NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.1
Volume:	257.576
LogP:	1.745
LogD:	2.325
LogS:	-1.67
# Rotatable Bonds:	3
TPSA:	53.47
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	3.39
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.536
MDCK Permeability:	2.6582150894682854e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	80.29759216308594%
Volume Distribution (VD):	1.654
Pgp-substrate:	25.752471923828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.438
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.576
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	2.698
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.887
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.737
Carcinogencity:	0.331
Eye Corrosion:	0.004
Eye Irritation:	0.715
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC284559

Natural Product ID:	NPC284559
*Common Name:**	FMLNWBVUWATIIH-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FMLNWBVUWATIIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14N2O3/c1-17-11-8-9-4-6-15-10-5-7-16-13(12(9)10)14(11,18-2)19-3/h4-8H,1-3H3
SMILES:	COC1=Cc2ccnc3ccnc(c23)C1(OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450982
PubChem CID:	11086414
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0001857] Naphthyridines

*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
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	southern Australian	n.a.	PMID[11908980]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	Singapore	n.a.	PMID[15043446]
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20451377]
NPO13586	Aaptos suberitoides	Species	Suberitidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[23282083]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599282]
NPO13586	Aaptos suberitoides	Species	Suberitidae	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
ED50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	59.0	ug ml-1	PMID[490224]
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	51.2	%	PMID[490225]

☑ 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 NPC284559 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	500
0.1-0.2	3808
0.2-0.3	13264
0.3-0.4	16478
0.4-0.5	4384
0.5-0.6	2440
0.6-0.7	1660
0.7-0.8	162
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
0.7923	Intermediate Similarity	NPC118084
0.7842	Intermediate Similarity	NPC287437
0.7778	Intermediate Similarity	NPC162530
0.7766	Intermediate Similarity	NPC198673
0.7708	Intermediate Similarity	NPC234197
0.7692	Intermediate Similarity	NPC470164
0.7692	Intermediate Similarity	NPC323345
0.7656	Intermediate Similarity	NPC476582
0.7656	Intermediate Similarity	NPC4071
0.7656	Intermediate Similarity	NPC476578
0.7653	Intermediate Similarity	NPC313189
0.7641	Intermediate Similarity	NPC36229
0.7641	Intermediate Similarity	NPC476581
0.7641	Intermediate Similarity	NPC16452
0.7638	Intermediate Similarity	NPC53069
0.7638	Intermediate Similarity	NPC202768
0.7638	Intermediate Similarity	NPC296482
0.7622	Intermediate Similarity	NPC284678
0.7619	Intermediate Similarity	NPC133140
0.7619	Intermediate Similarity	NPC195268
0.7617	Intermediate Similarity	NPC477019
0.7604	Intermediate Similarity	NPC168911
0.7604	Intermediate Similarity	NPC239954
0.7581	Intermediate Similarity	NPC20249
0.7574	Intermediate Similarity	NPC473513
0.7563	Intermediate Similarity	NPC135549
0.7552	Intermediate Similarity	NPC267928
0.7552	Intermediate Similarity	NPC106824
0.7551	Intermediate Similarity	NPC327592
0.755	Intermediate Similarity	NPC171409
0.755	Intermediate Similarity	NPC96405
0.7537	Intermediate Similarity	NPC173080
0.7528	Intermediate Similarity	NPC97367
0.7513	Intermediate Similarity	NPC317373
0.7487	Intermediate Similarity	NPC31930
0.7486	Intermediate Similarity	NPC150048
0.7486	Intermediate Similarity	NPC203754
0.7474	Intermediate Similarity	NPC123395
0.7474	Intermediate Similarity	NPC284338
0.7459	Intermediate Similarity	NPC476518
0.7427	Intermediate Similarity	NPC471323
0.7419	Intermediate Similarity	NPC161887
0.7419	Intermediate Similarity	NPC266551
0.7419	Intermediate Similarity	NPC219963
0.7418	Intermediate Similarity	NPC121658
0.7418	Intermediate Similarity	NPC14651
0.7396	Intermediate Similarity	NPC329541
0.7391	Intermediate Similarity	NPC134586
0.7376	Intermediate Similarity	NPC202605
0.7376	Intermediate Similarity	NPC112206
0.7376	Intermediate Similarity	NPC318299
0.7374	Intermediate Similarity	NPC177404
0.7363	Intermediate Similarity	NPC290689
0.736	Intermediate Similarity	NPC472062
0.736	Intermediate Similarity	NPC472069
0.736	Intermediate Similarity	NPC472063
0.7351	Intermediate Similarity	NPC211997
0.7347	Intermediate Similarity	NPC19872
0.734	Intermediate Similarity	NPC317752
0.7333	Intermediate Similarity	NPC212213
0.7323	Intermediate Similarity	NPC476138
0.7323	Intermediate Similarity	NPC245816
0.7313	Intermediate Similarity	NPC472070
0.731	Intermediate Similarity	NPC232727
0.7306	Intermediate Similarity	NPC226202
0.7286	Intermediate Similarity	NPC165349
0.7286	Intermediate Similarity	NPC264166
0.7286	Intermediate Similarity	NPC274291
0.7286	Intermediate Similarity	NPC285558
0.7286	Intermediate Similarity	NPC118832
0.7286	Intermediate Similarity	NPC329708
0.7286	Intermediate Similarity	NPC47059
0.7283	Intermediate Similarity	NPC111624
0.7277	Intermediate Similarity	NPC167860
0.7277	Intermediate Similarity	NPC123976
0.7273	Intermediate Similarity	NPC328318
0.7273	Intermediate Similarity	NPC328596
0.7264	Intermediate Similarity	NPC287208
0.7259	Intermediate Similarity	NPC176538
0.7259	Intermediate Similarity	NPC315957
0.725	Intermediate Similarity	NPC472064
0.725	Intermediate Similarity	NPC472065
0.7238	Intermediate Similarity	NPC263439
0.7236	Intermediate Similarity	NPC475774
0.7228	Intermediate Similarity	NPC185782
0.7228	Intermediate Similarity	NPC174758
0.7228	Intermediate Similarity	NPC174672
0.7225	Intermediate Similarity	NPC216612
0.7211	Intermediate Similarity	NPC62510
0.7206	Intermediate Similarity	NPC251160
0.7198	Intermediate Similarity	NPC471178
0.7192	Intermediate Similarity	NPC188420
0.7188	Intermediate Similarity	NPC296527
0.7178	Intermediate Similarity	NPC18348
0.7178	Intermediate Similarity	NPC82548
0.7172	Intermediate Similarity	NPC121772
0.7163	Intermediate Similarity	NPC17565
0.7163	Intermediate Similarity	NPC193267
0.7163	Intermediate Similarity	NPC213530
0.715	Intermediate Similarity	NPC76748
0.7143	Intermediate Similarity	NPC13880
0.7143	Intermediate Similarity	NPC118511
0.7143	Intermediate Similarity	NPC469589
0.7136	Intermediate Similarity	NPC235076
0.7136	Intermediate Similarity	NPC314954
0.7135	Intermediate Similarity	NPC249614
0.7128	Intermediate Similarity	NPC307963
0.7127	Intermediate Similarity	NPC25899
0.7122	Intermediate Similarity	NPC26679
0.7113	Intermediate Similarity	NPC92111
0.7109	Intermediate Similarity	NPC65277
0.7109	Intermediate Similarity	NPC322482
0.7105	Intermediate Similarity	NPC48938
0.7101	Intermediate Similarity	NPC477110
0.7095	Intermediate Similarity	NPC63562
0.7094	Intermediate Similarity	NPC477111
0.7092	Intermediate Similarity	NPC135950
0.7087	Intermediate Similarity	NPC271215
0.7087	Intermediate Similarity	NPC149471
0.7087	Intermediate Similarity	NPC476287
0.7081	Intermediate Similarity	NPC473764
0.7081	Intermediate Similarity	NPC314940
0.7068	Intermediate Similarity	NPC207851
0.7056	Intermediate Similarity	NPC251090
0.7056	Intermediate Similarity	NPC194967
0.7043	Intermediate Similarity	NPC158129
0.7039	Intermediate Similarity	NPC118940
0.7039	Intermediate Similarity	NPC26872
0.7037	Intermediate Similarity	NPC469554
0.7035	Intermediate Similarity	NPC103361
0.7033	Intermediate Similarity	NPC100079
0.7033	Intermediate Similarity	NPC322976
0.7033	Intermediate Similarity	NPC324203
0.7033	Intermediate Similarity	NPC63338
0.7033	Intermediate Similarity	NPC23614
0.7019	Intermediate Similarity	NPC274982
0.7019	Intermediate Similarity	NPC8022
0.7019	Intermediate Similarity	NPC470799
0.7017	Intermediate Similarity	NPC132680
0.7017	Intermediate Similarity	NPC269919
0.7017	Intermediate Similarity	NPC26850
0.701	Intermediate Similarity	NPC266249
0.701	Intermediate Similarity	NPC472289
0.7	Intermediate Similarity	NPC46451
0.6995	Remote Similarity	NPC204385
0.6995	Remote Similarity	NPC471177
0.6995	Remote Similarity	NPC59779
0.6995	Remote Similarity	NPC48192
0.6995	Remote Similarity	NPC477113
0.6995	Remote Similarity	NPC124542
0.699	Remote Similarity	NPC208284
0.6974	Remote Similarity	NPC469489
0.697	Remote Similarity	NPC109922
0.6968	Remote Similarity	NPC312872
0.6963	Remote Similarity	NPC470474
0.6963	Remote Similarity	NPC206201
0.6959	Remote Similarity	NPC206251
0.6959	Remote Similarity	NPC74382
0.6959	Remote Similarity	NPC101543
0.6959	Remote Similarity	NPC46580
0.6957	Remote Similarity	NPC316981
0.6952	Remote Similarity	NPC204446
0.6952	Remote Similarity	NPC314270
0.6952	Remote Similarity	NPC252590
0.6947	Remote Similarity	NPC141377
0.6947	Remote Similarity	NPC133261
0.6946	Remote Similarity	NPC212125
0.6943	Remote Similarity	NPC188387
0.6943	Remote Similarity	NPC42591
0.6943	Remote Similarity	NPC282103
0.6943	Remote Similarity	NPC163421
0.6942	Remote Similarity	NPC123839
0.6942	Remote Similarity	NPC5145
0.694	Remote Similarity	NPC131718
0.6935	Remote Similarity	NPC224928
0.6934	Remote Similarity	NPC60621
0.6931	Remote Similarity	NPC84347
0.6923	Remote Similarity	NPC236668
0.6923	Remote Similarity	NPC469592
0.6923	Remote Similarity	NPC471080
0.6919	Remote Similarity	NPC29702
0.6919	Remote Similarity	NPC328029
0.6915	Remote Similarity	NPC329793
0.6912	Remote Similarity	NPC260434
0.6912	Remote Similarity	NPC472111
0.6912	Remote Similarity	NPC238457
0.6911	Remote Similarity	NPC168486
0.6911	Remote Similarity	NPC222592
0.6901	Remote Similarity	NPC118121
0.6893	Remote Similarity	NPC86288
0.6891	Remote Similarity	NPC84478
0.689	Remote Similarity	NPC146976
0.6887	Remote Similarity	NPC174049
0.6882	Remote Similarity	NPC41717
0.6878	Remote Similarity	NPC30540
0.6875	Remote Similarity	NPC314394
0.6872	Remote Similarity	NPC473822
0.6866	Remote Similarity	NPC476167
0.6865	Remote Similarity	NPC211187
0.6865	Remote Similarity	NPC102423

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 NPC284559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	654
0.2-0.3	850
0.3-0.4	1605
0.4-0.5	2802
0.5-0.6	1970
0.6-0.7	936
0.7-0.8	64
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
0.7907	Intermediate Similarity	NPD2581	Approved
0.7907	Intermediate Similarity	NPD2582	Approved
0.7892	Intermediate Similarity	NPD8063	Discontinued
0.7657	Intermediate Similarity	NPD5255	Approved
0.7638	Intermediate Similarity	NPD3816	Phase 1
0.7638	Intermediate Similarity	NPD3815	Phase 1
0.7619	Intermediate Similarity	NPD3923	Approved
0.7619	Intermediate Similarity	NPD3924	Approved
0.7619	Intermediate Similarity	NPD3922	Approved
0.7619	Intermediate Similarity	NPD3921	Approved
0.7592	Intermediate Similarity	NPD3477	Phase 2
0.7592	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6569	Phase 2
0.7486	Intermediate Similarity	NPD926	Approved
0.7486	Intermediate Similarity	NPD925	Approved
0.7475	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD1032	Phase 2
0.7407	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1034	Phase 3
0.7377	Intermediate Similarity	NPD2076	Approved
0.7377	Intermediate Similarity	NPD2077	Approved
0.735	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD9705	Discontinued
0.7318	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD112	Approved
0.7308	Intermediate Similarity	NPD5862	Discovery
0.7306	Intermediate Similarity	NPD4528	Approved
0.7306	Intermediate Similarity	NPD4526	Approved
0.7306	Intermediate Similarity	NPD4529	Approved
0.7297	Intermediate Similarity	NPD5100	Phase 3
0.7286	Intermediate Similarity	NPD4033	Approved
0.7286	Intermediate Similarity	NPD31	Approved
0.7286	Intermediate Similarity	NPD4036	Approved
0.7286	Intermediate Similarity	NPD4037	Approved
0.7286	Intermediate Similarity	NPD4122	Approved
0.7286	Intermediate Similarity	NPD4034	Approved
0.7286	Intermediate Similarity	NPD4039	Approved
0.7286	Intermediate Similarity	NPD4038	Approved
0.7286	Intermediate Similarity	NPD4035	Approved
0.7286	Intermediate Similarity	NPD32	Approved
0.7259	Intermediate Similarity	NPD1740	Approved
0.7259	Intermediate Similarity	NPD1739	Approved
0.7253	Intermediate Similarity	NPD425	Approved
0.7253	Intermediate Similarity	NPD424	Approved
0.7251	Intermediate Similarity	NPD1649	Discontinued
0.724	Intermediate Similarity	NPD6281	Approved
0.7211	Intermediate Similarity	NPD3082	Discontinued
0.72	Intermediate Similarity	NPD4795	Phase 2
0.7179	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1392	Approved
0.7128	Intermediate Similarity	NPD3920	Phase 2
0.7128	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD1038	Approved
0.7127	Intermediate Similarity	NPD1741	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4889	Approved
0.7077	Intermediate Similarity	NPD4372	Phase 1
0.7074	Intermediate Similarity	NPD4072	Approved
0.7074	Intermediate Similarity	NPD4071	Approved
0.7073	Intermediate Similarity	NPD3939	Suspended
0.7053	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3330	Phase 1
0.7033	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6227	Discontinued
0.7029	Intermediate Similarity	NPD3813	Approved
0.702	Intermediate Similarity	NPD1229	Phase 2
0.7017	Intermediate Similarity	NPD9383	Approved
0.7017	Intermediate Similarity	NPD9382	Approved
0.7011	Intermediate Similarity	NPD2780	Approved
0.7011	Intermediate Similarity	NPD2782	Approved
0.7006	Intermediate Similarity	NPD4703	Approved
0.7006	Intermediate Similarity	NPD4702	Approved
0.7	Intermediate Similarity	NPD3763	Approved
0.6995	Remote Similarity	NPD5256	Discontinued
0.6995	Remote Similarity	NPD4375	Approved
0.699	Remote Similarity	NPD4131	Phase 3
0.6984	Remote Similarity	NPD8123	Approved
0.6984	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8122	Approved
0.6981	Remote Similarity	NPD1856	Discontinued
0.6976	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD9690	Approved
0.6963	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7674	Phase 3
0.6963	Remote Similarity	NPD3386	Phase 2
0.6963	Remote Similarity	NPD4204	Approved
0.6963	Remote Similarity	NPD7675	Phase 3
0.6963	Remote Similarity	NPD4203	Approved
0.6963	Remote Similarity	NPD7426	Phase 1
0.6959	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD9695	Approved
0.6952	Remote Similarity	NPD4429	Discontinued
0.695	Remote Similarity	NPD5999	Phase 2
0.6946	Remote Similarity	NPD9284	Approved
0.6942	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4148	Approved
0.6939	Remote Similarity	NPD5913	Phase 3
0.6935	Remote Similarity	NPD1622	Discontinued
0.6935	Remote Similarity	NPD2781	Approved
0.693	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6494	Phase 2
0.6927	Remote Similarity	NPD5658	Approved
0.6923	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2060	Approved
0.6907	Remote Similarity	NPD706	Phase 1
0.6905	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4886	Phase 2
0.6897	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6158	Phase 2
0.6889	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD3321	Discontinued
0.6888	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9506	Approved
0.6878	Remote Similarity	NPD5065	Approved
0.6878	Remote Similarity	NPD7222	Phase 2
0.6862	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2334	Discontinued
0.685	Remote Similarity	NPD2952	Discontinued
0.6849	Remote Similarity	NPD7558	Phase 2
0.6845	Remote Similarity	NPD5529	Phase 1
0.6845	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2380	Approved
0.6842	Remote Similarity	NPD2382	Approved
0.6842	Remote Similarity	NPD2381	Approved
0.684	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD1602	Discontinued
0.6834	Remote Similarity	NPD4427	Phase 2
0.6831	Remote Similarity	NPD820	Phase 3
0.6827	Remote Similarity	NPD5475	Discontinued
0.6824	Remote Similarity	NPD715	Phase 3
0.6822	Remote Similarity	NPD1954	Phase 1
0.6821	Remote Similarity	NPD4919	Phase 3
0.6821	Remote Similarity	NPD4921	Phase 3
0.6821	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2757	Phase 2
0.6818	Remote Similarity	NPD3404	Approved
0.6816	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD565	Phase 2
0.6809	Remote Similarity	NPD5319	Approved
0.6809	Remote Similarity	NPD5320	Approved
0.6806	Remote Similarity	NPD6159	Phase 2
0.6804	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6750	Phase 2
0.6798	Remote Similarity	NPD3911	Approved
0.6796	Remote Similarity	NPD2882	Phase 1
0.6796	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5022	Discontinued
0.6787	Remote Similarity	NPD5891	Approved
0.6784	Remote Similarity	NPD5428	Discontinued
0.6784	Remote Similarity	NPD802	Phase 2
0.6784	Remote Similarity	NPD4551	Phase 2
0.6782	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1768	Approved
0.6777	Remote Similarity	NPD5612	Discontinued
0.6776	Remote Similarity	NPD6298	Discontinued
0.6772	Remote Similarity	NPD2123	Phase 3
0.6771	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4699	Discontinued
0.6766	Remote Similarity	NPD4673	Phase 2
0.6765	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3794	Approved
0.6762	Remote Similarity	NPD5945	Phase 1
0.6762	Remote Similarity	NPD5944	Phase 1
0.6762	Remote Similarity	NPD3795	Approved
0.6761	Remote Similarity	NPD3402	Phase 1
0.6761	Remote Similarity	NPD7404	Approved
0.6754	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4021	Phase 2
0.675	Remote Similarity	NPD3396	Approved
0.675	Remote Similarity	NPD3395	Approved
0.6749	Remote Similarity	NPD2332	Discontinued
0.6748	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3003	Approved
0.6746	Remote Similarity	NPD9080	Approved
0.6746	Remote Similarity	NPD5067	Phase 2
0.6746	Remote Similarity	NPD3570	Phase 2
0.6746	Remote Similarity	NPD5066	Phase 2
0.6742	Remote Similarity	NPD6964	Approved
0.6742	Remote Similarity	NPD1352	Discontinued
0.6742	Remote Similarity	NPD6963	Approved
0.6739	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2600	Approved
0.6736	Remote Similarity	NPD2599	Approved
0.6736	Remote Similarity	NPD2601	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