FAIRMol

Z126938578

ID 1244

DB fairmolThis detail page is pinned to the current database context.
Back to results Open docking pose (4)
2D structure

SMILES: O=C(c1ccc2c(c1)OCO2)N1CCC(n2c(=O)[nH]c3ccccc32)CC1

Formula: C20H19N3O4 | MW: 365.3890000000001

LogP: 2.5356000000000005 | TPSA: 76.56

HBA/HBD: 4/1 | RotB: 2

InChIKey: NIEKONUYMYXIRN-UHFFFAOYSA-N

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern P-gp efflux flag Clear highlight

Bio motif

Catechol N-Methyl amide ×2 H-bond acceptor N ×3 H-bond acceptor O ×4 H-bond donor Gatekeeper aromatic ×2 Metal chelator PAINS — catechol P-gp efflux flag

Functional group

Carbonyl Amide Tertiary amine Lactam Aryl ether ×2 Ether ×2 Acetal

Ring system

Benzene ×2 Benzimidazole Imidazole Benzodioxole Pipecolinyl ring

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-1.113940-
DOCK_BASE_INTER_RANK-0.984230-
DOCK_BASE_INTER_RANK-0.872657-
DOCK_BASE_INTER_RANK-1.175110-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT10.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CLASH_COUNT11.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CONTACT_COUNT12.000000-
DOCK_CONTACT_COUNT13.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT18.000000-
DOCK_EXPERIMENTT07-
DOCK_EXPERIMENTT08-
DOCK_EXPERIMENTT03-
DOCK_EXPERIMENTT14-
DOCK_EXPERIMENT_ID14-
DOCK_EXPERIMENT_ID3-
DOCK_EXPERIMENT_ID8-
DOCK_EXPERIMENT_ID7-
DOCK_FINAL_RANK2.148201-
DOCK_FINAL_RANK0.929869-
DOCK_FINAL_RANK2.197549-
DOCK_FINAL_RANK1.652558-
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_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_IFP::A:ALA321-
DOCK_IFP::A:ALA961-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG2421-
DOCK_IFP::A:ARG3371-
DOCK_IFP::A:ARG971-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP2431-
DOCK_IFP::A:ASP3851-
DOCK_IFP::A:ASP521-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:GLU3841-
DOCK_IFP::A:GLY1571-
DOCK_IFP::A:GLY2401-
DOCK_IFP::A:ILE451-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU3391-
DOCK_IFP::A:LEU941-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS511-
DOCK_IFP::A:LYS571-
DOCK_IFP::A:LYS951-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET531-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE3831-
DOCK_IFP::A:PHE561-
DOCK_IFP::A:PHE911-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:PRO991-
DOCK_IFP::A:SER2821-
DOCK_IFP::A:THR2411-
DOCK_IFP::A:THR831-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TYR1621-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR981-
DOCK_IFP::A:TYR981-
DOCK_IFP::A:VAL1561-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL301-
DOCK_IFP::A:VAL311-
DOCK_IFP::A:VAL3351-
DOCK_IFP::A:VAL3361-
DOCK_IFP::A:VAL871-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.642218-
DOCK_MAX_CLASH_OVERLAP0.642072-
DOCK_MAX_CLASH_OVERLAP0.642148-
DOCK_MAX_CLASH_OVERLAP0.642172-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.166363-
DOCK_PRE_RANK1.613638-
DOCK_PRE_RANK0.897152-
DOCK_PRE_RANK2.126488-
DOCK_PRIMARY_POSE_ID4561-
DOCK_PRIMARY_POSE_ID9322-
DOCK_PRIMARY_POSE_ID5257-
DOCK_PRIMARY_POSE_ID1887-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t14-
DOCK_REPORT_IDselection_import_t08-
DOCK_REPORT_IDselection_import_t07-
DOCK_REPORT_IDselection_import_t03-
DOCK_RESIDUE_CONTACTSA:ARG14;A:ASP161;A:CYS168;A:LEU209;A:LYS178;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:PRO99;A:TRP221;A:TYR174;A:TYR98;A:VAL206-
DOCK_RESIDUE_CONTACTSA:ALA32;A:ARG97;A:ASP52;A:GLY157;A:ILE45;A:LEU94;A:LYS57;A:LYS95;A:MET53;A:NDP301;A:PHE56;A:PHE91;A:THR83;A:TYR162;A:VAL156;A:VAL30;A:VAL31;A:VAL87-
DOCK_RESIDUE_CONTACTSA:ARG242;A:ARG337;A:ASP243;A:ASP385;A:GLU384;A:GLY240;A:LEU339;A:LYS51;A:PHE383;A:SER282;A:THR241;A:VAL335;A:VAL336-
DOCK_RESIDUE_CONTACTSA:ALA96;A:ARG14;A:ASP161;A:CYS168;A:LEU208;A:LEU209;A:NAP301;A:PHE97;A:PRO210;A:TRP221;A:TYR174;A:TYR98-
DOCK_SCAFFOLDO=C(c1ccc2c(c1)OCO2)N1CCC(n2c(=O)[nH]c3ccccc32)CC1-
DOCK_SCAFFOLDO=C(c1ccc2c(c1)OCO2)N1CCC(n2c(=O)[nH]c3ccccc32)CC1-
DOCK_SCAFFOLDO=C(c1ccc2c(c1)OCO2)N1CCC(n2c(=O)[nH]c3ccccc32)CC1-
DOCK_SCAFFOLDO=C(c1ccc2c(c1)OCO2)N1CCC(n2c(=O)[nH]c3ccccc32)CC1-
DOCK_SCORE-22.867200-
DOCK_SCORE-28.015400-
DOCK_SCORE-27.039300-
DOCK_SCORE-26.475600-
DOCK_SCORE_INTER-31.728100-
DOCK_SCORE_INTER-23.561700-
DOCK_SCORE_INTER-26.574200-
DOCK_SCORE_INTER-30.076400-
DOCK_SCORE_INTER_KCAL-5.627618-
DOCK_SCORE_INTER_KCAL-7.183628-
DOCK_SCORE_INTER_KCAL-6.347141-
DOCK_SCORE_INTER_KCAL-7.578130-
DOCK_SCORE_INTER_NORM-0.984230-
DOCK_SCORE_INTER_NORM-1.175110-
DOCK_SCORE_INTER_NORM-0.872657-
DOCK_SCORE_INTER_NORM-1.113940-
DOCK_SCORE_INTRA3.712700-
DOCK_SCORE_INTRA0.098637-
DOCK_SCORE_INTRA3.037160-
DOCK_SCORE_INTRA0.694477-
DOCK_SCORE_INTRA_KCAL0.725414-
DOCK_SCORE_INTRA_KCAL0.023559-
DOCK_SCORE_INTRA_KCAL0.165873-
DOCK_SCORE_INTRA_KCAL0.886764-
DOCK_SCORE_INTRA_NORM0.137507-
DOCK_SCORE_INTRA_NORM0.112487-
DOCK_SCORE_INTRA_NORM0.003653-
DOCK_SCORE_INTRA_NORM0.025721-
DOCK_SCORE_KCAL-6.691366-
DOCK_SCORE_KCAL-6.323591-
DOCK_SCORE_KCAL-6.458229-
DOCK_SCORE_KCAL-5.461739-
DOCK_SCORE_NORM-0.980576-
DOCK_SCORE_NORM-0.846935-
DOCK_SCORE_NORM-1.001450-
DOCK_SCORE_NORM-1.037610-
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_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_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_SOURCE_FILET08_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET07_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET14_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET03_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC20H19N3O4-
DOCK_SOURCE_FORMULAC20H19N3O4-
DOCK_SOURCE_FORMULAC20H19N3O4-
DOCK_SOURCE_FORMULAC20H19N3O4-
DOCK_SOURCE_HBA4.000000-
DOCK_SOURCE_HBA4.000000-
DOCK_SOURCE_HBA4.000000-
DOCK_SOURCE_HBA4.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HBD1.000000-
DOCK_SOURCE_HEAVY_ATOMS27.000000-
DOCK_SOURCE_HEAVY_ATOMS27.000000-
DOCK_SOURCE_HEAVY_ATOMS27.000000-
DOCK_SOURCE_HEAVY_ATOMS27.000000-
DOCK_SOURCE_LOGP2.535600-
DOCK_SOURCE_LOGP2.535600-
DOCK_SOURCE_LOGP2.535600-
DOCK_SOURCE_LOGP2.535600-
DOCK_SOURCE_MW365.389000-
DOCK_SOURCE_MW365.389000-
DOCK_SOURCE_MW365.389000-
DOCK_SOURCE_MW365.389000-
DOCK_SOURCE_NAMEZ126938578-
DOCK_SOURCE_NAMEZ126938578-
DOCK_SOURCE_NAMEZ126938578-
DOCK_SOURCE_NAMEZ126938578-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_TPSA76.560000-
DOCK_SOURCE_TPSA76.560000-
DOCK_SOURCE_TPSA76.560000-
DOCK_SOURCE_TPSA76.560000-
DOCK_STRAIN_DELTA25.299617-
DOCK_STRAIN_DELTA24.325857-
DOCK_STRAIN_DELTA17.417669-
DOCK_STRAIN_DELTA28.975564-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK1-
DOCK_TARGETT07-
DOCK_TARGETT08-
DOCK_TARGETT14-
DOCK_TARGETT03-
EXACT_MASS365.13755608800005Da
FORMULAC20H19N3O4-
HBA4-
HBD1-
LOGP2.5356000000000005-
MOL_WEIGHT365.3890000000001g/mol
QED_SCORE0.7571505800242982-
ROTATABLE_BONDS2-
TPSA76.56A^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
T08 T08 selection_import_t08 1
native pose available
 0.9298687402047414 -28.0154 11 0.58 - Best pose
T07 T07 selection_import_t07 1
native pose available
 1.6525578724986323 -27.0393 15 0.79 - Best pose
T03 T03 selection_import_t03 1
native pose available
 2.14820113608716 -26.4756 16 0.80 - Best pose
T14 T14 selection_import_t14 1
native pose available
 2.197549195052648 -22.8672 8 0.53 - Best pose
T08 — T08 1 poses · report selection_import_t08
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
516 0.9298687402047414 -1.17511 -28.0154 6 12 11 0.58 0.50 0.60 0.80 - no geometry warning; 13 clashes; 4 protein contact clashes; 2 cofactor-context clashes; moderate strain Δ 25.3 Open pose
T07 — T07 1 poses · report selection_import_t07
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
498 1.6525578724986323 -1.11394 -27.0393 3 15 15 0.79 0.17 0.20 0.20 - no geometry warning; 11 clashes; 1 protein clash; moderate strain Δ 29.0 Open pose
T03 — T03 1 poses · report selection_import_t03
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
532 2.14820113608716 -0.98423 -26.4756 2 18 16 0.80 0.29 0.40 0.40 - no geometry warning; 13 clashes; 1 protein clash 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
514 2.197549195052648 -0.872657 -22.8672 5 13 8 0.53 0.00 0.20 0.20 - no geometry warning; 10 clashes; 1 protein clash; moderate strain Δ 24.3 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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