FAIRMol

OHD_Leishmania_134

ID 483

DB SELECTIONThis detail page is pinned to the current database context.
Back to results Open docking pose (5)
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-KRWDZBQOSA-O

Recognized patterns

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

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-0.840735-
DOCK_BASE_INTER_RANK-1.267410-
DOCK_BASE_INTER_RANK-0.768227-
DOCK_BASE_INTER_RANK-0.789949-
DOCK_BASE_INTER_RANK-0.566535-
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_COUNT15.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CLASH_COUNT13.000000-
DOCK_CLASH_COUNT12.000000-
DOCK_CONTACT_COUNT20.000000-
DOCK_CONTACT_COUNT20.000000-
DOCK_CONTACT_COUNT21.000000-
DOCK_CONTACT_COUNT20.000000-
DOCK_CONTACT_COUNT13.000000-
DOCK_EXPERIMENTT01-
DOCK_EXPERIMENTT08-
DOCK_EXPERIMENTT09-
DOCK_EXPERIMENTT12-
DOCK_EXPERIMENTT20-
DOCK_EXPERIMENT_ID1-
DOCK_EXPERIMENT_ID8-
DOCK_EXPERIMENT_ID9-
DOCK_EXPERIMENT_ID12-
DOCK_EXPERIMENT_ID20-
DOCK_FINAL_RANK2.767879-
DOCK_FINAL_RANK2.600551-
DOCK_FINAL_RANK3.425641-
DOCK_FINAL_RANK5.229915-
DOCK_FINAL_RANK2.106954-
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:ALA1021-
DOCK_IFP::A:ALA1701-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG1401-
DOCK_IFP::A:ARG1441-
DOCK_IFP::A:ASN1061-
DOCK_IFP::A:ASN4021-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP221-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:GLU2171-
DOCK_IFP::A:GLU311-
DOCK_IFP::A:GLU4661-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:GLY211-
DOCK_IFP::A:HIS1051-
DOCK_IFP::A:HIS1411-
DOCK_IFP::A:HIS4611-
DOCK_IFP::A:ILE611-
DOCK_IFP::A:ILE81-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU231-
DOCK_IFP::A:LEU3991-
DOCK_IFP::A:LEU681-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS2201-
DOCK_IFP::A:MET1011-
DOCK_IFP::A:MET1691-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET3931-
DOCK_IFP::A:NAP2011-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE351-
DOCK_IFP::A:PHE3961-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:PRO271-
DOCK_IFP::A:PRO3981-
DOCK_IFP::A:PRO4621-
DOCK_IFP::A:PRO621-
DOCK_IFP::A:SER3941-
DOCK_IFP::A:SER3951-
DOCK_IFP::A:SER4641-
DOCK_IFP::A:SER601-
DOCK_IFP::A:SER951-
DOCK_IFP::A:THR1371-
DOCK_IFP::A:THR3971-
DOCK_IFP::A:THR4631-
DOCK_IFP::A:THR571-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TRP251-
DOCK_IFP::A:TYR1221-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR341-
DOCK_IFP::A:TYR971-
DOCK_IFP::A:VAL1161-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL91-
DOCK_IFP::B:ALA321-
DOCK_IFP::B:ARG1161-
DOCK_IFP::B:ARG461-
DOCK_IFP::B:ARG971-
DOCK_IFP::B:ASP131-
DOCK_IFP::B:ASP521-
DOCK_IFP::B:CYS721-
DOCK_IFP::B:GLY731-
DOCK_IFP::B:GLY771-
DOCK_IFP::B:HIS141-
DOCK_IFP::B:ILE151-
DOCK_IFP::B:ILE761-
DOCK_IFP::B:LEU1791-
DOCK_IFP::B:LEU941-
DOCK_IFP::B:LYS571-
DOCK_IFP::B:MET531-
DOCK_IFP::B:MET781-
DOCK_IFP::B:MET791-
DOCK_IFP::B:PHE551-
DOCK_IFP::B:PHE561-
DOCK_IFP::B:PHE911-
DOCK_IFP::B:PRO881-
DOCK_IFP::B:SER741-
DOCK_IFP::B:THR1801-
DOCK_IFP::B:THR831-
DOCK_IFP::B:TYR1621-
DOCK_IFP::B:TYR1781-
DOCK_IFP::B:TYR491-
DOCK_IFP::B:VAL1561-
DOCK_IFP::B:VAL301-
DOCK_IFP::B:VAL311-
DOCK_IFP::B:VAL871-
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_OVERLAP0.677171-
DOCK_MAX_CLASH_OVERLAP0.688400-
DOCK_MAX_CLASH_OVERLAP0.688358-
DOCK_MAX_CLASH_OVERLAP0.690090-
DOCK_MAX_CLASH_OVERLAP0.677223-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.626423-
DOCK_PRE_RANK2.529406-
DOCK_PRE_RANK3.349931-
DOCK_PRE_RANK5.136802-
DOCK_PRE_RANK1.979105-
DOCK_PRIMARY_POSE_ID17-
DOCK_PRIMARY_POSE_ID4760-
DOCK_PRIMARY_POSE_ID5431-
DOCK_PRIMARY_POSE_ID7462-
DOCK_PRIMARY_POSE_ID12892-
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_t01-
DOCK_REPORT_IDselection_import_t08-
DOCK_REPORT_IDselection_import_t09-
DOCK_REPORT_IDselection_import_t12-
DOCK_REPORT_IDselection_import_t20-
DOCK_RESIDUE_CONTACTSA:ALA10;A:ASP22;A:GLU31;A:GLY21;A:ILE61;A:ILE8;A:LEU23;A:LEU68;A:NAP201;A:PHE35;A:PRO27;A:PRO62;A:SER60;A:THR137;A:THR57;A:TRP25;A:TYR122;A:TYR34;A:VAL116;A:VAL9-
DOCK_RESIDUE_CONTACTSA:ALA170;A:ARG14;A:ASP161;A:CYS168;A:GLU217;A:GLY205;A:LEU208;A:LEU209;A:LYS178;A:LYS220;A:MET169;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:SER95;A:TRP221;A:TYR174;A:VAL206-
DOCK_RESIDUE_CONTACTSA:NDP301;B:ALA32;B:ARG97;B:ASP52;B:LEU179;B:LEU94;B:LYS57;B:MET53;B:MET79;B:PHE55;B:PHE56;B:PHE91;B:PRO88;B:THR180;B:THR83;B:TYR162;B:TYR178;B:VAL156;B:VAL30;B:VAL31;B:VAL87-
DOCK_RESIDUE_CONTACTSA:ALA102;A:ARG140;A:ARG144;A:ASN106;A:HIS105;A:HIS141;A:MET101;A:TYR97;B:ARG116;B:ARG46;B:ASP13;B:CYS72;B:GLY73;B:GLY77;B:HIS14;B:ILE15;B:ILE76;B:MET78;B:SER74;B:TYR49-
DOCK_RESIDUE_CONTACTSA:ASN402;A:GLU466;A:HIS461;A:LEU399;A:MET393;A:PHE396;A:PRO398;A:PRO462;A:SER394;A:SER395;A:SER464;A:THR397;A:THR463-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCC1-
DOCK_SCAFFOLDO=C(Cc1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCC1-
DOCK_SCORE-30.215900-
DOCK_SCORE-46.987400-
DOCK_SCORE-26.192000-
DOCK_SCORE-24.928500-
DOCK_SCORE-19.996800-
DOCK_SCORE_INTER-29.425700-
DOCK_SCORE_INTER-44.359300-
DOCK_SCORE_INTER-26.888000-
DOCK_SCORE_INTER-27.648200-
DOCK_SCORE_INTER-19.828700-
DOCK_SCORE_INTER_KCAL-7.028211-
DOCK_SCORE_INTER_KCAL-10.595041-
DOCK_SCORE_INTER_KCAL-6.422091-
DOCK_SCORE_INTER_KCAL-6.603662-
DOCK_SCORE_INTER_KCAL-4.736006-
DOCK_SCORE_INTER_NORM-0.840735-
DOCK_SCORE_INTER_NORM-1.267410-
DOCK_SCORE_INTER_NORM-0.768227-
DOCK_SCORE_INTER_NORM-0.789949-
DOCK_SCORE_INTER_NORM-0.566535-
DOCK_SCORE_INTRA-0.790138-
DOCK_SCORE_INTRA-2.628060-
DOCK_SCORE_INTRA0.695958-
DOCK_SCORE_INTRA2.719650-
DOCK_SCORE_INTRA-0.168104-
DOCK_SCORE_INTRA_KCAL-0.188721-
DOCK_SCORE_INTRA_KCAL-0.627702-
DOCK_SCORE_INTRA_KCAL0.166227-
DOCK_SCORE_INTRA_KCAL0.649578-
DOCK_SCORE_INTRA_KCAL-0.040151-
DOCK_SCORE_INTRA_NORM-0.022575-
DOCK_SCORE_INTRA_NORM-0.075087-
DOCK_SCORE_INTRA_NORM0.019884-
DOCK_SCORE_INTRA_NORM0.077704-
DOCK_SCORE_INTRA_NORM-0.004803-
DOCK_SCORE_KCAL-7.216947-
DOCK_SCORE_KCAL-11.222753-
DOCK_SCORE_KCAL-6.255854-
DOCK_SCORE_KCAL-5.954073-
DOCK_SCORE_KCAL-4.776156-
DOCK_SCORE_NORM-0.863310-
DOCK_SCORE_NORM-1.342500-
DOCK_SCORE_NORM-0.748343-
DOCK_SCORE_NORM-0.712244-
DOCK_SCORE_NORM-0.571338-
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_FILET01_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET08_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET09_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET12_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET20_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_FORMULAC23H30N9O3+-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
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_HBD4.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HEAVY_ATOMS35.000000-
DOCK_SOURCE_HEAVY_ATOMS35.000000-
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_LOGP-0.588900-
DOCK_SOURCE_LOGP-0.588900-
DOCK_SOURCE_MW480.553000-
DOCK_SOURCE_MW480.553000-
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_NAMEOHD_Leishmania_134-
DOCK_SOURCE_NAMEOHD_Leishmania_134-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
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_SOURCE_TPSA191.720000-
DOCK_SOURCE_TPSA191.720000-
DOCK_STRAIN_DELTA71.095936-
DOCK_STRAIN_DELTA44.311078-
DOCK_STRAIN_DELTA46.212439-
DOCK_STRAIN_DELTA53.153066-
DOCK_STRAIN_DELTA66.162299-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT01-
DOCK_TARGETT08-
DOCK_TARGETT09-
DOCK_TARGETT12-
DOCK_TARGETT20-
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
T20 T20 selection_import_t20 1
native pose available
 2.106954150751916 -19.9968 6 0.75 - Best pose
T08 T08 selection_import_t08 1
native pose available
 2.6005507690572345 -46.9874 16 0.84 - Best pose
T01 T01 selection_import_t01 1
native pose available
 2.7678789075782624 -30.2159 17 0.81 - Best pose
T09 T09 selection_import_t09 1
native pose available
 3.4256406135165247 -26.192 18 0.86 - Best pose
T12 T12 selection_import_t12 1
native pose available
 5.2299146119473345 -24.9285 15 0.94 - Best pose
T20 — T20 1 poses · report selection_import_t20
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 2.106954150751916 -0.566535 -19.9968 7 13 6 0.75 0.00 0.00 0.00 - no geometry warning; 12 clashes; 7 protein contact clashes; high strain Δ 66.2 Open 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
19 2.6005507690572345 -1.26741 -46.9874 12 20 16 0.84 0.83 0.80 0.80 - no geometry warning; 15 clashes; 1 protein clash; 3 cofactor-context clashes; high strain Δ 44.3 Open pose
T01 — T01 1 poses · report selection_import_t01
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
17 2.7678789075782624 -0.840735 -30.2159 10 20 17 0.81 0.80 0.80 0.80 - no geometry warning; 14 clashes; 1 protein clash; 1 cofactor-context clash; high strain Δ 71.1 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
13 3.4256406135165247 -0.768227 -26.192 9 21 18 0.86 0.57 0.67 0.67 - no geometry warning; 12 clashes; 1 protein clash; high strain Δ 46.2 Open pose
T12 — T12 1 poses · report selection_import_t12
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
10 5.2299146119473345 -0.789949 -24.9285 10 20 15 0.94 0.33 0.40 0.50 - no geometry warning; 13 clashes; 3 protein clashes; high strain Δ 53.2 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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