FAIRMol

OHD_Leishmania_127

ID 647 ★ Native ligand

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

Native ligand reference

This compound is marked as the uploaded native ligand reference for docking comparison and docking IFP projection overlay.
Target T08 Report selection_import_t08
2D structure

SMILES: COC(=O)C1CCN(C(=O)c2ccc(N(CCCO)Cc3cnc4nc(N)nc(N)c4n3)cc2)CC1

Formula: C24H30N8O4 | MW: 494.5560000000004

LogP: 0.9984000000000006 | TPSA: 173.67999999999998

HBA/HBD: 11/3 | RotB: 8

InChIKey: NKRKEQBTIYLTPA-UHFFFAOYSA-N

Recognized patterns

Click a named motif to highlight it in the 2D depiction or launch reverse search.
Highlighted: 1 pattern Ionizable base 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 Alcohol Tertiary amine ×2 Lactam Ether

Ring system

Benzene Pyrimidine Pyrazine Pipecolinyl ring

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.857405-
DOCK_BASE_INTER_RANK-0.780992-
DOCK_BASE_INTER_RANK-0.794938-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT20.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CLASH_COUNT16.000000-
DOCK_CONTACT_COUNT22.000000-
DOCK_CONTACT_COUNT21.000000-
DOCK_CONTACT_COUNT15.000000-
DOCK_EXPERIMENTT04-
DOCK_EXPERIMENTT03-
DOCK_EXPERIMENTT01-
DOCK_EXPERIMENT_ID4-
DOCK_EXPERIMENT_ID1-
DOCK_EXPERIMENT_ID3-
DOCK_FINAL_RANK4.731024-
DOCK_FINAL_RANK1.843412-
DOCK_FINAL_RANK4.392977-
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:ALA321-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG171-
DOCK_IFP::A:ARG971-
DOCK_IFP::A:ASN651-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP2321-
DOCK_IFP::A:ASP521-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:GLN361-
DOCK_IFP::A:GLU311-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:HIS2411-
DOCK_IFP::A:ILE451-
DOCK_IFP::A:ILE611-
DOCK_IFP::A:ILE81-
DOCK_IFP::A:LEU1881-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU2261-
DOCK_IFP::A:LEU2291-
DOCK_IFP::A:LEU231-
DOCK_IFP::A:LEU681-
DOCK_IFP::A:LEU941-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS1781-
DOCK_IFP::A:LYS1981-
DOCK_IFP::A:LYS571-
DOCK_IFP::A:LYS951-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET2331-
DOCK_IFP::A:MET531-
DOCK_IFP::A:NAP2011-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NDP3011-
DOCK_IFP::A:NDP3021-
DOCK_IFP::A:PHE1131-
DOCK_IFP::A:PHE1351-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE321-
DOCK_IFP::A:PHE351-
DOCK_IFP::A:PHE551-
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:PRO621-
DOCK_IFP::A:PRO881-
DOCK_IFP::A:PRO991-
DOCK_IFP::A:PRO991-
DOCK_IFP::A:SER1111-
DOCK_IFP::A:SER2071-
DOCK_IFP::A:SER2071-
DOCK_IFP::A:SER601-
DOCK_IFP::A:SER861-
DOCK_IFP::A:SER951-
DOCK_IFP::A:SER951-
DOCK_IFP::A:THR1371-
DOCK_IFP::A:THR1801-
DOCK_IFP::A:THR571-
DOCK_IFP::A:THR831-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TYR1221-
DOCK_IFP::A:TYR1621-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR1781-
DOCK_IFP::A:TYR1911-
DOCK_IFP::A:TYR1941-
DOCK_IFP::A:TYR341-
DOCK_IFP::A:TYR981-
DOCK_IFP::A:TYR981-
DOCK_IFP::A:VAL1161-
DOCK_IFP::A:VAL1361-
DOCK_IFP::A:VAL1561-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL2301-
DOCK_IFP::A:VAL301-
DOCK_IFP::A:VAL311-
DOCK_IFP::A:VAL871-
DOCK_IFP::A:VAL91-
DOCK_IFP::D:ARG2871-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.695401-
DOCK_MAX_CLASH_OVERLAP0.682172-
DOCK_MAX_CLASH_OVERLAP0.682260-
DOCK_NATIVE_REFERENCE1-
DOCK_NATIVE_REFERENCE1-
DOCK_NATIVE_REPORT_IDselection_import_t07-
DOCK_NATIVE_REPORT_IDselection_import_t08-
DOCK_NATIVE_TARGETT07-
DOCK_NATIVE_TARGETT08-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK4.332295-
DOCK_PRE_RANK4.668859-
DOCK_PRE_RANK1.785602-
DOCK_PRIMARY_POSE_ID5418-
DOCK_PRIMARY_POSE_ID12-
DOCK_PRIMARY_POSE_ID4741-
DOCK_PRIMARY_POSE_ID1365-
DOCK_PRIMARY_POSE_ID2039-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t04-
DOCK_REPORT_IDselection_import_t01-
DOCK_REPORT_IDselection_import_t03-
DOCK_RESIDUE_CONTACTSA:ALA32;A:ARG97;A:ASP52;A:ILE45;A:LEU94;A:LYS57;A:LYS95;A:MET53;A:NDP301;A:PHE55;A:PHE56;A:PHE91;A:PRO88;A:SER86;A:THR180;A:THR83;A:TYR162;A:TYR178;A:VAL156;A:VAL30;A:VAL31;A:VAL87-
DOCK_RESIDUE_CONTACTSA:ALA10;A:ASN65;A:GLN36;A:GLU31;A:ILE61;A:ILE8;A:LEU23;A:LEU68;A:NAP201;A:PHE135;A:PHE32;A:PHE35;A:PRO62;A:SER60;A:THR137;A:THR57;A:TYR122;A:TYR34;A:VAL116;A:VAL136;A:VAL9-
DOCK_RESIDUE_CONTACTSA:ARG17;A:ASP232;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:LYS198;A:MET233;A:NDP302;A:PHE113;A:SER111;A:TYR191;A:TYR194;A:VAL230;D:ARG287-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3ncncc3n2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3ncncc3n2)cc1)N1CCCCC1-
DOCK_SCAFFOLDO=C(c1ccc(NCc2cnc3ncncc3n2)cc1)N1CCCCC1-
DOCK_SCORE-31.400400-
DOCK_SCORE-30.784600-
DOCK_SCORE-23.634200-
DOCK_SCORE_INTER-30.866600-
DOCK_SCORE_INTER-28.617800-
DOCK_SCORE_INTER-28.115700-
DOCK_SCORE_INTER_KCAL-7.372364-
DOCK_SCORE_INTER_KCAL-6.835247-
DOCK_SCORE_INTER_KCAL-6.715322-
DOCK_SCORE_INTER_NORM-0.794938-
DOCK_SCORE_INTER_NORM-0.780992-
DOCK_SCORE_INTER_NORM-0.857405-
DOCK_SCORE_INTRA-2.782580-
DOCK_SCORE_INTRA-2.668850-
DOCK_SCORE_INTRA7.232360-
DOCK_SCORE_INTRA_KCAL-0.664608-
DOCK_SCORE_INTRA_KCAL1.727420-
DOCK_SCORE_INTRA_KCAL-0.637444-
DOCK_SCORE_INTRA_NORM0.200899-
DOCK_SCORE_INTRA_NORM-0.077294-
DOCK_SCORE_INTRA_NORM-0.074135-
DOCK_SCORE_KCAL-7.499860-
DOCK_SCORE_KCAL-5.644934-
DOCK_SCORE_KCAL-7.352779-
DOCK_SCORE_NORM-0.656506-
DOCK_SCORE_NORM-0.855127-
DOCK_SCORE_NORM-0.872232-
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_FILET01_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET03_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET04_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC24H30N8O4-
DOCK_SOURCE_FORMULAC24H30N8O4-
DOCK_SOURCE_FORMULAC24H30N8O4-
DOCK_SOURCE_HBA11.000000-
DOCK_SOURCE_HBA11.000000-
DOCK_SOURCE_HBA11.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HBD3.000000-
DOCK_SOURCE_HEAVY_ATOMS36.000000-
DOCK_SOURCE_HEAVY_ATOMS36.000000-
DOCK_SOURCE_HEAVY_ATOMS36.000000-
DOCK_SOURCE_LOGP0.998400-
DOCK_SOURCE_LOGP0.998400-
DOCK_SOURCE_LOGP0.998400-
DOCK_SOURCE_MW494.556000-
DOCK_SOURCE_MW494.556000-
DOCK_SOURCE_MW494.556000-
DOCK_SOURCE_NAMEOHD_Leishmania_127-
DOCK_SOURCE_NAMEOHD_Leishmania_127-
DOCK_SOURCE_NAMEOHD_Leishmania_127-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_RINGS4.000000-
DOCK_SOURCE_TPSA173.680000-
DOCK_SOURCE_TPSA173.680000-
DOCK_SOURCE_TPSA173.680000-
DOCK_STRAIN_DELTA38.470634-
DOCK_STRAIN_DELTA40.433378-
DOCK_STRAIN_DELTA39.771409-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT03-
DOCK_TARGETT04-
DOCK_TARGETT01-
EXACT_MASS494.2390014399999Da
FORMULAC24H30N8O4-
HBA11-
HBD3-
LOGP0.9984000000000006-
MOL_WEIGHT494.5560000000004g/mol
QED_SCORE0.38106119031911095-
ROTATABLE_BONDS8-
TPSA173.67999999999998A^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
T03 T03 selection_import_t03 1
native pose available
 1.8434120926030078 -30.7846 19 0.95 - Best pose
T04 T04 selection_import_t04 1
native pose available
 4.392976696001355 -23.6342 14 0.74 - Best pose
T01 T01 selection_import_t01 1
native pose available
 4.73102392041183 -31.4004 18 0.86 - Best pose
T07 T07 selection_import_t07 1
native pose available
 - - 19 1.00 - Best pose
T08 T08 selection_import_t08 1
native pose available
 - - 19 1.00 - Best 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
10 1.8434120926030078 -0.780992 -30.7846 12 22 19 0.95 0.57 0.80 0.80 - no geometry warning; 16 clashes; 5 protein contact clashes; high strain Δ 38.5 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
6 4.392976696001355 -0.857405 -23.6342 6 15 14 0.74 0.67 0.80 0.80 - no geometry warning; 20 clashes; 2 protein clashes; 3 cofactor-context clashes; high strain Δ 39.8 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
12 4.73102392041183 -0.794938 -31.4004 10 21 18 0.86 0.20 0.40 0.40 - no geometry warning; 16 clashes; 3 protein clashes; high strain Δ 40.4 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
- ★ Native - - - 6 19 19 1.00 1.00 1.00 1.00 - no Native reference ligand 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
- ★ Native - - - 6 19 19 1.00 1.00 1.00 1.00 - no Native reference ligand 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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