Compound detail

SMILES: COc1ccc(CN(C)Cc2ccncc2)cc1-c1ccc(S(=O)(=O)NC2CCC2)s1

Formula: C23H27N3O3S2 | MW: 457.6210000000002

LogP: 4.281500000000004 | TPSA: 71.53

HBA/HBD: 6/1 | RotB: 9

InChIKey: SPPHPPMRHOBINH-UHFFFAOYSA-N

Recognized patterns

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

Highlighted: 1 pattern Aryl ether Clear highlight

Bio motif

Sulfonamide bioisostere H-bond acceptor N ×2 H-bond acceptor O ×3 H-bond donor Gatekeeper aromatic P-gp efflux flag

Functional group

Tertiary amine Sulfonamide Aryl ether Ether

Ring system

Benzene Pyridine Thiophene Cyclobutane

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.783142	-
DOCK_BASE_INTER_RANK	-0.927754	-
DOCK_BASE_INTER_RANK	-0.731697	-
DOCK_BASE_INTER_RANK	-0.665842	-
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	7.000000	-
DOCK_CLASH_COUNT	9.000000	-
DOCK_CLASH_COUNT	8.000000	-
DOCK_CLASH_COUNT	7.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_CONTACT_COUNT	17.000000	-
DOCK_CONTACT_COUNT	15.000000	-
DOCK_CONTACT_COUNT	11.000000	-
DOCK_EXPERIMENT	T11	-
DOCK_EXPERIMENT	T12	-
DOCK_EXPERIMENT	T18	-
DOCK_EXPERIMENT	T20	-
DOCK_EXPERIMENT_ID	11	-
DOCK_EXPERIMENT_ID	12	-
DOCK_EXPERIMENT_ID	18	-
DOCK_EXPERIMENT_ID	20	-
DOCK_FINAL_RANK	2.777253	-
DOCK_FINAL_RANK	4.687977	-
DOCK_FINAL_RANK	2.820680	-
DOCK_FINAL_RANK	2.137495	-
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:ALA40	1	-
DOCK_IFP::A:ARG140	1	-
DOCK_IFP::A:ARG144	1	-
DOCK_IFP::A:ASN106	1	-
DOCK_IFP::A:ASN125	1	-
DOCK_IFP::A:ASN402	1	-
DOCK_IFP::A:ASP105	1	-
DOCK_IFP::A:CYS52	1	-
DOCK_IFP::A:GLN124	1	-
DOCK_IFP::A:GLU18	1	-
DOCK_IFP::A:GLU192	1	-
DOCK_IFP::A:GLU467	1	-
DOCK_IFP::A:GLY13	1	-
DOCK_IFP::A:GLY191	1	-
DOCK_IFP::A:GLY39	1	-
DOCK_IFP::A:GLY49	1	-
DOCK_IFP::A:HIS105	1	-
DOCK_IFP::A:HIS141	1	-
DOCK_IFP::A:HIS144	1	-
DOCK_IFP::A:HIS222	1	-
DOCK_IFP::A:ILE106	1	-
DOCK_IFP::A:ILE126	1	-
DOCK_IFP::A:ILE339	1	-
DOCK_IFP::A:LEU17	1	-
DOCK_IFP::A:LEU194	1	-
DOCK_IFP::A:LEU399	1	-
DOCK_IFP::A:LEU95	1	-
DOCK_IFP::A:LYS410	1	-
DOCK_IFP::A:MET101	1	-
DOCK_IFP::A:MET113	1	-
DOCK_IFP::A:MET400	1	-
DOCK_IFP::A:PHE189	1	-
DOCK_IFP::A:PHE190	1	-
DOCK_IFP::A:PHE396	1	-
DOCK_IFP::A:PHE51	1	-
DOCK_IFP::A:PHE74	1	-
DOCK_IFP::A:PRO223	1	-
DOCK_IFP::A:PRO398	1	-
DOCK_IFP::A:SER109	1	-
DOCK_IFP::A:SER14	1	-
DOCK_IFP::A:SER395	1	-
DOCK_IFP::A:SER464	1	-
DOCK_IFP::A:THR335	1	-
DOCK_IFP::A:THR397	1	-
DOCK_IFP::A:THR463	1	-
DOCK_IFP::A:TRP21	1	-
DOCK_IFP::A:TYR110	1	-
DOCK_IFP::A:TYR97	1	-
DOCK_IFP::A:VAL187	1	-
DOCK_IFP::A:VAL188	1	-
DOCK_IFP::A:VAL221	1	-
DOCK_IFP::A:VAL53	1	-
DOCK_IFP::B:ARG116	1	-
DOCK_IFP::B:ARG46	1	-
DOCK_IFP::B:ASP13	1	-
DOCK_IFP::B:CYS72	1	-
DOCK_IFP::B:GLY73	1	-
DOCK_IFP::B:HIS14	1	-
DOCK_IFP::B:ILE15	1	-
DOCK_IFP::B:ILE76	1	-
DOCK_IFP::B:SER74	1	-
DOCK_IFP::B:TYR49	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	0.650462	-
DOCK_MAX_CLASH_OVERLAP	0.650527	-
DOCK_MAX_CLASH_OVERLAP	0.650534	-
DOCK_MAX_CLASH_OVERLAP	0.650535	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	2.747397	-
DOCK_PRE_RANK	4.660057	-
DOCK_PRE_RANK	2.786171	-
DOCK_PRE_RANK	2.110079	-
DOCK_PRIMARY_POSE_ID	6916	-
DOCK_PRIMARY_POSE_ID	7570	-
DOCK_PRIMARY_POSE_ID	11683	-
DOCK_PRIMARY_POSE_ID	13064	-
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_t11	-
DOCK_REPORT_ID	selection_import_t12	-
DOCK_REPORT_ID	selection_import_t18	-
DOCK_REPORT_ID	selection_import_t20	-
DOCK_RESIDUE_CONTACTS	A:ALA40;A:ASN125;A:GLN124;A:GLU192;A:GLY191;A:GLY39;A:HIS144;A:HIS222;A:ILE126;A:LEU194;A:LEU95;A:PHE189;A:PHE190;A:PHE51;A:PHE74;A:PRO223;A:VAL187;A:VAL188;A:VAL221	-
DOCK_RESIDUE_CONTACTS	A:ARG140;A:ARG144;A:ASN106;A:HIS105;A:HIS141;A:MET101;A:TYR97;B:ARG116;B:ARG46;B:ASP13;B:CYS72;B:GLY73;B:HIS14;B:ILE15;B:ILE76;B:SER74;B:TYR49	-
DOCK_RESIDUE_CONTACTS	A:ASP105;A:CYS52;A:GLU18;A:GLY13;A:GLY49;A:ILE106;A:ILE339;A:LEU17;A:MET113;A:SER109;A:SER14;A:THR335;A:TRP21;A:TYR110;A:VAL53	-
DOCK_RESIDUE_CONTACTS	A:ASN402;A:GLU467;A:LEU399;A:LYS410;A:MET400;A:PHE396;A:PRO398;A:SER395;A:SER464;A:THR397;A:THR463	-
DOCK_SCAFFOLD	O=S(=O)(NC1CCC1)c1ccc(-c2cccc(CNCc3ccncc3)c2)s1	-
DOCK_SCAFFOLD	O=S(=O)(NC1CCC1)c1ccc(-c2cccc(CNCc3ccncc3)c2)s1	-
DOCK_SCAFFOLD	O=S(=O)(NC1CCC1)c1ccc(-c2cccc(CNCc3ccncc3)c2)s1	-
DOCK_SCAFFOLD	O=S(=O)(NC1CCC1)c1ccc(-c2cccc(CNCc3ccncc3)c2)s1	-
DOCK_SCORE	-21.378000	-
DOCK_SCORE	-27.902600	-
DOCK_SCORE	-22.286100	-
DOCK_SCORE	-20.212200	-
DOCK_SCORE_INTER	-24.277400	-
DOCK_SCORE_INTER	-28.760400	-
DOCK_SCORE_INTER	-22.682600	-
DOCK_SCORE_INTER	-20.641100	-
DOCK_SCORE_INTER_KCAL	-5.798560	-
DOCK_SCORE_INTER_KCAL	-6.869306	-
DOCK_SCORE_INTER_KCAL	-5.417648	-
DOCK_SCORE_INTER_KCAL	-4.930044	-
DOCK_SCORE_INTER_NORM	-0.783142	-
DOCK_SCORE_INTER_NORM	-0.927754	-
DOCK_SCORE_INTER_NORM	-0.731697	-
DOCK_SCORE_INTER_NORM	-0.665842	-
DOCK_SCORE_INTRA	2.899410	-
DOCK_SCORE_INTRA	0.857739	-
DOCK_SCORE_INTRA	0.396481	-
DOCK_SCORE_INTRA	0.428887	-
DOCK_SCORE_INTRA_KCAL	0.692512	-
DOCK_SCORE_INTRA_KCAL	0.204868	-
DOCK_SCORE_INTRA_KCAL	0.094698	-
DOCK_SCORE_INTRA_KCAL	0.102438	-
DOCK_SCORE_INTRA_NORM	0.093529	-
DOCK_SCORE_INTRA_NORM	0.027669	-
DOCK_SCORE_INTRA_NORM	0.012790	-
DOCK_SCORE_INTRA_NORM	0.013835	-
DOCK_SCORE_KCAL	-5.106050	-
DOCK_SCORE_KCAL	-6.664424	-
DOCK_SCORE_KCAL	-5.322946	-
DOCK_SCORE_KCAL	-4.827603	-
DOCK_SCORE_NORM	-0.689612	-
DOCK_SCORE_NORM	-0.900085	-
DOCK_SCORE_NORM	-0.718907	-
DOCK_SCORE_NORM	-0.652007	-
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	T11_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T12_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T18_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T20_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C23H27N3O3S2	-
DOCK_SOURCE_FORMULA	C23H27N3O3S2	-
DOCK_SOURCE_FORMULA	C23H27N3O3S2	-
DOCK_SOURCE_FORMULA	C23H27N3O3S2	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBA	6.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HBD	1.000000	-
DOCK_SOURCE_HEAVY_ATOMS	31.000000	-
DOCK_SOURCE_HEAVY_ATOMS	31.000000	-
DOCK_SOURCE_HEAVY_ATOMS	31.000000	-
DOCK_SOURCE_HEAVY_ATOMS	31.000000	-
DOCK_SOURCE_LOGP	4.281500	-
DOCK_SOURCE_LOGP	4.281500	-
DOCK_SOURCE_LOGP	4.281500	-
DOCK_SOURCE_LOGP	4.281500	-
DOCK_SOURCE_MW	457.621000	-
DOCK_SOURCE_MW	457.621000	-
DOCK_SOURCE_MW	457.621000	-
DOCK_SOURCE_MW	457.621000	-
DOCK_SOURCE_NAME	KB_chagas_146	-
DOCK_SOURCE_NAME	KB_chagas_146	-
DOCK_SOURCE_NAME	KB_chagas_146	-
DOCK_SOURCE_NAME	KB_chagas_146	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	71.530000	-
DOCK_SOURCE_TPSA	71.530000	-
DOCK_SOURCE_TPSA	71.530000	-
DOCK_SOURCE_TPSA	71.530000	-
DOCK_STRAIN_DELTA	23.453356	-
DOCK_STRAIN_DELTA	22.135382	-
DOCK_STRAIN_DELTA	26.403233	-
DOCK_STRAIN_DELTA	21.781754	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_TARGET	T11	-
DOCK_TARGET	T12	-
DOCK_TARGET	T18	-
DOCK_TARGET	T20	-
EXACT_MASS	457.1493837240001	Da
FORMULA	C23H27N3O3S2	-
HBA	6	-
HBD	1	-
LOGP	4.281500000000004	-
MOL_WEIGHT	457.6210000000002	g/mol
QED_SCORE	0.5192498388293774	-
ROTATABLE_BONDS	9	-
TPSA	71.53	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
T20	T20	selection_import_t20	1 native pose available	2.1374948191649445	-20.2122	6	0.75	-	Best pose
T11	T11	selection_import_t11	1 native pose available	2.7772525615488326	-21.378	13	0.72	-	Best pose
T18	T18	selection_import_t18	1 native pose available	2.820679519399628	-22.2861	9	0.69	-	Best pose
T12	T12	selection_import_t12	1 native pose available	4.687977126069968	-27.9026	14	0.88	-	Best pose

T20 — T20 1 poses · report selection_import_t20

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
185	2.1374948191649445	-0.665842	-20.2122	5	11	6	0.75	0.00	0.00	0.00	-	no	geometry warning; 7 clashes; 1 protein clash; moderate strain Δ 21.8	Open pose

T11 — T11 1 poses · report selection_import_t11

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
142	2.7772525615488326	-0.783142	-21.378	6	19	13	0.72	0.20	0.20	0.25	-	no	geometry warning; 7 clashes; 2 protein clashes; moderate strain Δ 23.5	Open pose

T18 — T18 1 poses · report selection_import_t18

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
162	2.820679519399628	-0.731697	-22.2861	4	15	9	0.69	-	-	-	-	no	geometry warning; 8 clashes; 2 protein clashes; moderate strain Δ 26.4	Open pose

T12 — T12 1 poses · report selection_import_t12

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
118	4.687977126069968	-0.927754	-27.9026	10	17	14	0.88	0.42	0.30	0.40	-	no	geometry warning; 9 clashes; 3 protein clashes; moderate strain Δ 22.1	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_chagas_146

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