FAIRMol

OHD_Leishmania_134

ID 1020

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

SMILES: NC(=O)[C@H]1CCCN1C(=O)Cc1ccc(N(CCCO)Cc2cnc3nc(N)nc(N)c3[nH+]2)cc1

Formula: C23H30N9O3+ | MW: 480.55300000000034

LogP: -0.5888999999999962 | TPSA: 191.72

HBA/HBD: 9/4 | RotB: 9

InChIKey: GGQMXOYQALOJNY-QGZVFWFLSA-O

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern Proline-like ring Clear highlight

Bio motif

Peptide backbone ATP mimic pyrimidine Proline-like ring N-Methyl amide ×2 H-bond acceptor N ×6 H-bond acceptor O ×2 H-bond donor ×5 Gatekeeper aromatic Ionizable base ×2 Metal chelator ×2 Retro-amide P-gp efflux flag ×2

Functional group

Carbonyl ×2 Amide ×2 Primary amine ×3 Alcohol Tertiary amine ×2 Lactam

Ring system

Benzene Pyrimidine Pyrazine

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.812027-
DOCK_BASE_INTER_RANK-0.709407-
DOCK_BASE_INTER_RANK-0.649489-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_CONTACT_COUNT16.000000-
DOCK_EXPERIMENTT02-
DOCK_EXPERIMENTT11-
DOCK_EXPERIMENTT14-
DOCK_EXPERIMENT_ID2-
DOCK_EXPERIMENT_ID11-
DOCK_EXPERIMENT_ID14-
DOCK_FINAL_RANK3.624858-
DOCK_FINAL_RANK2.770343-
DOCK_FINAL_RANK2.332695-
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:ALA101-
DOCK_IFP::A:ARG221-
DOCK_IFP::A:ARG2421-
DOCK_IFP::A:ARG3371-
DOCK_IFP::A:ARG501-
DOCK_IFP::A:ASN201-
DOCK_IFP::A:ASP221-
DOCK_IFP::A:ASP2431-
DOCK_IFP::A:ASP3851-
DOCK_IFP::A:ASP441-
DOCK_IFP::A:GLN1241-
DOCK_IFP::A:GLN2201-
DOCK_IFP::A:GLU1921-
DOCK_IFP::A:GLU311-
DOCK_IFP::A:GLU3841-
DOCK_IFP::A:GLY1911-
DOCK_IFP::A:HIS1441-
DOCK_IFP::A:HIS2221-
DOCK_IFP::A:ILE1261-
DOCK_IFP::A:ILE611-
DOCK_IFP::A:ILE81-
DOCK_IFP::A:LEU1941-
DOCK_IFP::A:LEU231-
DOCK_IFP::A:LEU3391-
DOCK_IFP::A:LEU681-
DOCK_IFP::A:NAP2011-
DOCK_IFP::A:PHE1351-
DOCK_IFP::A:PHE1891-
DOCK_IFP::A:PHE1901-
DOCK_IFP::A:PHE321-
DOCK_IFP::A:PHE351-
DOCK_IFP::A:PHE3831-
DOCK_IFP::A:PHE741-
DOCK_IFP::A:PRO2231-
DOCK_IFP::A:PRO261-
DOCK_IFP::A:PRO271-
DOCK_IFP::A:PRO621-
DOCK_IFP::A:SER2821-
DOCK_IFP::A:SER601-
DOCK_IFP::A:THR1371-
DOCK_IFP::A:THR211-
DOCK_IFP::A:THR2851-
DOCK_IFP::A:THR571-
DOCK_IFP::A:TRP251-
DOCK_IFP::A:TYR1221-
DOCK_IFP::A:TYR341-
DOCK_IFP::A:VAL1161-
DOCK_IFP::A:VAL1871-
DOCK_IFP::A:VAL1881-
DOCK_IFP::A:VAL2211-
DOCK_IFP::A:VAL3351-
DOCK_IFP::A:VAL3361-
DOCK_IFP::A:VAL91-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.677624-
DOCK_MAX_CLASH_OVERLAP0.688280-
DOCK_MAX_CLASH_OVERLAP0.677535-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK3.548388-
DOCK_PRE_RANK2.708255-
DOCK_PRE_RANK2.232498-
DOCK_PRIMARY_POSE_ID690-
DOCK_PRIMARY_POSE_ID6787-
DOCK_PRIMARY_POSE_ID8819-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t02-
DOCK_REPORT_IDselection_import_t11-
DOCK_REPORT_IDselection_import_t14-
DOCK_RESIDUE_CONTACTSA:ALA10;A:ASP22;A:GLU31;A:ILE61;A:ILE8;A:LEU23;A:LEU68;A:NAP201;A:PHE135;A:PHE32;A:PHE35;A:PRO26;A:PRO27;A:PRO62;A:SER60;A:THR137;A:THR57;A:TRP25;A:TYR122;A:TYR34;A:VAL116;A:VAL9-
DOCK_RESIDUE_CONTACTSA:GLN124;A:GLN220;A:GLU192;A:GLY191;A:HIS144;A:HIS222;A:ILE126;A:LEU194;A:PHE189;A:PHE190;A:PHE74;A:PRO223;A:VAL187;A:VAL188;A:VAL221-
DOCK_RESIDUE_CONTACTSA:ARG22;A:ARG242;A:ARG337;A:ARG50;A:ASN20;A:ASP243;A:ASP385;A:ASP44;A:GLU384;A:LEU339;A:PHE383;A:SER282;A:THR21;A:THR285;A:VAL335;A:VAL336-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCC1-
DOCK_SCORE-31.955600-
DOCK_SCORE-20.430100-
DOCK_SCORE-22.531300-
DOCK_SCORE_INTER-28.420900-
DOCK_SCORE_INTER-24.829200-
DOCK_SCORE_INTER-22.732100-
DOCK_SCORE_INTER_KCAL-6.788218-
DOCK_SCORE_INTER_KCAL-5.930355-
DOCK_SCORE_INTER_KCAL-5.429471-
DOCK_SCORE_INTER_NORM-0.812027-
DOCK_SCORE_INTER_NORM-0.709407-
DOCK_SCORE_INTER_NORM-0.649489-
DOCK_SCORE_INTRA-3.534670-
DOCK_SCORE_INTRA4.399180-
DOCK_SCORE_INTRA0.200812-
DOCK_SCORE_INTRA_KCAL-0.844242-
DOCK_SCORE_INTRA_KCAL1.050727-
DOCK_SCORE_INTRA_KCAL0.047963-
DOCK_SCORE_INTRA_NORM-0.100991-
DOCK_SCORE_INTRA_NORM0.125691-
DOCK_SCORE_INTRA_NORM0.005737-
DOCK_SCORE_KCAL-7.632467-
DOCK_SCORE_KCAL-4.879648-
DOCK_SCORE_KCAL-5.381511-
DOCK_SCORE_NORM-0.913018-
DOCK_SCORE_NORM-0.583716-
DOCK_SCORE_NORM-0.643752-
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_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_FILET02_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET11_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET14_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HEAVY_ATOMS35.000000-
DOCK_SOURCE_HEAVY_ATOMS35.000000-
DOCK_SOURCE_HEAVY_ATOMS35.000000-
DOCK_SOURCE_LOGP-0.588900-
DOCK_SOURCE_LOGP-0.588900-
DOCK_SOURCE_LOGP-0.588900-
DOCK_SOURCE_MW480.553000-
DOCK_SOURCE_MW480.553000-
DOCK_SOURCE_MW480.553000-
DOCK_SOURCE_NAMEOHD_Leishmania_134-
DOCK_SOURCE_NAMEOHD_Leishmania_134-
DOCK_SOURCE_NAMEOHD_Leishmania_134-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA191.720000-
DOCK_SOURCE_TPSA191.720000-
DOCK_SOURCE_TPSA191.720000-
DOCK_STRAIN_DELTA46.524791-
DOCK_STRAIN_DELTA40.399070-
DOCK_STRAIN_DELTA55.875913-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT02-
DOCK_TARGETT11-
DOCK_TARGETT14-
EXACT_MASS480.24661224009Da
FORMULAC23H30N9O3+-
HBA9-
HBD4-
LOGP-0.5888999999999962-
MOL_WEIGHT480.55300000000034g/mol
QED_SCORE0.30973432353438796-
ROTATABLE_BONDS9-
TPSA191.72A^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
T14 T14 selection_import_t14 1
native pose available
 2.3326950438436285 -22.5313 8 0.53 - Best pose
T11 T11 selection_import_t11 1
native pose available
 2.7703431775692176 -20.4301 14 0.78 - Best pose
T02 T02 selection_import_t02 1
native pose available
 3.624857535893448 -31.9556 17 0.81 - Best 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
11 2.3326950438436285 -0.649489 -22.5313 9 16 8 0.53 0.33 0.40 0.40 - no geometry warning; 13 clashes; 9 protein contact clashes; high strain Δ 55.9 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
13 2.7703431775692176 -0.709407 -20.4301 6 15 14 0.78 0.20 0.40 0.25 - no geometry warning; 13 clashes; 1 protein clash; high strain Δ 40.4 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
12 3.624857535893448 -0.812027 -31.9556 8 22 17 0.81 0.60 0.60 0.60 - no geometry warning; 13 clashes; 2 protein clashes; high strain Δ 46.5 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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