NPASS Compound

Structure

NPC476418 OpenBabel07101719122D 22 23 0 0 1 0 0 0 0 0999 V2000 -7.6771 2.5377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0704 1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9144 0.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9090 -0.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.7065 1.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3157 0.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7930 1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4090 -0.9056 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -9.2938 1.0819 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.9840 0.8621 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5726 1.5431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.6885 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 19 1 0 0 0 0 12 21 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	433.96
Volume:	312.034
LogP:	1.919
LogD:	2.594
LogS:	-4.017
# Rotatable Bonds:	6
TPSA:	92.05
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	3.072
Fsp3:	0.385
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.029
MDCK Permeability:	1.6458910977235064e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.885
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	92.15997314453125%
Volume Distribution (VD):	1.017
Pgp-substrate:	7.538517475128174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.294
CYP1A2-substrate:	0.659
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.267
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	3.894
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.494
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.037
Carcinogencity:	0.533
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.047

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476418

Natural Product ID:	NPC476418
*Common Name:**	Midpacamide
IUPAC Name:	4,5-dibromo-1-methyl-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]pyrrole-2-carboxamide
Synonyms:	Midpacamide
Standard InCHIKey:	OMOGWRPVZKQNGZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H16Br2N4O3/c1-18-9(6-7(14)10(18)15)11(20)16-5-3-4-8-12(21)19(2)13(22)17-8/h6,8H,3-5H2,1-2H3,(H,16,20)(H,17,22)
SMILES:	CN1C(=CC(=C1Br)Br)C(=O)NCCCC2C(=O)N(C(=O)N2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598733
PubChem CID:	11026484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002491] Azolidines [CHEMONTID:0000250] Imidazolidines [CHEMONTID:0001149] Imidazolidinones [CHEMONTID:0001150] Imidazolidinediones [CHEMONTID:0002273] Hydantoins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1
Others	2

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	46.7	%	PMID[475346]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	46000.0	nM	PMID[475346]
NPT20972	CELL-LINE	SU.86.86	Homo sapiens	Activity	>	20.0	%	PMID[475347]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC476418 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1327
0.1-0.2	15731
0.2-0.3	17821
0.3-0.4	3241
0.4-0.5	3025
0.5-0.6	1297
0.6-0.7	190
0.7-0.8	31
0.8-0.85	22
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC97106
0.9006	High Similarity	NPC136441
0.8846	High Similarity	NPC27296
0.8742	High Similarity	NPC206148
0.869	High Similarity	NPC112489
0.865	High Similarity	NPC80528
0.8599	High Similarity	NPC474236
0.8589	High Similarity	NPC28096
0.8589	High Similarity	NPC476421
0.8589	High Similarity	NPC226835
0.8589	High Similarity	NPC227489
0.858	High Similarity	NPC46022
0.8571	High Similarity	NPC474383
0.8547	High Similarity	NPC476413
0.8509	High Similarity	NPC306160
0.8497	Intermediate Similarity	NPC476414
0.8476	Intermediate Similarity	NPC54214
0.8387	Intermediate Similarity	NPC260041
0.8343	Intermediate Similarity	NPC46811
0.8263	Intermediate Similarity	NPC37268
0.8246	Intermediate Similarity	NPC469814
0.815	Intermediate Similarity	NPC63571
0.815	Intermediate Similarity	NPC111566
0.8129	Intermediate Similarity	NPC472861
0.8129	Intermediate Similarity	NPC184932
0.8103	Intermediate Similarity	NPC310633
0.8092	Intermediate Similarity	NPC150592
0.8061	Intermediate Similarity	NPC73687
0.8049	Intermediate Similarity	NPC473706
0.7989	Intermediate Similarity	NPC476423
0.7908	Intermediate Similarity	NPC20021
0.7877	Intermediate Similarity	NPC19342
0.7778	Intermediate Similarity	NPC271927
0.7772	Intermediate Similarity	NPC9635
0.776	Intermediate Similarity	NPC19696
0.776	Intermediate Similarity	NPC136957
0.773	Intermediate Similarity	NPC469716
0.7719	Intermediate Similarity	NPC469976
0.7692	Intermediate Similarity	NPC48117
0.7692	Intermediate Similarity	NPC476526
0.7692	Intermediate Similarity	NPC329765
0.7657	Intermediate Similarity	NPC314281
0.7657	Intermediate Similarity	NPC40530
0.765	Intermediate Similarity	NPC174281
0.765	Intermediate Similarity	NPC475286
0.7647	Intermediate Similarity	NPC474696
0.7588	Intermediate Similarity	NPC2414
0.7435	Intermediate Similarity	NPC476524
0.7377	Intermediate Similarity	NPC210123
0.7374	Intermediate Similarity	NPC270834
0.7365	Intermediate Similarity	NPC109158
0.7344	Intermediate Similarity	NPC476525
0.7273	Intermediate Similarity	NPC469717
0.7267	Intermediate Similarity	NPC472288
0.716	Intermediate Similarity	NPC472260
0.7158	Intermediate Similarity	NPC476527
0.7101	Intermediate Similarity	NPC52110
0.7076	Intermediate Similarity	NPC298288
0.6936	Remote Similarity	NPC142688
0.6933	Remote Similarity	NPC291517
0.6893	Remote Similarity	NPC233380
0.6832	Remote Similarity	NPC71236
0.6829	Remote Similarity	NPC23215
0.6788	Remote Similarity	NPC474389
0.6754	Remote Similarity	NPC474180
0.6754	Remote Similarity	NPC188821
0.6687	Remote Similarity	NPC98156
0.6687	Remote Similarity	NPC64661
0.6687	Remote Similarity	NPC167200
0.6687	Remote Similarity	NPC292434
0.6687	Remote Similarity	NPC14448
0.6687	Remote Similarity	NPC195704
0.6687	Remote Similarity	NPC138596
0.6687	Remote Similarity	NPC200397
0.6667	Remote Similarity	NPC477004
0.665	Remote Similarity	NPC470703
0.6618	Remote Similarity	NPC50562
0.6601	Remote Similarity	NPC470702
0.6601	Remote Similarity	NPC473218
0.6585	Remote Similarity	NPC67658
0.6561	Remote Similarity	NPC133003
0.6559	Remote Similarity	NPC265710
0.6541	Remote Similarity	NPC476419
0.6529	Remote Similarity	NPC12831
0.6529	Remote Similarity	NPC48171
0.6529	Remote Similarity	NPC169308
0.6529	Remote Similarity	NPC74928
0.6529	Remote Similarity	NPC77582
0.6529	Remote Similarity	NPC302717
0.6529	Remote Similarity	NPC129753
0.6529	Remote Similarity	NPC3698
0.6529	Remote Similarity	NPC205604
0.6529	Remote Similarity	NPC244087
0.6529	Remote Similarity	NPC97230
0.6529	Remote Similarity	NPC286529
0.6529	Remote Similarity	NPC209281
0.6529	Remote Similarity	NPC59839
0.6524	Remote Similarity	NPC16659
0.652	Remote Similarity	NPC469715
0.6513	Remote Similarity	NPC77061
0.6497	Remote Similarity	NPC33229
0.6491	Remote Similarity	NPC58268
0.6491	Remote Similarity	NPC101130
0.6491	Remote Similarity	NPC129412
0.6491	Remote Similarity	NPC114033
0.6486	Remote Similarity	NPC186068
0.6486	Remote Similarity	NPC469529
0.6477	Remote Similarity	NPC243716
0.6461	Remote Similarity	NPC74357
0.6417	Remote Similarity	NPC473380
0.6417	Remote Similarity	NPC240088
0.6404	Remote Similarity	NPC75135
0.64	Remote Similarity	NPC100726
0.6398	Remote Similarity	NPC243633
0.6398	Remote Similarity	NPC175150
0.6384	Remote Similarity	NPC66642
0.6383	Remote Similarity	NPC11126
0.6368	Remote Similarity	NPC470205
0.6364	Remote Similarity	NPC475736
0.6349	Remote Similarity	NPC182940
0.6344	Remote Similarity	NPC161861
0.6344	Remote Similarity	NPC288074
0.634	Remote Similarity	NPC324091
0.6335	Remote Similarity	NPC477003
0.6335	Remote Similarity	NPC21429
0.6333	Remote Similarity	NPC168209
0.6313	Remote Similarity	NPC209362
0.6302	Remote Similarity	NPC474258
0.63	Remote Similarity	NPC77241
0.63	Remote Similarity	NPC166209
0.63	Remote Similarity	NPC13456
0.63	Remote Similarity	NPC269203
0.6286	Remote Similarity	NPC467188
0.628	Remote Similarity	NPC471194
0.628	Remote Similarity	NPC153980
0.628	Remote Similarity	NPC6865
0.628	Remote Similarity	NPC471193
0.6269	Remote Similarity	NPC94752
0.6263	Remote Similarity	NPC91179
0.625	Remote Similarity	NPC228835
0.625	Remote Similarity	NPC474318
0.625	Remote Similarity	NPC475914
0.625	Remote Similarity	NPC268744
0.625	Remote Similarity	NPC153123
0.625	Remote Similarity	NPC220797
0.625	Remote Similarity	NPC201266
0.6237	Remote Similarity	NPC473946
0.6236	Remote Similarity	NPC471655
0.6236	Remote Similarity	NPC473878
0.6232	Remote Similarity	NPC72956
0.6231	Remote Similarity	NPC262898
0.623	Remote Similarity	NPC253687
0.6226	Remote Similarity	NPC474195
0.6216	Remote Similarity	NPC109447
0.6215	Remote Similarity	NPC105811
0.6207	Remote Similarity	NPC317701
0.6196	Remote Similarity	NPC247987
0.6181	Remote Similarity	NPC179701
0.618	Remote Similarity	NPC13432
0.6178	Remote Similarity	NPC477042
0.6176	Remote Similarity	NPC473376
0.6169	Remote Similarity	NPC237414
0.6168	Remote Similarity	NPC313823
0.6167	Remote Similarity	NPC251391
0.6154	Remote Similarity	NPC17059
0.6154	Remote Similarity	NPC213914
0.6146	Remote Similarity	NPC471191
0.6142	Remote Similarity	NPC476460
0.6122	Remote Similarity	NPC209917
0.6122	Remote Similarity	NPC213629
0.6119	Remote Similarity	NPC171317
0.6114	Remote Similarity	NPC471192
0.6111	Remote Similarity	NPC474196
0.6108	Remote Similarity	NPC274981
0.6105	Remote Similarity	NPC151635
0.6103	Remote Similarity	NPC17273
0.6103	Remote Similarity	NPC141612
0.6103	Remote Similarity	NPC135601
0.6102	Remote Similarity	NPC470440
0.6098	Remote Similarity	NPC88115
0.6094	Remote Similarity	NPC234403
0.6091	Remote Similarity	NPC268966
0.6089	Remote Similarity	NPC123906
0.6087	Remote Similarity	NPC470680
0.6087	Remote Similarity	NPC100104
0.6085	Remote Similarity	NPC64055
0.6082	Remote Similarity	NPC110158
0.6077	Remote Similarity	NPC281094
0.6064	Remote Similarity	NPC471943
0.6057	Remote Similarity	NPC238499
0.6043	Remote Similarity	NPC114637
0.6043	Remote Similarity	NPC49217
0.6041	Remote Similarity	NPC473666
0.6034	Remote Similarity	NPC104049
0.6033	Remote Similarity	NPC474492
0.6031	Remote Similarity	NPC159125
0.6029	Remote Similarity	NPC471944
0.6027	Remote Similarity	NPC156003
0.6022	Remote Similarity	NPC217021
0.6022	Remote Similarity	NPC70406

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	1061
0.2-0.3	1670
0.3-0.4	2315
0.4-0.5	2686
0.5-0.6	1095
0.6-0.7	58
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7419	Intermediate Similarity	NPD7459	Phase 2
0.7135	Intermediate Similarity	NPD5686	Approved
0.7135	Intermediate Similarity	NPD5685	Approved
0.7037	Intermediate Similarity	NPD2290	Phase 3
0.7037	Intermediate Similarity	NPD2289	Phase 3
0.697	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1031	Discontinued
0.6515	Remote Similarity	NPD7817	Phase 1
0.6489	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD1096	Discontinued
0.6398	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD5643	Phase 2
0.6392	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.635	Remote Similarity	NPD5017	Discontinued
0.635	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2367	Phase 2
0.6275	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5199	Approved
0.6256	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5198	Approved
0.6244	Remote Similarity	NPD2442	Approved
0.6244	Remote Similarity	NPD460	Discontinued
0.6244	Remote Similarity	NPD2443	Approved
0.6235	Remote Similarity	NPD272	Approved
0.6231	Remote Similarity	NPD1952	Discontinued
0.623	Remote Similarity	NPD3178	Discontinued
0.6224	Remote Similarity	NPD1658	Discontinued
0.6214	Remote Similarity	NPD3968	Approved
0.6214	Remote Similarity	NPD1600	Suspended
0.6211	Remote Similarity	NPD3077	Approved
0.6211	Remote Similarity	NPD3079	Approved
0.6211	Remote Similarity	NPD3078	Approved
0.6211	Remote Similarity	NPD3076	Approved
0.6196	Remote Similarity	NPD1631	Approved
0.6188	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7026	Phase 2
0.615	Remote Similarity	NPD1573	Approved
0.615	Remote Similarity	NPD6210	Phase 3
0.615	Remote Similarity	NPD1575	Approved
0.615	Remote Similarity	NPD6579	Phase 2
0.615	Remote Similarity	NPD6664	Approved
0.6149	Remote Similarity	NPD2222	Discontinued
0.6149	Remote Similarity	NPD9599	Approved
0.6146	Remote Similarity	NPD3967	Approved
0.6129	Remote Similarity	NPD439	Approved
0.6129	Remote Similarity	NPD438	Approved
0.612	Remote Similarity	NPD1630	Approved
0.6117	Remote Similarity	NPD3411	Phase 2
0.6117	Remote Similarity	NPD3410	Approved
0.6117	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD510	Phase 1
0.61	Remote Similarity	NPD7027	Phase 3
0.6098	Remote Similarity	NPD8169	Discontinued
0.6093	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2405	Phase 3
0.6078	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD3041	Approved
0.6071	Remote Similarity	NPD4988	Discontinued
0.6059	Remote Similarity	NPD4961	Approved
0.6058	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD2408	Discontinued
0.6056	Remote Similarity	NPD6470	Phase 3
0.6053	Remote Similarity	NPD4883	Approved
0.605	Remote Similarity	NPD7619	Phase 3
0.605	Remote Similarity	NPD7618	Phase 3
0.6041	Remote Similarity	NPD5016	Approved
0.604	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD1506	Discontinued
0.6031	Remote Similarity	NPD3318	Approved
0.6031	Remote Similarity	NPD1745	Approved
0.6031	Remote Similarity	NPD3320	Approved
0.6031	Remote Similarity	NPD3319	Phase 1
0.6029	Remote Similarity	NPD4962	Approved
0.6029	Remote Similarity	NPD4963	Approved
0.6029	Remote Similarity	NPD7727	Phase 2
0.6027	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2128	Phase 1
0.6021	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5809	Phase 3
0.6019	Remote Similarity	NPD8114	Approved
0.6019	Remote Similarity	NPD8115	Approved
0.6012	Remote Similarity	NPD1781	Discontinued
0.601	Remote Similarity	NPD4960	Approved
0.601	Remote Similarity	NPD3927	Phase 2
0.601	Remote Similarity	NPD4959	Approved
0.6	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5787	Discontinued
0.599	Remote Similarity	NPD2008	Discontinued
0.599	Remote Similarity	NPD7568	Phase 1
0.599	Remote Similarity	NPD6271	Approved
0.599	Remote Similarity	NPD3246	Discontinued
0.598	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4024	Phase 3
0.5977	Remote Similarity	NPD200	Phase 2
0.5977	Remote Similarity	NPD201	Phase 2
0.5976	Remote Similarity	NPD4811	Discontinued
0.5968	Remote Similarity	NPD6771	Discontinued
0.5967	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD1982	Phase 1
0.596	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD2061	Approved
0.595	Remote Similarity	NPD5974	Approved
0.595	Remote Similarity	NPD5973	Phase 2
0.5939	Remote Similarity	NPD4940	Approved
0.5939	Remote Similarity	NPD9598	Discontinued
0.5939	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5020	Approved
0.5931	Remote Similarity	NPD7308	Discontinued
0.5924	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6802	Phase 3
0.5922	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6268	Phase 1
0.5918	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7564	Discontinued
0.5917	Remote Similarity	NPD7716	Approved
0.5917	Remote Similarity	NPD7717	Approved
0.5916	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD750	Phase 2
0.5911	Remote Similarity	NPD1174	Phase 2
0.5911	Remote Similarity	NPD2880	Discontinued
0.5911	Remote Similarity	NPD5446	Phase 2
0.5907	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5510	Approved
0.5904	Remote Similarity	NPD509	Phase 3
0.59	Remote Similarity	NPD2892	Phase 1
0.5899	Remote Similarity	NPD4047	Discontinued
0.5899	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD7656	Approved
0.5896	Remote Similarity	NPD7657	Approved
0.5888	Remote Similarity	NPD3353	Approved
0.5885	Remote Similarity	NPD4128	Approved
0.5885	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD4415	Approved
0.5879	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD7175	Phase 1
0.5877	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1587	Approved
0.5874	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD3890	Phase 2
0.5874	Remote Similarity	NPD3891	Phase 2
0.5872	Remote Similarity	NPD809	Discontinued
0.587	Remote Similarity	NPD1003	Phase 2
0.5867	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD2130	Discontinued
0.5859	Remote Similarity	NPD645	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD7232	Discontinued
0.5855	Remote Similarity	NPD6044	Discontinued
0.5854	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5854	Approved
0.5852	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD3583	Phase 2
0.585	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.585	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD1618	Phase 2
0.5845	Remote Similarity	NPD6173	Approved
0.5842	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD2547	Discontinued
0.5841	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7970	Approved
0.5833	Remote Similarity	NPD4524	Discontinued
0.5833	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1623	Approved
0.583	Remote Similarity	NPD5935	Discontinued
0.5829	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD3961	Discontinued
0.5825	Remote Similarity	NPD4155	Approved
0.5825	Remote Similarity	NPD4181	Approved
0.5824	Remote Similarity	NPD499	Phase 3
0.5822	Remote Similarity	NPD2411	Approved
0.5819	Remote Similarity	NPD7044	Discontinued
0.5815	Remote Similarity	NPD180	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD7406	Phase 2
0.5813	Remote Similarity	NPD5855	Phase 3
0.5813	Remote Similarity	NPD5853	Phase 3
0.5811	Remote Similarity	NPD7887	Approved
0.5811	Remote Similarity	NPD7888	Approved
0.581	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD1586	Approved
0.5803	Remote Similarity	NPD7297	Phase 2
0.5794	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD9396	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data