Compound detail

SMILES: O=C(CN1C(=O)[C@@H]2[C@H](C1=O)[C@H]1C=C[C@@H]2C1)Nc1n[nH]c(SCc2ccc(Cl)cc2)n1

Formula: C20H18ClN5O3S | MW: 443.9160000000001

LogP: 2.4960000000000004 | TPSA: 108.05

HBA/HBD: 6/2 | RotB: 6

InChIKey: NWSJRKVKWADPHV-CRJCFHLZSA-N

Recognized patterns

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

Highlighted: 1 pattern Hinge binder (NH-C=O) Clear highlight

Bio motif

Peptide backbone Hinge binder (C=O-NH) Hinge binder (NH-C=O) N-Methyl amide ×4 H-bond acceptor N ×4 H-bond acceptor O ×3 H-bond donor ×2 Gatekeeper aromatic Metal chelator ×3 Retro-amide P-gp efflux flag

Functional group

Carbonyl ×3 Amide ×3 Secondary amine Tertiary amine Lactam ×2 Chlorine Imide Sulfide Alkene

Ring system

Benzene 1,2,4-Triazole Cyclopentane

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.854448	-
DOCK_BASE_INTER_RANK	-0.762105	-
DOCK_BASE_INTER_RANK	-0.961311	-
DOCK_BASE_INTER_RANK	-0.851339	-
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	12.000000	-
DOCK_CLASH_COUNT	7.000000	-
DOCK_CLASH_COUNT	8.000000	-
DOCK_CLASH_COUNT	6.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_CONTACT_COUNT	13.000000	-
DOCK_CONTACT_COUNT	13.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT	T09	-
DOCK_EXPERIMENT	T02	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	21	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	9	-
DOCK_EXPERIMENT_ID	2	-
DOCK_FINAL_RANK	2.346952	-
DOCK_FINAL_RANK	2.622510	-
DOCK_FINAL_RANK	0.277597	-
DOCK_FINAL_RANK	1.832386	-
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:ALA10	1	-
DOCK_IFP::A:ALA34	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ASN65	1	-
DOCK_IFP::A:ASP22	1	-
DOCK_IFP::A:GLN56	1	-
DOCK_IFP::A:GLU31	1	-
DOCK_IFP::A:GLU50	1	-
DOCK_IFP::A:GLY117	1	-
DOCK_IFP::A:GLY21	1	-
DOCK_IFP::A:HIS102	1	-
DOCK_IFP::A:HIS138	1	-
DOCK_IFP::A:ILE160	1	-
DOCK_IFP::A:ILE47	1	-
DOCK_IFP::A:ILE51	1	-
DOCK_IFP::A:ILE61	1	-
DOCK_IFP::A:ILE8	1	-
DOCK_IFP::A:LEU23	1	-
DOCK_IFP::A:LEU68	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:MET55	1	-
DOCK_IFP::A:MET98	1	-
DOCK_IFP::A:NAP201	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:PHE32	1	-
DOCK_IFP::A:PHE35	1	-
DOCK_IFP::A:PHE58	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PRO52	1	-
DOCK_IFP::A:PRO62	1	-
DOCK_IFP::A:PRO91	1	-
DOCK_IFP::A:SER60	1	-
DOCK_IFP::A:THR57	1	-
DOCK_IFP::A:TYR122	1	-
DOCK_IFP::A:TYR94	1	-
DOCK_IFP::A:VAL116	1	-
DOCK_IFP::A:VAL33	1	-
DOCK_IFP::A:VAL9	1	-
DOCK_IFP::B:ALA32	1	-
DOCK_IFP::B:ARG113	1	-
DOCK_IFP::B:ARG48	1	-
DOCK_IFP::B:ASP52	1	-
DOCK_IFP::B:CYS69	1	-
DOCK_IFP::B:GLY70	1	-
DOCK_IFP::B:HIS11	1	-
DOCK_IFP::B:ILE182	1	-
DOCK_IFP::B:ILE45	1	-
DOCK_IFP::B:MET53	1	-
DOCK_IFP::B:PHE56	1	-
DOCK_IFP::B:PRO12	1	-
DOCK_IFP::B:PRO50	1	-
DOCK_IFP::B:SER71	1	-
DOCK_IFP::B:THR83	1	-
DOCK_IFP::B:TRP47	1	-
DOCK_IFP::B:TYR46	1	-
DOCK_IFP::B:VAL156	1	-
DOCK_IFP::B:VAL49	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	0.617968	-
DOCK_MAX_CLASH_OVERLAP	0.617196	-
DOCK_MAX_CLASH_OVERLAP	0.637705	-
DOCK_MAX_CLASH_OVERLAP	0.617940	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	0.241171	-
DOCK_PRE_RANK	2.593530	-
DOCK_PRE_RANK	2.323362	-
DOCK_PRE_RANK	1.767137	-
DOCK_PRIMARY_POSE_ID	1201	-
DOCK_PRIMARY_POSE_ID	14049	-
DOCK_PRIMARY_POSE_ID	3853	-
DOCK_PRIMARY_POSE_ID	5901	-
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_t21	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_REPORT_ID	selection_import_t09	-
DOCK_REPORT_ID	selection_import_t02	-
DOCK_RESIDUE_CONTACTS	A:ALA10;A:ASN65;A:ASP22;A:GLU31;A:GLY117;A:GLY21;A:ILE61;A:ILE8;A:LEU23;A:LEU68;A:NAP201;A:PHE32;A:PHE35;A:PRO62;A:SER60;A:THR57;A:TYR122;A:VAL116;A:VAL9	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG59;A:GLN56;A:GLU50;A:ILE160;A:ILE47;A:ILE51;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:PRO52;A:PRO91;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG141;A:HIS102;A:HIS138;A:MET98;A:TYR94;B:ARG113;B:CYS69;B:GLY70;B:HIS11;B:PRO12;B:SER71;B:TYR46	-
DOCK_RESIDUE_CONTACTS	A:NDP301;B:ALA32;B:ARG48;B:ASP52;B:ILE182;B:ILE45;B:MET53;B:PHE56;B:PRO50;B:THR83;B:TRP47;B:VAL156;B:VAL49	-
DOCK_SCAFFOLD	O=C(CN1C(=O)C2C3C=CC(C3)C2C1=O)Nc1n[nH]c(SCc2ccccc2)n1	-
DOCK_SCAFFOLD	O=C(CN1C(=O)C2C3C=CC(C3)C2C1=O)Nc1n[nH]c(SCc2ccccc2)n1	-
DOCK_SCAFFOLD	O=C1C2C3C=CC(C3)C2C(=O)N1CC=Nc1nc(SCc2ccccc2)n[nH]1	-
DOCK_SCAFFOLD	O=C(CN1C(=O)C2C3C=CC(C3)C2C1=O)Nc1n[nH]c(SCc2ccccc2)n1	-
DOCK_SCORE	-25.408000	-
DOCK_SCORE	-27.784600	-
DOCK_SCORE	-28.058000	-
DOCK_SCORE	-25.846000	-
DOCK_SCORE_INTER	-25.540200	-
DOCK_SCORE_INTER	-22.863200	-
DOCK_SCORE_INTER	-25.633400	-
DOCK_SCORE_INTER	-28.839300	-
DOCK_SCORE_INTER_KCAL	-5.460784	-
DOCK_SCORE_INTER_KCAL	-6.100175	-
DOCK_SCORE_INTER_KCAL	-6.122435	-
DOCK_SCORE_INTER_KCAL	-6.888151	-
DOCK_SCORE_INTER_NORM	-0.961311	-
DOCK_SCORE_INTER_NORM	-0.851339	-
DOCK_SCORE_INTER_NORM	-0.762105	-
DOCK_SCORE_INTER_NORM	-0.854448	-
DOCK_SCORE_INTRA	-2.734450	-
DOCK_SCORE_INTRA	0.781310	-
DOCK_SCORE_INTRA	-0.305834	-
DOCK_SCORE_INTRA	-2.151110	-
DOCK_SCORE_INTRA_KCAL	-0.073047	-
DOCK_SCORE_INTRA_KCAL	-0.653112	-
DOCK_SCORE_INTRA_KCAL	-0.513784	-
DOCK_SCORE_INTRA_KCAL	0.186613	-
DOCK_SCORE_INTRA_NORM	-0.091148	-
DOCK_SCORE_INTRA_NORM	-0.010195	-
DOCK_SCORE_INTRA_NORM	0.026044	-
DOCK_SCORE_INTRA_NORM	-0.071704	-
DOCK_SCORE_KCAL	-6.068599	-
DOCK_SCORE_KCAL	-6.173214	-
DOCK_SCORE_KCAL	-6.636241	-
DOCK_SCORE_KCAL	-6.701541	-
DOCK_SCORE_NORM	-0.846935	-
DOCK_SCORE_NORM	-0.861534	-
DOCK_SCORE_NORM	-0.935267	-
DOCK_SCORE_NORM	-0.926152	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.189568	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.006319	-
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	T02_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T06_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T09_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T21_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C20H18ClN5O3S	-
DOCK_SOURCE_FORMULA	C20H18ClN5O3S	-
DOCK_SOURCE_FORMULA	C20H18ClN5O3S	-
DOCK_SOURCE_FORMULA	C20H18ClN5O3S	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
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	2.496000	-
DOCK_SOURCE_LOGP	2.496000	-
DOCK_SOURCE_LOGP	3.145500	-
DOCK_SOURCE_LOGP	2.496000	-
DOCK_SOURCE_MW	443.916000	-
DOCK_SOURCE_MW	443.916000	-
DOCK_SOURCE_MW	443.916000	-
DOCK_SOURCE_MW	443.916000	-
DOCK_SOURCE_NAME	Z28978240	-
DOCK_SOURCE_NAME	Z28978240	-
DOCK_SOURCE_NAME	Z28978240	-
DOCK_SOURCE_NAME	Z28978240	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_TPSA	108.050000	-
DOCK_SOURCE_TPSA	108.050000	-
DOCK_SOURCE_TPSA	108.050000	-
DOCK_SOURCE_TPSA	111.540000	-
DOCK_STRAIN_DELTA	18.937605	-
DOCK_STRAIN_DELTA	22.864883	-
DOCK_STRAIN_DELTA	41.787950	-
DOCK_STRAIN_DELTA	27.545044	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	1	-
DOCK_TARGET	T09	-
DOCK_TARGET	T21	-
DOCK_TARGET	T06	-
DOCK_TARGET	T02	-
EXACT_MASS	443.0818881160001	Da
FORMULA	C20H18ClN5O3S	-
HBA	6	-
HBD	2	-
LOGP	2.4960000000000004	-
MOL_WEIGHT	443.9160000000001	g/mol
QED_SCORE	0.40317173197426387	-
ROTATABLE_BONDS	6	-
TPSA	108.05	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	0.2775974985117356	-25.408	11	0.52	-	Best pose
T02	T02	selection_import_t02	1 native pose available	1.832385519737991	-28.058	19	0.90	-	Best pose
T09	T09	selection_import_t09	1 native pose available	2.346952227036073	-25.846	8	0.38	-	Best pose
T21	T21	selection_import_t21	1 native pose available	2.6225100394025977	-27.7846	10	0.71	-	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
467	0.2775974985117356	-0.762105	-25.408	0	16	11	0.52	0.00	0.00	0.00	-	no	geometry warning; 7 clashes; 1 protein contact clash; moderate strain Δ 27.5	Open pose

T02 — T02 1 poses · report selection_import_t02

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
523	1.832385519737991	-0.961311	-28.058	1	19	19	0.90	0.20	0.20	0.20	-	no	geometry warning; 12 clashes; 1 protein clash; high strain Δ 41.8	Open pose

T09 — T09 1 poses · report selection_import_t09

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
483	2.346952227036073	-0.851339	-25.846	4	13	8	0.38	0.00	0.17	0.17	-	no	geometry warning; 6 clashes; 2 protein clashes	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
491	2.6225100394025977	-0.854448	-27.7846	9	13	10	0.71	0.25	0.22	0.25	-	no	geometry warning; 8 clashes; 1 protein clash; moderate strain Δ 22.9	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

Z28978240

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