FAIRMol

OHD_Leishmania_477

ID 3747

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

SMILES: COc1cc([C@@H]2CC(c3cccc(NC(=O)Nc4ccc(Cl)cc4)c3)=NN2C(=O)c2cccnc2)ccc1O

Formula: C29H24ClN5O4 | MW: 541.9950000000002

LogP: 6.084700000000005 | TPSA: 116.15

HBA/HBD: 6/3 | RotB: 6

InChIKey: CWOIDDQYPOMTMD-VWLOTQADSA-N

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern H-bond acceptor O Clear highlight

Bio motif

Catechol Hinge binder (C=O-NH) ×2 Hinge binder (NH-C=O) ×2 N-Methyl amide H-bond acceptor N ×3 H-bond acceptor O ×3 H-bond donor ×3 Gatekeeper aromatic ×3 Metal chelator ×3

Functional group

Carbonyl ×2 Amide ×3 Secondary amine ×2 Phenol Lactam Chlorine Urea Aryl ether Imine Ether

Ring system

Benzene ×3 Pyridine

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.663814-
DOCK_BASE_INTER_RANK-0.712507-
DOCK_BASE_INTER_RANK-0.605523-
DOCK_BASE_INTER_RANK-0.622988-
DOCK_BASE_INTER_RANK-0.633908-
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_COUNT18.000000-
DOCK_CLASH_COUNT18.000000-
DOCK_CLASH_COUNT18.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CONTACT_COUNT17.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT14.000000-
DOCK_CONTACT_COUNT18.000000-
DOCK_EXPERIMENTT11-
DOCK_EXPERIMENTT15-
DOCK_EXPERIMENTT17-
DOCK_EXPERIMENTT20-
DOCK_EXPERIMENTT21-
DOCK_EXPERIMENT_ID11-
DOCK_EXPERIMENT_ID15-
DOCK_EXPERIMENT_ID17-
DOCK_EXPERIMENT_ID20-
DOCK_EXPERIMENT_ID21-
DOCK_FINAL_RANK2.920101-
DOCK_FINAL_RANK2.439587-
DOCK_FINAL_RANK3.249970-
DOCK_FINAL_RANK2.941099-
DOCK_FINAL_RANK3.056103-
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:ALA2841-
DOCK_IFP::A:ALA3651-
DOCK_IFP::A:ARG1371-
DOCK_IFP::A:ARG1401-
DOCK_IFP::A:ARG1411-
DOCK_IFP::A:ARG2871-
DOCK_IFP::A:ARG3311-
DOCK_IFP::A:ARG4721-
DOCK_IFP::A:ASN1031-
DOCK_IFP::A:ASN1931-
DOCK_IFP::A:ASN4021-
DOCK_IFP::A:ASP3301-
DOCK_IFP::A:GLU1351-
DOCK_IFP::A:GLU1361-
DOCK_IFP::A:GLU1921-
DOCK_IFP::A:GLU4671-
DOCK_IFP::A:GLY1911-
DOCK_IFP::A:GLY1971-
DOCK_IFP::A:GLY2291-
DOCK_IFP::A:GLY2861-
DOCK_IFP::A:GLY3761-
DOCK_IFP::A:HIS1021-
DOCK_IFP::A:HIS1441-
DOCK_IFP::A:HIS2221-
DOCK_IFP::A:HIS4281-
DOCK_IFP::A:ILE1261-
DOCK_IFP::A:ILE1991-
DOCK_IFP::A:ILE3781-
DOCK_IFP::A:LEU1941-
DOCK_IFP::A:LEU3321-
DOCK_IFP::A:LEU3341-
DOCK_IFP::A:LEU3771-
DOCK_IFP::A:LEU3991-
DOCK_IFP::A:MET3331-
DOCK_IFP::A:MET4001-
DOCK_IFP::A:MET4711-
DOCK_IFP::A:PHE1891-
DOCK_IFP::A:PHE1901-
DOCK_IFP::A:PHE1981-
DOCK_IFP::A:PHE2301-
DOCK_IFP::A:PHE3961-
DOCK_IFP::A:PHE511-
DOCK_IFP::A:PHE741-
DOCK_IFP::A:PRO2231-
DOCK_IFP::A:PRO3981-
DOCK_IFP::A:SER3641-
DOCK_IFP::A:SER3941-
DOCK_IFP::A:SER3951-
DOCK_IFP::A:SER4641-
DOCK_IFP::A:SER4701-
DOCK_IFP::A:SER751-
DOCK_IFP::A:THR3741-
DOCK_IFP::A:THR4631-
DOCK_IFP::A:THR4731-
DOCK_IFP::A:THR771-
DOCK_IFP::A:VAL1871-
DOCK_IFP::A:VAL1881-
DOCK_IFP::A:VAL2211-
DOCK_IFP::A:VAL3661-
DOCK_IFP::A:VAL3811-
DOCK_IFP::B:ALA2091-
DOCK_IFP::B:ALA2441-
DOCK_IFP::B:ALA901-
DOCK_IFP::B:ARG741-
DOCK_IFP::B:ASN2451-
DOCK_IFP::B:ASP101-
DOCK_IFP::B:CYS691-
DOCK_IFP::B:GLY701-
DOCK_IFP::B:GLY721-
DOCK_IFP::B:GLY741-
DOCK_IFP::B:HIS111-
DOCK_IFP::B:ILE731-
DOCK_IFP::B:LEU731-
DOCK_IFP::B:LYS2111-
DOCK_IFP::B:LYS891-
DOCK_IFP::B:MET701-
DOCK_IFP::B:PRO121-
DOCK_IFP::B:PRO1871-
DOCK_IFP::B:PRO2121-
DOCK_IFP::B:PRO2131-
DOCK_IFP::B:SER431-
DOCK_IFP::B:SER711-
DOCK_IFP::B:TYR2101-
DOCK_IFP::B:TYR4081-
DOCK_IFP::B:TYR461-
DOCK_IFP::B:VAL881-
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_OVERLAP0.653240-
DOCK_MAX_CLASH_OVERLAP0.653200-
DOCK_MAX_CLASH_OVERLAP0.653204-
DOCK_MAX_CLASH_OVERLAP0.653224-
DOCK_MAX_CLASH_OVERLAP0.658974-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.842053-
DOCK_PRE_RANK2.359032-
DOCK_PRE_RANK3.216581-
DOCK_PRE_RANK2.865342-
DOCK_PRE_RANK2.984706-
DOCK_PRIMARY_POSE_ID6807-
DOCK_PRIMARY_POSE_ID9501-
DOCK_PRIMARY_POSE_ID10870-
DOCK_PRIMARY_POSE_ID12912-
DOCK_PRIMARY_POSE_ID13579-
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_t11-
DOCK_REPORT_IDselection_import_t15-
DOCK_REPORT_IDselection_import_t17-
DOCK_REPORT_IDselection_import_t20-
DOCK_REPORT_IDselection_import_t21-
DOCK_RESIDUE_CONTACTSA:ASN193;A:GLU192;A:GLY191;A:HIS144;A:HIS222;A:ILE126;A:LEU194;A:PHE189;A:PHE190;A:PHE51;A:PHE74;A:PRO223;A:SER75;A:THR77;A:VAL187;A:VAL188;A:VAL221-
DOCK_RESIDUE_CONTACTSB:ALA209;B:ALA244;B:ALA90;B:ARG74;B:ASN245;B:LEU73;B:LYS211;B:LYS89;B:MET70;B:PRO187;B:PRO212;B:PRO213;B:TYR210;B:TYR408;B:VAL88-
DOCK_RESIDUE_CONTACTSA:ALA284;A:ALA365;A:ARG287;A:ARG331;A:ASP330;A:GLY197;A:GLY229;A:GLY286;A:GLY376;A:HIS428;A:ILE199;A:ILE378;A:LEU332;A:LEU334;A:LEU377;A:MET333;A:PHE198;A:PHE230;A:SER364;A:THR374;A:VAL366;A:VAL381-
DOCK_RESIDUE_CONTACTSA:ARG472;A:ASN402;A:GLU467;A:LEU399;A:MET400;A:MET471;A:PHE396;A:PRO398;A:SER394;A:SER395;A:SER464;A:SER470;A:THR463;A:THR473-
DOCK_RESIDUE_CONTACTSA:ARG137;A:ARG140;A:ARG141;A:ASN103;A:GLU135;A:GLU136;A:HIS102;B:ASP10;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER43;B:SER71;B:TYR46-
DOCK_SCAFFOLDO=C(Nc1ccccc1)Nc1cccc(C2=NN(C(=O)c3cccnc3)C(c3ccccc3)C2)c1-
DOCK_SCAFFOLDO=C(Nc1ccccc1)Nc1cccc(C2=NN(C(=O)c3cccnc3)C(c3ccccc3)C2)c1-
DOCK_SCAFFOLDO=C(Nc1ccccc1)Nc1cccc(C2=NN(C(=O)c3cccnc3)C(c3ccccc3)C2)c1-
DOCK_SCAFFOLDO=C(Nc1ccccc1)Nc1cccc(C2=NN(C(=O)c3cccnc3)C(c3ccccc3)C2)c1-
DOCK_SCAFFOLDO=C(Nc1ccccc1)Nc1cccc(C2=NN(C(=O)c3cccnc3)C(c3ccccc3)C2)c1-
DOCK_SCORE-16.135000-
DOCK_SCORE-20.192300-
DOCK_SCORE-19.296500-
DOCK_SCORE-17.206200-
DOCK_SCORE-14.100400-
DOCK_SCORE_INTER-25.888700-
DOCK_SCORE_INTER-27.787800-
DOCK_SCORE_INTER-23.615400-
DOCK_SCORE_INTER-24.296500-
DOCK_SCORE_INTER-24.722400-
DOCK_SCORE_INTER_KCAL-6.183412-
DOCK_SCORE_INTER_KCAL-6.637005-
DOCK_SCORE_INTER_KCAL-5.640444-
DOCK_SCORE_INTER_KCAL-5.803122-
DOCK_SCORE_INTER_KCAL-5.904846-
DOCK_SCORE_INTER_NORM-0.663814-
DOCK_SCORE_INTER_NORM-0.712507-
DOCK_SCORE_INTER_NORM-0.605523-
DOCK_SCORE_INTER_NORM-0.622988-
DOCK_SCORE_INTER_NORM-0.633908-
DOCK_SCORE_INTRA9.753780-
DOCK_SCORE_INTRA7.365430-
DOCK_SCORE_INTRA4.318860-
DOCK_SCORE_INTRA6.939570-
DOCK_SCORE_INTRA10.123400-
DOCK_SCORE_INTRA_KCAL2.329651-
DOCK_SCORE_INTRA_KCAL1.759203-
DOCK_SCORE_INTRA_KCAL1.031542-
DOCK_SCORE_INTRA_KCAL1.657489-
DOCK_SCORE_INTRA_KCAL2.417934-
DOCK_SCORE_INTRA_NORM0.250097-
DOCK_SCORE_INTRA_NORM0.188857-
DOCK_SCORE_INTRA_NORM0.110740-
DOCK_SCORE_INTRA_NORM0.177938-
DOCK_SCORE_INTRA_NORM0.259576-
DOCK_SCORE_KCAL-3.853780-
DOCK_SCORE_KCAL-4.822850-
DOCK_SCORE_KCAL-4.608892-
DOCK_SCORE_KCAL-4.109632-
DOCK_SCORE_KCAL-3.367824-
DOCK_SCORE_NORM-0.413717-
DOCK_SCORE_NORM-0.517751-
DOCK_SCORE_NORM-0.494783-
DOCK_SCORE_NORM-0.441186-
DOCK_SCORE_NORM-0.361549-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.230051-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.150701-
DOCK_SCORE_RESTR0.498566-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.005899-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.003864-
DOCK_SCORE_RESTR_NORM0.012784-
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_FILET11_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET15_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET17_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET20_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET21_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC29H24ClN5O4-
DOCK_SOURCE_FORMULAC29H24ClN5O4-
DOCK_SOURCE_FORMULAC29H24ClN5O4-
DOCK_SOURCE_FORMULAC29H24ClN5O4-
DOCK_SOURCE_FORMULAC29H24ClN5O4-
DOCK_SOURCE_HBA6.000000-
DOCK_SOURCE_HBA6.000000-
DOCK_SOURCE_HBA6.000000-
DOCK_SOURCE_HBA6.000000-
DOCK_SOURCE_HBA6.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HEAVY_ATOMS39.000000-
DOCK_SOURCE_HEAVY_ATOMS39.000000-
DOCK_SOURCE_HEAVY_ATOMS39.000000-
DOCK_SOURCE_HEAVY_ATOMS39.000000-
DOCK_SOURCE_HEAVY_ATOMS39.000000-
DOCK_SOURCE_LOGP6.084700-
DOCK_SOURCE_LOGP6.084700-
DOCK_SOURCE_LOGP6.084700-
DOCK_SOURCE_LOGP6.084700-
DOCK_SOURCE_LOGP6.084700-
DOCK_SOURCE_MW541.995000-
DOCK_SOURCE_MW541.995000-
DOCK_SOURCE_MW541.995000-
DOCK_SOURCE_MW541.995000-
DOCK_SOURCE_MW541.995000-
DOCK_SOURCE_NAMEOHD_Leishmania_477-
DOCK_SOURCE_NAMEOHD_Leishmania_477-
DOCK_SOURCE_NAMEOHD_Leishmania_477-
DOCK_SOURCE_NAMEOHD_Leishmania_477-
DOCK_SOURCE_NAMEOHD_Leishmania_477-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_TPSA116.150000-
DOCK_SOURCE_TPSA116.150000-
DOCK_SOURCE_TPSA116.150000-
DOCK_SOURCE_TPSA116.150000-
DOCK_SOURCE_TPSA116.150000-
DOCK_STRAIN_DELTA47.170748-
DOCK_STRAIN_DELTA48.188705-
DOCK_STRAIN_DELTA25.718114-
DOCK_STRAIN_DELTA46.231797-
DOCK_STRAIN_DELTA44.417256-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT11-
DOCK_TARGETT15-
DOCK_TARGETT17-
DOCK_TARGETT20-
DOCK_TARGETT21-
EXACT_MASS541.151681928Da
FORMULAC29H24ClN5O4-
HBA6-
HBD3-
LOGP6.084700000000005-
MOL_WEIGHT541.9950000000002g/mol
QED_SCORE0.2732086841036333-
ROTATABLE_BONDS6-
TPSA116.15A^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
T15 T15 selection_import_t15 1
native pose available
 2.4395873276642837 -20.1923 8 0.62 - Best pose
T11 T11 selection_import_t11 1
native pose available
 2.9201007805750137 -16.135 14 0.78 - Best pose
T20 T20 selection_import_t20 1
native pose available
 2.94109877306006 -17.2062 7 0.88 - Best pose
T21 T21 selection_import_t21 1
native pose available
 3.0561031500942453 -14.1004 13 0.93 - Best pose
T17 T17 selection_import_t17 1
native pose available
 3.2499699785463396 -19.2965 11 0.92 - Best pose
T15 — T15 1 poses · report selection_import_t15
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
15 2.4395873276642837 -0.712507 -20.1923 6 15 8 0.62 - - - - no geometry warning; 18 clashes; 7 protein contact clashes; high strain Δ 48.2 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
33 2.9201007805750137 -0.663814 -16.135 5 17 14 0.78 0.40 0.40 0.50 - no geometry warning; 18 clashes; 1 protein clash; high strain Δ 47.2 Open 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
33 2.94109877306006 -0.622988 -17.2062 5 14 7 0.88 0.00 0.00 0.00 - no geometry warning; 16 clashes; 1 protein clash; high strain Δ 46.2 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
21 3.0561031500942453 -0.633908 -14.1004 6 18 13 0.93 0.17 0.11 0.12 - no geometry warning; 16 clashes; 1 protein clash; high strain Δ 44.4 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
27 3.2499699785463396 -0.605523 -19.2965 3 22 11 0.92 0.00 0.00 0.00 - no geometry warning; 18 clashes; 1 protein clash; moderate strain Δ 25.7 Open pose
Loading PharmaFP-250 analysis…

Drug Similarity

Shared structural fragments with approved drugs — based on faircheckmol profile fingerprint.
Loading drug matches…

Structural Profile Fingerprint

Named-bit fingerprint from curated SMARTS patterns. Each bit = one chemical pattern.

Loading…

ADMET Profile

Computed from structure using RDKit. Indicative only — not a substitute for experimental data.

Loading…

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.
Loading…