FAIRMol

OHD_Leishmania_19

ID 2683

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

SMILES: Cc1ncc([N+](=O)O)n1CCSCCOC(=O)c1cc(O)c(O)c(O)c1

Formula: C15H18N3O7S+ | MW: 384.3900000000001

LogP: 1.6981199999999994 | TPSA: 145.12

HBA/HBD: 8/4 | RotB: 8

InChIKey: YRXJKUKGBNFOMW-UHFFFAOYSA-O

Recognized patterns

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

Bio motif

Catechol ×2 Resorcinol H-bond acceptor N ×2 H-bond acceptor O ×3 H-bond donor ×4 Gatekeeper aromatic Metal chelator PAINS — catechol ×2

Functional group

Carbonyl Ester Phenol ×3 Sulfide Ether

Ring system

Benzene

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-1.107140-
DOCK_BASE_INTER_RANK-1.184760-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT6.000000-
DOCK_CLASH_COUNT6.000000-
DOCK_CONTACT_COUNT17.000000-
DOCK_CONTACT_COUNT12.000000-
DOCK_EXPERIMENTT21-
DOCK_EXPERIMENTT07-
DOCK_EXPERIMENT_ID7-
DOCK_EXPERIMENT_ID21-
DOCK_FINAL_RANK-0.172806-
DOCK_FINAL_RANK3.028251-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_IFP::A:ARG1371-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG1411-
DOCK_IFP::A:ASN1031-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:GLU2171-
DOCK_IFP::A:HIS1021-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:MET2131-
DOCK_IFP::A:MET981-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:PHE1711-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:SER951-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR941-
DOCK_IFP::B:ARG1131-
DOCK_IFP::B:ASP101-
DOCK_IFP::B:CYS691-
DOCK_IFP::B:GLY701-
DOCK_IFP::B:GLY721-
DOCK_IFP::B:GLY741-
DOCK_IFP::B:HIS111-
DOCK_IFP::B:ILE731-
DOCK_IFP::B:PRO121-
DOCK_IFP::B:SER711-
DOCK_IFP::B:TYR461-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.610749-
DOCK_MAX_CLASH_OVERLAP0.607766-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.922886-
DOCK_PRE_RANK-0.289298-
DOCK_PRIMARY_POSE_ID4064-
DOCK_PRIMARY_POSE_ID13559-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t21-
DOCK_REPORT_IDselection_import_t07-
DOCK_RESIDUE_CONTACTSA:ARG137;A:ARG141;A:ASN103;A:HIS102;A:MET98;A:TYR94;B:ARG113;B:ASP10;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER71;B:TYR46-
DOCK_RESIDUE_CONTACTSA:ARG14;A:ASP161;A:GLU217;A:LEU209;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:SER95;A:TRP221;A:TYR174-
DOCK_SCAFFOLDO=C(OCCSCCn1ccnc1)c1ccccc1-
DOCK_SCAFFOLDO=C(OCCSCCn1ccnc1)c1ccccc1-
DOCK_SCORE-28.133900-
DOCK_SCORE-25.543500-
DOCK_SCORE_INTER-28.785700-
DOCK_SCORE_INTER-30.803800-
DOCK_SCORE_INTER_KCAL-6.875349-
DOCK_SCORE_INTER_KCAL-7.357364-
DOCK_SCORE_INTER_NORM-1.107140-
DOCK_SCORE_INTER_NORM-1.184760-
DOCK_SCORE_INTRA3.242200-
DOCK_SCORE_INTRA2.669880-
DOCK_SCORE_INTRA_KCAL0.637690-
DOCK_SCORE_INTRA_KCAL0.774387-
DOCK_SCORE_INTRA_NORM0.124700-
DOCK_SCORE_INTRA_NORM0.102688-
DOCK_SCORE_KCAL-6.719669-
DOCK_SCORE_KCAL-6.100963-
DOCK_SCORE_NORM-0.982441-
DOCK_SCORE_NORM-1.082070-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_RESTR_NORM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SCORE_SYSTEM_NORM0.000000-
DOCK_SELECTION_EXCLUDED0-
DOCK_SELECTION_EXCLUDED0-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SEVERE_CLASH_COUNT0.000000-
DOCK_SOURCE_FILET21_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET07_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC15H18N3O7S+-
DOCK_SOURCE_FORMULAC15H18N3O7S+-
DOCK_SOURCE_HBA8.000000-
DOCK_SOURCE_HBA8.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HBD4.000000-
DOCK_SOURCE_HEAVY_ATOMS26.000000-
DOCK_SOURCE_HEAVY_ATOMS26.000000-
DOCK_SOURCE_LOGP1.698120-
DOCK_SOURCE_LOGP1.698120-
DOCK_SOURCE_MW384.390000-
DOCK_SOURCE_MW384.390000-
DOCK_SOURCE_NAMEOHD_Leishmania_19-
DOCK_SOURCE_NAMEOHD_Leishmania_19-
DOCK_SOURCE_RINGS2.000000-
DOCK_SOURCE_RINGS2.000000-
DOCK_SOURCE_TPSA145.120000-
DOCK_SOURCE_TPSA145.120000-
DOCK_STRAIN_DELTA61.989728-
DOCK_STRAIN_DELTA57.834916-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT07-
DOCK_TARGETT21-
EXACT_MASS384.08599733609Da
FORMULAC15H18N3O7S+-
HBA8-
HBD4-
LOGP1.6981199999999994-
MOL_WEIGHT384.3900000000001g/mol
QED_SCORE0.23109369693139487-
ROTATABLE_BONDS8-
TPSA145.12A^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
T07 T07 selection_import_t07 1
native pose available
 -0.1728060123477814 -28.1339 11 0.58 - Best pose
T21 T21 selection_import_t21 1
native pose available
 3.028251281531995 -25.5435 13 0.93 - Best 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
1 -0.1728060123477814 -1.18476 -28.1339 11 12 11 0.58 0.67 0.60 0.60 - no geometry warning; 6 clashes; 1 protein contact clash; 2 severe cofactor-context clashes; high strain Δ 62.0 Open pose
T21 — T21 1 poses · report selection_import_t21
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
1 3.028251281531995 -1.10714 -25.5435 11 17 13 0.93 0.50 0.67 0.88 - no geometry warning; 6 clashes; 2 protein clashes; high strain Δ 57.8 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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