FAIRMol

Z15821830

ID 2629

DB fairmolThis detail page is pinned to the current database context.
Back to results Open docking pose (3)
2D structure

SMILES: Cc1ccc(NC(=O)COC(=O)[C@H](NS(=O)(=O)c2ccc(Cl)cc2)[C@@H](C)O)cc1C

Formula: C20H23ClN2O6S | MW: 454.9320000000003

LogP: 2.1664399999999997 | TPSA: 121.80000000000001

HBA/HBD: 6/3 | RotB: 8

InChIKey: LBJWZYUUHUKGJB-AUUYWEPGSA-N

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

Hinge binder (C=O-NH) Hinge binder (NH-C=O) Sulfonamide bioisostere H-bond acceptor O ×5 H-bond donor ×3 Gatekeeper aromatic ×2 Metal chelator ×2 Retro-amide

Functional group

Carbonyl ×2 Amide Ester Secondary amine Alcohol Sulfonamide Chlorine Ether

Ring system

Benzene ×2

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.811856-
DOCK_BASE_INTER_RANK-0.857518-
DOCK_BASE_INTER_RANK-0.875317-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CLASH_COUNT11.000000-
DOCK_CLASH_COUNT14.000000-
DOCK_CONTACT_COUNT13.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT21.000000-
DOCK_EXPERIMENTT10-
DOCK_EXPERIMENTT21-
DOCK_EXPERIMENTT06-
DOCK_EXPERIMENT_ID6-
DOCK_EXPERIMENT_ID10-
DOCK_EXPERIMENT_ID21-
DOCK_FINAL_RANK2.716969-
DOCK_FINAL_RANK4.149014-
DOCK_FINAL_RANK3.337239-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_IFP::A:ALA151-
DOCK_IFP::A:ALA341-
DOCK_IFP::A:ARG1001-
DOCK_IFP::A:ARG1161-
DOCK_IFP::A:ARG1371-
DOCK_IFP::A:ARG1401-
DOCK_IFP::A:ARG1411-
DOCK_IFP::A:ARG1441-
DOCK_IFP::A:ARG591-
DOCK_IFP::A:ASN1061-
DOCK_IFP::A:ASP541-
DOCK_IFP::A:CYS721-
DOCK_IFP::A:GLY1611-
DOCK_IFP::A:GLY731-
DOCK_IFP::A:GLY771-
DOCK_IFP::A:HIS1021-
DOCK_IFP::A:HIS1051-
DOCK_IFP::A:HIS1381-
DOCK_IFP::A:HIS141-
DOCK_IFP::A:HIS1411-
DOCK_IFP::A:HIS1821-
DOCK_IFP::A:ILE1601-
DOCK_IFP::A:ILE471-
DOCK_IFP::A:LEU1361-
DOCK_IFP::A:LEU901-
DOCK_IFP::A:LEU971-
DOCK_IFP::A:MET551-
DOCK_IFP::A:MET981-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:PHE581-
DOCK_IFP::A:PHE941-
DOCK_IFP::A:PRO911-
DOCK_IFP::A:SER461-
DOCK_IFP::A:THR1841-
DOCK_IFP::A:THR741-
DOCK_IFP::A:THR861-
DOCK_IFP::A:TYR1661-
DOCK_IFP::A:TYR491-
DOCK_IFP::A:TYR571-
DOCK_IFP::A:TYR941-
DOCK_IFP::A:VAL321-
DOCK_IFP::A:VAL331-
DOCK_IFP::B:ASP101-
DOCK_IFP::B:CYS691-
DOCK_IFP::B:GLY701-
DOCK_IFP::B:HIS111-
DOCK_IFP::B:PRO121-
DOCK_IFP::B:SER711-
DOCK_IFP::B:TYR461-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.617751-
DOCK_MAX_CLASH_OVERLAP0.617710-
DOCK_MAX_CLASH_OVERLAP0.617778-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK3.292192-
DOCK_PRE_RANK4.093908-
DOCK_PRE_RANK2.670055-
DOCK_PRIMARY_POSE_ID3879-
DOCK_PRIMARY_POSE_ID6598-
DOCK_PRIMARY_POSE_ID14080-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t06-
DOCK_REPORT_IDselection_import_t10-
DOCK_REPORT_IDselection_import_t21-
DOCK_RESIDUE_CONTACTSA:ALA15;A:ARG116;A:ARG140;A:ARG144;A:ASN106;A:CYS72;A:GLY73;A:GLY77;A:HIS105;A:HIS14;A:HIS141;A:LEU136;A:SER46;A:THR74;A:TYR49-
DOCK_RESIDUE_CONTACTSA:ALA34;A:ARG100;A:ARG59;A:ASP54;A:GLY161;A:HIS182;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:PRO91;A:THR184;A:THR86;A:TYR166;A:TYR57;A:VAL32;A:VAL33-
DOCK_RESIDUE_CONTACTSA:ARG137;A:ARG141;A:HIS102;A:HIS138;A:MET98;A:TYR94;B:ASP10;B:CYS69;B:GLY70;B:HIS11;B:PRO12;B:SER71;B:TYR46-
DOCK_SCAFFOLDO=C(COC(=O)CNS(=O)(=O)c1ccccc1)Nc1ccccc1-
DOCK_SCAFFOLDO=C(COC(=O)CNS(=O)(=O)c1ccccc1)Nc1ccccc1-
DOCK_SCAFFOLDO=C(COC(=O)CNS(=O)(=O)c1ccccc1)Nc1ccccc1-
DOCK_SCORE-23.840600-
DOCK_SCORE-24.847100-
DOCK_SCORE-22.670800-
DOCK_SCORE_INTER-26.259500-
DOCK_SCORE_INTER-24.355700-
DOCK_SCORE_INTER-25.725600-
DOCK_SCORE_INTER_KCAL-5.817262-
DOCK_SCORE_INTER_KCAL-6.271977-
DOCK_SCORE_INTER_KCAL-6.144457-
DOCK_SCORE_INTER_NORM-0.857518-
DOCK_SCORE_INTER_NORM-0.875317-
DOCK_SCORE_INTER_NORM-0.811856-
DOCK_SCORE_INTRA2.704330-
DOCK_SCORE_INTRA1.884910-
DOCK_SCORE_INTRA-0.491454-
DOCK_SCORE_INTRA_KCAL0.645918-
DOCK_SCORE_INTRA_KCAL0.450203-
DOCK_SCORE_INTRA_KCAL-0.117382-
DOCK_SCORE_INTRA_NORM0.090144-
DOCK_SCORE_INTRA_NORM0.062830-
DOCK_SCORE_INTRA_NORM-0.016382-
DOCK_SCORE_KCAL-5.414830-
DOCK_SCORE_KCAL-5.694232-
DOCK_SCORE_KCAL-5.934630-
DOCK_SCORE_NORM-0.794688-
DOCK_SCORE_NORM-0.828238-
DOCK_SCORE_NORM-0.755694-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.884356-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.029479-
DOCK_SCORE_RESTR_NORM0.000000-
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_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SOURCE_FILET21_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET10_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET06_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC20H23ClN2O6S-
DOCK_SOURCE_FORMULAC20H23ClN2O6S-
DOCK_SOURCE_FORMULAC20H23ClN2O6S-
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_HEAVY_ATOMS30.000000-
DOCK_SOURCE_HEAVY_ATOMS30.000000-
DOCK_SOURCE_HEAVY_ATOMS30.000000-
DOCK_SOURCE_LOGP2.166440-
DOCK_SOURCE_LOGP2.166440-
DOCK_SOURCE_LOGP2.166440-
DOCK_SOURCE_MW454.932000-
DOCK_SOURCE_MW454.932000-
DOCK_SOURCE_MW454.932000-
DOCK_SOURCE_NAMEZ15821830-
DOCK_SOURCE_NAMEZ15821830-
DOCK_SOURCE_NAMEZ15821830-
DOCK_SOURCE_RINGS2.000000-
DOCK_SOURCE_RINGS2.000000-
DOCK_SOURCE_RINGS2.000000-
DOCK_SOURCE_TPSA121.800000-
DOCK_SOURCE_TPSA121.800000-
DOCK_SOURCE_TPSA121.800000-
DOCK_STRAIN_DELTA37.219355-
DOCK_STRAIN_DELTA33.235573-
DOCK_STRAIN_DELTA32.279076-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT10-
DOCK_TARGETT21-
DOCK_TARGETT06-
EXACT_MASS454.096535136Da
FORMULAC20H23ClN2O6S-
HBA6-
HBD3-
LOGP2.1664399999999997-
MOL_WEIGHT454.9320000000003g/mol
QED_SCORE0.5253074655263783-
ROTATABLE_BONDS8-
TPSA121.80000000000001A^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
T06 T06 selection_import_t06 1
native pose available
 2.716968997486293 -22.6708 18 0.86 - Best pose
T21 T21 selection_import_t21 1
native pose available
 3.337239377939873 -24.8471 11 0.79 - Best pose
T10 T10 selection_import_t10 1
native pose available
 4.149014367180202 -23.8406 13 0.76 - Best 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.
PoseFinal rankInter normScoreHBContactsNative overlapNative recallHB strictHB roleHB residueRMSDExcludedNotes
493 2.716968997486293 -0.875317 -22.6708 1 21 18 0.86 0.00 0.00 0.00 - no geometry warning; 12 clashes; 1 protein clash; high strain Δ 33.2 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
522 3.337239377939873 -0.811856 -24.8471 7 13 11 0.79 0.17 0.22 0.25 - no geometry warning; 11 clashes; 2 protein clashes; high strain Δ 32.3 Open pose
T10 — T10 1 poses · report selection_import_t10
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
502 4.149014367180202 -0.857518 -23.8406 10 15 13 0.76 0.46 0.45 0.45 - no geometry warning; 14 clashes; 2 protein clashes; high strain Δ 37.2 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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