Compound detail

SMILES: O=C(C[C@@H]1Sc2ccccc2NC1=O)OCc1cc(=O)oc2cc(O)ccc12

Formula: C20H15NO6S | MW: 397.4080000000002

LogP: 3.0449 | TPSA: 105.83999999999999

HBA/HBD: 7/2 | RotB: 4

InChIKey: CPLUPJVUVTZVJN-KRWDZBQOSA-N

Recognized patterns

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

Bio motif

Hinge binder (C=O-NH) Hinge binder (NH-C=O) H-bond acceptor O ×5 H-bond donor ×2 Gatekeeper aromatic ×2 Metal chelator ×2

Functional group

Carbonyl ×2 Amide Ester Secondary amine Phenol Lactam Sulfide Ether

Ring system

Benzene ×2 Coumarin

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-1.176040	-
DOCK_BASE_INTER_RANK	-0.832144	-
DOCK_BASE_INTER_RANK	-0.825934	-
DOCK_BASE_INTER_RANK	-0.926931	-
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	11.000000	-
DOCK_CLASH_COUNT	11.000000	-
DOCK_CLASH_COUNT	11.000000	-
DOCK_CLASH_COUNT	14.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_CONTACT_COUNT	18.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_CONTACT_COUNT	15.000000	-
DOCK_EXPERIMENT	T05	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT	T17	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	5	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	17	-
DOCK_EXPERIMENT_ID	21	-
DOCK_FINAL_RANK	2.054521	-
DOCK_FINAL_RANK	4.101927	-
DOCK_FINAL_RANK	4.451491	-
DOCK_FINAL_RANK	1.716567	-
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:ALA363	1	-
DOCK_IFP::A:ALA365	1	-
DOCK_IFP::A:ARG100	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG17	1	-
DOCK_IFP::A:ARG331	1	-
DOCK_IFP::A:ARG361	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ASN103	1	-
DOCK_IFP::A:ASP181	1	-
DOCK_IFP::A:CYS375	1	-
DOCK_IFP::A:GLN56	1	-
DOCK_IFP::A:GLY161	1	-
DOCK_IFP::A:GLY225	1	-
DOCK_IFP::A:GLY376	1	-
DOCK_IFP::A:HIS102	1	-
DOCK_IFP::A:HIS138	1	-
DOCK_IFP::A:ILE160	1	-
DOCK_IFP::A:ILE47	1	-
DOCK_IFP::A:LEU188	1	-
DOCK_IFP::A:LEU226	1	-
DOCK_IFP::A:LEU229	1	-
DOCK_IFP::A:LEU332	1	-
DOCK_IFP::A:LEU334	1	-
DOCK_IFP::A:LEU377	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:MET183	1	-
DOCK_IFP::A:MET333	1	-
DOCK_IFP::A:MET55	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:PHE58	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PRO115	1	-
DOCK_IFP::A:PRO91	1	-
DOCK_IFP::A:SER364	1	-
DOCK_IFP::A:THR360	1	-
DOCK_IFP::A:THR374	1	-
DOCK_IFP::A:THR86	1	-
DOCK_IFP::A:TYR114	1	-
DOCK_IFP::A:TYR166	1	-
DOCK_IFP::A:TYR191	1	-
DOCK_IFP::A:TYR194	1	-
DOCK_IFP::A:VAL228	1	-
DOCK_IFP::A:VAL230	1	-
DOCK_IFP::A:VAL32	1	-
DOCK_IFP::A:VAL33	1	-
DOCK_IFP::A:VAL362	1	-
DOCK_IFP::A:VAL366	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	0.613938	-
DOCK_MAX_CLASH_OVERLAP	0.613426	-
DOCK_MAX_CLASH_OVERLAP	0.614088	-
DOCK_MAX_CLASH_OVERLAP	0.614028	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	2.027500	-
DOCK_PRE_RANK	4.074005	-
DOCK_PRE_RANK	4.427011	-
DOCK_PRE_RANK	1.679174	-
DOCK_PRIMARY_POSE_ID	3074	-
DOCK_PRIMARY_POSE_ID	3766	-
DOCK_PRIMARY_POSE_ID	11296	-
DOCK_PRIMARY_POSE_ID	13979	-
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_t05	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_REPORT_ID	selection_import_t17	-
DOCK_REPORT_ID	selection_import_t21	-
DOCK_RESIDUE_CONTACTS	A:ARG17;A:ASP181;A:GLY225;A:LEU188;A:LEU226;A:LEU229;A:MET183;A:NDP302;A:PHE113;A:PRO115;A:TYR114;A:TYR191;A:TYR194;A:VAL228;A:VAL230;D:ARG287	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG100;A:ARG59;A:GLN56;A:GLY161;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:PRO91;A:THR86;A:TYR166;A:VAL32;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ALA363;A:ALA365;A:ARG331;A:ARG361;A:CYS375;A:GLY376;A:LEU332;A:LEU334;A:LEU377;A:MET333;A:PHE198;A:PHE230;A:SER364;A:THR360;A:THR374;A:VAL362;A:VAL366	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG141;A:ASN103;A:HIS102;A:HIS138;B:ARG113;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER71;B:TYR46	-
DOCK_SCAFFOLD	O=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12	-
DOCK_SCAFFOLD	O=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12	-
DOCK_SCAFFOLD	O=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12	-
DOCK_SCAFFOLD	O=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12	-
DOCK_SCORE	-25.543600	-
DOCK_SCORE	-21.224600	-
DOCK_SCORE	-20.342400	-
DOCK_SCORE	-25.259400	-
DOCK_SCORE_INTER	-32.929300	-
DOCK_SCORE_INTER	-23.300000	-
DOCK_SCORE_INTER	-23.126100	-
DOCK_SCORE_INTER	-25.954100	-
DOCK_SCORE_INTER_KCAL	-7.865032	-
DOCK_SCORE_INTER_KCAL	-5.565112	-
DOCK_SCORE_INTER_KCAL	-5.523576	-
DOCK_SCORE_INTER_KCAL	-6.199033	-
DOCK_SCORE_INTER_NORM	-1.176040	-
DOCK_SCORE_INTER_NORM	-0.832144	-
DOCK_SCORE_INTER_NORM	-0.825934	-
DOCK_SCORE_INTER_NORM	-0.926931	-
DOCK_SCORE_INTRA	7.385610	-
DOCK_SCORE_INTRA	1.294600	-
DOCK_SCORE_INTRA	2.783770	-
DOCK_SCORE_INTRA	0.694635	-
DOCK_SCORE_INTRA_KCAL	1.764023	-
DOCK_SCORE_INTRA_KCAL	0.309210	-
DOCK_SCORE_INTRA_KCAL	0.664892	-
DOCK_SCORE_INTRA_KCAL	0.165911	-
DOCK_SCORE_INTRA_NORM	0.263772	-
DOCK_SCORE_INTRA_NORM	0.046236	-
DOCK_SCORE_INTRA_NORM	0.099420	-
DOCK_SCORE_INTRA_NORM	0.024808	-
DOCK_SCORE_KCAL	-6.100987	-
DOCK_SCORE_KCAL	-5.069411	-
DOCK_SCORE_KCAL	-4.858701	-
DOCK_SCORE_KCAL	-6.033107	-
DOCK_SCORE_NORM	-0.912273	-
DOCK_SCORE_NORM	-0.758022	-
DOCK_SCORE_NORM	-0.726514	-
DOCK_SCORE_NORM	-0.902123	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.780816	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.027886	-
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	T05_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T06_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	C20H15NO6S	-
DOCK_SOURCE_FORMULA	C20H15NO6S	-
DOCK_SOURCE_FORMULA	C20H15NO6S	-
DOCK_SOURCE_FORMULA	C20H15NO6S	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBA	7.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_HEAVY_ATOMS	28.000000	-
DOCK_SOURCE_LOGP	3.044900	-
DOCK_SOURCE_LOGP	3.044900	-
DOCK_SOURCE_LOGP	3.044900	-
DOCK_SOURCE_LOGP	3.044900	-
DOCK_SOURCE_MW	397.408000	-
DOCK_SOURCE_MW	397.408000	-
DOCK_SOURCE_MW	397.408000	-
DOCK_SOURCE_MW	397.408000	-
DOCK_SOURCE_NAME	Z16383985	-
DOCK_SOURCE_NAME	Z16383985	-
DOCK_SOURCE_NAME	Z16383985	-
DOCK_SOURCE_NAME	Z16383985	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	105.840000	-
DOCK_SOURCE_TPSA	105.840000	-
DOCK_SOURCE_TPSA	105.840000	-
DOCK_SOURCE_TPSA	105.840000	-
DOCK_STRAIN_DELTA	21.501955	-
DOCK_STRAIN_DELTA	22.137098	-
DOCK_STRAIN_DELTA	19.627584	-
DOCK_STRAIN_DELTA	28.106305	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_TARGET	T05	-
DOCK_TARGET	T06	-
DOCK_TARGET	T17	-
DOCK_TARGET	T21	-
EXACT_MASS	397.0620082	Da
FORMULA	C20H15NO6S	-
HBA	7	-
HBD	2	-
LOGP	3.0449	-
MOL_WEIGHT	397.4080000000002	g/mol
QED_SCORE	0.514766835784493	-
ROTATABLE_BONDS	4	-
TPSA	105.83999999999999	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
T21	T21	selection_import_t21	1 native pose available	1.7165668534412548	-25.2594	13	0.93	-	Best pose
T05	T05	selection_import_t05	1 native pose available	2.0545206570759786	-25.5436	12	0.71	-	Best pose
T06	T06	selection_import_t06	1 native pose available	4.101926987256495	-21.2246	14	0.67	-	Best pose
T17	T17	selection_import_t17	1 native pose available	4.451490659921485	-20.3424	10	0.83	-	Best 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
421	1.7165668534412548	-0.926931	-25.2594	10	15	13	0.93	0.50	0.56	0.75	-	no	geometry warning; 14 clashes; 7 protein contact clashes; moderate strain Δ 28.1	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
364	2.0545206570759786	-1.17604	-25.5436	7	16	12	0.71	0.43	0.50	0.60	-	no	geometry warning; 11 clashes; 1 protein clash; 1 severe cofactor-context clash; moderate strain Δ 21.5	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
380	4.101926987256495	-0.832144	-21.2246	4	18	14	0.67	0.00	0.00	0.00	-	no	geometry warning; 11 clashes; 2 protein clashes; moderate strain Δ 22.1	Open 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
453	4.451490659921485	-0.825934	-20.3424	4	17	10	0.83	1.00	1.00	1.00	-	no	geometry warning; 11 clashes; 3 protein clashes	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

Z16383985

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