Compound detail

SMILES: O=C1C[C@@H](/C(O)=N/c2nc(-c3ccccn3)cs2)CN1c1ccc2c(c1)OCCO2

Formula: C21H18N4O4S | MW: 422.4660000000003

LogP: 3.6174000000000026 | TPSA: 97.14

HBA/HBD: 7/1 | RotB: 4

InChIKey: IANKKUUQOWXLNS-CYBMUJFWSA-N

Recognized patterns

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

Bio motif

Catechol N-Methyl amide ×2 H-bond acceptor N ×4 H-bond acceptor O ×3 H-bond donor Gatekeeper aromatic Metal chelator ×2 P-gp efflux flag

Functional group

Carbonyl Amide Tertiary amine Lactam Aryl ether ×2 Imine Ether ×2

Ring system

Benzene Pyridine Thiazole Benzodioxane

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.894811	-
DOCK_BASE_INTER_RANK	-1.046830	-
DOCK_BASE_INTER_RANK	-0.830626	-
DOCK_BASE_INTER_RANK	-0.804378	-
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	10.000000	-
DOCK_CLASH_COUNT	12.000000	-
DOCK_CLASH_COUNT	11.000000	-
DOCK_CLASH_COUNT	15.000000	-
DOCK_CONTACT_COUNT	18.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_EXPERIMENT	T03	-
DOCK_EXPERIMENT	T05	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	3	-
DOCK_EXPERIMENT_ID	5	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	21	-
DOCK_FINAL_RANK	1.341193	-
DOCK_FINAL_RANK	3.192527	-
DOCK_FINAL_RANK	1.145752	-
DOCK_FINAL_RANK	2.092694	-
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:ALA32	1	-
DOCK_IFP::A:ALA34	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG140	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG17	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ARG97	1	-
DOCK_IFP::A:ASN103	1	-
DOCK_IFP::A:ASP181	1	-
DOCK_IFP::A:ASP52	1	-
DOCK_IFP::A:ASP54	1	-
DOCK_IFP::A:GLN56	1	-
DOCK_IFP::A:GLY225	1	-
DOCK_IFP::A:HIS102	1	-
DOCK_IFP::A:HIS138	1	-
DOCK_IFP::A:ILE160	1	-
DOCK_IFP::A:ILE45	1	-
DOCK_IFP::A:ILE47	1	-
DOCK_IFP::A:LEU179	1	-
DOCK_IFP::A:LEU188	1	-
DOCK_IFP::A:LEU226	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU94	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:LYS57	1	-
DOCK_IFP::A:LYS95	1	-
DOCK_IFP::A:MET183	1	-
DOCK_IFP::A:MET53	1	-
DOCK_IFP::A:MET55	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:NDP302	1	-
DOCK_IFP::A:PHE113	1	-
DOCK_IFP::A:PHE55	1	-
DOCK_IFP::A:PHE56	1	-
DOCK_IFP::A:PHE58	1	-
DOCK_IFP::A:PHE91	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PRO187	1	-
DOCK_IFP::A:SER111	1	-
DOCK_IFP::A:SER112	1	-
DOCK_IFP::A:THR180	1	-
DOCK_IFP::A:THR184	1	-
DOCK_IFP::A:THR195	1	-
DOCK_IFP::A:TYR114	1	-
DOCK_IFP::A:TYR166	1	-
DOCK_IFP::A:TYR178	1	-
DOCK_IFP::A:TYR191	1	-
DOCK_IFP::A:TYR194	1	-
DOCK_IFP::A:TYR57	1	-
DOCK_IFP::A:VAL230	1	-
DOCK_IFP::A:VAL30	1	-
DOCK_IFP::A:VAL31	1	-
DOCK_IFP::A:VAL32	1	-
DOCK_IFP::A:VAL33	1	-
DOCK_IFP::A:VAL87	1	-
DOCK_IFP::B:ASP10	1	-
DOCK_IFP::B:ASP45	1	-
DOCK_IFP::B:CYS69	1	-
DOCK_IFP::B:GLY70	1	-
DOCK_IFP::B:HIS11	1	-
DOCK_IFP::B:PRO12	1	-
DOCK_IFP::B:SER43	1	-
DOCK_IFP::B:SER71	1	-
DOCK_IFP::B:TYR46	1	-
DOCK_IFP::B:VAL44	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	0.655007	-
DOCK_MAX_CLASH_OVERLAP	0.655054	-
DOCK_MAX_CLASH_OVERLAP	0.655641	-
DOCK_MAX_CLASH_OVERLAP	0.655075	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	1.291671	-
DOCK_PRE_RANK	3.154055	-
DOCK_PRE_RANK	1.103906	-
DOCK_PRE_RANK	2.028998	-
DOCK_PRIMARY_POSE_ID	1847	-
DOCK_PRIMARY_POSE_ID	3144	-
DOCK_PRIMARY_POSE_ID	3836	-
DOCK_PRIMARY_POSE_ID	14034	-
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_t03	-
DOCK_REPORT_ID	selection_import_t05	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_REPORT_ID	selection_import_t21	-
DOCK_RESIDUE_CONTACTS	A:ALA32;A:ARG97;A:ASP52;A:ILE45;A:LEU179;A:LEU94;A:LYS57;A:LYS95;A:MET53;A:NDP301;A:PHE55;A:PHE56;A:PHE91;A:THR180;A:TYR178;A:VAL30;A:VAL31;A:VAL87	-
DOCK_RESIDUE_CONTACTS	A:ARG17;A:ASP181;A:GLY225;A:LEU188;A:LEU226;A:MET183;A:NDP302;A:PHE113;A:PRO187;A:SER111;A:SER112;A:THR195;A:TYR114;A:TYR191;A:TYR194;A:VAL230;D:ARG287	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG59;A:ASP54;A:GLN56;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:THR184;A:TYR166;A:TYR57;A:VAL32;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG140;A:ARG141;A:ASN103;A:HIS102;A:HIS138;B:ASP10;B:ASP45;B:CYS69;B:GLY70;B:HIS11;B:PRO12;B:SER43;B:SER71;B:TYR46;B:VAL44	-
DOCK_SCAFFOLD	O=C1CC(C=Nc2nc(-c3ccccn3)cs2)CN1c1ccc2c(c1)OCCO2	-
DOCK_SCAFFOLD	O=C1CC(C=Nc2nc(-c3ccccn3)cs2)CN1c1ccc2c(c1)OCCO2	-
DOCK_SCAFFOLD	O=C(Nc1nc(-c2ccccn2)cs1)C1CC(=O)N(c2ccc3c(c2)OCCO3)C1	-
DOCK_SCAFFOLD	O=C1CC(C=Nc2nc(-c3ccccn3)cs2)CN1c1ccc2c(c1)OCCO2	-
DOCK_SCORE	-32.906000	-
DOCK_SCORE	-33.261500	-
DOCK_SCORE	-17.216200	-
DOCK_SCORE	-30.789200	-
DOCK_SCORE_INTER	-26.844300	-
DOCK_SCORE_INTER	-31.405000	-
DOCK_SCORE_INTER	-24.918800	-
DOCK_SCORE_INTER	-24.131300	-
DOCK_SCORE_INTER_KCAL	-6.411654	-
DOCK_SCORE_INTER_KCAL	-7.500959	-
DOCK_SCORE_INTER_KCAL	-5.951756	-
DOCK_SCORE_INTER_KCAL	-5.763664	-
DOCK_SCORE_INTER_NORM	-0.894811	-
DOCK_SCORE_INTER_NORM	-1.046830	-
DOCK_SCORE_INTER_NORM	-0.830626	-
DOCK_SCORE_INTER_NORM	-0.804378	-
DOCK_SCORE_INTRA	-6.061630	-
DOCK_SCORE_INTRA	-1.856440	-
DOCK_SCORE_INTRA	7.702590	-
DOCK_SCORE_INTRA	-6.974780	-
DOCK_SCORE_INTRA_KCAL	-1.447796	-
DOCK_SCORE_INTRA_KCAL	-0.443403	-
DOCK_SCORE_INTRA_KCAL	1.839733	-
DOCK_SCORE_INTRA_KCAL	-1.665898	-
DOCK_SCORE_INTRA_NORM	-0.202054	-
DOCK_SCORE_INTRA_NORM	-0.061881	-
DOCK_SCORE_INTRA_NORM	0.256753	-
DOCK_SCORE_INTRA_NORM	-0.232493	-
DOCK_SCORE_KCAL	-7.859466	-
DOCK_SCORE_KCAL	-7.944376	-
DOCK_SCORE_KCAL	-4.112021	-
DOCK_SCORE_KCAL	-7.353877	-
DOCK_SCORE_NORM	-1.096870	-
DOCK_SCORE_NORM	-1.108720	-
DOCK_SCORE_NORM	-0.573873	-
DOCK_SCORE_NORM	-1.026310	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.316903	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.010563	-
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	T03_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_FILE	T21_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C21H18N4O4S	-
DOCK_SOURCE_FORMULA	C21H18N4O4S	-
DOCK_SOURCE_FORMULA	C21H18N4O4S	-
DOCK_SOURCE_FORMULA	C21H18N4O4S	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HEAVY_ATOMS	30.000000	-
DOCK_SOURCE_HEAVY_ATOMS	30.000000	-
DOCK_SOURCE_HEAVY_ATOMS	30.000000	-
DOCK_SOURCE_HEAVY_ATOMS	30.000000	-
DOCK_SOURCE_LOGP	3.617400	-
DOCK_SOURCE_LOGP	3.617400	-
DOCK_SOURCE_LOGP	2.967900	-
DOCK_SOURCE_LOGP	3.617400	-
DOCK_SOURCE_MW	422.466000	-
DOCK_SOURCE_MW	422.466000	-
DOCK_SOURCE_MW	422.466000	-
DOCK_SOURCE_MW	422.466000	-
DOCK_SOURCE_NAME	Z29466466	-
DOCK_SOURCE_NAME	Z29466466	-
DOCK_SOURCE_NAME	Z29466466	-
DOCK_SOURCE_NAME	Z29466466	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_TPSA	97.140000	-
DOCK_SOURCE_TPSA	97.140000	-
DOCK_SOURCE_TPSA	93.650000	-
DOCK_SOURCE_TPSA	97.140000	-
DOCK_STRAIN_DELTA	34.539160	-
DOCK_STRAIN_DELTA	28.722996	-
DOCK_STRAIN_DELTA	30.586956	-
DOCK_STRAIN_DELTA	41.109099	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_TARGET	T03	-
DOCK_TARGET	T05	-
DOCK_TARGET	T06	-
DOCK_TARGET	T21	-
EXACT_MASS	422.10487605599997	Da
FORMULA	C21H18N4O4S	-
HBA	7	-
HBD	1	-
LOGP	3.6174000000000026	-
MOL_WEIGHT	422.4660000000003	g/mol
QED_SCORE	0.5095276468573028	-
ROTATABLE_BONDS	4	-
TPSA	97.14	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
T06	T06	selection_import_t06	1 native pose available	1.1457515134075142	-17.2162	15	0.71	-	Best pose
T03	T03	selection_import_t03	1 native pose available	1.3411933317363585	-32.906	14	0.70	-	Best pose
T21	T21	selection_import_t21	1 native pose available	2.0926937225473776	-30.7892	12	0.86	-	Best pose
T05	T05	selection_import_t05	1 native pose available	3.19252741198437	-33.2615	11	0.65	-	Best 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
450	1.1457515134075142	-0.830626	-17.2162	2	17	15	0.71	0.20	0.25	0.50	-	no	geometry warning; 11 clashes; 4 protein contact clashes; high strain Δ 30.6	Open pose

T03 — T03 1 poses · report selection_import_t03

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
492	1.3411933317363585	-0.894811	-32.906	4	18	14	0.70	0.14	0.20	0.20	-	no	geometry warning; 10 clashes; 6 protein contact clashes; high strain Δ 34.5	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
476	2.0926937225473776	-0.804378	-30.7892	8	16	12	0.86	0.17	0.22	0.25	-	no	geometry warning; 15 clashes; 7 protein contact clashes; high strain Δ 41.1	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
434	3.19252741198437	-1.04683	-33.2615	6	17	11	0.65	0.43	0.50	0.60	-	no	geometry warning; 12 clashes; 1 protein clash; 3 cofactor-context clashes; moderate strain Δ 28.7	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

Z29466466

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