FAIRMol

KB_Leish_31

ID 1008

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

SMILES: N#Cc1ccccc1S(=O)(=O)N1CCN(C(=O)CNC(=O)c2ccc3c(c2)OCO3)CC1

Formula: C21H20N4O6S | MW: 456.48000000000036

LogP: 0.5498800000000001 | TPSA: 129.04

HBA/HBD: 7/1 | RotB: 5

InChIKey: GWEZMXDRLZJLML-UHFFFAOYSA-N

Recognized patterns

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

Bio motif

Catechol Peptide backbone Hinge binder (C=O-NH) Hinge binder (NH-C=O) Sulfonamide bioisostere N-Methyl amide ×2 H-bond acceptor N ×3 H-bond acceptor O ×6 H-bond donor Gatekeeper aromatic ×2 β-Turn mimetic ×2 Metal chelator ×2 Retro-amide PAINS — catechol P-gp efflux flag

Functional group

Carbonyl ×2 Amide ×2 Secondary amine Nitrile Tertiary amine Lactam Sulfonamide Aryl ether ×2 Ether ×2 Acetal

Ring system

Benzene ×2 Benzodioxole

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.755698-
DOCK_BASE_INTER_RANK-0.882408-
DOCK_BASE_INTER_RANK-0.794759-
DOCK_BASE_INTER_RANK-0.763793-
DOCK_BASE_INTER_RANK-0.809113-
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_COUNT11.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CLASH_COUNT14.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT19.000000-
DOCK_CONTACT_COUNT17.000000-
DOCK_CONTACT_COUNT12.000000-
DOCK_CONTACT_COUNT13.000000-
DOCK_EXPERIMENTT02-
DOCK_EXPERIMENTT15-
DOCK_EXPERIMENTT13-
DOCK_EXPERIMENTT04-
DOCK_EXPERIMENTT09-
DOCK_EXPERIMENT_ID13-
DOCK_EXPERIMENT_ID2-
DOCK_EXPERIMENT_ID4-
DOCK_EXPERIMENT_ID15-
DOCK_EXPERIMENT_ID9-
DOCK_FINAL_RANK1.677935-
DOCK_FINAL_RANK5.420151-
DOCK_FINAL_RANK3.391565-
DOCK_FINAL_RANK1.350598-
DOCK_FINAL_RANK2.065796-
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:ALA671-
DOCK_IFP::A:ARG2771-
DOCK_IFP::A:ASN3271-
DOCK_IFP::A:ASN651-
DOCK_IFP::A:ASP221-
DOCK_IFP::A:ASP2321-
DOCK_IFP::A:ASP3321-
DOCK_IFP::A:CYS3281-
DOCK_IFP::A:GLN361-
DOCK_IFP::A:GLY1991-
DOCK_IFP::A:GLY2361-
DOCK_IFP::A:GLY2371-
DOCK_IFP::A:GLY2761-
DOCK_IFP::A:GLY3931-
DOCK_IFP::A:HIS1971-
DOCK_IFP::A:HIS2411-
DOCK_IFP::A:HIS3331-
DOCK_IFP::A:ILE611-
DOCK_IFP::A:ILE81-
DOCK_IFP::A:LEU1881-
DOCK_IFP::A:LEU2261-
DOCK_IFP::A:LEU2291-
DOCK_IFP::A:LEU231-
DOCK_IFP::A:LEU681-
DOCK_IFP::A:LYS691-
DOCK_IFP::A:MET2331-
DOCK_IFP::A:NAP2011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:NDP3021-
DOCK_IFP::A:PHE1131-
DOCK_IFP::A:PHE321-
DOCK_IFP::A:PHE351-
DOCK_IFP::A:PRO271-
DOCK_IFP::A:PRO2751-
DOCK_IFP::A:PRO621-
DOCK_IFP::A:SER2001-
DOCK_IFP::A:SER601-
DOCK_IFP::A:TYR1221-
DOCK_IFP::A:TYR1911-
DOCK_IFP::A:TYR1941-
DOCK_IFP::A:TYR2781-
DOCK_IFP::A:TYR3311-
DOCK_IFP::A:TYR3891-
DOCK_IFP::A:VAL1161-
DOCK_IFP::A:VAL2301-
DOCK_IFP::A:VAL3921-
DOCK_IFP::A:VAL91-
DOCK_IFP::B:ALA2091-
DOCK_IFP::B:ALA321-
DOCK_IFP::B:ALA901-
DOCK_IFP::B:ARG481-
DOCK_IFP::B:ASN2081-
DOCK_IFP::B:ASP521-
DOCK_IFP::B:GLY2141-
DOCK_IFP::B:GLY2151-
DOCK_IFP::B:ILE451-
DOCK_IFP::B:LYS2111-
DOCK_IFP::B:LYS891-
DOCK_IFP::B:MET531-
DOCK_IFP::B:MET701-
DOCK_IFP::B:PHE561-
DOCK_IFP::B:PRO1871-
DOCK_IFP::B:PRO2121-
DOCK_IFP::B:PRO2131-
DOCK_IFP::B:PRO881-
DOCK_IFP::B:SER441-
DOCK_IFP::B:SER861-
DOCK_IFP::B:TRP471-
DOCK_IFP::B:TYR2101-
DOCK_IFP::B:VAL301-
DOCK_IFP::B:VAL311-
DOCK_IFP::B:VAL491-
DOCK_IFP::B:VAL871-
DOCK_IFP::B:VAL881-
DOCK_IFP::D:ARG2871-
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_OVERLAP0.699624-
DOCK_MAX_CLASH_OVERLAP0.643304-
DOCK_MAX_CLASH_OVERLAP0.643284-
DOCK_MAX_CLASH_OVERLAP0.642681-
DOCK_MAX_CLASH_OVERLAP0.682301-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.035708-
DOCK_PRE_RANK1.311885-
DOCK_PRE_RANK5.333076-
DOCK_PRE_RANK1.641976-
DOCK_PRE_RANK3.346865-
DOCK_PRIMARY_POSE_ID2099-
DOCK_PRIMARY_POSE_ID8213-
DOCK_PRIMARY_POSE_ID6052-
DOCK_PRIMARY_POSE_ID819-
DOCK_PRIMARY_POSE_ID10136-
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_t04-
DOCK_REPORT_IDselection_import_t09-
DOCK_REPORT_IDselection_import_t02-
DOCK_REPORT_IDselection_import_t15-
DOCK_REPORT_IDselection_import_t13-
DOCK_RESIDUE_CONTACTSA:ALA67;A:ARG277;A:ASN327;A:ASP332;A:CYS328;A:GLY199;A:GLY236;A:GLY237;A:GLY276;A:GLY393;A:HIS197;A:HIS333;A:LYS69;A:PRO275;A:SER200;A:TYR278;A:TYR331;A:TYR389;A:VAL392-
DOCK_RESIDUE_CONTACTSB:ALA209;B:ALA90;B:ASN208;B:GLY214;B:GLY215;B:LYS211;B:LYS89;B:MET70;B:PRO187;B:PRO212;B:PRO213;B:TYR210;B:VAL88-
DOCK_RESIDUE_CONTACTSA:NDP301;B:ALA32;B:ARG48;B:ASP52;B:ILE45;B:MET53;B:PHE56;B:PRO88;B:SER44;B:SER86;B:TRP47;B:VAL30;B:VAL31;B:VAL49;B:VAL87-
DOCK_RESIDUE_CONTACTSA:ALA10;A:ASN65;A:ASP22;A:GLN36;A:ILE61;A:ILE8;A:LEU23;A:LEU68;A:NAP201;A:PHE32;A:PHE35;A:PRO27;A:PRO62;A:SER60;A:TYR122;A:VAL116;A:VAL9-
DOCK_RESIDUE_CONTACTSA:ASP232;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:MET233;A:NDP302;A:PHE113;A:TYR191;A:TYR194;A:VAL230;D:ARG287-
DOCK_SCAFFOLDO=C(NCC(=O)N1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccc2c(c1)OCO2-
DOCK_SCAFFOLDO=C(NCC(=O)N1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccc2c(c1)OCO2-
DOCK_SCAFFOLDO=C(NCC(=O)N1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccc2c(c1)OCO2-
DOCK_SCAFFOLDO=C(NCC(=O)N1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccc2c(c1)OCO2-
DOCK_SCAFFOLDO=C(NCC(=O)N1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccc2c(c1)OCO2-
DOCK_SCORE-17.641000-
DOCK_SCORE-23.115200-
DOCK_SCORE-23.529100-
DOCK_SCORE-24.532100-
DOCK_SCORE-24.730100-
DOCK_SCORE_INTER-28.237100-
DOCK_SCORE_INTER-24.441400-
DOCK_SCORE_INTER-24.182300-
DOCK_SCORE_INTER-25.891600-
DOCK_SCORE_INTER-25.432300-
DOCK_SCORE_INTER_KCAL-6.074403-
DOCK_SCORE_INTER_KCAL-5.775846-
DOCK_SCORE_INTER_KCAL-6.184105-
DOCK_SCORE_INTER_KCAL-6.744318-
DOCK_SCORE_INTER_KCAL-5.837731-
DOCK_SCORE_INTER_NORM-0.763793-
DOCK_SCORE_INTER_NORM-0.809113-
DOCK_SCORE_INTER_NORM-0.794759-
DOCK_SCORE_INTER_NORM-0.882408-
DOCK_SCORE_INTER_NORM-0.755698-
DOCK_SCORE_INTRA2.362490-
DOCK_SCORE_INTRA2.317120-
DOCK_SCORE_INTRA6.541360-
DOCK_SCORE_INTRA-0.288742-
DOCK_SCORE_INTRA3.704970-
DOCK_SCORE_INTRA_KCAL0.884917-
DOCK_SCORE_INTRA_KCAL1.562378-
DOCK_SCORE_INTRA_KCAL0.553435-
DOCK_SCORE_INTRA_KCAL-0.068965-
DOCK_SCORE_INTRA_KCAL0.564271-
DOCK_SCORE_INTRA_NORM-0.009023-
DOCK_SCORE_INTRA_NORM0.073828-
DOCK_SCORE_INTRA_NORM0.204418-
DOCK_SCORE_INTRA_NORM0.115780-
DOCK_SCORE_INTRA_NORM0.072410-
DOCK_SCORE_KCAL-5.906685-
DOCK_SCORE_KCAL-5.520973-
DOCK_SCORE_KCAL-5.859394-
DOCK_SCORE_KCAL-4.213482-
DOCK_SCORE_KCAL-5.619831-
DOCK_SCORE_NORM-0.551281-
DOCK_SCORE_NORM-0.766628-
DOCK_SCORE_NORM-0.722349-
DOCK_SCORE_NORM-0.772816-
DOCK_SCORE_NORM-0.735285-
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_FILET15_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET09_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET13_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET02_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET04_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC21H20N4O6S-
DOCK_SOURCE_FORMULAC21H20N4O6S-
DOCK_SOURCE_FORMULAC21H20N4O6S-
DOCK_SOURCE_FORMULAC21H20N4O6S-
DOCK_SOURCE_FORMULAC21H20N4O6S-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HEAVY_ATOMS32.000000-
DOCK_SOURCE_HEAVY_ATOMS32.000000-
DOCK_SOURCE_HEAVY_ATOMS32.000000-
DOCK_SOURCE_HEAVY_ATOMS32.000000-
DOCK_SOURCE_HEAVY_ATOMS32.000000-
DOCK_SOURCE_LOGP0.549880-
DOCK_SOURCE_LOGP0.549880-
DOCK_SOURCE_LOGP0.549880-
DOCK_SOURCE_LOGP0.549880-
DOCK_SOURCE_LOGP0.549880-
DOCK_SOURCE_MW456.480000-
DOCK_SOURCE_MW456.480000-
DOCK_SOURCE_MW456.480000-
DOCK_SOURCE_MW456.480000-
DOCK_SOURCE_MW456.480000-
DOCK_SOURCE_NAMEKB_Leish_31-
DOCK_SOURCE_NAMEZ32154728-
DOCK_SOURCE_NAMEZ32154728-
DOCK_SOURCE_NAMEKB_Leish_31-
DOCK_SOURCE_NAMEKB_Leish_31-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA129.040000-
DOCK_SOURCE_TPSA129.040000-
DOCK_SOURCE_TPSA129.040000-
DOCK_SOURCE_TPSA129.040000-
DOCK_SOURCE_TPSA129.040000-
DOCK_STRAIN_DELTA50.791137-
DOCK_STRAIN_DELTA32.098845-
DOCK_STRAIN_DELTA27.269972-
DOCK_STRAIN_DELTA28.859249-
DOCK_STRAIN_DELTA23.607262-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT02-
DOCK_TARGETT09-
DOCK_TARGETT13-
DOCK_TARGETT04-
DOCK_TARGETT15-
EXACT_MASS456.1103553599999Da
FORMULAC21H20N4O6S-
HBA7-
HBD1-
LOGP0.5498800000000001-
MOL_WEIGHT456.48000000000036g/mol
QED_SCORE0.6955604732172063-
ROTATABLE_BONDS5-
TPSA129.04A^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
T04 T04 selection_import_t04 1
native pose available
 1.3505982434811619 -17.641 11 0.58 - Best pose
T15 T15 selection_import_t15 1
native pose available
 1.6779348296445458 -24.7301 9 0.69 - Best pose
T09 T09 selection_import_t09 1
native pose available
 2.0657957641371216 -23.5291 11 0.52 - Best pose
T02 T02 selection_import_t02 1
native pose available
 3.3915646375584045 -23.1152 16 0.76 - Best pose
T13 T13 selection_import_t13 1
native pose available
 5.420150559491577 -24.5321 13 0.68 - Best pose
T04 — T04 1 poses · report selection_import_t04
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
66 1.3505982434811619 -0.755698 -17.641 1 12 11 0.58 0.17 0.20 0.20 - no geometry warning; 12 clashes; 4 protein contact clashes; 1 cofactor-context clash; moderate strain Δ 28.9 Open 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
650 1.6779348296445458 -0.763793 -24.7301 4 13 9 0.69 - - - - no geometry warning; 13 clashes; 6 protein contact clashes; moderate strain Δ 27.3 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
634 2.0657957641371216 -0.809113 -23.5291 3 15 11 0.52 0.00 0.00 0.00 - no geometry warning; 11 clashes; 1 protein clash; 1 cofactor-context clash; moderate strain Δ 23.6 Open pose
T02 — T02 1 poses · report selection_import_t02
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 3.3915646375584045 -0.794759 -23.1152 3 17 16 0.76 0.20 0.20 0.20 - no geometry warning; 14 clashes; 2 protein clashes; high strain Δ 32.1 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
83 5.420150559491577 -0.882408 -24.5321 11 19 13 0.68 0.56 0.43 0.57 - no geometry warning; 16 clashes; 3 protein clashes; high strain Δ 50.8 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…