Compound detail

SMILES: C[N@@H+]1Cc2ccc(OCc3ccc(-c4ccc(Cl)cc4)cc3)cc2[C@@H](O)C1

Formula: C23H23ClNO2+ | MW: 380.89500000000004

LogP: 3.647700000000002 | TPSA: 33.900000000000006

HBA/HBD: 2/2 | RotB: 4

InChIKey: KITWWCSRMHIZBP-QHCPKHFHSA-O

Recognized patterns

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

Highlighted: 1 pattern Ether Clear highlight

Bio motif

Biphenyl H-bond acceptor O H-bond donor ×2 Gatekeeper aromatic ×3

Functional group

Alcohol Chlorine Aryl ether Ether

Ring system

Benzene ×3

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.703477	-
DOCK_BASE_INTER_RANK	-1.119430	-
DOCK_BASE_INTER_RANK	-0.938614	-
DOCK_BASE_INTER_RANK	-1.179660	-
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	16.000000	-
DOCK_CLASH_COUNT	13.000000	-
DOCK_CLASH_COUNT	12.000000	-
DOCK_CLASH_COUNT	12.000000	-
DOCK_CONTACT_COUNT	18.000000	-
DOCK_CONTACT_COUNT	7.000000	-
DOCK_CONTACT_COUNT	20.000000	-
DOCK_CONTACT_COUNT	15.000000	-
DOCK_EXPERIMENT	T07	-
DOCK_EXPERIMENT	T06	-
DOCK_EXPERIMENT	T20	-
DOCK_EXPERIMENT	T22	-
DOCK_EXPERIMENT_ID	7	-
DOCK_EXPERIMENT_ID	22	-
DOCK_EXPERIMENT_ID	6	-
DOCK_EXPERIMENT_ID	20	-
DOCK_FINAL_RANK	3.064813	-
DOCK_FINAL_RANK	2.532392	-
DOCK_FINAL_RANK	1.389516	-
DOCK_FINAL_RANK	0.387824	-
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:ALA24	1	-
DOCK_IFP::A:ALA34	1	-
DOCK_IFP::A:ARG100	1	-
DOCK_IFP::A:ARG14	1	-
DOCK_IFP::A:ARG59	1	-
DOCK_IFP::A:ASN126	1	-
DOCK_IFP::A:ASN402	1	-
DOCK_IFP::A:ASP129	1	-
DOCK_IFP::A:ASP161	1	-
DOCK_IFP::A:ASP54	1	-
DOCK_IFP::A:ASP68	1	-
DOCK_IFP::A:CYS168	1	-
DOCK_IFP::A:GLN42	1	-
DOCK_IFP::A:GLU21	1	-
DOCK_IFP::A:GLU467	1	-
DOCK_IFP::A:GLU73	1	-
DOCK_IFP::A:GLY23	1	-
DOCK_IFP::A:GLY25	1	-
DOCK_IFP::A:GLY71	1	-
DOCK_IFP::A:ILE160	1	-
DOCK_IFP::A:ILE47	1	-
DOCK_IFP::A:LEU130	1	-
DOCK_IFP::A:LEU208	1	-
DOCK_IFP::A:LEU209	1	-
DOCK_IFP::A:LEU90	1	-
DOCK_IFP::A:LEU97	1	-
DOCK_IFP::A:LYS127	1	-
DOCK_IFP::A:LYS159	1	-
DOCK_IFP::A:LYS26	1	-
DOCK_IFP::A:LYS407	1	-
DOCK_IFP::A:MET213	1	-
DOCK_IFP::A:MET55	1	-
DOCK_IFP::A:NAP301	1	-
DOCK_IFP::A:NDP301	1	-
DOCK_IFP::A:PHE171	1	-
DOCK_IFP::A:PHE38	1	-
DOCK_IFP::A:PHE396	1	-
DOCK_IFP::A:PHE58	1	-
DOCK_IFP::A:PHE94	1	-
DOCK_IFP::A:PHE97	1	-
DOCK_IFP::A:PRO210	1	-
DOCK_IFP::A:PRO91	1	-
DOCK_IFP::A:SER207	1	-
DOCK_IFP::A:SER22	1	-
DOCK_IFP::A:SER27	1	-
DOCK_IFP::A:SER28	1	-
DOCK_IFP::A:SER394	1	-
DOCK_IFP::A:SER395	1	-
DOCK_IFP::A:SER95	1	-
DOCK_IFP::A:THR184	1	-
DOCK_IFP::A:THR397	1	-
DOCK_IFP::A:THR44	1	-
DOCK_IFP::A:THR69	1	-
DOCK_IFP::A:TRP221	1	-
DOCK_IFP::A:TRP49	1	-
DOCK_IFP::A:TYR174	1	-
DOCK_IFP::A:TYR57	1	-
DOCK_IFP::A:VAL206	1	-
DOCK_IFP::A:VAL32	1	-
DOCK_IFP::A:VAL33	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	0.712641	-
DOCK_MAX_CLASH_OVERLAP	0.649555	-
DOCK_MAX_CLASH_OVERLAP	0.638756	-
DOCK_MAX_CLASH_OVERLAP	0.636800	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	3.029349	-
DOCK_PRE_RANK	1.345923	-
DOCK_PRE_RANK	2.498858	-
DOCK_PRE_RANK	0.359277	-
DOCK_PRIMARY_POSE_ID	14270	-
DOCK_PRIMARY_POSE_ID	4116	-
DOCK_PRIMARY_POSE_ID	3442	-
DOCK_PRIMARY_POSE_ID	12941	-
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_t20	-
DOCK_REPORT_ID	selection_import_t07	-
DOCK_REPORT_ID	selection_import_t06	-
DOCK_REPORT_ID	selection_import_t22	-
DOCK_RESIDUE_CONTACTS	A:ARG14;A:ASP161;A:CYS168;A:LEU208;A:LEU209;A:MET213;A:NAP301;A:PHE171;A:PHE97;A:PRO210;A:SER207;A:SER95;A:TRP221;A:TYR174;A:VAL206	-
DOCK_RESIDUE_CONTACTS	A:ALA34;A:ARG100;A:ARG59;A:ASP54;A:ILE160;A:ILE47;A:LEU90;A:LEU97;A:MET55;A:NDP301;A:PHE58;A:PHE94;A:PRO91;A:THR184;A:TRP49;A:TYR57;A:VAL32;A:VAL33	-
DOCK_RESIDUE_CONTACTS	A:ALA24;A:ASN126;A:ASP129;A:ASP68;A:GLN42;A:GLU21;A:GLU73;A:GLY23;A:GLY25;A:GLY71;A:LEU130;A:LYS127;A:LYS159;A:LYS26;A:PHE38;A:SER22;A:SER27;A:SER28;A:THR44;A:THR69	-
DOCK_RESIDUE_CONTACTS	A:ASN402;A:GLU467;A:LYS407;A:PHE396;A:SER394;A:SER395;A:THR397	-
DOCK_SCAFFOLD	c1ccc(-c2ccc(COc3ccc4c(c3)CC[NH2+]C4)cc2)cc1	-
DOCK_SCAFFOLD	c1ccc(-c2ccc(COc3ccc4c(c3)CC[NH2+]C4)cc2)cc1	-
DOCK_SCAFFOLD	c1ccc(-c2ccc(COc3ccc4c(c3)CC[NH2+]C4)cc2)cc1	-
DOCK_SCAFFOLD	c1ccc(-c2ccc(COc3ccc4c(c3)CC[NH2+]C4)cc2)cc1	-
DOCK_SCORE	-20.137400	-
DOCK_SCORE	-30.106200	-
DOCK_SCORE	-14.459600	-
DOCK_SCORE	-27.237800	-
DOCK_SCORE_INTER	-30.224600	-
DOCK_SCORE_INTER	-25.342600	-
DOCK_SCORE_INTER	-31.850800	-
DOCK_SCORE_INTER	-18.993900	-
DOCK_SCORE_INTER_KCAL	-4.536617	-
DOCK_SCORE_INTER_KCAL	-6.052979	-
DOCK_SCORE_INTER_KCAL	-7.219025	-
DOCK_SCORE_INTER_KCAL	-7.607436	-
DOCK_SCORE_INTER_NORM	-0.703477	-
DOCK_SCORE_INTER_NORM	-1.179660	-
DOCK_SCORE_INTER_NORM	-0.938614	-
DOCK_SCORE_INTER_NORM	-1.119430	-
DOCK_SCORE_INTRA	1.744530	-
DOCK_SCORE_INTRA	4.271420	-
DOCK_SCORE_INTRA	4.534260	-
DOCK_SCORE_INTRA	2.986850	-
DOCK_SCORE_INTRA_KCAL	0.713397	-
DOCK_SCORE_INTRA_KCAL	0.416674	-
DOCK_SCORE_INTRA_KCAL	1.020212	-
DOCK_SCORE_INTRA_KCAL	1.082990	-
DOCK_SCORE_INTRA_NORM	0.158201	-
DOCK_SCORE_INTRA_NORM	0.167935	-
DOCK_SCORE_INTRA_NORM	0.064612	-
DOCK_SCORE_INTRA_NORM	0.110624	-
DOCK_SCORE_KCAL	-7.190745	-
DOCK_SCORE_KCAL	-3.453618	-
DOCK_SCORE_KCAL	-4.809737	-
DOCK_SCORE_KCAL	-6.505640	-
DOCK_SCORE_NORM	-1.115050	-
DOCK_SCORE_NORM	-0.535542	-
DOCK_SCORE_NORM	-0.745829	-
DOCK_SCORE_NORM	-1.008810	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.933759	-
DOCK_SCORE_RESTR_NORM	0.034584	-
DOCK_SCORE_RESTR_NORM	0.000000	-
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	T07_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T20_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T22_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T06_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C23H23ClNO2+	-
DOCK_SOURCE_FORMULA	C23H23ClNO2+	-
DOCK_SOURCE_FORMULA	C23H23ClNO2+	-
DOCK_SOURCE_FORMULA	C23H23ClNO2+	-
DOCK_SOURCE_HBA	2.000000	-
DOCK_SOURCE_HBA	2.000000	-
DOCK_SOURCE_HBA	2.000000	-
DOCK_SOURCE_HBA	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HBD	2.000000	-
DOCK_SOURCE_HEAVY_ATOMS	27.000000	-
DOCK_SOURCE_HEAVY_ATOMS	27.000000	-
DOCK_SOURCE_HEAVY_ATOMS	27.000000	-
DOCK_SOURCE_HEAVY_ATOMS	27.000000	-
DOCK_SOURCE_LOGP	3.647700	-
DOCK_SOURCE_LOGP	3.647700	-
DOCK_SOURCE_LOGP	3.647700	-
DOCK_SOURCE_LOGP	3.647700	-
DOCK_SOURCE_MW	380.895000	-
DOCK_SOURCE_MW	380.895000	-
DOCK_SOURCE_MW	380.895000	-
DOCK_SOURCE_MW	380.895000	-
DOCK_SOURCE_NAME	OHD_TB2021_37	-
DOCK_SOURCE_NAME	OHD_TB2021_37	-
DOCK_SOURCE_NAME	OHD_TB2021_37	-
DOCK_SOURCE_NAME	OHD_TB2021_37	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	33.900000	-
DOCK_SOURCE_TPSA	33.900000	-
DOCK_SOURCE_TPSA	33.900000	-
DOCK_SOURCE_TPSA	33.900000	-
DOCK_STRAIN_DELTA	25.807842	-
DOCK_STRAIN_DELTA	31.519418	-
DOCK_STRAIN_DELTA	22.568766	-
DOCK_STRAIN_DELTA	26.976364	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	1	-
DOCK_STRAIN_OK	0	-
DOCK_TARGET	T22	-
DOCK_TARGET	T20	-
DOCK_TARGET	T07	-
DOCK_TARGET	T06	-
EXACT_MASS	380.14118307609004	Da
FORMULA	C23H23ClNO2+	-
HBA	2	-
HBD	2	-
LOGP	3.647700000000002	-
MOL_WEIGHT	380.89500000000004	g/mol
QED_SCORE	0.7240917692335797	-
ROTATABLE_BONDS	4	-
TPSA	33.900000000000006	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
T07	T07	selection_import_t07	1 native pose available	0.38782382149013206	-30.1062	15	0.79	-	Best pose
T06	T06	selection_import_t06	1 native pose available	1.389516464842362	-20.1374	16	0.76	-	Best pose
T20	T20	selection_import_t20	1 native pose available	2.532392372412851	-14.4596	5	0.62	-	Best pose
T22	T22	selection_import_t22	1 native pose available	3.064812850486778	-27.2378	16	0.76	-	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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
53	0.38782382149013206	-1.17966	-30.1062	3	15	15	0.79	0.33	0.40	0.40	-	no	geometry warning; 12 clashes; 1 protein contact clash; 1 cofactor-context clash; moderate strain Δ 22.6	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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
56	1.389516464842362	-0.938614	-20.1374	2	18	16	0.76	0.40	0.25	0.25	-	no	geometry warning; 16 clashes; 3 protein contact clashes; high strain Δ 31.5	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
62	2.532392372412851	-0.703477	-14.4596	4	7	5	0.62	0.00	0.00	0.00	-	no	geometry warning; 12 clashes; 1 protein clash; moderate strain Δ 25.8	Open pose

T22 — T22 1 poses · report selection_import_t22

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
32	3.064812850486778	-1.11943	-27.2378	6	20	16	0.76	0.27	0.27	0.36	-	no	geometry warning; 13 clashes; 2 protein clashes; moderate strain Δ 27.0	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

OHD_TB2021_37

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