Compound detail

SMILES: O=C(c1ccc(Cl)cc1)N1CCCC[C@@H](Sc2nnc(-c3ccc4c(c3)OCO4)o2)C1=O

Formula: C22H18ClN3O5S | MW: 471.92200000000025

LogP: 4.432300000000002 | TPSA: 94.76000000000002

HBA/HBD: 8/- | RotB: 4

InChIKey: GVMQVAYHFJDREY-GOSISDBHSA-N

Recognized patterns

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

Highlighted: 1 pattern Tertiary amine Clear highlight

Bio motif

Catechol N-Methyl amide ×4 H-bond acceptor N ×3 H-bond acceptor O ×5 Gatekeeper aromatic ×2 Metal chelator ×2 P-gp efflux flag

Functional group

Carbonyl ×2 Amide ×2 Tertiary amine Lactam ×2 Chlorine Aryl ether ×2 Imide Sulfide Ether ×2 Acetal

Ring system

Benzene ×2 Benzodioxole Oxadiazole 1,3,4-Oxadiazole

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.942546	-
DOCK_BASE_INTER_RANK	-0.980047	-
DOCK_BASE_INTER_RANK	-0.718628	-
DOCK_BASE_INTER_RANK	-0.794718	-
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	8.000000	-
DOCK_CLASH_COUNT	10.000000	-
DOCK_CLASH_COUNT	9.000000	-
DOCK_CLASH_COUNT	10.000000	-
DOCK_CONTACT_COUNT	15.000000	-
DOCK_CONTACT_COUNT	14.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_EXPERIMENT	T03	-
DOCK_EXPERIMENT	T05	-
DOCK_EXPERIMENT	T17	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	3	-
DOCK_EXPERIMENT_ID	5	-
DOCK_EXPERIMENT_ID	17	-
DOCK_EXPERIMENT_ID	21	-
DOCK_FINAL_RANK	2.099053	-
DOCK_FINAL_RANK	3.276619	-
DOCK_FINAL_RANK	0.982042	-
DOCK_FINAL_RANK	4.476669	-
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:ALA284	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG17	1	-
DOCK_IFP::A:ARG228	1	-
DOCK_IFP::A:ARG287	1	-
DOCK_IFP::A:ARG331	1	-
DOCK_IFP::A:ARG39	1	-
DOCK_IFP::A:ARG97	1	-
DOCK_IFP::A:ASN103	1	-
DOCK_IFP::A:ASP330	1	-
DOCK_IFP::A:GLY196	1	-
DOCK_IFP::A:GLY197	1	-
DOCK_IFP::A:GLY286	1	-
DOCK_IFP::A:HIS102	1	-
DOCK_IFP::A:HIS138	1	-
DOCK_IFP::A:HIS241	1	-
DOCK_IFP::A:ILE199	1	-
DOCK_IFP::A:ILE45	1	-
DOCK_IFP::A:LEU188	1	-
DOCK_IFP::A:LEU226	1	-
DOCK_IFP::A:LEU227	1	-
DOCK_IFP::A:LEU229	1	-
DOCK_IFP::A:LEU332	1	-
DOCK_IFP::A:LEU94	1	-
DOCK_IFP::A:LYS57	1	-
DOCK_IFP::A:LYS95	1	-
DOCK_IFP::A:MET333	1	-
DOCK_IFP::A:MET53	1	-
DOCK_IFP::A:MET98	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:NDP302	1	-
DOCK_IFP::A:PHE113	1	-
DOCK_IFP::A:PHE198	1	-
DOCK_IFP::A:PHE230	1	-
DOCK_IFP::A:PHE56	1	-
DOCK_IFP::A:PHE91	1	-
DOCK_IFP::A:PRO88	1	-
DOCK_IFP::A:SER111	1	-
DOCK_IFP::A:SER112	1	-
DOCK_IFP::A:SER200	1	-
DOCK_IFP::A:TYR114	1	-
DOCK_IFP::A:TYR162	1	-
DOCK_IFP::A:TYR194	1	-
DOCK_IFP::A:TYR221	1	-
DOCK_IFP::A:TYR94	1	-
DOCK_IFP::A:VAL156	1	-
DOCK_IFP::A:VAL230	1	-
DOCK_IFP::A:VAL30	1	-
DOCK_IFP::A:VAL31	1	-
DOCK_IFP::A:VAL87	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: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	0.641358	-
DOCK_MAX_CLASH_OVERLAP	0.641313	-
DOCK_MAX_CLASH_OVERLAP	0.641316	-
DOCK_MAX_CLASH_OVERLAP	0.641220	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	2.051485	-
DOCK_PRE_RANK	3.245548	-
DOCK_PRE_RANK	0.952602	-
DOCK_PRE_RANK	4.433039	-
DOCK_PRIMARY_POSE_ID	1795	-
DOCK_PRIMARY_POSE_ID	3078	-
DOCK_PRIMARY_POSE_ID	11297	-
DOCK_PRIMARY_POSE_ID	13982	-
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_t17	-
DOCK_REPORT_ID	selection_import_t21	-
DOCK_RESIDUE_CONTACTS	A:ARG97;A:ILE45;A:LEU94;A:LYS57;A:LYS95;A:MET53;A:NDP301;A:PHE56;A:PHE91;A:PRO88;A:TYR162;A:VAL156;A:VAL30;A:VAL31;A:VAL87	-
DOCK_RESIDUE_CONTACTS	A:ARG17;A:ARG39;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:NDP302;A:PHE113;A:SER111;A:SER112;A:TYR114;A:TYR194;A:VAL230;D:ARG287	-
DOCK_RESIDUE_CONTACTS	A:ALA284;A:ARG228;A:ARG287;A:ARG331;A:ASP330;A:GLY196;A:GLY197;A:GLY286;A:ILE199;A:LEU227;A:LEU332;A:MET333;A:PHE198;A:PHE230;A:SER200;A:TYR221	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG141;A:ASN103;A:HIS102;A:HIS138;A:MET98;A:TYR94;B:ARG113;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER71;B:TYR46	-
DOCK_SCAFFOLD	O=C(c1ccccc1)N1CCCCC(Sc2nnc(-c3ccc4c(c3)OCO4)o2)C1=O	-
DOCK_SCAFFOLD	O=C(c1ccccc1)N1CCCCC(Sc2nnc(-c3ccc4c(c3)OCO4)o2)C1=O	-
DOCK_SCAFFOLD	O=C(c1ccccc1)N1CCCCC(Sc2nnc(-c3ccc4c(c3)OCO4)o2)C1=O	-
DOCK_SCAFFOLD	O=C(c1ccccc1)N1CCCCC(Sc2nnc(-c3ccc4c(c3)OCO4)o2)C1=O	-
DOCK_SCORE	-22.961400	-
DOCK_SCORE	-28.503800	-
DOCK_SCORE	-21.656800	-
DOCK_SCORE	-17.711600	-
DOCK_SCORE_INTER	-30.161500	-
DOCK_SCORE_INTER	-31.361500	-
DOCK_SCORE_INTER	-22.996100	-
DOCK_SCORE_INTER	-25.431000	-
DOCK_SCORE_INTER_KCAL	-7.203954	-
DOCK_SCORE_INTER_KCAL	-7.490569	-
DOCK_SCORE_INTER_KCAL	-5.492527	-
DOCK_SCORE_INTER_KCAL	-6.074093	-
DOCK_SCORE_INTER_NORM	-0.942546	-
DOCK_SCORE_INTER_NORM	-0.980047	-
DOCK_SCORE_INTER_NORM	-0.718628	-
DOCK_SCORE_INTER_NORM	-0.794718	-
DOCK_SCORE_INTRA	7.200110	-
DOCK_SCORE_INTRA	2.287500	-
DOCK_SCORE_INTRA	1.339340	-
DOCK_SCORE_INTRA	7.719400	-
DOCK_SCORE_INTRA_KCAL	1.719717	-
DOCK_SCORE_INTRA_KCAL	0.546360	-
DOCK_SCORE_INTRA_KCAL	0.319896	-
DOCK_SCORE_INTRA_KCAL	1.843748	-
DOCK_SCORE_INTRA_NORM	0.225003	-
DOCK_SCORE_INTRA_NORM	0.071485	-
DOCK_SCORE_INTRA_NORM	0.041854	-
DOCK_SCORE_INTRA_NORM	0.241231	-
DOCK_SCORE_KCAL	-5.484239	-
DOCK_SCORE_KCAL	-6.808019	-
DOCK_SCORE_KCAL	-5.172640	-
DOCK_SCORE_KCAL	-4.230345	-
DOCK_SCORE_NORM	-0.717543	-
DOCK_SCORE_NORM	-0.890745	-
DOCK_SCORE_NORM	-0.676774	-
DOCK_SCORE_NORM	-0.553487	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.570156	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.017817	-
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	T03_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T05_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T17_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T21_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C22H18ClN3O5S	-
DOCK_SOURCE_FORMULA	C22H18ClN3O5S	-
DOCK_SOURCE_FORMULA	C22H18ClN3O5S	-
DOCK_SOURCE_FORMULA	C22H18ClN3O5S	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBD	0.000000	-
DOCK_SOURCE_HBD	0.000000	-
DOCK_SOURCE_HBD	0.000000	-
DOCK_SOURCE_HBD	0.000000	-
DOCK_SOURCE_HEAVY_ATOMS	32.000000	-
DOCK_SOURCE_HEAVY_ATOMS	32.000000	-
DOCK_SOURCE_HEAVY_ATOMS	32.000000	-
DOCK_SOURCE_HEAVY_ATOMS	32.000000	-
DOCK_SOURCE_LOGP	4.432300	-
DOCK_SOURCE_LOGP	4.432300	-
DOCK_SOURCE_LOGP	4.432300	-
DOCK_SOURCE_LOGP	4.432300	-
DOCK_SOURCE_MW	471.922000	-
DOCK_SOURCE_MW	471.922000	-
DOCK_SOURCE_MW	471.922000	-
DOCK_SOURCE_MW	471.922000	-
DOCK_SOURCE_NAME	Z19456089	-
DOCK_SOURCE_NAME	Z19456089	-
DOCK_SOURCE_NAME	Z19456089	-
DOCK_SOURCE_NAME	Z19456089	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_RINGS	5.000000	-
DOCK_SOURCE_TPSA	94.760000	-
DOCK_SOURCE_TPSA	94.760000	-
DOCK_SOURCE_TPSA	94.760000	-
DOCK_SOURCE_TPSA	94.760000	-
DOCK_STRAIN_DELTA	33.566113	-
DOCK_STRAIN_DELTA	24.250941	-
DOCK_STRAIN_DELTA	23.175213	-
DOCK_STRAIN_DELTA	31.538909	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	0	-
DOCK_TARGET	T03	-
DOCK_TARGET	T05	-
DOCK_TARGET	T17	-
DOCK_TARGET	T21	-
EXACT_MASS	471.0655693559999	Da
FORMULA	C22H18ClN3O5S	-
HBA	8	-
HBD	0	-
LOGP	4.432300000000002	-
MOL_WEIGHT	471.92200000000025	g/mol
QED_SCORE	0.5154908481471429	-
ROTATABLE_BONDS	4	-
TPSA	94.76000000000002	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
T17	T17	selection_import_t17	1 native pose available	0.9820416630673475	-21.6568	6	0.50	-	Best pose
T03	T03	selection_import_t03	1 native pose available	2.0990534002216545	-22.9614	14	0.70	-	Best pose
T05	T05	selection_import_t05	1 native pose available	3.276619061336012	-28.5038	11	0.65	-	Best pose
T21	T21	selection_import_t21	1 native pose available	4.476669211177931	-17.7116	13	0.93	-	Best pose

T17 — T17 1 poses · report selection_import_t17

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
454	0.9820416630673475	-0.718628	-21.6568	2	16	6	0.50	0.00	0.00	0.00	-	no	geometry warning; 9 clashes; 4 protein contact clashes; moderate strain Δ 23.2	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
440	2.0990534002216545	-0.942546	-22.9614	3	15	14	0.70	0.29	0.20	0.20	-	no	geometry warning; 8 clashes; 1 protein clash; high strain Δ 33.6	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
368	3.276619061336012	-0.980047	-28.5038	7	14	11	0.65	0.29	0.33	0.60	-	no	geometry warning; 10 clashes; 2 protein clashes; 1 severe cofactor-context clash; moderate strain Δ 24.3	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
424	4.476669211177931	-0.794718	-17.7116	12	17	13	0.93	0.50	0.56	0.62	-	no	geometry warning; 10 clashes; 2 protein clashes; high strain Δ 31.5	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

Z19456089

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