FAIRMol

Z16383985

ID 1924

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

SMILES: O=C(C[C@H]1Sc2ccccc2NC1=O)OCc1cc(=O)oc2cc(O)ccc12

Formula: C20H15NO6S | MW: 397.4080000000002

LogP: 3.0449 | TPSA: 105.83999999999999

HBA/HBD: 7/2 | RotB: 4

InChIKey: CPLUPJVUVTZVJN-QGZVFWFLSA-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) H-bond acceptor O ×5 H-bond donor ×2 Gatekeeper aromatic ×2 Metal chelator ×2

Functional group

Carbonyl ×2 Amide Ester Secondary amine Phenol Lactam Sulfide Ether

Ring system

Benzene ×2 Coumarin

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.987817-
DOCK_BASE_INTER_RANK-0.820251-
DOCK_BASE_INTER_RANK-0.979960-
DOCK_BASE_INTER_RANK-0.934900-
DOCK_BASE_INTER_RANK-0.917555-
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_COUNT14.000000-
DOCK_CLASH_COUNT11.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CLASH_COUNT11.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CONTACT_COUNT14.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT14.000000-
DOCK_CONTACT_COUNT23.000000-
DOCK_CONTACT_COUNT16.000000-
DOCK_EXPERIMENTT10-
DOCK_EXPERIMENTT14-
DOCK_EXPERIMENTT09-
DOCK_EXPERIMENTT13-
DOCK_EXPERIMENTT04-
DOCK_EXPERIMENT_ID9-
DOCK_EXPERIMENT_ID10-
DOCK_EXPERIMENT_ID4-
DOCK_EXPERIMENT_ID14-
DOCK_EXPERIMENT_ID13-
DOCK_FINAL_RANK2.947179-
DOCK_FINAL_RANK5.014011-
DOCK_FINAL_RANK3.259786-
DOCK_FINAL_RANK5.143590-
DOCK_FINAL_RANK2.228205-
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:ALA1111-
DOCK_IFP::A:ALA2831-
DOCK_IFP::A:ARG1161-
DOCK_IFP::A:ARG1401-
DOCK_IFP::A:ARG1441-
DOCK_IFP::A:ARG1541-
DOCK_IFP::A:ARG171-
DOCK_IFP::A:ARG221-
DOCK_IFP::A:ARG2771-
DOCK_IFP::A:ARG501-
DOCK_IFP::A:ASN1061-
DOCK_IFP::A:ASN1121-
DOCK_IFP::A:ASP1811-
DOCK_IFP::A:ASP2331-
DOCK_IFP::A:ASP3851-
DOCK_IFP::A:ASP441-
DOCK_IFP::A:ASP471-
DOCK_IFP::A:ASP881-
DOCK_IFP::A:CYS261-
DOCK_IFP::A:CYS721-
DOCK_IFP::A:GLN3411-
DOCK_IFP::A:GLU2741-
DOCK_IFP::A:GLU3841-
DOCK_IFP::A:GLY2351-
DOCK_IFP::A:GLY2361-
DOCK_IFP::A:GLY2371-
DOCK_IFP::A:GLY2761-
DOCK_IFP::A:GLY731-
DOCK_IFP::A:GLY751-
DOCK_IFP::A:GLY771-
DOCK_IFP::A:HIS1051-
DOCK_IFP::A:HIS141-
DOCK_IFP::A:HIS1411-
DOCK_IFP::A:HIS1971-
DOCK_IFP::A:HIS2411-
DOCK_IFP::A:ILE761-
DOCK_IFP::A:LEU1011-
DOCK_IFP::A:LEU1881-
DOCK_IFP::A:LEU2261-
DOCK_IFP::A:LEU2291-
DOCK_IFP::A:LEU251-
DOCK_IFP::A:LEU3821-
DOCK_IFP::A:LYS691-
DOCK_IFP::A:MET2331-
DOCK_IFP::A:MET781-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:NDP3021-
DOCK_IFP::A:PHE1131-
DOCK_IFP::A:PHE1701-
DOCK_IFP::A:PHE1961-
DOCK_IFP::A:PHE2381-
DOCK_IFP::A:PHE2841-
DOCK_IFP::A:PRO1131-
DOCK_IFP::A:PRO2751-
DOCK_IFP::A:SER1111-
DOCK_IFP::A:SER1951-
DOCK_IFP::A:SER2001-
DOCK_IFP::A:SER2821-
DOCK_IFP::A:THR1321-
DOCK_IFP::A:THR211-
DOCK_IFP::A:THR2851-
DOCK_IFP::A:THR741-
DOCK_IFP::A:TYR1911-
DOCK_IFP::A:TYR1941-
DOCK_IFP::A:TYR2781-
DOCK_IFP::A:TYR3891-
DOCK_IFP::A:TYR491-
DOCK_IFP::A:VAL2301-
DOCK_IFP::B:ALA321-
DOCK_IFP::B:ARG481-
DOCK_IFP::B:ASP521-
DOCK_IFP::B:ILE451-
DOCK_IFP::B:LEU941-
DOCK_IFP::B:MET531-
DOCK_IFP::B:PHE561-
DOCK_IFP::B:PRO501-
DOCK_IFP::B:SER441-
DOCK_IFP::B:TRP471-
DOCK_IFP::B:VAL1561-
DOCK_IFP::B:VAL311-
DOCK_IFP::B:VAL491-
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_OVERLAP0.614291-
DOCK_MAX_CLASH_OVERLAP0.614278-
DOCK_MAX_CLASH_OVERLAP0.614334-
DOCK_MAX_CLASH_OVERLAP0.645167-
DOCK_MAX_CLASH_OVERLAP0.613552-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.209452-
DOCK_PRE_RANK3.223495-
DOCK_PRE_RANK2.918544-
DOCK_PRE_RANK4.987172-
DOCK_PRE_RANK5.119519-
DOCK_PRIMARY_POSE_ID2433-
DOCK_PRIMARY_POSE_ID8521-
DOCK_PRIMARY_POSE_ID5830-
DOCK_PRIMARY_POSE_ID6469-
DOCK_PRIMARY_POSE_ID9216-
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_t13-
DOCK_REPORT_IDselection_import_t14-
DOCK_REPORT_IDselection_import_t04-
DOCK_REPORT_IDselection_import_t10-
DOCK_RESIDUE_CONTACTSA:ALA283;A:ARG22;A:ARG50;A:ASP385;A:ASP44;A:ASP47;A:CYS26;A:GLN341;A:GLU384;A:LEU25;A:LEU382;A:PHE284;A:SER282;A:THR21;A:THR285-
DOCK_RESIDUE_CONTACTSA:NDP301;B:ALA32;B:ARG48;B:ASP52;B:ILE45;B:LEU94;B:MET53;B:PHE56;B:PRO50;B:SER44;B:TRP47;B:VAL156;B:VAL31;B:VAL49-
DOCK_RESIDUE_CONTACTSA:ALA111;A:ARG154;A:ARG277;A:ASN112;A:ASP233;A:ASP88;A:GLU274;A:GLY235;A:GLY236;A:GLY237;A:GLY276;A:HIS197;A:LYS69;A:PHE170;A:PHE196;A:PHE238;A:PRO113;A:PRO275;A:SER195;A:SER200;A:THR132;A:TYR278;A:TYR389-
DOCK_RESIDUE_CONTACTSA:ARG116;A:ARG140;A:ARG144;A:ASN106;A:CYS72;A:GLY73;A:GLY75;A:GLY77;A:HIS105;A:HIS14;A:HIS141;A:ILE76;A:LEU101;A:MET78;A:THR74;A:TYR49-
DOCK_RESIDUE_CONTACTSA:ARG17;A:ASP181;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:MET233;A:NDP302;A:PHE113;A:SER111;A:TYR191;A:TYR194;A:VAL230;D:ARG287-
DOCK_SCAFFOLDO=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12-
DOCK_SCAFFOLDO=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12-
DOCK_SCAFFOLDO=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12-
DOCK_SCAFFOLDO=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12-
DOCK_SCAFFOLDO=C(CC1Sc2ccccc2NC1=O)OCc1cc(=O)oc2ccccc12-
DOCK_SCORE-12.202100-
DOCK_SCORE-25.578000-
DOCK_SCORE-23.987400-
DOCK_SCORE-22.121500-
DOCK_SCORE-21.358200-
DOCK_SCORE_INTER-27.658900-
DOCK_SCORE_INTER-25.691600-
DOCK_SCORE_INTER-27.438900-
DOCK_SCORE_INTER-26.177200-
DOCK_SCORE_INTER-22.967000-
DOCK_SCORE_INTER_KCAL-6.606218-
DOCK_SCORE_INTER_KCAL-6.553672-
DOCK_SCORE_INTER_KCAL-5.485576-
DOCK_SCORE_INTER_KCAL-6.136336-
DOCK_SCORE_INTER_KCAL-6.252320-
DOCK_SCORE_INTER_NORM-0.917555-
DOCK_SCORE_INTER_NORM-0.987817-
DOCK_SCORE_INTER_NORM-0.979960-
DOCK_SCORE_INTER_NORM-0.820251-
DOCK_SCORE_INTER_NORM-0.934900-
DOCK_SCORE_INTRA1.608850-
DOCK_SCORE_INTRA3.451460-
DOCK_SCORE_INTRA0.599199-
DOCK_SCORE_INTRA5.537340-
DOCK_SCORE_INTRA13.489400-
DOCK_SCORE_INTRA_KCAL0.824367-
DOCK_SCORE_INTRA_KCAL1.322572-
DOCK_SCORE_INTRA_KCAL3.221889-
DOCK_SCORE_INTRA_KCAL0.143116-
DOCK_SCORE_INTRA_KCAL0.384267-
DOCK_SCORE_INTRA_NORM0.481766-
DOCK_SCORE_INTRA_NORM0.021400-
DOCK_SCORE_INTRA_NORM0.057459-
DOCK_SCORE_INTRA_NORM0.197762-
DOCK_SCORE_INTRA_NORM0.123266-
DOCK_SCORE_KCAL-2.914423-
DOCK_SCORE_KCAL-5.729295-
DOCK_SCORE_KCAL-6.109203-
DOCK_SCORE_KCAL-5.101321-
DOCK_SCORE_KCAL-5.283632-
DOCK_SCORE_NORM-0.913500-
DOCK_SCORE_NORM-0.435789-
DOCK_SCORE_NORM-0.762792-
DOCK_SCORE_NORM-0.790055-
DOCK_SCORE_NORM-0.856693-
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_FILET10_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET04_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET09_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET14_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET13_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC20H15NO6S-
DOCK_SOURCE_FORMULAC20H15NO6S-
DOCK_SOURCE_FORMULAC20H15NO6S-
DOCK_SOURCE_FORMULAC20H15NO6S-
DOCK_SOURCE_FORMULAC20H15NO6S-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HEAVY_ATOMS28.000000-
DOCK_SOURCE_HEAVY_ATOMS28.000000-
DOCK_SOURCE_HEAVY_ATOMS28.000000-
DOCK_SOURCE_HEAVY_ATOMS28.000000-
DOCK_SOURCE_HEAVY_ATOMS28.000000-
DOCK_SOURCE_LOGP3.044900-
DOCK_SOURCE_LOGP3.044900-
DOCK_SOURCE_LOGP3.044900-
DOCK_SOURCE_LOGP3.044900-
DOCK_SOURCE_LOGP3.044900-
DOCK_SOURCE_MW397.408000-
DOCK_SOURCE_MW397.408000-
DOCK_SOURCE_MW397.408000-
DOCK_SOURCE_MW397.408000-
DOCK_SOURCE_MW397.408000-
DOCK_SOURCE_NAMEZ16383985-
DOCK_SOURCE_NAMEZ16383985-
DOCK_SOURCE_NAMEZ16383985-
DOCK_SOURCE_NAMEZ16383985-
DOCK_SOURCE_NAMEZ16383985-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA105.840000-
DOCK_SOURCE_TPSA105.840000-
DOCK_SOURCE_TPSA105.840000-
DOCK_SOURCE_TPSA105.840000-
DOCK_SOURCE_TPSA105.840000-
DOCK_STRAIN_DELTA22.629898-
DOCK_STRAIN_DELTA27.465747-
DOCK_STRAIN_DELTA19.313452-
DOCK_STRAIN_DELTA14.804180-
DOCK_STRAIN_DELTA21.372584-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_TARGETT13-
DOCK_TARGETT09-
DOCK_TARGETT04-
DOCK_TARGETT14-
DOCK_TARGETT10-
EXACT_MASS397.0620082Da
FORMULAC20H15NO6S-
HBA7-
HBD2-
LOGP3.0449-
MOL_WEIGHT397.4080000000002g/mol
QED_SCORE0.514766835784493-
ROTATABLE_BONDS4-
TPSA105.83999999999999A^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
T09 T09 selection_import_t09 1
native pose available
 2.2282048565114194 -25.578 9 0.43 - Best pose
T04 T04 selection_import_t04 1
native pose available
 2.9471794262273776 -12.2021 14 0.74 - Best pose
T14 T14 selection_import_t14 1
native pose available
 3.2597862975616207 -21.3582 7 0.47 - Best pose
T13 T13 selection_import_t13 1
native pose available
 5.01401130935189 -22.1215 15 0.79 - Best pose
T10 T10 selection_import_t10 1
native pose available
 5.1435904455655335 -23.9874 15 0.88 - Best 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
412 2.2282048565114194 -0.9349 -25.578 4 14 9 0.43 0.00 0.00 0.00 - no geometry warning; 11 clashes; 1 protein clash Open 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
400 2.9471794262273776 -0.917555 -12.2021 7 14 14 0.74 0.50 0.60 0.60 - no geometry warning; 12 clashes; 2 protein clashes; 5 cofactor-context clashes; moderate strain Δ 22.6 Open pose
T14 — T14 1 poses · report selection_import_t14
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
408 3.2597862975616207 -0.820251 -21.3582 9 15 7 0.47 0.17 0.40 0.40 - no geometry warning; 14 clashes; 1 protein clash; moderate strain Δ 27.5 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
391 5.01401130935189 -0.987817 -22.1215 9 23 15 0.79 0.44 0.57 0.57 - no geometry warning; 11 clashes; 3 protein clashes; moderate strain Δ 21.4 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
373 5.1435904455655335 -0.97996 -23.9874 10 16 15 0.88 0.54 0.55 0.82 - no geometry warning; 12 clashes; 3 protein clashes 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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