NPASS Compound

Structure

NPC295276 OpenBabel07101718322D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.4057 2.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9041 4.1471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2864 0.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7686 1.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2338 1.5239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2200 0.9729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2028 2.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8868 -0.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 -0.3472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0267 1.1751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0690 3.6649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5213 0.3472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5429 1.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2028 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8042 1.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6014 1.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2028 0.6944 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.6944 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0864 0.9605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8042 1.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6014 1.0417 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2338 4.1471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3283 2.0676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0380 -0.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6394 2.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6398 1.5950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0690 2.7005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 12 6 1 1 0 0 0 13 18 1 0 0 0 0 13 24 2 0 0 0 0 14 17 1 0 0 0 0 14 25 2 0 0 0 0 15 20 1 0 0 0 0 15 26 1 6 0 0 0 16 21 1 1 0 0 0 16 28 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 1 0 0 0 18 21 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 1 0 0 0 19 27 1 0 0 0 0 21 5 1 1 0 0 0 22 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	397.038
LogP:	1.728
LogD:	0.568
LogS:	-3.575
# Rotatable Bonds:	2
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	6.186
Fsp3:	0.773
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:	-5.424
MDCK Permeability:	9.266456618206576e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.672
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	46.487648010253906%
Volume Distribution (VD):	0.873
Pgp-substrate:	60.701560974121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	5.116
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.204
Carcinogencity:	0.257
Eye Corrosion:	0.019
Eye Irritation:	0.02
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC295276

Natural Product ID:	NPC295276
*Common Name:**	Tenuifolin H
IUPAC Name:	n.a.
Synonyms:	Tenuifolin H
Standard InCHIKey:	WVKGNTPHONPKBB-VHLOLGLTSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-10-12-6-13(24)18-21(5)16(28-11(2)23)7-15(26)20(3,4)17(21)14(25)9-22(18,8-12)19(10)27/h12,15-19,26-27H,1,6-9H2,2-5H3/t12-,15+,16+,17-,18+,19-,21-,22+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H](O)C([C@@H]2[C@]1(C)[C@@H]1C(=O)C[C@@H]3C[C@@]1(CC2=O)[C@H](O)C3=C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334481
PubChem CID:	71579126
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327668]
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25375202]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000.0	nM	PMID[521920]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[521920]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[521920]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[521920]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[521920]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[521920]

☑ 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 NPC295276 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	220
0.1-0.2	1686
0.2-0.3	5504
0.3-0.4	10684
0.4-0.5	10570
0.5-0.6	5931
0.6-0.7	5631
0.7-0.8	2170
0.8-0.85	194
0.85-0.9	74
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC253886
0.9579	High Similarity	NPC121218
0.9286	High Similarity	NPC47281
0.9278	High Similarity	NPC170615
0.9192	High Similarity	NPC37600
0.9192	High Similarity	NPC50535
0.9091	High Similarity	NPC84928
0.9	High Similarity	NPC28791
0.9	High Similarity	NPC295366
0.899	High Similarity	NPC216114
0.8969	High Similarity	NPC38296
0.8969	High Similarity	NPC38471
0.8969	High Similarity	NPC98837
0.8969	High Similarity	NPC20479
0.8969	High Similarity	NPC162459
0.8969	High Similarity	NPC89099
0.8969	High Similarity	NPC28864
0.8911	High Similarity	NPC86852
0.8911	High Similarity	NPC251824
0.89	High Similarity	NPC98603
0.8889	High Similarity	NPC286519
0.8889	High Similarity	NPC246736
0.8889	High Similarity	NPC148628
0.8889	High Similarity	NPC214946
0.8889	High Similarity	NPC76866
0.8889	High Similarity	NPC304832
0.8889	High Similarity	NPC88203
0.8878	High Similarity	NPC293866
0.8866	High Similarity	NPC10864
0.8846	High Similarity	NPC40608
0.883	High Similarity	NPC100313
0.88	High Similarity	NPC266
0.88	High Similarity	NPC469985
0.8788	High Similarity	NPC289148
0.8788	High Similarity	NPC163963
0.8788	High Similarity	NPC39683
0.8788	High Similarity	NPC52899
0.8788	High Similarity	NPC46848
0.8763	High Similarity	NPC470387
0.8763	High Similarity	NPC29410
0.8763	High Similarity	NPC200054
0.875	High Similarity	NPC280804
0.8725	High Similarity	NPC471246
0.8713	High Similarity	NPC474558
0.871	High Similarity	NPC472497
0.87	High Similarity	NPC275990
0.8687	High Similarity	NPC37047
0.8687	High Similarity	NPC180733
0.8687	High Similarity	NPC287676
0.8687	High Similarity	NPC41971
0.866	High Similarity	NPC98639
0.866	High Similarity	NPC470232
0.8654	High Similarity	NPC255655
0.8646	High Similarity	NPC294263
0.8632	High Similarity	NPC123252
0.8632	High Similarity	NPC194485
0.8632	High Similarity	NPC53890
0.8632	High Similarity	NPC219937
0.8614	High Similarity	NPC87927
0.86	High Similarity	NPC471790
0.86	High Similarity	NPC75941
0.8586	High Similarity	NPC78427
0.8586	High Similarity	NPC471038
0.8586	High Similarity	NPC16911
0.8571	High Similarity	NPC13949
0.8571	High Similarity	NPC329910
0.8571	High Similarity	NPC94650
0.8557	High Similarity	NPC470385
0.8557	High Similarity	NPC475118
0.8557	High Similarity	NPC470386
0.8542	High Similarity	NPC198054
0.8529	High Similarity	NPC301787
0.8511	High Similarity	NPC472495
0.85	High Similarity	NPC94906
0.8469	Intermediate Similarity	NPC470229
0.8462	Intermediate Similarity	NPC231278
0.8462	Intermediate Similarity	NPC218123
0.8462	Intermediate Similarity	NPC112895
0.8454	Intermediate Similarity	NPC224060
0.8454	Intermediate Similarity	NPC26046
0.8454	Intermediate Similarity	NPC472496
0.8454	Intermediate Similarity	NPC244356
0.8447	Intermediate Similarity	NPC285927
0.8447	Intermediate Similarity	NPC200957
0.8447	Intermediate Similarity	NPC138908
0.8447	Intermediate Similarity	NPC222833
0.8431	Intermediate Similarity	NPC139347
0.8421	Intermediate Similarity	NPC160304
0.8416	Intermediate Similarity	NPC71706
0.8416	Intermediate Similarity	NPC252614
0.84	Intermediate Similarity	NPC472028
0.84	Intermediate Similarity	NPC474724
0.84	Intermediate Similarity	NPC474793
0.8384	Intermediate Similarity	NPC234564
0.8384	Intermediate Similarity	NPC140242
0.8367	Intermediate Similarity	NPC153775
0.8367	Intermediate Similarity	NPC29247
0.8367	Intermediate Similarity	NPC261333
0.8367	Intermediate Similarity	NPC47853
0.8367	Intermediate Similarity	NPC289539
0.8367	Intermediate Similarity	NPC111524
0.8367	Intermediate Similarity	NPC292374
0.8367	Intermediate Similarity	NPC469982
0.8367	Intermediate Similarity	NPC91772
0.8367	Intermediate Similarity	NPC101233
0.8367	Intermediate Similarity	NPC129004
0.8367	Intermediate Similarity	NPC104371
0.8367	Intermediate Similarity	NPC215271
0.8365	Intermediate Similarity	NPC166993
0.8365	Intermediate Similarity	NPC201908
0.8365	Intermediate Similarity	NPC176949
0.8351	Intermediate Similarity	NPC250753
0.8351	Intermediate Similarity	NPC130840
0.8351	Intermediate Similarity	NPC198242
0.8351	Intermediate Similarity	NPC211403
0.835	Intermediate Similarity	NPC202793
0.835	Intermediate Similarity	NPC29705
0.8333	Intermediate Similarity	NPC124544
0.8333	Intermediate Similarity	NPC309388
0.8333	Intermediate Similarity	NPC475803
0.8333	Intermediate Similarity	NPC194642
0.8317	Intermediate Similarity	NPC55503
0.8317	Intermediate Similarity	NPC470388
0.8317	Intermediate Similarity	NPC108371
0.8317	Intermediate Similarity	NPC156324
0.8317	Intermediate Similarity	NPC218383
0.8316	Intermediate Similarity	NPC153604
0.8302	Intermediate Similarity	NPC98633
0.8302	Intermediate Similarity	NPC124053
0.8302	Intermediate Similarity	NPC130302
0.8286	Intermediate Similarity	NPC273155
0.8283	Intermediate Similarity	NPC241047
0.8283	Intermediate Similarity	NPC210214
0.8283	Intermediate Similarity	NPC288906
0.8283	Intermediate Similarity	NPC266431
0.8283	Intermediate Similarity	NPC263135
0.828	Intermediate Similarity	NPC472498
0.8269	Intermediate Similarity	NPC4115
0.8269	Intermediate Similarity	NPC278628
0.8269	Intermediate Similarity	NPC231530
0.8265	Intermediate Similarity	NPC181594
0.8265	Intermediate Similarity	NPC147272
0.8265	Intermediate Similarity	NPC144739
0.8252	Intermediate Similarity	NPC96217
0.8252	Intermediate Similarity	NPC277074
0.8252	Intermediate Similarity	NPC209298
0.8252	Intermediate Similarity	NPC122811
0.8252	Intermediate Similarity	NPC140723
0.8252	Intermediate Similarity	NPC470310
0.8241	Intermediate Similarity	NPC285086
0.8235	Intermediate Similarity	NPC236585
0.8235	Intermediate Similarity	NPC148279
0.8224	Intermediate Similarity	NPC56025
0.8218	Intermediate Similarity	NPC119036
0.82	Intermediate Similarity	NPC256227
0.82	Intermediate Similarity	NPC306797
0.82	Intermediate Similarity	NPC169270
0.82	Intermediate Similarity	NPC292718
0.82	Intermediate Similarity	NPC104568
0.82	Intermediate Similarity	NPC111834
0.82	Intermediate Similarity	NPC135548
0.82	Intermediate Similarity	NPC264979
0.8191	Intermediate Similarity	NPC263974
0.8191	Intermediate Similarity	NPC299963
0.8182	Intermediate Similarity	NPC64006
0.8182	Intermediate Similarity	NPC3359
0.8173	Intermediate Similarity	NPC13149
0.8172	Intermediate Similarity	NPC170985
0.8163	Intermediate Similarity	NPC299185
0.8163	Intermediate Similarity	NPC476168
0.8163	Intermediate Similarity	NPC470230
0.8155	Intermediate Similarity	NPC271980
0.8155	Intermediate Similarity	NPC193934
0.8148	Intermediate Similarity	NPC473352
0.8137	Intermediate Similarity	NPC293890
0.8137	Intermediate Similarity	NPC267921
0.8131	Intermediate Similarity	NPC471093
0.8125	Intermediate Similarity	NPC174619
0.8119	Intermediate Similarity	NPC190080
0.8119	Intermediate Similarity	NPC111187
0.8119	Intermediate Similarity	NPC253586
0.8113	Intermediate Similarity	NPC211224
0.8113	Intermediate Similarity	NPC94529
0.8113	Intermediate Similarity	NPC63841
0.81	Intermediate Similarity	NPC157686
0.81	Intermediate Similarity	NPC205173
0.81	Intermediate Similarity	NPC84018
0.81	Intermediate Similarity	NPC259042
0.81	Intermediate Similarity	NPC138245
0.81	Intermediate Similarity	NPC231060
0.81	Intermediate Similarity	NPC197158
0.81	Intermediate Similarity	NPC471624
0.8095	Intermediate Similarity	NPC12823
0.8095	Intermediate Similarity	NPC196528
0.8085	Intermediate Similarity	NPC471037
0.8081	Intermediate Similarity	NPC199543
0.8081	Intermediate Similarity	NPC476189
0.8077	Intermediate Similarity	NPC159442
0.8073	Intermediate Similarity	NPC962
0.8061	Intermediate Similarity	NPC180849

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 NPC295276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	2084
0.2-0.3	3983
0.3-0.4	1886
0.4-0.5	509
0.5-0.6	208
0.6-0.7	185
0.7-0.8	84
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
0.78	Intermediate Similarity	NPD8035	Phase 2
0.78	Intermediate Similarity	NPD8034	Phase 2
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7757	Intermediate Similarity	NPD7128	Approved
0.7757	Intermediate Similarity	NPD6675	Approved
0.7757	Intermediate Similarity	NPD6402	Approved
0.7757	Intermediate Similarity	NPD5739	Approved
0.7732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6373	Approved
0.7706	Intermediate Similarity	NPD6372	Approved
0.7692	Intermediate Similarity	NPD7638	Approved
0.7685	Intermediate Similarity	NPD5701	Approved
0.7685	Intermediate Similarity	NPD5697	Approved
0.7615	Intermediate Similarity	NPD6881	Approved
0.7615	Intermediate Similarity	NPD6899	Approved
0.7615	Intermediate Similarity	NPD7320	Approved
0.7593	Intermediate Similarity	NPD6008	Approved
0.7568	Intermediate Similarity	NPD6649	Approved
0.7568	Intermediate Similarity	NPD6650	Approved
0.7545	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD6012	Approved
0.7545	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD5696	Approved
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7477	Intermediate Similarity	NPD7102	Approved
0.7455	Intermediate Similarity	NPD6011	Approved
0.7455	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7411	Intermediate Similarity	NPD8130	Phase 1
0.7411	Intermediate Similarity	NPD6617	Approved
0.7411	Intermediate Similarity	NPD6869	Approved
0.7411	Intermediate Similarity	NPD6847	Approved
0.7379	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD6115	Approved
0.7368	Intermediate Similarity	NPD6697	Approved
0.7368	Intermediate Similarity	NPD6118	Approved
0.7368	Intermediate Similarity	NPD6114	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7345	Intermediate Similarity	NPD6882	Approved
0.7345	Intermediate Similarity	NPD8297	Approved
0.7339	Intermediate Similarity	NPD5141	Approved
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.729	Intermediate Similarity	NPD5286	Approved
0.729	Intermediate Similarity	NPD4696	Approved
0.729	Intermediate Similarity	NPD5285	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7257	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5328	Approved
0.7241	Intermediate Similarity	NPD6009	Approved
0.7234	Intermediate Similarity	NPD3703	Phase 2
0.719	Intermediate Similarity	NPD7507	Approved
0.7172	Intermediate Similarity	NPD4788	Approved
0.717	Intermediate Similarity	NPD4697	Phase 3
0.7158	Intermediate Similarity	NPD6117	Approved
0.7156	Intermediate Similarity	NPD5225	Approved
0.7156	Intermediate Similarity	NPD5224	Approved
0.7156	Intermediate Similarity	NPD4633	Approved
0.7156	Intermediate Similarity	NPD5226	Approved
0.7155	Intermediate Similarity	NPD6274	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD7748	Approved
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7115	Intermediate Similarity	NPD6079	Approved
0.7115	Intermediate Similarity	NPD7515	Phase 2
0.7107	Intermediate Similarity	NPD7492	Approved
0.7103	Intermediate Similarity	NPD7902	Approved
0.7091	Intermediate Similarity	NPD5174	Approved
0.7091	Intermediate Similarity	NPD5175	Approved
0.7083	Intermediate Similarity	NPD6116	Phase 1
0.7075	Intermediate Similarity	NPD4629	Approved
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7075	Intermediate Similarity	NPD5210	Approved
0.7073	Intermediate Similarity	NPD7736	Approved
0.7064	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7049	Intermediate Similarity	NPD6616	Approved
0.7048	Intermediate Similarity	NPD4202	Approved
0.7025	Intermediate Similarity	NPD7604	Phase 2
0.7018	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5222	Approved
0.7009	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.6992	Remote Similarity	NPD7078	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6949	Remote Similarity	NPD6317	Approved
0.6949	Remote Similarity	NPD7115	Discovery
0.6947	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5173	Approved
0.6942	Remote Similarity	NPD5988	Approved
0.6942	Remote Similarity	NPD6370	Approved
0.6937	Remote Similarity	NPD4754	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD4786	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4753	Phase 2
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6336	Discontinued
0.6903	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD3667	Approved
0.6891	Remote Similarity	NPD6313	Approved
0.6891	Remote Similarity	NPD6335	Approved
0.6891	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD3702	Approved
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6908	Approved
0.686	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD4729	Approved
0.6842	Remote Similarity	NPD4730	Approved
0.6842	Remote Similarity	NPD5128	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7637	Suspended
0.6783	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6053	Discontinued
0.675	Remote Similarity	NPD7328	Approved
0.675	Remote Similarity	NPD7327	Approved
0.6748	Remote Similarity	NPD8328	Phase 3
0.6737	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5777	Approved
0.6737	Remote Similarity	NPD6081	Approved
0.6737	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6727	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5249	Phase 3
0.6724	Remote Similarity	NPD5251	Approved
0.6724	Remote Similarity	NPD5247	Approved
0.6724	Remote Similarity	NPD5250	Approved
0.6724	Remote Similarity	NPD5248	Approved
0.6723	Remote Similarity	NPD6868	Approved
0.6721	Remote Similarity	NPD6921	Approved
0.6702	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3698	Phase 2
0.6694	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD4244	Approved
0.6632	Remote Similarity	NPD4245	Approved
0.6609	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1700	Approved
0.6604	Remote Similarity	NPD6904	Approved
0.6604	Remote Similarity	NPD6673	Approved
0.6604	Remote Similarity	NPD6080	Approved
0.6585	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD8378	Approved
0.6585	Remote Similarity	NPD8296	Approved
0.6585	Remote Similarity	NPD8380	Approved
0.6581	Remote Similarity	NPD5135	Approved
0.6581	Remote Similarity	NPD5169	Approved
0.6581	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD3573	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD6435	Approved
0.6559	Remote Similarity	NPD4224	Phase 2
0.6552	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD7525	Registered
0.6535	Remote Similarity	NPD6033	Approved
0.6525	Remote Similarity	NPD5127	Approved
0.6509	Remote Similarity	NPD5208	Approved
0.6505	Remote Similarity	NPD6695	Phase 3

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