Compound detail

SMILES: COc1cc(/C=[NH+]/N=c2/nc[nH]c3c(Nc4cccc(OCCCO)c4)[nH+]cnc23)ccc1O

Formula: C23H25N7O4+2 | MW: 463.4980000000001

LogP: 0.006400000000000683 | TPSA: 152.99

HBA/HBD: 8/5 | RotB: 9

InChIKey: IPFRGVWUGQBPLU-KVSWJAHQSA-P

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

Catechol ATP mimic pyrimidine ×2 H-bond acceptor N ×5 H-bond acceptor O ×2 H-bond donor ×6 Gatekeeper aromatic ×2 Ionizable base ×2

Functional group

Secondary amine Alcohol Phenol Aryl ether ×2 Ether ×2

Ring system

Benzene ×2 Pyrimidine ×2

Properties

Name	Value	Unit
DOCK_BASE_INTER_RANK	-0.684285	-
DOCK_BASE_INTER_RANK	-0.555888	-
DOCK_BASE_INTER_RANK	-0.878702	-
DOCK_BASE_INTER_RANK	-0.908199	-
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	14.000000	-
DOCK_CLASH_COUNT	15.000000	-
DOCK_CLASH_COUNT	17.000000	-
DOCK_CLASH_COUNT	14.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_CONTACT_COUNT	19.000000	-
DOCK_CONTACT_COUNT	8.000000	-
DOCK_CONTACT_COUNT	16.000000	-
DOCK_EXPERIMENT	T16	-
DOCK_EXPERIMENT	T01	-
DOCK_EXPERIMENT	T20	-
DOCK_EXPERIMENT	T02	-
DOCK_EXPERIMENT_ID	16	-
DOCK_EXPERIMENT_ID	20	-
DOCK_EXPERIMENT_ID	1	-
DOCK_EXPERIMENT_ID	2	-
DOCK_FINAL_RANK	2.702659	-
DOCK_FINAL_RANK	4.661053	-
DOCK_FINAL_RANK	3.326514	-
DOCK_FINAL_RANK	4.581793	-
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:ALA10	1	-
DOCK_IFP::A:ALA10	1	-
DOCK_IFP::A:ALA209	1	-
DOCK_IFP::A:ALA77	1	-
DOCK_IFP::A:ALA90	1	-
DOCK_IFP::A:ARG29	1	-
DOCK_IFP::A:ARG29	1	-
DOCK_IFP::A:ARG74	1	-
DOCK_IFP::A:ASN402	1	-
DOCK_IFP::A:ASN65	1	-
DOCK_IFP::A:ASN65	1	-
DOCK_IFP::A:GLU31	1	-
DOCK_IFP::A:GLU31	1	-
DOCK_IFP::A:GLU467	1	-
DOCK_IFP::A:ILE61	1	-
DOCK_IFP::A:ILE61	1	-
DOCK_IFP::A:ILE8	1	-
DOCK_IFP::A:ILE8	1	-
DOCK_IFP::A:LEU23	1	-
DOCK_IFP::A:LEU23	1	-
DOCK_IFP::A:LEU28	1	-
DOCK_IFP::A:LEU28	1	-
DOCK_IFP::A:LEU399	1	-
DOCK_IFP::A:LEU68	1	-
DOCK_IFP::A:LEU68	1	-
DOCK_IFP::A:LEU73	1	-
DOCK_IFP::A:LYS211	1	-
DOCK_IFP::A:LYS89	1	-
DOCK_IFP::A:MET70	1	-
DOCK_IFP::A:NAP201	1	-
DOCK_IFP::A:NAP201	1	-
DOCK_IFP::A:PHE32	1	-
DOCK_IFP::A:PHE32	1	-
DOCK_IFP::A:PHE35	1	-
DOCK_IFP::A:PHE35	1	-
DOCK_IFP::A:PHE396	1	-
DOCK_IFP::A:PHE83	1	-
DOCK_IFP::A:PRO212	1	-
DOCK_IFP::A:PRO213	1	-
DOCK_IFP::A:PRO27	1	-
DOCK_IFP::A:PRO27	1	-
DOCK_IFP::A:PRO398	1	-
DOCK_IFP::A:PRO62	1	-
DOCK_IFP::A:PRO62	1	-
DOCK_IFP::A:SER394	1	-
DOCK_IFP::A:SER395	1	-
DOCK_IFP::A:SER86	1	-
DOCK_IFP::A:SER87	1	-
DOCK_IFP::A:THR397	1	-
DOCK_IFP::A:THR57	1	-
DOCK_IFP::A:THR57	1	-
DOCK_IFP::A:TRP25	1	-
DOCK_IFP::A:TRP25	1	-
DOCK_IFP::A:TYR122	1	-
DOCK_IFP::A:TYR122	1	-
DOCK_IFP::A:TYR210	1	-
DOCK_IFP::A:TYR69	1	-
DOCK_IFP::A:VAL116	1	-
DOCK_IFP::A:VAL116	1	-
DOCK_IFP::A:VAL88	1	-
DOCK_IFP::A:VAL9	1	-
DOCK_IFP::A:VAL9	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	0.672837	-
DOCK_MAX_CLASH_OVERLAP	0.662188	-
DOCK_MAX_CLASH_OVERLAP	0.672700	-
DOCK_MAX_CLASH_OVERLAP	0.672718	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_POSE_COUNT	1	-
DOCK_PRE_RANK	2.612992	-
DOCK_PRE_RANK	4.526973	-
DOCK_PRE_RANK	4.463523	-
DOCK_PRE_RANK	3.172893	-
DOCK_PRIMARY_POSE_ID	426	-
DOCK_PRIMARY_POSE_ID	10593	-
DOCK_PRIMARY_POSE_ID	13244	-
DOCK_PRIMARY_POSE_ID	1086	-
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_t01	-
DOCK_REPORT_ID	selection_import_t16	-
DOCK_REPORT_ID	selection_import_t20	-
DOCK_REPORT_ID	selection_import_t02	-
DOCK_RESIDUE_CONTACTS	A:ASN402;A:GLU467;A:LEU399;A:PHE396;A:PRO398;A:SER394;A:SER395;A:THR397	-
DOCK_RESIDUE_CONTACTS	A:ALA209;A:ALA77;A:ALA90;A:ARG74;A:LEU73;A:LYS211;A:LYS89;A:MET70;A:PHE83;A:PRO212;A:PRO213;A:SER86;A:SER87;A:TYR210;A:TYR69;A:VAL88	-
DOCK_RESIDUE_CONTACTS	A:ALA10;A:ARG29;A:ASN65;A:GLU31;A:ILE61;A:ILE8;A:LEU23;A:LEU28;A:LEU68;A:NAP201;A:PHE32;A:PHE35;A:PRO27;A:PRO62;A:THR57;A:TRP25;A:TYR122;A:VAL116;A:VAL9	-
DOCK_RESIDUE_CONTACTS	A:ALA10;A:ARG29;A:ASN65;A:GLU31;A:ILE61;A:ILE8;A:LEU23;A:LEU28;A:LEU68;A:NAP201;A:PHE32;A:PHE35;A:PRO27;A:PRO62;A:THR57;A:TRP25;A:TYR122;A:VAL116;A:VAL9	-
DOCK_SCAFFOLD	C(=[NH+]N=c1nc[nH]c2c(Nc3ccccc3)[nH+]cnc12)c1ccccc1	-
DOCK_SCAFFOLD	C(=[NH+]N=c1nc[nH]c2c(Nc3ccccc3)[nH+]cnc12)c1ccccc1	-
DOCK_SCAFFOLD	C(=[NH+]N=c1[nH]cnc2c(Nc3ccccc3)[nH+]cnc12)c1ccccc1	-
DOCK_SCAFFOLD	C(=[NH+]N=c1nc[nH]c2c(Nc3ccccc3)[nH+]cnc12)c1ccccc1	-
DOCK_SCORE	-13.289100	-
DOCK_SCORE	-24.011900	-
DOCK_SCORE	-20.759600	-
DOCK_SCORE	-24.709600	-
DOCK_SCORE_INTER	-18.900200	-
DOCK_SCORE_INTER	-30.878800	-
DOCK_SCORE_INTER	-23.265700	-
DOCK_SCORE_INTER	-29.875900	-
DOCK_SCORE_INTER_KCAL	-5.556919	-
DOCK_SCORE_INTER_KCAL	-7.135739	-
DOCK_SCORE_INTER_KCAL	-7.375278	-
DOCK_SCORE_INTER_KCAL	-4.514237	-
DOCK_SCORE_INTER_NORM	-0.684285	-
DOCK_SCORE_INTER_NORM	-0.908199	-
DOCK_SCORE_INTER_NORM	-0.878702	-
DOCK_SCORE_INTER_NORM	-0.555888	-
DOCK_SCORE_INTRA	6.169150	-
DOCK_SCORE_INTRA	5.611060	-
DOCK_SCORE_INTRA	2.506050	-
DOCK_SCORE_INTRA	5.863920	-
DOCK_SCORE_INTRA_KCAL	1.340179	-
DOCK_SCORE_INTRA_KCAL	1.473477	-
DOCK_SCORE_INTRA_KCAL	0.598560	-
DOCK_SCORE_INTRA_KCAL	1.400574	-
DOCK_SCORE_INTRA_NORM	0.165031	-
DOCK_SCORE_INTRA_NORM	0.172468	-
DOCK_SCORE_INTRA_NORM	0.181446	-
DOCK_SCORE_INTRA_NORM	0.073707	-
DOCK_SCORE_KCAL	-4.958347	-
DOCK_SCORE_KCAL	-5.901789	-
DOCK_SCORE_KCAL	-3.174048	-
DOCK_SCORE_KCAL	-5.735146	-
DOCK_SCORE_NORM	-0.390857	-
DOCK_SCORE_NORM	-0.706234	-
DOCK_SCORE_NORM	-0.726753	-
DOCK_SCORE_NORM	-0.610578	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR	0.000000	-
DOCK_SCORE_RESTR_NORM	0.000000	-
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	T20_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T16_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T02_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FILE	T01_top5_kcal_zscore_compound_names.sdf	-
DOCK_SOURCE_FORMULA	C23H25N7O4+2	-
DOCK_SOURCE_FORMULA	C23H25N7O4+2	-
DOCK_SOURCE_FORMULA	C23H25N7O4+2	-
DOCK_SOURCE_FORMULA	C23H25N7O4+2	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBA	8.000000	-
DOCK_SOURCE_HBD	5.000000	-
DOCK_SOURCE_HBD	5.000000	-
DOCK_SOURCE_HBD	5.000000	-
DOCK_SOURCE_HBD	5.000000	-
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	0.006400	-
DOCK_SOURCE_LOGP	0.006400	-
DOCK_SOURCE_LOGP	0.006400	-
DOCK_SOURCE_LOGP	0.006400	-
DOCK_SOURCE_MW	463.498000	-
DOCK_SOURCE_MW	463.498000	-
DOCK_SOURCE_MW	463.498000	-
DOCK_SOURCE_MW	463.498000	-
DOCK_SOURCE_NAME	OHD_MAC_15	-
DOCK_SOURCE_NAME	OHD_MAC_15	-
DOCK_SOURCE_NAME	OHD_MAC_15	-
DOCK_SOURCE_NAME	OHD_MAC_15	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_RINGS	4.000000	-
DOCK_SOURCE_TPSA	152.990000	-
DOCK_SOURCE_TPSA	152.990000	-
DOCK_SOURCE_TPSA	152.990000	-
DOCK_SOURCE_TPSA	152.990000	-
DOCK_STRAIN_DELTA	51.810369	-
DOCK_STRAIN_DELTA	68.428830	-
DOCK_STRAIN_DELTA	62.647076	-
DOCK_STRAIN_DELTA	75.463165	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_STRAIN_OK	0	-
DOCK_TARGET	T16	-
DOCK_TARGET	T20	-
DOCK_TARGET	T01	-
DOCK_TARGET	T02	-
EXACT_MASS	463.19570512018004	Da
FORMULA	C23H25N7O4+2	-
HBA	8	-
HBD	5	-
LOGP	0.006400000000000683	-
MOL_WEIGHT	463.4980000000001	g/mol
QED_SCORE	0.13309442638693506	-
ROTATABLE_BONDS	9	-
TPSA	152.99	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
T16	T16	selection_import_t16	1 native pose available	2.702658847280366	-20.7596	11	0.92	-	Best pose
T20	T20	selection_import_t20	1 native pose available	3.3265135327684106	-13.2891	7	0.88	-	Best pose
T02	T02	selection_import_t02	1 native pose available	4.581792920673776	-24.7096	15	0.71	-	Best pose
T01	T01	selection_import_t01	1 native pose available	4.66105274577834	-24.0119	15	0.71	-	Best pose

T16 — T16 1 poses · report selection_import_t16

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
428	2.702658847280366	-0.684285	-20.7596	7	16	11	0.92	-	-	-	-	no	geometry warning; 17 clashes; 1 protein clash; high strain Δ 51.8	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
365	3.3265135327684106	-0.555888	-13.2891	5	8	7	0.88	1.00	1.00	1.00	-	no	geometry warning; 15 clashes; 1 protein clash; high strain Δ 75.5	Open pose

T02 — T02 1 poses · report selection_import_t02

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
408	4.581792920673776	-0.908199	-24.7096	5	19	15	0.71	0.20	0.40	0.40	-	no	geometry warning; 14 clashes; 3 protein clashes; high strain Δ 62.6	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.

Pose	Final rank	Inter norm	Score	HB	Contacts	Native overlap	Native recall	HB strict	HB role	HB residue	RMSD	Excluded	Notes
426	4.66105274577834	-0.878702	-24.0119	6	19	15	0.71	0.20	0.40	0.40	-	no	geometry warning; 14 clashes; 3 protein clashes; 1 cofactor-context clash; high strain Δ 68.4	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_MAC_15

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