FAIRMol

KB_chagas_146

ID 298

DB fairmolThis detail page is pinned to the current database context.
Back to results Open docking pose (5)
2D structure

SMILES: COc1ccc(C[N@@H+](C)Cc2ccncc2)cc1-c1ccc(S(=O)(=O)NC2CCC2)s1

Formula: C23H28N3O3S2+ | MW: 458.6290000000002

LogP: 2.8644000000000007 | TPSA: 72.73

HBA/HBD: 5/2 | RotB: 9

InChIKey: SPPHPPMRHOBINH-UHFFFAOYSA-O

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern Hinge binder (C=O-NH) Clear highlight

Bio motif

Sulfonamide bioisostere H-bond acceptor N H-bond acceptor O ×3 H-bond donor ×2 Gatekeeper aromatic

Functional group

Sulfonamide Aryl ether Ether

Ring system

Benzene Pyridine Thiophene Cyclobutane

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-1.039160-
DOCK_BASE_INTER_RANK-0.749402-
DOCK_BASE_INTER_RANK-0.871784-
DOCK_BASE_INTER_RANK-0.917573-
DOCK_BASE_INTER_RANK-0.844926-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT8.000000-
DOCK_CLASH_COUNT7.000000-
DOCK_CLASH_COUNT6.000000-
DOCK_CLASH_COUNT8.000000-
DOCK_CLASH_COUNT10.000000-
DOCK_CONTACT_COUNT17.000000-
DOCK_CONTACT_COUNT14.000000-
DOCK_CONTACT_COUNT21.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT23.000000-
DOCK_EXPERIMENTT01-
DOCK_EXPERIMENTT16-
DOCK_EXPERIMENTT09-
DOCK_EXPERIMENTT22-
DOCK_EXPERIMENTT13-
DOCK_EXPERIMENT_ID22-
DOCK_EXPERIMENT_ID9-
DOCK_EXPERIMENT_ID1-
DOCK_EXPERIMENT_ID13-
DOCK_EXPERIMENT_ID16-
DOCK_FINAL_RANK1.896748-
DOCK_FINAL_RANK5.205269-
DOCK_FINAL_RANK4.060504-
DOCK_FINAL_RANK2.066095-
DOCK_FINAL_RANK3.370145-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_IFP::A:ALA101-
DOCK_IFP::A:ALA1111-
DOCK_IFP::A:ALA1581-
DOCK_IFP::A:ALA2091-
DOCK_IFP::A:ALA241-
DOCK_IFP::A:ALA401-
DOCK_IFP::A:ALA671-
DOCK_IFP::A:ALA901-
DOCK_IFP::A:ALA901-
DOCK_IFP::A:ARG1541-
DOCK_IFP::A:ARG2771-
DOCK_IFP::A:ARG291-
DOCK_IFP::A:ASN1121-
DOCK_IFP::A:ASN1261-
DOCK_IFP::A:ASN411-
DOCK_IFP::A:ASP1291-
DOCK_IFP::A:ASP221-
DOCK_IFP::A:ASP3321-
DOCK_IFP::A:ASP681-
DOCK_IFP::A:CYS701-
DOCK_IFP::A:GLN421-
DOCK_IFP::A:GLU2741-
DOCK_IFP::A:GLU311-
DOCK_IFP::A:GLU731-
DOCK_IFP::A:GLY1991-
DOCK_IFP::A:GLY211-
DOCK_IFP::A:GLY2141-
DOCK_IFP::A:GLY2151-
DOCK_IFP::A:GLY231-
DOCK_IFP::A:GLY2351-
DOCK_IFP::A:GLY2361-
DOCK_IFP::A:GLY2371-
DOCK_IFP::A:GLY251-
DOCK_IFP::A:GLY2761-
DOCK_IFP::A:GLY711-
DOCK_IFP::A:HIS1971-
DOCK_IFP::A:ILE611-
DOCK_IFP::A:ILE81-
DOCK_IFP::A:LEU1301-
DOCK_IFP::A:LEU231-
DOCK_IFP::A:LEU281-
DOCK_IFP::A:LEU391-
DOCK_IFP::A:LYS1271-
DOCK_IFP::A:LYS1591-
DOCK_IFP::A:LYS2111-
DOCK_IFP::A:LYS261-
DOCK_IFP::A:LYS691-
DOCK_IFP::A:LYS891-
DOCK_IFP::A:MET701-
DOCK_IFP::A:NAP2011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:PHE1701-
DOCK_IFP::A:PHE2381-
DOCK_IFP::A:PHE321-
DOCK_IFP::A:PHE351-
DOCK_IFP::A:PHE381-
DOCK_IFP::A:PRO1131-
DOCK_IFP::A:PRO1871-
DOCK_IFP::A:PRO2121-
DOCK_IFP::A:PRO2131-
DOCK_IFP::A:PRO271-
DOCK_IFP::A:PRO2751-
DOCK_IFP::A:PRO621-
DOCK_IFP::A:SER1571-
DOCK_IFP::A:SER2001-
DOCK_IFP::A:SER271-
DOCK_IFP::A:SER281-
DOCK_IFP::A:SER601-
DOCK_IFP::A:SER861-
DOCK_IFP::A:SER871-
DOCK_IFP::A:THR1371-
DOCK_IFP::A:THR441-
DOCK_IFP::A:THR571-
DOCK_IFP::A:THR691-
DOCK_IFP::A:TRP251-
DOCK_IFP::A:TYR1221-
DOCK_IFP::A:TYR2101-
DOCK_IFP::A:TYR3891-
DOCK_IFP::A:VAL1161-
DOCK_IFP::A:VAL881-
DOCK_IFP::A:VAL91-
DOCK_IFP::B:ALA321-
DOCK_IFP::B:ARG971-
DOCK_IFP::B:ASP521-
DOCK_IFP::B:ILE451-
DOCK_IFP::B:LEU941-
DOCK_IFP::B:LYS571-
DOCK_IFP::B:LYS951-
DOCK_IFP::B:MET531-
DOCK_IFP::B:PHE561-
DOCK_IFP::B:PHE911-
DOCK_IFP::B:PRO881-
DOCK_IFP::B:PRO931-
DOCK_IFP::B:TRP471-
DOCK_IFP::B:VAL1561-
DOCK_IFP::B:VAL311-
DOCK_IFP::B:VAL871-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.650590-
DOCK_MAX_CLASH_OVERLAP0.650637-
DOCK_MAX_CLASH_OVERLAP0.650763-
DOCK_MAX_CLASH_OVERLAP0.650589-
DOCK_MAX_CLASH_OVERLAP0.650560-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK3.334827-
DOCK_PRE_RANK2.022772-
DOCK_PRE_RANK1.854828-
DOCK_PRE_RANK4.009499-
DOCK_PRE_RANK5.160336-
DOCK_PRIMARY_POSE_ID8242-
DOCK_PRIMARY_POSE_ID183-
DOCK_PRIMARY_POSE_ID14351-
DOCK_PRIMARY_POSE_ID10297-
DOCK_PRIMARY_POSE_ID5559-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t09-
DOCK_REPORT_IDselection_import_t22-
DOCK_REPORT_IDselection_import_t13-
DOCK_REPORT_IDselection_import_t01-
DOCK_REPORT_IDselection_import_t16-
DOCK_RESIDUE_CONTACTSA:ALA111;A:ALA67;A:ALA90;A:ARG154;A:ARG277;A:ASN112;A:ASP332;A:CYS70;A:GLU274;A:GLY199;A:GLY235;A:GLY236;A:GLY237;A:GLY276;A:HIS197;A:LYS69;A:PHE170;A:PHE238;A:PRO113;A:PRO275;A:SER200;A:TYR389-
DOCK_RESIDUE_CONTACTSA:NDP301;B:ALA32;B:ARG97;B:ASP52;B:ILE45;B:LEU94;B:LYS57;B:LYS95;B:MET53;B:PHE56;B:PHE91;B:PRO88;B:PRO93;B:TRP47;B:VAL156;B:VAL31;B:VAL87-
DOCK_RESIDUE_CONTACTSA:ALA10;A:ARG29;A:ASP22;A:GLU31;A:GLY21;A:ILE61;A:ILE8;A:LEU23;A:LEU28;A:NAP201;A:PHE32;A:PHE35;A:PRO27;A:PRO62;A:SER60;A:THR137;A:THR57;A:TRP25;A:TYR122;A:VAL116;A:VAL9-
DOCK_RESIDUE_CONTACTSA:ALA158;A:ALA24;A:ALA40;A:ASN126;A:ASN41;A:ASP129;A:ASP68;A:GLN42;A:GLU73;A:GLY23;A:GLY25;A:GLY71;A:LEU130;A:LEU39;A:LYS127;A:LYS159;A:LYS26;A:PHE38;A:SER157;A:SER27;A:SER28;A:THR44;A:THR69-
DOCK_RESIDUE_CONTACTSA:ALA209;A:ALA90;A:GLY214;A:GLY215;A:LYS211;A:LYS89;A:MET70;A:PRO187;A:PRO212;A:PRO213;A:SER86;A:SER87;A:TYR210;A:VAL88-
DOCK_SCAFFOLDO=S(=O)(NC1CCC1)c1ccc(-c2cccc(C[NH2+]Cc3ccncc3)c2)s1-
DOCK_SCAFFOLDO=S(=O)(NC1CCC1)c1ccc(-c2cccc(C[NH2+]Cc3ccncc3)c2)s1-
DOCK_SCAFFOLDO=S(=O)(NC1CCC1)c1ccc(-c2cccc(C[NH2+]Cc3ccncc3)c2)s1-
DOCK_SCAFFOLDO=S(=O)(NC1CCC1)c1ccc(-c2cccc(C[NH2+]Cc3ccncc3)c2)s1-
DOCK_SCAFFOLDO=S(=O)(NC1CCC1)c1ccc(-c2cccc(C[NH2+]Cc3ccncc3)c2)s1-
DOCK_SCORE-24.365100-
DOCK_SCORE-26.546400-
DOCK_SCORE-26.159500-
DOCK_SCORE-24.035800-
DOCK_SCORE-21.486600-
DOCK_SCORE_INTER-28.444800-
DOCK_SCORE_INTER-26.192700-
DOCK_SCORE_INTER-27.025300-
DOCK_SCORE_INTER-32.214100-
DOCK_SCORE_INTER-23.231400-
DOCK_SCORE_INTER_KCAL-7.694209-
DOCK_SCORE_INTER_KCAL-6.256022-
DOCK_SCORE_INTER_KCAL-6.454885-
DOCK_SCORE_INTER_KCAL-5.548727-
DOCK_SCORE_INTER_KCAL-6.793927-
DOCK_SCORE_INTER_NORM-0.844926-
DOCK_SCORE_INTER_NORM-0.871784-
DOCK_SCORE_INTER_NORM-1.039160-
DOCK_SCORE_INTER_NORM-0.917573-
DOCK_SCORE_INTER_NORM-0.749402-
DOCK_SCORE_INTRA-0.804308-
DOCK_SCORE_INTRA5.538670-
DOCK_SCORE_INTRA0.033159-
DOCK_SCORE_INTRA5.667690-
DOCK_SCORE_INTRA4.079650-
DOCK_SCORE_INTRA_KCAL-0.192106-
DOCK_SCORE_INTRA_KCAL1.322889-
DOCK_SCORE_INTRA_KCAL1.353705-
DOCK_SCORE_INTRA_KCAL0.007920-
DOCK_SCORE_INTRA_KCAL0.974408-
DOCK_SCORE_INTRA_NORM0.001070-
DOCK_SCORE_INTRA_NORM0.182829-
DOCK_SCORE_INTRA_NORM0.178667-
DOCK_SCORE_INTRA_NORM-0.025945-
DOCK_SCORE_INTRA_NORM0.131602-
DOCK_SCORE_KCAL-5.740855-
DOCK_SCORE_KCAL-5.819507-
DOCK_SCORE_KCAL-6.248092-
DOCK_SCORE_KCAL-6.340501-
DOCK_SCORE_KCAL-5.131988-
DOCK_SCORE_NORM-0.843856-
DOCK_SCORE_NORM-0.856334-
DOCK_SCORE_NORM-0.693117-
DOCK_SCORE_NORM-0.775347-
DOCK_SCORE_NORM-0.785971-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SOURCE_FILET09_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET22_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET16_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET13_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET01_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC23H28N3O3S2+-
DOCK_SOURCE_FORMULAC23H28N3O3S2+-
DOCK_SOURCE_FORMULAC23H28N3O3S2+-
DOCK_SOURCE_FORMULAC23H28N3O3S2+-
DOCK_SOURCE_FORMULAC23H28N3O3S2+-
DOCK_SOURCE_HBA5.000000-
DOCK_SOURCE_HBA5.000000-
DOCK_SOURCE_HBA5.000000-
DOCK_SOURCE_HBA5.000000-
DOCK_SOURCE_HBA5.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HEAVY_ATOMS31.000000-
DOCK_SOURCE_HEAVY_ATOMS31.000000-
DOCK_SOURCE_HEAVY_ATOMS31.000000-
DOCK_SOURCE_HEAVY_ATOMS31.000000-
DOCK_SOURCE_HEAVY_ATOMS31.000000-
DOCK_SOURCE_LOGP2.864400-
DOCK_SOURCE_LOGP2.864400-
DOCK_SOURCE_LOGP2.864400-
DOCK_SOURCE_LOGP2.864400-
DOCK_SOURCE_LOGP2.864400-
DOCK_SOURCE_MW458.629000-
DOCK_SOURCE_MW458.629000-
DOCK_SOURCE_MW458.629000-
DOCK_SOURCE_MW458.629000-
DOCK_SOURCE_MW458.629000-
DOCK_SOURCE_NAMEKB_chagas_146-
DOCK_SOURCE_NAMEKB_chagas_146-
DOCK_SOURCE_NAMEKB_chagas_146-
DOCK_SOURCE_NAMEKB_chagas_146-
DOCK_SOURCE_NAMEKB_chagas_146-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA72.730000-
DOCK_SOURCE_TPSA72.730000-
DOCK_SOURCE_TPSA72.730000-
DOCK_SOURCE_TPSA72.730000-
DOCK_SOURCE_TPSA72.730000-
DOCK_STRAIN_DELTA30.627146-
DOCK_STRAIN_DELTA32.219404-
DOCK_STRAIN_DELTA35.264618-
DOCK_STRAIN_DELTA26.889291-
DOCK_STRAIN_DELTA31.376794-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT16-
DOCK_TARGETT22-
DOCK_TARGETT09-
DOCK_TARGETT01-
DOCK_TARGETT13-
EXACT_MASS458.15666017609Da
FORMULAC23H28N3O3S2+-
HBA5-
HBD2-
LOGP2.8644000000000007-
MOL_WEIGHT458.6290000000002g/mol
QED_SCORE0.517259791348676-
ROTATABLE_BONDS9-
TPSA72.73A^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
TargetExperimentReportPosesBest rankBest scoreNative overlapNative recallRMSD
T01 T01 selection_import_t01 1
native pose available
 1.8967482424734206 -21.4866 17 0.81 - Best pose
T09 T09 selection_import_t09 1
native pose available
 2.066095302338495 -26.1595 14 0.67 - Best pose
T16 T16 selection_import_t16 1
native pose available
 3.370144819325612 -24.0358 8 0.67 - Best pose
T22 T22 selection_import_t22 1
native pose available
 4.060504241383809 -26.5464 19 0.90 - Best pose
T13 T13 selection_import_t13 1
native pose available
 5.20526856742621 -24.3651 16 0.84 - Best pose
T01 — T01 1 poses · report selection_import_t01
Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
183 1.8967482424734206 -0.871784 -21.4866 2 21 17 0.81 0.00 0.00 0.00 - no geometry warning; 6 clashes; 1 protein clash; 1 cofactor-context clash; high strain Δ 30.6 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
141 2.066095302338495 -0.844926 -26.1595 4 17 14 0.67 0.29 0.17 0.17 - no geometry warning; 8 clashes; 1 protein clash; high strain Δ 31.4 Open pose
T16 — T16 1 poses · report selection_import_t16
Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
132 3.370144819325612 -0.749402 -24.0358 5 14 8 0.67 - - - - no geometry warning; 8 clashes; 2 protein clashes; moderate strain Δ 26.9 Open pose
T22 — T22 1 poses · report selection_import_t22
Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
113 4.060504241383809 -1.03916 -26.5464 10 23 19 0.90 0.53 0.55 0.55 - no geometry warning; 7 clashes; 3 protein clashes; high strain Δ 35.3 Open pose
T13 — T13 1 poses · report selection_import_t13
Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
112 5.20526856742621 -0.917573 -24.3651 9 22 16 0.84 0.44 0.57 0.57 - no geometry warning; 10 clashes; 3 protein clashes; high strain Δ 32.2 Open pose
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Drug Similarity

Shared structural fragments with approved drugs — based on faircheckmol profile fingerprint.
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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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