FAIRMol

OHD_Leishmania_135

ID 2648

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

SMILES: CCOC(=O)C1CCN(C(=O)c2ccc(N(CC)Cc3cnc4[nH+]c(N)nc(N)c4n3)cc2)CC1

Formula: C24H31N8O3+ | MW: 479.56500000000034

LogP: 1.4451 | TPSA: 154.7

HBA/HBD: 9/2 | RotB: 7

InChIKey: HEPDQIIFCBFHRJ-UHFFFAOYSA-O

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern H-bond acceptor N Clear highlight

Bio motif

ATP mimic pyrimidine N-Methyl amide ×2 H-bond acceptor N ×6 H-bond acceptor O ×3 H-bond donor ×3 Gatekeeper aromatic Ionizable base ×2 Metal chelator ×2 P-gp efflux flag ×2

Functional group

Carbonyl ×2 Amide Ester Primary amine ×2 Tertiary amine ×2 Lactam Ether

Ring system

Benzene Pyrimidine Pyrazine Pipecolinyl ring

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.713349-
DOCK_BASE_INTER_RANK-1.052550-
DOCK_BASE_INTER_RANK-1.021330-
DOCK_BASE_INTER_RANK-0.794446-
DOCK_BASE_INTER_RANK-0.679060-
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_COUNT16.000000-
DOCK_CLASH_COUNT15.000000-
DOCK_CLASH_COUNT14.000000-
DOCK_CLASH_COUNT18.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT20.000000-
DOCK_CONTACT_COUNT19.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT21.000000-
DOCK_EXPERIMENTT06-
DOCK_EXPERIMENTT07-
DOCK_EXPERIMENTT08-
DOCK_EXPERIMENTT09-
DOCK_EXPERIMENTT11-
DOCK_EXPERIMENT_ID6-
DOCK_EXPERIMENT_ID7-
DOCK_EXPERIMENT_ID8-
DOCK_EXPERIMENT_ID9-
DOCK_EXPERIMENT_ID11-
DOCK_FINAL_RANK4.134283-
DOCK_FINAL_RANK2.326527-
DOCK_FINAL_RANK2.193963-
DOCK_FINAL_RANK4.649434-
DOCK_FINAL_RANK4.955806-
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:ALA2121-
DOCK_IFP::A:ALA341-
DOCK_IFP::A:ALA401-
DOCK_IFP::A:ALA961-
DOCK_IFP::A:ARG1001-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG591-
DOCK_IFP::A:ASN1251-
DOCK_IFP::A:ASP1271-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP541-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:GLN1241-
DOCK_IFP::A:GLN561-
DOCK_IFP::A:GLU1921-
DOCK_IFP::A:GLU2171-
DOCK_IFP::A:GLU2171-
DOCK_IFP::A:GLY1911-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:HIS1441-
DOCK_IFP::A:HIS1821-
DOCK_IFP::A:HIS2221-
DOCK_IFP::A:ILE1261-
DOCK_IFP::A:ILE1601-
DOCK_IFP::A:ILE471-
DOCK_IFP::A:ILE481-
DOCK_IFP::A:LEU1941-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU901-
DOCK_IFP::A:LEU951-
DOCK_IFP::A:LEU971-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS2201-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET551-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE1891-
DOCK_IFP::A:PHE1901-
DOCK_IFP::A:PHE511-
DOCK_IFP::A:PHE581-
DOCK_IFP::A:PHE741-
DOCK_IFP::A:PHE941-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:PRO2231-
DOCK_IFP::A:PRO521-
DOCK_IFP::A:PRO991-
DOCK_IFP::A:SER2071-
DOCK_IFP::A:SER891-
DOCK_IFP::A:SER951-
DOCK_IFP::A:SER951-
DOCK_IFP::A:THR1841-
DOCK_IFP::A:THR711-
DOCK_IFP::A:THR861-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TYR1661-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR571-
DOCK_IFP::A:VAL1871-
DOCK_IFP::A:VAL1881-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL2211-
DOCK_IFP::A:VAL321-
DOCK_IFP::A:VAL331-
DOCK_IFP::B:ALA321-
DOCK_IFP::B:ARG971-
DOCK_IFP::B:ASP521-
DOCK_IFP::B:CYS1551-
DOCK_IFP::B:GLY1571-
DOCK_IFP::B:ILE451-
DOCK_IFP::B:LEU941-
DOCK_IFP::B:LYS571-
DOCK_IFP::B:LYS951-
DOCK_IFP::B:MET531-
DOCK_IFP::B:PHE551-
DOCK_IFP::B:PHE561-
DOCK_IFP::B:PHE911-
DOCK_IFP::B:SER861-
DOCK_IFP::B:THR1801-
DOCK_IFP::B:THR831-
DOCK_IFP::B:TYR1621-
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_OVERLAP0.729187-
DOCK_MAX_CLASH_OVERLAP0.690092-
DOCK_MAX_CLASH_OVERLAP0.690113-
DOCK_MAX_CLASH_OVERLAP0.677287-
DOCK_MAX_CLASH_OVERLAP0.677277-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK4.096676-
DOCK_PRE_RANK2.273639-
DOCK_PRE_RANK2.107204-
DOCK_PRE_RANK4.540391-
DOCK_PRE_RANK4.846875-
DOCK_PRIMARY_POSE_ID3400-
DOCK_PRIMARY_POSE_ID4080-
DOCK_PRIMARY_POSE_ID4761-
DOCK_PRIMARY_POSE_ID5432-
DOCK_PRIMARY_POSE_ID6788-
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_t06-
DOCK_REPORT_IDselection_import_t07-
DOCK_REPORT_IDselection_import_t08-
DOCK_REPORT_IDselection_import_t09-
DOCK_REPORT_IDselection_import_t11-
DOCK_RESIDUE_CONTACTSA:ALA34;A:ARG100;A:ARG59;A:ASP54;A:GLN56;A:HIS182;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:PRO52;A:SER89;A:THR184;A:THR86;A:TYR166;A:TYR57;A:VAL32;A:VAL33-
DOCK_RESIDUE_CONTACTSA:ALA96;A:ARG14;A:ASP161;A:CYS168;A:GLU217;A:GLY205;A:LEU208;A:LEU209;A:LYS178;A:LYS220;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:SER207;A:SER95;A:TRP221;A:TYR174;A:VAL206-
DOCK_RESIDUE_CONTACTSA:ALA212;A:ARG14;A:ASP161;A:CYS168;A:GLU217;A:GLY205;A:LEU208;A:LEU209;A:LYS178;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:PRO99;A:SER95;A:TRP221;A:TYR174;A:VAL206-
DOCK_RESIDUE_CONTACTSA:NDP301;B:ALA32;B:ARG97;B:ASP52;B:CYS155;B:GLY157;B:ILE45;B:LEU94;B:LYS57;B:LYS95;B:MET53;B:PHE55;B:PHE56;B:PHE91;B:SER86;B:THR180;B:THR83;B:TYR162;B:VAL156;B:VAL30;B:VAL31;B:VAL87-
DOCK_RESIDUE_CONTACTSA:ALA40;A:ASN125;A:ASP127;A:GLN124;A:GLU192;A:GLY191;A:HIS144;A:HIS222;A:ILE126;A:ILE48;A:LEU194;A:LEU95;A:PHE189;A:PHE190;A:PHE51;A:PHE74;A:PRO223;A:THR71;A:VAL187;A:VAL188;A:VAL221-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3[nH+]cncc3n2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3ncncc3[nH+]2)cc1)N1CCCCC1-
DOCK_SCORE-16.154200-
DOCK_SCORE-36.641400-
DOCK_SCORE-33.722900-
DOCK_SCORE-29.576600-
DOCK_SCORE-20.175900-
DOCK_SCORE_INTER-24.967200-
DOCK_SCORE_INTER-36.839400-
DOCK_SCORE_INTER-35.746400-
DOCK_SCORE_INTER-27.805600-
DOCK_SCORE_INTER-23.767100-
DOCK_SCORE_INTER_KCAL-5.963316-
DOCK_SCORE_INTER_KCAL-8.798943-
DOCK_SCORE_INTER_KCAL-8.537885-
DOCK_SCORE_INTER_KCAL-6.641256-
DOCK_SCORE_INTER_KCAL-5.676677-
DOCK_SCORE_INTER_NORM-0.713349-
DOCK_SCORE_INTER_NORM-1.052550-
DOCK_SCORE_INTER_NORM-1.021330-
DOCK_SCORE_INTER_NORM-0.794446-
DOCK_SCORE_INTER_NORM-0.679060-
DOCK_SCORE_INTRA8.654600-
DOCK_SCORE_INTRA0.197995-
DOCK_SCORE_INTRA2.023500-
DOCK_SCORE_INTRA-1.771030-
DOCK_SCORE_INTRA3.591190-
DOCK_SCORE_INTRA_KCAL2.067117-
DOCK_SCORE_INTRA_KCAL0.047290-
DOCK_SCORE_INTRA_KCAL0.483305-
DOCK_SCORE_INTRA_KCAL-0.423003-
DOCK_SCORE_INTRA_KCAL0.857741-
DOCK_SCORE_INTRA_NORM0.247274-
DOCK_SCORE_INTRA_NORM0.005657-
DOCK_SCORE_INTRA_NORM0.057814-
DOCK_SCORE_INTRA_NORM-0.050601-
DOCK_SCORE_INTRA_NORM0.102605-
DOCK_SCORE_KCAL-3.858366-
DOCK_SCORE_KCAL-8.751652-
DOCK_SCORE_KCAL-8.054580-
DOCK_SCORE_KCAL-7.064253-
DOCK_SCORE_KCAL-4.818933-
DOCK_SCORE_NORM-0.461548-
DOCK_SCORE_NORM-1.046900-
DOCK_SCORE_NORM-0.963512-
DOCK_SCORE_NORM-0.845047-
DOCK_SCORE_NORM-0.576455-
DOCK_SCORE_RESTR0.158455-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR_NORM0.004527-
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_FILET06_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET07_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_FILET11_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC24H31N8O3+-
DOCK_SOURCE_FORMULAC24H31N8O3+-
DOCK_SOURCE_FORMULAC24H31N8O3+-
DOCK_SOURCE_FORMULAC24H31N8O3+-
DOCK_SOURCE_FORMULAC24H31N8O3+-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBA9.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
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_LOGP1.445100-
DOCK_SOURCE_LOGP1.445100-
DOCK_SOURCE_LOGP1.445100-
DOCK_SOURCE_LOGP1.445100-
DOCK_SOURCE_LOGP1.445100-
DOCK_SOURCE_MW479.565000-
DOCK_SOURCE_MW479.565000-
DOCK_SOURCE_MW479.565000-
DOCK_SOURCE_MW479.565000-
DOCK_SOURCE_MW479.565000-
DOCK_SOURCE_NAMEOHD_Leishmania_135-
DOCK_SOURCE_NAMEOHD_Leishmania_135-
DOCK_SOURCE_NAMEOHD_Leishmania_135-
DOCK_SOURCE_NAMEOHD_Leishmania_135-
DOCK_SOURCE_NAMEOHD_Leishmania_135-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA154.700000-
DOCK_SOURCE_TPSA154.700000-
DOCK_SOURCE_TPSA154.700000-
DOCK_SOURCE_TPSA154.700000-
DOCK_SOURCE_TPSA154.700000-
DOCK_STRAIN_DELTA28.229409-
DOCK_STRAIN_DELTA36.170872-
DOCK_STRAIN_DELTA50.666469-
DOCK_STRAIN_DELTA59.216661-
DOCK_STRAIN_DELTA59.175204-
DOCK_STRAIN_OK1-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT06-
DOCK_TARGETT07-
DOCK_TARGETT08-
DOCK_TARGETT09-
DOCK_TARGETT11-
EXACT_MASS479.25136327209Da
FORMULAC24H31N8O3+-
HBA9-
HBD2-
LOGP1.4451-
MOL_WEIGHT479.56500000000034g/mol
QED_SCORE0.4789210563057314-
ROTATABLE_BONDS7-
TPSA154.7A^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
 2.1939628179865047 -33.7229 17 0.89 - Best pose
T07 T07 selection_import_t07 1
native pose available
 2.3265272319011476 -36.6414 17 0.89 - Best pose
T06 T06 selection_import_t06 1
native pose available
 4.134283078679938 -16.1542 18 0.86 - Best pose
T09 T09 selection_import_t09 1
native pose available
 4.649433580819565 -29.5766 20 0.95 - Best pose
T11 T11 selection_import_t11 1
native pose available
 4.955806310701608 -20.1759 14 0.78 - 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
20 2.1939628179865047 -1.02133 -33.7229 9 19 17 0.89 0.83 0.80 0.80 - no geometry warning; 14 clashes; 1 protein clash; 4 cofactor-context clashes; high strain Δ 50.7 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
17 2.3265272319011476 -1.05255 -36.6414 7 20 17 0.89 0.83 0.80 0.80 - no geometry warning; 15 clashes; 1 protein clash; 2 cofactor-context clashes; high strain Δ 36.2 Open 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
14 4.134283078679938 -0.713349 -16.1542 6 22 18 0.86 0.60 0.75 0.75 - no geometry warning; 16 clashes; 1 protein clash; moderate strain Δ 28.2 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
14 4.649433580819565 -0.794446 -29.5766 6 22 20 0.95 0.57 0.67 0.67 - no geometry warning; 18 clashes; 2 protein clashes; high strain Δ 59.2 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
14 4.955806310701608 -0.67906 -20.1759 5 21 14 0.78 0.40 0.40 0.75 - no geometry warning; 16 clashes; 2 protein clashes; high strain Δ 59.2 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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