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	21	-
DOCK_EXPERIMENT_ID	4	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	8	-
DOCK_FINAL_RANK	0.683930	-
DOCK_FINAL_RANK	2.452739	-
DOCK_FINAL_RANK	2.141478	-
DOCK_FINAL_RANK	1.384837	-
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:ALA34	1	-
DOCK_IFP::A:ARG100	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG14	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG17	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ASN103	1	-
DOCK_IFP::A:ASN175	1	-
DOCK_IFP::A:ASP161	1	-
DOCK_IFP::A:ASP54	1	-
DOCK_IFP::A:CYS168	1	-
DOCK_IFP::A:GLY205	1	-
DOCK_IFP::A:GLY240	1	-
DOCK_IFP::A:HIS102	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:LEU209	1	-
DOCK_IFP::A:LEU226	1	-
DOCK_IFP::A:LEU229	1	-
DOCK_IFP::A:LEU263	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:LYS244	1	-
DOCK_IFP::A:MET163	1	-
DOCK_IFP::A:MET55	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:PHE233	1	-
DOCK_IFP::A:PHE58	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PHE97	1	-
DOCK_IFP::A:PRO167	1	-
DOCK_IFP::A:PRO210	1	-
DOCK_IFP::A:PRO91	1	-
DOCK_IFP::A:SER111	1	-
DOCK_IFP::A:SER207	1	-
DOCK_IFP::A:SER95	1	-
DOCK_IFP::A:THR184	1	-
DOCK_IFP::A:THR86	1	-
DOCK_IFP::A:TRP221	1	-
DOCK_IFP::A:TYR174	1	-
DOCK_IFP::A:TYR194	1	-
DOCK_IFP::A:TYR57	1	-
DOCK_IFP::A:VAL164	1	-
DOCK_IFP::A:VAL206	1	-
DOCK_IFP::A:VAL237	1	-
DOCK_IFP::A:VAL32	1	-
DOCK_IFP::A:VAL33	1	-
DOCK_IFP::B:ALA41	1	-
DOCK_IFP::B:ARG113	1	-
DOCK_IFP::B:CYS69	1	-
DOCK_IFP::B:GLY70	1	-
DOCK_IFP::B:GLY72	1	-
DOCK_IFP::B:GLY74	1	-
DOCK_IFP::B:HIS11	1	-
DOCK_IFP::B:ILE73	1	-
DOCK_IFP::B:PRO12	1	-
DOCK_IFP::B:SER43	1	-
DOCK_IFP::B:SER71	1	-
DOCK_IFP::B:TYR46	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	0.616915	-
DOCK_MAX_CLASH_OVERLAP	0.616862	-
DOCK_MAX_CLASH_OVERLAP	0.616952	-
DOCK_MAX_CLASH_OVERLAP	0.616839	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	2.123202	-
DOCK_PRE_RANK	0.664377	-
DOCK_PRE_RANK	2.419844	-
DOCK_PRE_RANK	1.357958	-
DOCK_PRIMARY_POSE_ID	4889	-
DOCK_PRIMARY_POSE_ID	13656	-
DOCK_PRIMARY_POSE_ID	2100	-
DOCK_PRIMARY_POSE_ID	3505	-
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_t04	-
DOCK_REPORT_ID	selection_import_t08	-
DOCK_REPORT_ID	selection_import_t21	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG100;A:ARG59;A:ASP54;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE233;A:PHE58;A:PHE94;A:PRO91;A:THR184;A:THR86;A:TYR57;A:VAL32;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ARG14;A:ASN175;A:ASP161;A:CYS168;A:GLY205;A:LEU208;A:LEU209;A:LEU263;A:MET163;A:NAP301;A:PHE171;A:PHE97;A:PRO167;A:PRO210;A:SER207;A:SER95;A:TRP221;A:TYR174;A:VAL164;A:VAL206	-
DOCK_RESIDUE_CONTACTS	A:ARG17;A:GLY240;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:LYS244;A:NDP302;A:PHE113;A:SER111;A:TYR194;A:VAL237;D:ARG287	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG141;A:ASN103;A:HIS102;B:ALA41;B:ARG113;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER43;B:SER71;B:TYR46	-
DOCK_SCAFFOLD	O=C(CCc1ccc(-c2ccccc2)o1)N1CCN(c2ccccc2)CC1	-
DOCK_SCAFFOLD	O=C(CCc1ccc(-c2ccccc2)o1)N1CCN(c2ccccc2)CC1	-
DOCK_SCAFFOLD	O=C(CCc1ccc(-c2ccccc2)o1)N1CCN(c2ccccc2)CC1	-
DOCK_SCAFFOLD	O=C(CCc1ccc(-c2ccccc2)o1)N1CCN(c2ccccc2)CC1	-
DOCK_SCORE	-29.780200	-
DOCK_SCORE	-22.660500	-
DOCK_SCORE	-24.608900	-
DOCK_SCORE	-24.097400	-
DOCK_SCORE_INTER	-32.062500	-
DOCK_SCORE_INTER	-24.825800	-
DOCK_SCORE_INTER	-24.999700	-
DOCK_SCORE_INTER	-24.549900	-
DOCK_SCORE_INTER_KCAL	-5.929543	-
DOCK_SCORE_INTER_KCAL	-7.658000	-
DOCK_SCORE_INTER_KCAL	-5.971078	-
DOCK_SCORE_INTER_KCAL	-5.863645	-
DOCK_SCORE_INTER_NORM	-1.145090	-
DOCK_SCORE_INTER_NORM	-0.892848	-
DOCK_SCORE_INTER_NORM	-0.886636	-
DOCK_SCORE_INTER_NORM	-0.876783	-
DOCK_SCORE_INTRA	2.282330	-
DOCK_SCORE_INTRA	1.889410	-
DOCK_SCORE_INTRA	0.728454	-
DOCK_SCORE_INTRA	0.390826	-
DOCK_SCORE_INTRA_KCAL	0.451278	-
DOCK_SCORE_INTRA_KCAL	0.093347	-
DOCK_SCORE_INTRA_KCAL	0.173988	-
DOCK_SCORE_INTRA_KCAL	0.545125	-
DOCK_SCORE_INTRA_NORM	0.026016	-
DOCK_SCORE_INTRA_NORM	0.081512	-
DOCK_SCORE_INTRA_NORM	0.013958	-
DOCK_SCORE_INTRA_NORM	0.067479	-
DOCK_SCORE_KCAL	-5.755568	-
DOCK_SCORE_KCAL	-5.877737	-
DOCK_SCORE_KCAL	-5.412370	-
DOCK_SCORE_KCAL	-7.112882	-
DOCK_SCORE_NORM	-0.860620	-
DOCK_SCORE_NORM	-0.809304	-
DOCK_SCORE_NORM	-0.878890	-
DOCK_SCORE_NORM	-1.063580	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
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	T08_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T06_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T21_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T04_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C23H24N2O3	-
DOCK_SOURCE_FORMULA	C23H24N2O3	-
DOCK_SOURCE_FORMULA	C23H24N2O3	-
DOCK_SOURCE_FORMULA	C23H24N2O3	-
DOCK_SOURCE_HBA	4.000000	-
DOCK_SOURCE_HBA	4.000000	-
DOCK_SOURCE_HBA	4.000000	-
DOCK_SOURCE_HBA	4.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_LOGP	3.933600	-
DOCK_SOURCE_LOGP	3.933600	-
DOCK_SOURCE_LOGP	3.933600	-
DOCK_SOURCE_LOGP	3.933600	-
DOCK_SOURCE_MW	376.456000	-
DOCK_SOURCE_MW	376.456000	-
DOCK_SOURCE_MW	376.456000	-
DOCK_SOURCE_MW	376.456000	-
DOCK_SOURCE_NAME	KB_Leish_43	-
DOCK_SOURCE_NAME	KB_Leish_43	-
DOCK_SOURCE_NAME	KB_Leish_43	-
DOCK_SOURCE_NAME	KB_Leish_43	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	56.920000	-
DOCK_SOURCE_TPSA	56.920000	-
DOCK_SOURCE_TPSA	56.920000	-
DOCK_SOURCE_TPSA	56.920000	-
DOCK_STRAIN_DELTA	25.411153	-
DOCK_STRAIN_DELTA	14.353517	-
DOCK_STRAIN_DELTA	15.540408	-
DOCK_STRAIN_DELTA	21.401043	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_TARGET	T08	-
DOCK_TARGET	T04	-
DOCK_TARGET	T21	-
DOCK_TARGET	T06	-
EXACT_MASS	376.17869262799996	Da
FORMULA	C23H24N2O3	-
HBA	4	-
HBD	1	-
LOGP	3.933600000000003	-
MOL_WEIGHT	376.45600000000013	g/mol
QED_SCORE	0.7329489864532637	-
ROTATABLE_BONDS	5	-
TPSA	56.92	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
T04	T04	selection_import_t04	1 native pose available	0.6839298484108537	-24.6089	10	0.53	-	Best pose
T21	T21	selection_import_t21	1 native pose available	1.384836905943337	-22.6605	12	0.86	-	Best pose
T08	T08	selection_import_t08	1 native pose available	2.1414781620911882	-29.7802	15	0.79	-	Best pose
T06	T06	selection_import_t06	1 native pose available	2.4527390145860295	-24.0974	17	0.81	-	Best pose

T04 — T04 1 poses · report selection_import_t04

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
67	0.6839298484108537	-0.892848	-24.6089	6	13	10	0.53	0.33	0.20	0.20	-	no	geometry warning; 13 clashes; 1 protein contact clash; 1 severe cofactor-context clash	Open pose

T21 — T21 1 poses · report selection_import_t21

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
98	1.384836905943337	-0.876783	-22.6605	8	16	12	0.86	0.42	0.44	0.62	-	no	geometry warning; 10 clashes; 7 protein contact clashes; moderate strain Δ 21.4	Open 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
148	2.1414781620911882	-1.14509	-29.7802	3	20	15	0.79	0.00	0.00	0.20	-	no	geometry warning; 13 clashes; 1 protein clash; 1 cofactor-context clash	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
119	2.4527390145860295	-0.886636	-24.0974	2	19	17	0.81	0.40	0.50	0.50	-	no	geometry warning; 13 clashes; 1 protein clash; moderate strain Δ 25.4	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

KB_Leish_43

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