NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.06
Volume:	249.616
LogP:	1.742
LogD:	1.815
LogS:	-5.43
# Rotatable Bonds:	0
TPSA:	62.82
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	2.704
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	1.1998615264019463e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	97.13239288330078%
Volume Distribution (VD):	0.552
Pgp-substrate:	1.4120053052902222%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.397
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.5
CYP2C9-substrate:	0.342
CYP2D6-inhibitor:	0.544
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	2.998
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.892
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.474
Carcinogencity:	0.885
Eye Corrosion:	0.003
Eye Irritation:	0.321
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC40364

Natural Product ID:	NPC40364
*Common Name:**	Monomargine
IUPAC Name:	n.a.
Synonyms:	Monomargine
Standard InCHIKey:	QVJHQBASCBRCRU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8N2O2/c18-11-3-1-2-10-14(17-11)9-5-4-8-6-7-16-13(8)12(9)15(10)19/h1-7H,(H,17,18)
SMILES:	C1=CC(=O)NC2=c3ccc4=CC=Nc4c3C(=O)C2=C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488748
PubChem CID:	10243721
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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
NPO18362	Monocarpia marginalis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462006]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27324	Euphorbia petiolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23817	Asparagus falcatus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24206	Coreopsis senaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27483	Penicillium lanosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27266	Hoya parasitica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8793	Centaurea pumilio	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27430	Artemisia camphorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24237	Arthromeris mairei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21163	Lutzomyia longipalpis	Species	Psychodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18362	Monocarpia marginalis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.7	ug.mL-1	PMID[518168]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	0.7	ug.mL-1	PMID[518168]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.0	ug.mL-1	PMID[518168]

☑ 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 NPC40364 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	282
0.1-0.2	3649
0.2-0.3	13557
0.3-0.4	16488
0.4-0.5	6226
0.5-0.6	2244
0.6-0.7	225
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7762	Intermediate Similarity	NPC471164
0.7761	Intermediate Similarity	NPC254698
0.764	Intermediate Similarity	NPC28368
0.7619	Intermediate Similarity	NPC172170
0.7603	Intermediate Similarity	NPC136002
0.7552	Intermediate Similarity	NPC122553
0.7482	Intermediate Similarity	NPC209389
0.7407	Intermediate Similarity	NPC179605
0.7407	Intermediate Similarity	NPC279385
0.7397	Intermediate Similarity	NPC471574
0.7353	Intermediate Similarity	NPC103292
0.7343	Intermediate Similarity	NPC162417
0.7343	Intermediate Similarity	NPC316104
0.7324	Intermediate Similarity	NPC207428
0.7299	Intermediate Similarity	NPC268534
0.7285	Intermediate Similarity	NPC300596
0.7285	Intermediate Similarity	NPC237649
0.7208	Intermediate Similarity	NPC295021
0.7143	Intermediate Similarity	NPC117032
0.7095	Intermediate Similarity	NPC207554
0.708	Intermediate Similarity	NPC177684
0.708	Intermediate Similarity	NPC291962
0.7047	Intermediate Similarity	NPC2823
0.7047	Intermediate Similarity	NPC316202
0.7042	Intermediate Similarity	NPC307437
0.7042	Intermediate Similarity	NPC72473
0.7042	Intermediate Similarity	NPC58827
0.7029	Intermediate Similarity	NPC161956
0.7029	Intermediate Similarity	NPC112373
0.7029	Intermediate Similarity	NPC258531
0.702	Intermediate Similarity	NPC470822
0.6978	Remote Similarity	NPC257490
0.6972	Remote Similarity	NPC322433
0.6954	Remote Similarity	NPC314287
0.6944	Remote Similarity	NPC194562
0.6939	Remote Similarity	NPC300299
0.6929	Remote Similarity	NPC39818
0.6928	Remote Similarity	NPC324445
0.6909	Remote Similarity	NPC469529
0.6831	Remote Similarity	NPC192533
0.6829	Remote Similarity	NPC471943
0.6828	Remote Similarity	NPC472245
0.6828	Remote Similarity	NPC187231
0.679	Remote Similarity	NPC138293
0.679	Remote Similarity	NPC113056
0.6759	Remote Similarity	NPC150863
0.6725	Remote Similarity	NPC477003
0.6689	Remote Similarity	NPC83214
0.6687	Remote Similarity	NPC84317
0.6667	Remote Similarity	NPC316746
0.6644	Remote Similarity	NPC313722
0.6627	Remote Similarity	NPC284775
0.6626	Remote Similarity	NPC88970
0.6605	Remote Similarity	NPC154478
0.6599	Remote Similarity	NPC280807
0.6599	Remote Similarity	NPC477432
0.6591	Remote Similarity	NPC476460
0.6587	Remote Similarity	NPC355
0.6585	Remote Similarity	NPC189116
0.6558	Remote Similarity	NPC472241
0.6545	Remote Similarity	NPC471130
0.6535	Remote Similarity	NPC291070
0.6535	Remote Similarity	NPC246757
0.6533	Remote Similarity	NPC253476
0.6524	Remote Similarity	NPC214106
0.6506	Remote Similarity	NPC114637
0.6497	Remote Similarity	NPC259678
0.6494	Remote Similarity	NPC43477
0.6493	Remote Similarity	NPC473498
0.649	Remote Similarity	NPC173295
0.6486	Remote Similarity	NPC314431
0.6483	Remote Similarity	NPC226794
0.6479	Remote Similarity	NPC226143
0.6477	Remote Similarity	NPC473666
0.6471	Remote Similarity	NPC151635
0.6466	Remote Similarity	NPC38262
0.6466	Remote Similarity	NPC275467
0.6446	Remote Similarity	NPC115232
0.6446	Remote Similarity	NPC42372
0.6434	Remote Similarity	NPC27833
0.6434	Remote Similarity	NPC130931
0.6433	Remote Similarity	NPC472242
0.6429	Remote Similarity	NPC472243
0.6419	Remote Similarity	NPC122235
0.6379	Remote Similarity	NPC117027
0.6369	Remote Similarity	NPC130797
0.6364	Remote Similarity	NPC181527
0.6364	Remote Similarity	NPC469560
0.6358	Remote Similarity	NPC251391
0.6348	Remote Similarity	NPC324091
0.6347	Remote Similarity	NPC233380
0.6327	Remote Similarity	NPC474926
0.6325	Remote Similarity	NPC242116
0.6324	Remote Similarity	NPC55529
0.6323	Remote Similarity	NPC315051
0.6322	Remote Similarity	NPC191415
0.6316	Remote Similarity	NPC293216
0.6312	Remote Similarity	NPC105811
0.6307	Remote Similarity	NPC133003
0.6306	Remote Similarity	NPC478040
0.6301	Remote Similarity	NPC475094
0.6299	Remote Similarity	NPC287358
0.6296	Remote Similarity	NPC70406
0.6289	Remote Similarity	NPC467188
0.6288	Remote Similarity	NPC75496
0.6287	Remote Similarity	NPC265100
0.6286	Remote Similarity	NPC57051
0.6273	Remote Similarity	NPC123906
0.6259	Remote Similarity	NPC275410
0.6257	Remote Similarity	NPC252572
0.625	Remote Similarity	NPC477004
0.625	Remote Similarity	NPC21429
0.6235	Remote Similarity	NPC472118
0.6235	Remote Similarity	NPC313889
0.6231	Remote Similarity	NPC256452
0.6229	Remote Similarity	NPC270301
0.6228	Remote Similarity	NPC472121
0.6225	Remote Similarity	NPC126458
0.6216	Remote Similarity	NPC470343
0.6216	Remote Similarity	NPC472244
0.6203	Remote Similarity	NPC317701
0.6193	Remote Similarity	NPC470205
0.6188	Remote Similarity	NPC272458
0.6188	Remote Similarity	NPC478039
0.618	Remote Similarity	NPC17273
0.618	Remote Similarity	NPC87391
0.618	Remote Similarity	NPC135601
0.618	Remote Similarity	NPC141612
0.6176	Remote Similarity	NPC167336
0.6173	Remote Similarity	NPC241392
0.6172	Remote Similarity	NPC78154
0.6171	Remote Similarity	NPC88110
0.617	Remote Similarity	NPC35850
0.617	Remote Similarity	NPC276949
0.6168	Remote Similarity	NPC143457
0.6167	Remote Similarity	NPC154339
0.6164	Remote Similarity	NPC314186
0.6154	Remote Similarity	NPC304203
0.6154	Remote Similarity	NPC326422
0.6149	Remote Similarity	NPC317758
0.6148	Remote Similarity	NPC202613
0.6145	Remote Similarity	NPC213914
0.6141	Remote Similarity	NPC316282
0.6136	Remote Similarity	NPC472258
0.6136	Remote Similarity	NPC470677
0.6131	Remote Similarity	NPC471447
0.6127	Remote Similarity	NPC470550
0.6127	Remote Similarity	NPC113099
0.6121	Remote Similarity	NPC209362
0.612	Remote Similarity	NPC202812
0.6118	Remote Similarity	NPC279527
0.6118	Remote Similarity	NPC214960
0.6115	Remote Similarity	NPC130251
0.6115	Remote Similarity	NPC242933
0.6108	Remote Similarity	NPC474492
0.6107	Remote Similarity	NPC205946
0.6102	Remote Similarity	NPC102755
0.6087	Remote Similarity	NPC470579
0.6087	Remote Similarity	NPC102592
0.6087	Remote Similarity	NPC79356
0.6082	Remote Similarity	NPC70949
0.6076	Remote Similarity	NPC301760
0.6074	Remote Similarity	NPC473329
0.6071	Remote Similarity	NPC27904
0.6069	Remote Similarity	NPC177261
0.6066	Remote Similarity	NPC267343
0.6048	Remote Similarity	NPC76982
0.6045	Remote Similarity	NPC197335
0.6034	Remote Similarity	NPC475594
0.6029	Remote Similarity	NPC178681
0.6029	Remote Similarity	NPC471317
0.6026	Remote Similarity	NPC476950
0.6024	Remote Similarity	NPC229055
0.6023	Remote Similarity	NPC475761
0.6022	Remote Similarity	NPC18890
0.6014	Remote Similarity	NPC45033
0.6012	Remote Similarity	NPC80681
0.6011	Remote Similarity	NPC314659
0.6	Remote Similarity	NPC475607
0.6	Remote Similarity	NPC471743
0.6	Remote Similarity	NPC326792
0.6	Remote Similarity	NPC79698
0.5989	Remote Similarity	NPC471195
0.5989	Remote Similarity	NPC73994
0.5989	Remote Similarity	NPC471196
0.5988	Remote Similarity	NPC74357
0.5978	Remote Similarity	NPC110158
0.5976	Remote Similarity	NPC144691
0.5976	Remote Similarity	NPC309531
0.5976	Remote Similarity	NPC472102
0.5976	Remote Similarity	NPC13526
0.5976	Remote Similarity	NPC470680
0.5976	Remote Similarity	NPC100104
0.5967	Remote Similarity	NPC278434
0.5966	Remote Similarity	NPC474081
0.5965	Remote Similarity	NPC2414
0.5964	Remote Similarity	NPC281094
0.5959	Remote Similarity	NPC229353
0.5956	Remote Similarity	NPC92803
0.5956	Remote Similarity	NPC138370

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 NPC40364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	633
0.2-0.3	1181
0.3-0.4	1745
0.4-0.5	3593
0.5-0.6	1617
0.6-0.7	193
0.7-0.8	20
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
0.7481	Intermediate Similarity	NPD1079	Discontinued
0.7357	Intermediate Similarity	NPD1781	Discontinued
0.7153	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3248	Phase 1
0.7101	Intermediate Similarity	NPD1124	Approved
0.7101	Intermediate Similarity	NPD1123	Approved
0.7092	Intermediate Similarity	NPD1593	Approved
0.7071	Intermediate Similarity	NPD9539	Approved
0.7071	Intermediate Similarity	NPD9541	Approved
0.7034	Intermediate Similarity	NPD1541	Approved
0.7014	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1619	Phase 3
0.6972	Remote Similarity	NPD9540	Approved
0.6966	Remote Similarity	NPD1920	Approved
0.6966	Remote Similarity	NPD1919	Approved
0.6959	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7072	Phase 2
0.6899	Remote Similarity	NPD951	Approved
0.6879	Remote Similarity	NPD2790	Discontinued
0.6863	Remote Similarity	NPD6017	Discontinued
0.6839	Remote Similarity	NPD979	Approved
0.6818	Remote Similarity	NPD1524	Phase 1
0.6812	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2949	Approved
0.6803	Remote Similarity	NPD2950	Approved
0.68	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5918	Discontinued
0.6776	Remote Similarity	NPD6768	Approved
0.6765	Remote Similarity	NPD1175	Approved
0.6739	Remote Similarity	NPD1344	Phase 2
0.6733	Remote Similarity	NPD6342	Discontinued
0.6732	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4942	Approved
0.6712	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1527	Phase 2
0.6667	Remote Similarity	NPD1323	Discontinued
0.6667	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2360	Approved
0.6667	Remote Similarity	NPD1574	Approved
0.6644	Remote Similarity	NPD4549	Discontinued
0.6624	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD797	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2331	Discontinued
0.6594	Remote Similarity	NPD853	Approved
0.6594	Remote Similarity	NPD851	Approved
0.6577	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD441	Approved
0.6558	Remote Similarity	NPD6566	Discontinued
0.6509	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1854	Approved
0.6493	Remote Similarity	NPD1064	Approved
0.6493	Remote Similarity	NPD1065	Approved
0.6479	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1107	Approved
0.6471	Remote Similarity	NPD1626	Approved
0.6471	Remote Similarity	NPD1108	Approved
0.6456	Remote Similarity	NPD7088	Discontinued
0.6452	Remote Similarity	NPD167	Phase 2
0.6452	Remote Similarity	NPD168	Phase 1
0.6449	Remote Similarity	NPD480	Approved
0.6439	Remote Similarity	NPD813	Approved
0.6405	Remote Similarity	NPD4214	Discontinued
0.6402	Remote Similarity	NPD33	Approved
0.6402	Remote Similarity	NPD4393	Approved
0.6387	Remote Similarity	NPD2010	Phase 3
0.6386	Remote Similarity	NPD923	Approved
0.6385	Remote Similarity	NPD1100	Approved
0.6385	Remote Similarity	NPD1099	Approved
0.6382	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5748	Phase 2
0.6364	Remote Similarity	NPD7254	Discontinued
0.6364	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2479	Phase 3
0.6358	Remote Similarity	NPD2481	Approved
0.6333	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD2369	Discontinued
0.6327	Remote Similarity	NPD1036	Approved
0.6324	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4042	Phase 2
0.6319	Remote Similarity	NPD4045	Phase 2
0.6316	Remote Similarity	NPD1531	Approved
0.6306	Remote Similarity	NPD1625	Approved
0.6296	Remote Similarity	NPD563	Approved
0.6296	Remote Similarity	NPD564	Approved
0.6294	Remote Similarity	NPD922	Approved
0.6282	Remote Similarity	NPD4461	Discontinued
0.628	Remote Similarity	NPD7091	Discontinued
0.6277	Remote Similarity	NPD1342	Approved
0.6276	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1189	Approved
0.6236	Remote Similarity	NPD4988	Discontinued
0.6235	Remote Similarity	NPD7795	Phase 2
0.6233	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1190	Approved
0.6216	Remote Similarity	NPD2056	Discontinued
0.6214	Remote Similarity	NPD181	Approved
0.6211	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD1025	Discontinued
0.6194	Remote Similarity	NPD1532	Approved
0.6194	Remote Similarity	NPD1419	Approved
0.6194	Remote Similarity	NPD1417	Approved
0.6194	Remote Similarity	NPD2196	Discontinued
0.6188	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD2351	Discontinued
0.6181	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD9477	Approved
0.6176	Remote Similarity	NPD2192	Approved
0.6176	Remote Similarity	NPD2197	Approved
0.6175	Remote Similarity	NPD4848	Phase 1
0.6171	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.617	Remote Similarity	NPD23	Approved
0.6163	Remote Similarity	NPD3868	Phase 1
0.6149	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5840	Discontinued
0.6148	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD941	Approved
0.6143	Remote Similarity	NPD753	Approved
0.6139	Remote Similarity	NPD6512	Approved
0.6139	Remote Similarity	NPD6513	Approved
0.6133	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD272	Approved
0.6127	Remote Similarity	NPD1075	Approved
0.6127	Remote Similarity	NPD4883	Approved
0.6127	Remote Similarity	NPD1074	Approved
0.6127	Remote Similarity	NPD1073	Approved
0.6118	Remote Similarity	NPD2754	Discontinued
0.6118	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1270	Approved
0.6111	Remote Similarity	NPD4888	Discontinued
0.6105	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3319	Phase 1
0.6102	Remote Similarity	NPD3320	Approved
0.6102	Remote Similarity	NPD3318	Approved
0.6101	Remote Similarity	NPD5024	Approved
0.6089	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1663	Discontinued
0.608	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD1222	Discontinued
0.6074	Remote Similarity	NPD2193	Phase 2
0.6074	Remote Similarity	NPD2648	Phase 3
0.6067	Remote Similarity	NPD1321	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7564	Discontinued
0.6067	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD737	Phase 2
0.6058	Remote Similarity	NPD1677	Discontinued
0.6057	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD7142	Discontinued
0.6051	Remote Similarity	NPD3170	Approved
0.6048	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD787	Suspended
0.6043	Remote Similarity	NPD2678	Approved
0.6043	Remote Similarity	NPD2679	Approved
0.604	Remote Similarity	NPD2371	Approved
0.6038	Remote Similarity	NPD2365	Approved
0.6032	Remote Similarity	NPD6176	Phase 1
0.6027	Remote Similarity	NPD2210	Approved
0.6027	Remote Similarity	NPD2212	Approved
0.6025	Remote Similarity	NPD5931	Phase 3
0.6025	Remote Similarity	NPD5932	Phase 3
0.6025	Remote Similarity	NPD5933	Phase 3
0.6023	Remote Similarity	NPD3079	Approved
0.6023	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3078	Approved
0.6023	Remote Similarity	NPD3077	Approved
0.6023	Remote Similarity	NPD3076	Approved
0.6014	Remote Similarity	NPD993	Approved
0.6014	Remote Similarity	NPD990	Approved
0.6014	Remote Similarity	NPD5631	Phase 3
0.6012	Remote Similarity	NPD3776	Discontinued
0.6011	Remote Similarity	NPD4922	Phase 2
0.6	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2501	Discontinued
0.6	Remote Similarity	NPD6325	Discontinued
0.6	Remote Similarity	NPD2820	Phase 3
0.6	Remote Similarity	NPD3947	Discontinued
0.6	Remote Similarity	NPD479	Approved
0.6	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD5473	Discontinued
0.5989	Remote Similarity	NPD5146	Suspended
0.5989	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD7105	Phase 1
0.5988	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1343	Approved
0.5987	Remote Similarity	NPD4411	Phase 1
0.5987	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD1050	Approved
0.5987	Remote Similarity	NPD6358	Phase 2
0.5986	Remote Similarity	NPD1525	Approved
0.5986	Remote Similarity	NPD4733	Approved
0.5978	Remote Similarity	NPD4412	Phase 2

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