NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.08
Volume:	226.843
LogP:	2.13
LogD:	2.22
LogS:	-2.194
# Rotatable Bonds:	3
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.855
Synthetic Accessibility Score:	2.215
Fsp3:	0.154
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:	-4.73
MDCK Permeability:	2.1793999621877447e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.212
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	96.53284454345703%
Volume Distribution (VD):	1.136
Pgp-substrate:	1.7560200691223145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.564
CYP2D6-substrate:	0.824
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	13.036
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.194
Rat Oral Acute Toxicity:	0.377
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.28
Carcinogencity:	0.503
Eye Corrosion:	0.279
Eye Irritation:	0.895
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC472319

Natural Product ID:	NPC472319
*Common Name:**	WTKDFCHQROYLGC-QRRQSFLOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WTKDFCHQROYLGC-QRRQSFLOSA-N
Standard InCHI:	InChI=1S/C13H12O3/c14-11-7-9-13(15)16-12(11)8-6-10-4-2-1-3-5-10/h1-9,11-12,14H/b8-6+/t11?,12-/m0/s1
SMILES:	C1=CC=C(C=C1)C=CC2C(C=CC(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358621
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO33111	polyalthia parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25419616]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[525179]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[525179]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7900.0	nM	PMID[525179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14600.0	nM	PMID[525179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8100.0	nM	PMID[525179]

☑ 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 NPC472319 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	185
0.1-0.2	1210
0.2-0.3	4167
0.3-0.4	12017
0.4-0.5	14318
0.5-0.6	9270
0.6-0.7	1321
0.7-0.8	167
0.8-0.85	29
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC324835
0.9059	High Similarity	NPC308619
0.9059	High Similarity	NPC127491
0.8854	High Similarity	NPC280616
0.8854	High Similarity	NPC171831
0.8854	High Similarity	NPC242913
0.8673	High Similarity	NPC37115
0.8673	High Similarity	NPC136962
0.8605	High Similarity	NPC89950
0.8485	Intermediate Similarity	NPC472316
0.8485	Intermediate Similarity	NPC474376
0.8485	Intermediate Similarity	NPC475203
0.8485	Intermediate Similarity	NPC472315
0.8471	Intermediate Similarity	NPC176228
0.8444	Intermediate Similarity	NPC169050
0.8444	Intermediate Similarity	NPC286608
0.84	Intermediate Similarity	NPC472314
0.84	Intermediate Similarity	NPC277788
0.84	Intermediate Similarity	NPC475465
0.8391	Intermediate Similarity	NPC71795
0.8372	Intermediate Similarity	NPC78517
0.8372	Intermediate Similarity	NPC167577
0.8367	Intermediate Similarity	NPC82426
0.8367	Intermediate Similarity	NPC91820
0.8333	Intermediate Similarity	NPC154517
0.8333	Intermediate Similarity	NPC135951
0.8295	Intermediate Similarity	NPC99240
0.8252	Intermediate Similarity	NPC234376
0.8247	Intermediate Similarity	NPC80115
0.8202	Intermediate Similarity	NPC208183
0.8202	Intermediate Similarity	NPC243289
0.82	Intermediate Similarity	NPC472919
0.8191	Intermediate Similarity	NPC77273
0.8182	Intermediate Similarity	NPC303245
0.8173	Intermediate Similarity	NPC265002
0.814	Intermediate Similarity	NPC287790
0.814	Intermediate Similarity	NPC3672
0.8118	Intermediate Similarity	NPC206800
0.8118	Intermediate Similarity	NPC32203
0.8077	Intermediate Similarity	NPC158282
0.8061	Intermediate Similarity	NPC472318
0.8061	Intermediate Similarity	NPC98911
0.8023	Intermediate Similarity	NPC175393
0.8022	Intermediate Similarity	NPC53299
0.7961	Intermediate Similarity	NPC184633
0.7941	Intermediate Similarity	NPC477251
0.7938	Intermediate Similarity	NPC30361
0.7917	Intermediate Similarity	NPC23453
0.7864	Intermediate Similarity	NPC20485
0.7849	Intermediate Similarity	NPC96625
0.7841	Intermediate Similarity	NPC50192
0.7822	Intermediate Similarity	NPC234305
0.781	Intermediate Similarity	NPC43584
0.7789	Intermediate Similarity	NPC240108
0.7789	Intermediate Similarity	NPC213156
0.7757	Intermediate Similarity	NPC474641
0.7745	Intermediate Similarity	NPC85977
0.7736	Intermediate Similarity	NPC474314
0.7736	Intermediate Similarity	NPC185840
0.7736	Intermediate Similarity	NPC470825
0.7736	Intermediate Similarity	NPC477250
0.7717	Intermediate Similarity	NPC44546
0.7708	Intermediate Similarity	NPC119631
0.7684	Intermediate Similarity	NPC173443
0.7653	Intermediate Similarity	NPC473347
0.7647	Intermediate Similarity	NPC304638
0.7647	Intermediate Similarity	NPC160382
0.7619	Intermediate Similarity	NPC114741
0.7619	Intermediate Similarity	NPC182549
0.7596	Intermediate Similarity	NPC51174
0.7593	Intermediate Similarity	NPC474363
0.7579	Intermediate Similarity	NPC304760
0.7558	Intermediate Similarity	NPC155429
0.7556	Intermediate Similarity	NPC469894
0.7524	Intermediate Similarity	NPC156648
0.7524	Intermediate Similarity	NPC260952
0.7523	Intermediate Similarity	NPC217472
0.75	Intermediate Similarity	NPC127676
0.75	Intermediate Similarity	NPC272524
0.7477	Intermediate Similarity	NPC476003
0.7477	Intermediate Similarity	NPC323007
0.7453	Intermediate Similarity	NPC281604
0.7453	Intermediate Similarity	NPC206341
0.7451	Intermediate Similarity	NPC253746
0.7447	Intermediate Similarity	NPC58616
0.7426	Intermediate Similarity	NPC210529
0.7426	Intermediate Similarity	NPC160548
0.7426	Intermediate Similarity	NPC175852
0.7412	Intermediate Similarity	NPC78954
0.7412	Intermediate Similarity	NPC82770
0.7412	Intermediate Similarity	NPC239931
0.7379	Intermediate Similarity	NPC94343
0.7368	Intermediate Similarity	NPC476872
0.7353	Intermediate Similarity	NPC171843
0.7347	Intermediate Similarity	NPC317645
0.7328	Intermediate Similarity	NPC471466
0.7327	Intermediate Similarity	NPC289201
0.7321	Intermediate Similarity	NPC65791
0.7315	Intermediate Similarity	NPC183700
0.7304	Intermediate Similarity	NPC475328
0.7304	Intermediate Similarity	NPC11724
0.7297	Intermediate Similarity	NPC233669
0.7292	Intermediate Similarity	NPC194326
0.7292	Intermediate Similarity	NPC89377
0.7273	Intermediate Similarity	NPC95381
0.7273	Intermediate Similarity	NPC172525
0.7273	Intermediate Similarity	NPC87069
0.7248	Intermediate Similarity	NPC139946
0.7245	Intermediate Similarity	NPC185501
0.7241	Intermediate Similarity	NPC52097
0.7232	Intermediate Similarity	NPC470820
0.7232	Intermediate Similarity	NPC281277
0.7217	Intermediate Similarity	NPC229600
0.7207	Intermediate Similarity	NPC261453
0.7207	Intermediate Similarity	NPC33749
0.7207	Intermediate Similarity	NPC474685
0.7207	Intermediate Similarity	NPC328593
0.7204	Intermediate Similarity	NPC117180
0.7196	Intermediate Similarity	NPC47536
0.7184	Intermediate Similarity	NPC474308
0.7184	Intermediate Similarity	NPC118343
0.7182	Intermediate Similarity	NPC131530
0.7174	Intermediate Similarity	NPC170484
0.717	Intermediate Similarity	NPC152384
0.717	Intermediate Similarity	NPC37714
0.717	Intermediate Similarity	NPC269457
0.7157	Intermediate Similarity	NPC270654
0.7157	Intermediate Similarity	NPC249912
0.7157	Intermediate Similarity	NPC92754
0.7157	Intermediate Similarity	NPC276775
0.7143	Intermediate Similarity	NPC220893
0.7143	Intermediate Similarity	NPC474967
0.7143	Intermediate Similarity	NPC469527
0.7143	Intermediate Similarity	NPC276047
0.7143	Intermediate Similarity	NPC267733
0.713	Intermediate Similarity	NPC474364
0.713	Intermediate Similarity	NPC40178
0.7129	Intermediate Similarity	NPC81010
0.7129	Intermediate Similarity	NPC32977
0.7128	Intermediate Similarity	NPC99394
0.7128	Intermediate Similarity	NPC475199
0.7128	Intermediate Similarity	NPC283012
0.7128	Intermediate Similarity	NPC87299
0.7128	Intermediate Similarity	NPC329319
0.7128	Intermediate Similarity	NPC103326
0.7126	Intermediate Similarity	NPC169222
0.7126	Intermediate Similarity	NPC235059
0.7126	Intermediate Similarity	NPC16190
0.7119	Intermediate Similarity	NPC145287
0.7117	Intermediate Similarity	NPC308744
0.7115	Intermediate Similarity	NPC42211
0.7105	Intermediate Similarity	NPC309434
0.7105	Intermediate Similarity	NPC275519
0.7097	Intermediate Similarity	NPC121800
0.7091	Intermediate Similarity	NPC226250
0.7087	Intermediate Similarity	NPC179411
0.7087	Intermediate Similarity	NPC225060
0.7087	Intermediate Similarity	NPC35448
0.7087	Intermediate Similarity	NPC78701
0.7087	Intermediate Similarity	NPC317280
0.7087	Intermediate Similarity	NPC329387
0.7083	Intermediate Similarity	NPC99482
0.7083	Intermediate Similarity	NPC475710
0.7075	Intermediate Similarity	NPC148060
0.7075	Intermediate Similarity	NPC2518
0.7071	Intermediate Similarity	NPC26224
0.7069	Intermediate Similarity	NPC470849
0.7069	Intermediate Similarity	NPC470848
0.7059	Intermediate Similarity	NPC246679
0.7059	Intermediate Similarity	NPC79608
0.7059	Intermediate Similarity	NPC126991
0.7059	Intermediate Similarity	NPC257182
0.7059	Intermediate Similarity	NPC83218
0.7054	Intermediate Similarity	NPC29607
0.7054	Intermediate Similarity	NPC306740
0.7043	Intermediate Similarity	NPC263386
0.7043	Intermediate Similarity	NPC141791
0.7034	Intermediate Similarity	NPC472373
0.7034	Intermediate Similarity	NPC224208
0.7034	Intermediate Similarity	NPC474275
0.7027	Intermediate Similarity	NPC474176
0.7027	Intermediate Similarity	NPC266116
0.7019	Intermediate Similarity	NPC146351
0.7011	Intermediate Similarity	NPC311343
0.7009	Intermediate Similarity	NPC288760
0.7009	Intermediate Similarity	NPC227255
0.7	Intermediate Similarity	NPC477247
0.7	Intermediate Similarity	NPC471157
0.7	Intermediate Similarity	NPC252114
0.7	Intermediate Similarity	NPC260818
0.7	Intermediate Similarity	NPC474157
0.7	Intermediate Similarity	NPC61181
0.6991	Remote Similarity	NPC473507
0.699	Remote Similarity	NPC325499
0.6983	Remote Similarity	NPC202474
0.6983	Remote Similarity	NPC2058
0.6981	Remote Similarity	NPC301943
0.6981	Remote Similarity	NPC179686
0.6981	Remote Similarity	NPC474365
0.6979	Remote Similarity	NPC304538

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 NPC472319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	823
0.2-0.3	1670
0.3-0.4	3338
0.4-0.5	2190
0.5-0.6	854
0.6-0.7	104
0.7-0.8	6
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD689	Discontinued
0.8444	Intermediate Similarity	NPD1282	Approved
0.8118	Intermediate Similarity	NPD9716	Approved
0.7476	Intermediate Similarity	NPD6647	Phase 2
0.7426	Intermediate Similarity	NPD9495	Approved
0.7419	Intermediate Similarity	NPD3971	Phase 1
0.7407	Intermediate Similarity	NPD969	Suspended
0.7387	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1238	Approved
0.7083	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5909	Discontinued
0.7054	Intermediate Similarity	NPD2629	Approved
0.7037	Intermediate Similarity	NPD1358	Approved
0.6957	Remote Similarity	NPD9294	Approved
0.6923	Remote Similarity	NPD5926	Approved
0.6916	Remote Similarity	NPD1237	Approved
0.6909	Remote Similarity	NPD2067	Discontinued
0.6903	Remote Similarity	NPD690	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9258	Approved
0.69	Remote Similarity	NPD9256	Approved
0.6852	Remote Similarity	NPD5048	Discontinued
0.6842	Remote Similarity	NPD4198	Discontinued
0.6822	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3134	Approved
0.6727	Remote Similarity	NPD290	Approved
0.6701	Remote Similarity	NPD9491	Approved
0.6697	Remote Similarity	NPD9697	Approved
0.6696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6635	Remote Similarity	NPD6049	Phase 2
0.6635	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD9532	Phase 3
0.6542	Remote Similarity	NPD2066	Phase 3
0.6542	Remote Similarity	NPD7798	Approved
0.6538	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1202	Approved
0.6518	Remote Similarity	NPD2182	Approved
0.65	Remote Similarity	NPD9259	Approved
0.65	Remote Similarity	NPD9257	Approved
0.6496	Remote Similarity	NPD9493	Approved
0.6455	Remote Similarity	NPD164	Approved
0.6429	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5305	Approved
0.6417	Remote Similarity	NPD5306	Approved
0.6406	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD2684	Approved
0.6372	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD2626	Approved
0.6371	Remote Similarity	NPD2160	Approved
0.6371	Remote Similarity	NPD2627	Approved
0.6371	Remote Similarity	NPD2159	Approved
0.6371	Remote Similarity	NPD2625	Approved
0.6371	Remote Similarity	NPD2628	Approved
0.6364	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4136	Approved
0.6364	Remote Similarity	NPD1930	Approved
0.6364	Remote Similarity	NPD7266	Discontinued
0.6364	Remote Similarity	NPD1929	Approved
0.6364	Remote Similarity	NPD4106	Approved
0.6364	Remote Similarity	NPD4135	Approved
0.6354	Remote Similarity	NPD225	Approved
0.6354	Remote Similarity	NPD227	Approved
0.6346	Remote Similarity	NPD1239	Approved
0.6339	Remote Similarity	NPD6685	Approved
0.6339	Remote Similarity	NPD968	Approved
0.6327	Remote Similarity	NPD942	Approved
0.632	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD9713	Approved
0.6311	Remote Similarity	NPD1091	Approved
0.6311	Remote Similarity	NPD4807	Approved
0.6311	Remote Similarity	NPD4806	Approved
0.6311	Remote Similarity	NPD422	Phase 1
0.6311	Remote Similarity	NPD800	Approved
0.6289	Remote Similarity	NPD9490	Approved
0.6283	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5126	Approved
0.6281	Remote Similarity	NPD5125	Phase 3
0.6275	Remote Similarity	NPD4793	Discontinued
0.6273	Remote Similarity	NPD1932	Approved
0.6262	Remote Similarity	NPD1989	Approved
0.6261	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1090	Approved
0.625	Remote Similarity	NPD1894	Discontinued
0.625	Remote Similarity	NPD1086	Approved
0.625	Remote Similarity	NPD1089	Approved
0.625	Remote Similarity	NPD3673	Approved
0.625	Remote Similarity	NPD3672	Approved
0.6239	Remote Similarity	NPD9712	Approved
0.6231	Remote Similarity	NPD4340	Discontinued
0.623	Remote Similarity	NPD3496	Discontinued
0.6226	Remote Similarity	NPD1066	Discontinued
0.6224	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4628	Phase 3
0.6218	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5765	Approved
0.621	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4102	Approved
0.6198	Remote Similarity	NPD4105	Approved
0.619	Remote Similarity	NPD5647	Approved
0.619	Remote Similarity	NPD9365	Approved
0.6176	Remote Similarity	NPD6190	Approved
0.6176	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7008	Discontinued
0.6168	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1693	Approved
0.616	Remote Similarity	NPD3225	Approved
0.6154	Remote Similarity	NPD7843	Approved
0.6154	Remote Similarity	NPD5346	Phase 2
0.6154	Remote Similarity	NPD5347	Phase 2
0.6148	Remote Similarity	NPD1652	Phase 2
0.6147	Remote Similarity	NPD9609	Approved
0.6147	Remote Similarity	NPD9710	Approved
0.6147	Remote Similarity	NPD9611	Approved
0.6147	Remote Similarity	NPD9612	Approved
0.6147	Remote Similarity	NPD9711	Approved
0.6142	Remote Similarity	NPD5204	Approved
0.614	Remote Similarity	NPD9267	Approved
0.614	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.614	Remote Similarity	NPD9263	Approved
0.614	Remote Similarity	NPD9264	Approved
0.6132	Remote Similarity	NPD1088	Approved
0.6129	Remote Similarity	NPD9717	Approved
0.6124	Remote Similarity	NPD6798	Discontinued
0.6117	Remote Similarity	NPD650	Approved
0.6111	Remote Similarity	NPD2797	Approved
0.6111	Remote Similarity	NPD1203	Approved
0.6102	Remote Similarity	NPD1241	Discontinued
0.6094	Remote Similarity	NPD4617	Approved
0.6094	Remote Similarity	NPD5201	Approved
0.6094	Remote Similarity	NPD5203	Approved
0.6094	Remote Similarity	NPD4620	Approved
0.6087	Remote Similarity	NPD9266	Approved
0.6087	Remote Similarity	NPD74	Approved
0.6083	Remote Similarity	NPD5291	Approved
0.6083	Remote Similarity	NPD5292	Approved
0.6078	Remote Similarity	NPD111	Approved
0.6077	Remote Similarity	NPD4062	Phase 3
0.6077	Remote Similarity	NPD6233	Phase 2
0.6071	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6912	Phase 3
0.6068	Remote Similarity	NPD9508	Approved
0.6068	Remote Similarity	NPD228	Approved
0.6066	Remote Similarity	NPD1357	Approved
0.6061	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6653	Approved
0.6058	Remote Similarity	NPD531	Approved
0.6055	Remote Similarity	NPD1566	Phase 3
0.6055	Remote Similarity	NPD1564	Approved
0.6055	Remote Similarity	NPD1565	Approved
0.6053	Remote Similarity	NPD5705	Approved
0.6053	Remote Similarity	NPD5704	Approved
0.6053	Remote Similarity	NPD5706	Approved
0.605	Remote Similarity	NPD5951	Approved
0.6036	Remote Similarity	NPD2555	Approved
0.6036	Remote Similarity	NPD2550	Approved
0.6036	Remote Similarity	NPD2552	Approved
0.6036	Remote Similarity	NPD2553	Approved
0.6036	Remote Similarity	NPD2558	Approved
0.6036	Remote Similarity	NPD2549	Approved
0.6034	Remote Similarity	NPD5235	Approved
0.6034	Remote Similarity	NPD5239	Approved
0.6034	Remote Similarity	NPD5237	Approved
0.6034	Remote Similarity	NPD5240	Approved
0.6034	Remote Similarity	NPD5236	Approved
0.6033	Remote Similarity	NPD2347	Approved
0.6032	Remote Similarity	NPD2198	Approved
0.6032	Remote Similarity	NPD2199	Approved
0.6031	Remote Similarity	NPD4060	Phase 1
0.6028	Remote Similarity	NPD1653	Approved
0.6019	Remote Similarity	NPD2934	Approved
0.6019	Remote Similarity	NPD9260	Approved
0.6019	Remote Similarity	NPD2933	Approved
0.6017	Remote Similarity	NPD5277	Phase 2
0.6016	Remote Similarity	NPD9494	Approved
0.6016	Remote Similarity	NPD1778	Approved
0.6016	Remote Similarity	NPD3663	Approved
0.6016	Remote Similarity	NPD3664	Approved
0.6016	Remote Similarity	NPD4626	Approved
0.6016	Remote Similarity	NPD5723	Approved
0.6016	Remote Similarity	NPD3661	Approved
0.6016	Remote Similarity	NPD3662	Phase 3
0.6	Remote Similarity	NPD9250	Approved
0.6	Remote Similarity	NPD6637	Approved
0.6	Remote Similarity	NPD7157	Approved
0.6	Remote Similarity	NPD1048	Approved
0.5985	Remote Similarity	NPD6355	Discontinued
0.5985	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD230	Phase 1
0.5985	Remote Similarity	NPD5124	Phase 1
0.5984	Remote Similarity	NPD7741	Discontinued
0.5983	Remote Similarity	NPD2201	Approved
0.5982	Remote Similarity	NPD291	Approved
0.5982	Remote Similarity	NPD4188	Approved
0.5982	Remote Similarity	NPD855	Approved
0.5982	Remote Similarity	NPD854	Approved
0.5982	Remote Similarity	NPD4189	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