Compound detail

SMILES: COC(=O)c1cn(-c2ccc(O)cc2)c(=O)c2cc(NC(=O)OCc3ccccc3)c(=O)oc12

Formula: C24H18N2O8 | MW: 462.4140000000002

LogP: 3.184800000000001 | TPSA: 137.07000000000002

HBA/HBD: 8/2 | RotB: 5

InChIKey: OCSDSBOGXSTRHA-UHFFFAOYSA-N

Recognized patterns

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

Highlighted: 1 pattern H-bond acceptor O Clear highlight

Bio motif

Hinge binder (C=O-NH) Hinge binder (NH-C=O) H-bond acceptor N H-bond acceptor O ×7 H-bond donor ×2 Gatekeeper aromatic ×2 Metal chelator ×3

Functional group

Carbonyl ×2 Amide Ester ×2 Secondary amine Phenol Carbamate Ether ×2

Ring system

Benzene ×2 Pyridine

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.860383	-
DOCK_BASE_INTER_RANK	-1.003650	-
DOCK_BASE_INTER_RANK	-0.556999	-
DOCK_BASE_INTER_RANK	-0.815417	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_BOND_LENGTH_OUTLIERS	0.000000	-
DOCK_CLASH_COUNT	18.000000	-
DOCK_CLASH_COUNT	19.000000	-
DOCK_CLASH_COUNT	19.000000	-
DOCK_CLASH_COUNT	21.000000	-
DOCK_CONTACT_COUNT	12.000000	-
DOCK_CONTACT_COUNT	25.000000	-
DOCK_CONTACT_COUNT	13.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_EXPERIMENT	T03	-
DOCK_EXPERIMENT	T19	-
DOCK_EXPERIMENT	T20	-
DOCK_EXPERIMENT	T21	-
DOCK_EXPERIMENT_ID	3	-
DOCK_EXPERIMENT_ID	19	-
DOCK_EXPERIMENT_ID	20	-
DOCK_EXPERIMENT_ID	21	-
DOCK_FINAL_RANK	4.183202	-
DOCK_FINAL_RANK	5.197360	-
DOCK_FINAL_RANK	4.264488	-
DOCK_FINAL_RANK	3.559473	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOMETRY_ALERT	warning	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_GEOM_OK	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_HARD_GEOMETRY_FAIL	0	-
DOCK_IFP::A:ALA32	1	-
DOCK_IFP::A:ARG137	1	-
DOCK_IFP::A:ARG140	1	-
DOCK_IFP::A:ARG141	1	-
DOCK_IFP::A:ARG97	1	-
DOCK_IFP::A:ASN103	1	-
DOCK_IFP::A:ASN402	1	-
DOCK_IFP::A:ASP52	1	-
DOCK_IFP::A:GLU136	1	-
DOCK_IFP::A:GLU466	1	-
DOCK_IFP::A:GLU467	1	-
DOCK_IFP::A:HIS102	1	-
DOCK_IFP::A:HIS461	1	-
DOCK_IFP::A:LEU399	1	-
DOCK_IFP::A:LEU94	1	-
DOCK_IFP::A:LYS407	1	-
DOCK_IFP::A:LYS57	1	-
DOCK_IFP::A:LYS95	1	-
DOCK_IFP::A:MET53	1	-
DOCK_IFP::A:PHE396	1	-
DOCK_IFP::A:PHE56	1	-
DOCK_IFP::A:PHE91	1	-
DOCK_IFP::A:PRO398	1	-
DOCK_IFP::A:PRO462	1	-
DOCK_IFP::A:PRO93	1	-
DOCK_IFP::A:SER394	1	-
DOCK_IFP::A:SER395	1	-
DOCK_IFP::A:THR397	1	-
DOCK_IFP::A:THR463	1	-
DOCK_IFP::A:THR54	1	-
DOCK_IFP::A:TYR94	1	-
DOCK_IFP::A:VAL30	1	-
DOCK_IFP::B:ARG113	1	-
DOCK_IFP::B:ASP10	1	-
DOCK_IFP::B:CYS69	1	-
DOCK_IFP::B:GLY70	1	-
DOCK_IFP::B:GLY72	1	-
DOCK_IFP::B:GLY74	1	-
DOCK_IFP::B:HIS11	1	-
DOCK_IFP::B:ILE73	1	-
DOCK_IFP::B:PRO12	1	-
DOCK_IFP::B:SER43	1	-
DOCK_IFP::B:SER71	1	-
DOCK_IFP::B:TYR46	1	-
DOCK_IFP::C:ALA363	1	-
DOCK_IFP::C:ALA365	1	-
DOCK_IFP::C:ARG287	1	-
DOCK_IFP::C:ASP327	1	-
DOCK_IFP::C:CYS52	1	-
DOCK_IFP::C:CYS57	1	-
DOCK_IFP::C:GLN439	1	-
DOCK_IFP::C:GLU202	1	-
DOCK_IFP::C:GLY161	1	-
DOCK_IFP::C:GLY56	1	-
DOCK_IFP::C:ILE199	1	-
DOCK_IFP::C:ILE438	1	-
DOCK_IFP::C:LEU334	1	-
DOCK_IFP::C:LYS60	1	-
DOCK_IFP::C:NDP800	1	-
DOCK_IFP::C:PHE182	1	-
DOCK_IFP::C:PHE203	1	-
DOCK_IFP::C:PHE367	1	-
DOCK_IFP::C:PRO336	1	-
DOCK_IFP::C:PRO435	1	-
DOCK_IFP::C:SER162	1	-
DOCK_IFP::C:SER364	1	-
DOCK_IFP::C:THR335	1	-
DOCK_IFP::C:THR51	1	-
DOCK_IFP::C:VAL55	1	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_IMPORT_SCOPE	best_by_name	-
DOCK_MAX_CLASH_OVERLAP	0.687007	-
DOCK_MAX_CLASH_OVERLAP	0.668069	-
DOCK_MAX_CLASH_OVERLAP	0.668061	-
DOCK_MAX_CLASH_OVERLAP	0.668037	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	4.139056	-
DOCK_PRE_RANK	5.160662	-
DOCK_PRE_RANK	4.226179	-
DOCK_PRE_RANK	3.526678	-
DOCK_PRIMARY_POSE_ID	1599	-
DOCK_PRIMARY_POSE_ID	12416	-
DOCK_PRIMARY_POSE_ID	13122	-
DOCK_PRIMARY_POSE_ID	13708	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_RANKING_MODE	inter_strain_penalized	-
DOCK_REPORT_ID	selection_import_t03	-
DOCK_REPORT_ID	selection_import_t19	-
DOCK_REPORT_ID	selection_import_t20	-
DOCK_REPORT_ID	selection_import_t21	-
DOCK_RESIDUE_CONTACTS	A:ALA32;A:ARG97;A:ASP52;A:LEU94;A:LYS57;A:LYS95;A:MET53;A:PHE56;A:PHE91;A:PRO93;A:THR54;A:VAL30	-
DOCK_RESIDUE_CONTACTS	C:ALA363;C:ALA365;C:ARG287;C:ASP327;C:CYS52;C:CYS57;C:GLN439;C:GLU202;C:GLY161;C:GLY56;C:ILE199;C:ILE438;C:LEU334;C:LYS60;C:NDP800;C:PHE182;C:PHE203;C:PHE367;C:PRO336;C:PRO435;C:SER162;C:SER364;C:THR335;C:THR51;C:VAL55	-
DOCK_RESIDUE_CONTACTS	A:ASN402;A:GLU466;A:GLU467;A:HIS461;A:LEU399;A:LYS407;A:PHE396;A:PRO398;A:PRO462;A:SER394;A:SER395;A:THR397;A:THR463	-
DOCK_RESIDUE_CONTACTS	A:ARG137;A:ARG140;A:ARG141;A:ASN103;A:GLU136;A:HIS102;A:TYR94;B:ARG113;B:ASP10;B:CYS69;B:GLY70;B:GLY72;B:GLY74;B:HIS11;B:ILE73;B:PRO12;B:SER43;B:SER71;B:TYR46	-
DOCK_SCAFFOLD	O=C(Nc1cc2c(=O)n(-c3ccccc3)ccc2oc1=O)OCc1ccccc1	-
DOCK_SCAFFOLD	O=C(Nc1cc2c(=O)n(-c3ccccc3)ccc2oc1=O)OCc1ccccc1	-
DOCK_SCAFFOLD	O=C(Nc1cc2c(=O)n(-c3ccccc3)ccc2oc1=O)OCc1ccccc1	-
DOCK_SCAFFOLD	O=C(Nc1cc2c(=O)n(-c3ccccc3)ccc2oc1=O)OCc1ccccc1	-
DOCK_SCORE	-20.154800	-
DOCK_SCORE	-38.131600	-
DOCK_SCORE	-19.013500	-
DOCK_SCORE	-23.381200	-
DOCK_SCORE_INTER	-29.253000	-
DOCK_SCORE_INTER	-34.124200	-
DOCK_SCORE_INTER	-18.938000	-
DOCK_SCORE_INTER	-27.724200	-
DOCK_SCORE_INTER_KCAL	-6.986962	-
DOCK_SCORE_INTER_KCAL	-8.150429	-
DOCK_SCORE_INTER_KCAL	-4.523266	-
DOCK_SCORE_INTER_KCAL	-6.621814	-
DOCK_SCORE_INTER_NORM	-0.860383	-
DOCK_SCORE_INTER_NORM	-1.003650	-
DOCK_SCORE_INTER_NORM	-0.556999	-
DOCK_SCORE_INTER_NORM	-0.815417	-
DOCK_SCORE_INTRA	9.098260	-
DOCK_SCORE_INTRA	-4.443320	-
DOCK_SCORE_INTRA	-0.075513	-
DOCK_SCORE_INTRA	4.342970	-
DOCK_SCORE_INTRA_KCAL	2.173083	-
DOCK_SCORE_INTRA_KCAL	-1.061269	-
DOCK_SCORE_INTRA_KCAL	-0.018036	-
DOCK_SCORE_INTRA_KCAL	1.037301	-
DOCK_SCORE_INTRA_NORM	0.267596	-
DOCK_SCORE_INTRA_NORM	-0.130686	-
DOCK_SCORE_INTRA_NORM	-0.002221	-
DOCK_SCORE_INTRA_NORM	0.127735	-
DOCK_SCORE_KCAL	-4.813893	-
DOCK_SCORE_KCAL	-9.107580	-
DOCK_SCORE_KCAL	-4.541298	-
DOCK_SCORE_KCAL	-5.584506	-
DOCK_SCORE_NORM	-0.592787	-
DOCK_SCORE_NORM	-1.121520	-
DOCK_SCORE_NORM	-0.559220	-
DOCK_SCORE_NORM	-0.687683	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.435867	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.012820	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SCORE_SYSTEM_NORM	0.000000	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SELECTION_EXCLUDED	0	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SEVERE_CLASH_COUNT	0.000000	-
DOCK_SOURCE_FILE	T03_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T19_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T20_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T21_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C24H18N2O8	-
DOCK_SOURCE_FORMULA	C24H18N2O8	-
DOCK_SOURCE_FORMULA	C24H18N2O8	-
DOCK_SOURCE_FORMULA	C24H18N2O8	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HEAVY_ATOMS	34.000000	-
DOCK_SOURCE_HEAVY_ATOMS	34.000000	-
DOCK_SOURCE_HEAVY_ATOMS	34.000000	-
DOCK_SOURCE_HEAVY_ATOMS	34.000000	-
DOCK_SOURCE_LOGP	3.184800	-
DOCK_SOURCE_LOGP	3.184800	-
DOCK_SOURCE_LOGP	3.184800	-
DOCK_SOURCE_LOGP	3.184800	-
DOCK_SOURCE_MW	462.414000	-
DOCK_SOURCE_MW	462.414000	-
DOCK_SOURCE_MW	462.414000	-
DOCK_SOURCE_MW	462.414000	-
DOCK_SOURCE_NAME	ulfkktlib_2012	-
DOCK_SOURCE_NAME	ulfkktlib_2012	-
DOCK_SOURCE_NAME	ulfkktlib_2012	-
DOCK_SOURCE_NAME	ulfkktlib_2012	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	137.070000	-
DOCK_SOURCE_TPSA	137.070000	-
DOCK_SOURCE_TPSA	137.070000	-
DOCK_SOURCE_TPSA	137.070000	-
DOCK_STRAIN_DELTA	31.809384	-
DOCK_STRAIN_DELTA	27.703167	-
DOCK_STRAIN_DELTA	28.630836	-
DOCK_STRAIN_DELTA	25.348727	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_TARGET	T03	-
DOCK_TARGET	T19	-
DOCK_TARGET	T20	-
DOCK_TARGET	T21	-
EXACT_MASS	462.10631553599995	Da
FORMULA	C24H18N2O8	-
HBA	8	-
HBD	2	-
LOGP	3.184800000000001	-
MOL_WEIGHT	462.4140000000002	g/mol
QED_SCORE	0.4315986027037774	-
ROTATABLE_BONDS	5	-
TPSA	137.07000000000002	A^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

Target	Experiment	Report	Poses	Best rank	Best score	Native overlap	Native recall	RMSD
T21	T21	selection_import_t21	1 native pose available	3.5594730506349688	-23.3812	13	0.93	-	Best pose
T03	T03	selection_import_t03	1 native pose available	4.183201502208625	-20.1548	10	0.50	-	Best pose
T20	T20	selection_import_t20	1 native pose available	4.264488365437128	-19.0135	7	0.88	-	Best pose
T19	T19	selection_import_t19	1 native pose available	5.1973595992027075	-38.1316	8	0.30	-	Best 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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
150	3.5594730506349688	-0.815417	-23.3812	11	19	13	0.93	0.42	0.44	0.62	-	no	geometry warning; 21 clashes; 1 protein clash; moderate strain Δ 25.3	Open 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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
244	4.183201502208625	-0.860383	-20.1548	7	12	10	0.50	0.29	0.20	0.20	-	no	geometry warning; 18 clashes; 2 protein clashes; high strain Δ 31.8	Open 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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
243	4.264488365437128	-0.556999	-19.0135	8	13	7	0.88	0.00	0.00	0.00	-	no	geometry warning; 19 clashes; 1 protein clash; moderate strain Δ 28.6	Open pose

T19 — T19 1 poses · report selection_import_t19

Native comparison is calculated against the uploaded native ligand for the same experiment/target whenever it is available.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
215	5.1973595992027075	-1.00365	-38.1316	14	25	8	0.30	0.17	0.40	0.25	-	no	geometry warning; 19 clashes; 2 protein clashes; moderate strain Δ 27.7	Open pose

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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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Edit compound

ulfkktlib_2012

Recognized patterns

Bio motif

Functional group

Ring system

Properties

Docking across targets

Similar compounds (PharmaFP-250 Tanimoto)

Drug Similarity

Structural Profile Fingerprint

ADMET Profile

3D Conformer