FAIRMol

Z31287535

ID 2140

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

SMILES: CCOc1ccc(N2C(=O)/C(=C/NNC(=O)[C@H]3COc4ccccc4O3)c3ccccc3C2=O)cc1

Formula: C27H23N3O6 | MW: 485.4960000000002

LogP: 3.0740000000000016 | TPSA: 106.20000000000002

HBA/HBD: 7/2 | RotB: 6

InChIKey: QWUNEJRBNWSMST-INJUALFYSA-N

Recognized patterns

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

Bio motif

Acrylamide Catechol Michael acceptor Hinge binder (C=O-NH) Hinge binder (NH-C=O) N-Methyl amide ×4 Aza-Michael acceptor H-bond acceptor N H-bond acceptor O ×6 H-bond donor ×2 Gatekeeper aromatic ×3 Ionizable base Michael acceptor (extended) Metal chelator ×3 P-gp efflux flag

Functional group

Carbonyl ×3 Amide ×3 Tertiary amine Lactam ×2 Aryl ether ×3 Imide Enone Hydrazine Ether ×3 Alkene

Ring system

Benzene ×3 Benzodioxane

Properties

NameValueUnit
DOCK_BASE_INTER_RANK-0.997526-
DOCK_BASE_INTER_RANK-0.794939-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_BOND_LENGTH_OUTLIERS0.000000-
DOCK_CLASH_COUNT22.000000-
DOCK_CLASH_COUNT24.000000-
DOCK_CONTACT_COUNT16.000000-
DOCK_CONTACT_COUNT18.000000-
DOCK_EXPERIMENTT08-
DOCK_EXPERIMENTT05-
DOCK_EXPERIMENT_ID5-
DOCK_EXPERIMENT_ID8-
DOCK_FINAL_RANK3.018276-
DOCK_FINAL_RANK2.143592-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOMETRY_ALERTwarning-
DOCK_GEOM_OK0-
DOCK_GEOM_OK0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_HARD_GEOMETRY_FAIL0-
DOCK_IFP::A:ARG141-
DOCK_IFP::A:ARG171-
DOCK_IFP::A:ASP1611-
DOCK_IFP::A:ASP1811-
DOCK_IFP::A:CYS1681-
DOCK_IFP::A:GLY2051-
DOCK_IFP::A:GLY2251-
DOCK_IFP::A:HIS2411-
DOCK_IFP::A:LEU1881-
DOCK_IFP::A:LEU2081-
DOCK_IFP::A:LEU2091-
DOCK_IFP::A:LEU2261-
DOCK_IFP::A:LEU2291-
DOCK_IFP::A:LEU2631-
DOCK_IFP::A:LYS131-
DOCK_IFP::A:MET1631-
DOCK_IFP::A:MET1831-
DOCK_IFP::A:MET2331-
DOCK_IFP::A:NAP3011-
DOCK_IFP::A:NDP3021-
DOCK_IFP::A:PHE1131-
DOCK_IFP::A:PHE971-
DOCK_IFP::A:PRO2101-
DOCK_IFP::A:SER2071-
DOCK_IFP::A:SER951-
DOCK_IFP::A:TRP2211-
DOCK_IFP::A:TYR1741-
DOCK_IFP::A:TYR1911-
DOCK_IFP::A:TYR1941-
DOCK_IFP::A:VAL2061-
DOCK_IFP::A:VAL2301-
DOCK_IFP::A:VAL2371-
DOCK_IFP::D:ARG2871-
DOCK_IFP::D:HIS2671-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_IMPORT_SCOPEbest_by_name-
DOCK_MAX_CLASH_OVERLAP0.663229-
DOCK_MAX_CLASH_OVERLAP0.656897-
DOCK_POSE_COUNT1-
DOCK_POSE_COUNT1-
DOCK_PRE_RANK2.082985-
DOCK_PRE_RANK2.976227-
DOCK_PRIMARY_POSE_ID5140-
DOCK_PRIMARY_POSE_ID3061-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_RANKING_MODEinter_strain_penalized-
DOCK_REPORT_IDselection_import_t08-
DOCK_REPORT_IDselection_import_t05-
DOCK_RESIDUE_CONTACTSA:ARG14;A:ASP161;A:CYS168;A:GLY205;A:LEU208;A:LEU209;A:LEU263;A:LYS13;A:MET163;A:NAP301;A:PHE97;A:PRO210;A:SER207;A:SER95;A:TRP221;A:TYR174;A:VAL206;D:HIS267-
DOCK_RESIDUE_CONTACTSA:ARG17;A:ASP181;A:GLY225;A:HIS241;A:LEU188;A:LEU226;A:LEU229;A:MET183;A:MET233;A:NDP302;A:PHE113;A:TYR191;A:TYR194;A:VAL230;A:VAL237;D:ARG287-
DOCK_SCAFFOLDO=C1C(=CNN=CC2COc3ccccc3O2)c2ccccc2C(=O)N1c1ccccc1-
DOCK_SCAFFOLDO=C(NNC=C1C(=O)N(c2ccccc2)C(=O)c2ccccc21)C1COc2ccccc2O1-
DOCK_SCORE-28.749300-
DOCK_SCORE-34.532300-
DOCK_SCORE_INTER-28.617800-
DOCK_SCORE_INTER-35.910900-
DOCK_SCORE_INTER_KCAL-8.577175-
DOCK_SCORE_INTER_KCAL-6.835247-
DOCK_SCORE_INTER_NORM-0.794939-
DOCK_SCORE_INTER_NORM-0.997526-
DOCK_SCORE_INTRA1.378630-
DOCK_SCORE_INTRA-0.131451-
DOCK_SCORE_INTRA_KCAL0.329280-
DOCK_SCORE_INTRA_KCAL-0.031397-
DOCK_SCORE_INTRA_NORM-0.003651-
DOCK_SCORE_INTRA_NORM0.038295-
DOCK_SCORE_KCAL-8.247902-
DOCK_SCORE_KCAL-6.866655-
DOCK_SCORE_NORM-0.798591-
DOCK_SCORE_NORM-0.959231-
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_FILET08_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FILET05_top5_kcal_zscore_compound_names.sdf-
DOCK_SOURCE_FORMULAC27H23N3O6-
DOCK_SOURCE_FORMULAC27H23N3O6-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBA7.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HBD2.000000-
DOCK_SOURCE_HEAVY_ATOMS36.000000-
DOCK_SOURCE_HEAVY_ATOMS36.000000-
DOCK_SOURCE_LOGP3.074000-
DOCK_SOURCE_LOGP3.914300-
DOCK_SOURCE_MW485.496000-
DOCK_SOURCE_MW485.496000-
DOCK_SOURCE_NAMEZ31287535-
DOCK_SOURCE_NAMEZ31287535-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_RINGS5.000000-
DOCK_SOURCE_TPSA109.690000-
DOCK_SOURCE_TPSA106.200000-
DOCK_STRAIN_DELTA39.738053-
DOCK_STRAIN_DELTA30.696978-
DOCK_STRAIN_OK0-
DOCK_STRAIN_OK0-
DOCK_TARGETT05-
DOCK_TARGETT08-
EXACT_MASS485.158685456Da
FORMULAC27H23N3O6-
HBA7-
HBD2-
LOGP3.0740000000000016-
MOL_WEIGHT485.4960000000002g/mol
QED_SCORE0.31403027982737286-
ROTATABLE_BONDS6-
TPSA106.20000000000002A^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
T05 T05 selection_import_t05 1
native pose available
 2.14359219316684 -28.7493 13 0.76 - Best pose
T08 T08 selection_import_t08 1
native pose available
 3.018275984807697 -34.5323 14 0.74 - Best pose
T05 — T05 1 poses · report selection_import_t05
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
351 2.14359219316684 -0.794939 -28.7493 3 16 13 0.76 0.29 0.33 0.40 - no geometry warning; 24 clashes; 2 protein contact clashes; 1 cofactor-context clash; high strain Δ 39.7 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
399 3.018275984807697 -0.997526 -34.5323 10 18 14 0.74 0.17 0.20 0.60 - no geometry warning; 22 clashes; 10 protein contact clashes; 1 cofactor-context clash; high strain Δ 30.7 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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