NPASS Compound

Structure

CID324841 OpenBabel06191716172D 28 30 0 0 1 0 0 0 0 0999 V2000 -0.8381 1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3524 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8058 -2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3220 -3.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1852 1.1852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8381 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2505 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7181 -0.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 0.4839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3524 -0.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8695 0.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6762 -0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5804 -0.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8254 0.6523 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8381 -2.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1904 -1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7318 -1.8501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2647 1.5146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5355 -1.1782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -1.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2647 -0.2099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 22 1 1 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 6 0 0 0 17 24 2 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 6 0 0 0 19 25 1 0 0 0 0 19 28 1 0 0 0 0 21 22 1 1 0 0 0 22 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.24
Volume:	408.231
LogP:	3.843
LogD:	3.363
LogS:	-3.895
# Rotatable Bonds:	5
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	4.775
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:	-5.152
MDCK Permeability:	2.1202633433858864e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.085

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	96.06771087646484%
Volume Distribution (VD):	1.565
Pgp-substrate:	6.609541893005371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.117
CYP2C9-inhibitor:	0.338
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	5.235
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.325
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.303
Maximum Recommended Daily Dose:	0.114
Skin Sensitization:	0.341
Carcinogencity:	0.568
Eye Corrosion:	0.01
Eye Irritation:	0.081
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC324841

Natural Product ID:	NPC324841
*Common Name:**	Viteagnusin I
IUPAC Name:	[(1R,3R,4R,4aS,8aS)-4-hydroxy-4-[2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethyl]-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	ZHDFOHJIRGVVGC-XEBAKSHNSA-N
Standard InCHI:	InChI=1S/C22H34O6/c1-13-11-16(27-14(2)23)18-20(3,4)8-6-9-21(18,5)22(13,26)10-7-15-12-17(24)28-19(15)25/h12-13,16,18-19,25-26H,6-11H2,1-5H3/t13-,16-,18+,19?,21+,22-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](C)[C@]([C@@]2([C@@H]1C(C)(C)CCC2)C)(O)CCC1=CC(=O)OC1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436599
PubChem CID:	73349491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	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	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT994	Cell Line	ZR-75-30	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468430]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468430]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468430]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468430]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[468431]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	11300.0	nM	PMID[468431]

☑ 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 NPC324841 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	198
0.1-0.2	1390
0.2-0.3	4425
0.3-0.4	8564
0.4-0.5	12948
0.5-0.6	7033
0.6-0.7	6120
0.7-0.8	1751
0.8-0.85	203
0.85-0.9	54
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC105490
0.9348	High Similarity	NPC7349
0.9149	High Similarity	NPC472441
0.91	High Similarity	NPC38948
0.9082	High Similarity	NPC120009
0.9032	High Similarity	NPC78594
0.9032	High Similarity	NPC472811
0.901	High Similarity	NPC206618
0.9	High Similarity	NPC475074
0.9	High Similarity	NPC471205
0.898	High Similarity	NPC109195
0.898	High Similarity	NPC475038
0.898	High Similarity	NPC472815
0.8969	High Similarity	NPC16601
0.8947	High Similarity	NPC276110
0.8936	High Similarity	NPC472812
0.8878	High Similarity	NPC11974
0.883	High Similarity	NPC329842
0.8776	High Similarity	NPC228251
0.8776	High Similarity	NPC477972
0.8776	High Similarity	NPC219285
0.8776	High Similarity	NPC477716
0.8776	High Similarity	NPC477971
0.8776	High Similarity	NPC38855
0.8776	High Similarity	NPC161527
0.8776	High Similarity	NPC477721
0.8776	High Similarity	NPC20113
0.8776	High Similarity	NPC477968
0.8763	High Similarity	NPC477719
0.8763	High Similarity	NPC477718
0.8737	High Similarity	NPC472641
0.8737	High Similarity	NPC472640
0.8723	High Similarity	NPC78973
0.8713	High Similarity	NPC218158
0.8713	High Similarity	NPC51719
0.871	High Similarity	NPC472810
0.871	High Similarity	NPC472809
0.87	High Similarity	NPC281378
0.87	High Similarity	NPC471938
0.87	High Similarity	NPC160583
0.87	High Similarity	NPC45897
0.8687	High Similarity	NPC477717
0.8673	High Similarity	NPC325229
0.8673	High Similarity	NPC275086
0.8673	High Similarity	NPC278673
0.866	High Similarity	NPC165632
0.8646	High Similarity	NPC140277
0.8646	High Similarity	NPC469697
0.8646	High Similarity	NPC470255
0.8627	High Similarity	NPC122816
0.8617	High Similarity	NPC470734
0.8614	High Similarity	NPC471937
0.86	High Similarity	NPC162973
0.86	High Similarity	NPC471914
0.8571	High Similarity	NPC51499
0.8557	High Similarity	NPC471915
0.8544	High Similarity	NPC470024
0.8542	High Similarity	NPC53555
0.8529	High Similarity	NPC172867
0.8526	High Similarity	NPC472642
0.8511	High Similarity	NPC474629
0.8505	High Similarity	NPC471816
0.85	High Similarity	NPC222875
0.85	High Similarity	NPC25177
0.85	High Similarity	NPC295110
0.85	High Similarity	NPC268829
0.85	High Similarity	NPC471412
0.85	High Similarity	NPC247701
0.8495	Intermediate Similarity	NPC131813
0.8485	Intermediate Similarity	NPC473154
0.8478	Intermediate Similarity	NPC102048
0.8478	Intermediate Similarity	NPC471302
0.8469	Intermediate Similarity	NPC162346
0.8469	Intermediate Similarity	NPC209297
0.8469	Intermediate Similarity	NPC475380
0.8469	Intermediate Similarity	NPC194132
0.8462	Intermediate Similarity	NPC322912
0.8454	Intermediate Similarity	NPC298973
0.8454	Intermediate Similarity	NPC104925
0.8447	Intermediate Similarity	NPC109376
0.8421	Intermediate Similarity	NPC170633
0.8416	Intermediate Similarity	NPC476081
0.8416	Intermediate Similarity	NPC121423
0.8416	Intermediate Similarity	NPC238397
0.8416	Intermediate Similarity	NPC471363
0.8411	Intermediate Similarity	NPC471633
0.8411	Intermediate Similarity	NPC31354
0.8411	Intermediate Similarity	NPC69576
0.8411	Intermediate Similarity	NPC84949
0.8404	Intermediate Similarity	NPC166857
0.84	Intermediate Similarity	NPC476767
0.84	Intermediate Similarity	NPC251680
0.84	Intermediate Similarity	NPC471413
0.8387	Intermediate Similarity	NPC253604
0.8387	Intermediate Similarity	NPC42586
0.8387	Intermediate Similarity	NPC473251
0.8384	Intermediate Similarity	NPC100912
0.8384	Intermediate Similarity	NPC311241
0.8384	Intermediate Similarity	NPC475446
0.8384	Intermediate Similarity	NPC98112
0.8381	Intermediate Similarity	NPC177047
0.837	Intermediate Similarity	NPC476927
0.8367	Intermediate Similarity	NPC477969
0.8367	Intermediate Similarity	NPC135224
0.8365	Intermediate Similarity	NPC325054
0.8365	Intermediate Similarity	NPC181994
0.8365	Intermediate Similarity	NPC224660
0.835	Intermediate Similarity	NPC239961
0.835	Intermediate Similarity	NPC471206
0.835	Intermediate Similarity	NPC220217
0.835	Intermediate Similarity	NPC119855
0.8349	Intermediate Similarity	NPC83287
0.8333	Intermediate Similarity	NPC7613
0.8333	Intermediate Similarity	NPC472821
0.8333	Intermediate Similarity	NPC99620
0.8333	Intermediate Similarity	NPC470817
0.8333	Intermediate Similarity	NPC5311
0.8333	Intermediate Similarity	NPC187302
0.8333	Intermediate Similarity	NPC134270
0.8333	Intermediate Similarity	NPC193382
0.8333	Intermediate Similarity	NPC310341
0.8333	Intermediate Similarity	NPC475889
0.8333	Intermediate Similarity	NPC127933
0.8333	Intermediate Similarity	NPC189588
0.8333	Intermediate Similarity	NPC196471
0.8333	Intermediate Similarity	NPC199428
0.8333	Intermediate Similarity	NPC10232
0.8333	Intermediate Similarity	NPC97487
0.8333	Intermediate Similarity	NPC7644
0.8317	Intermediate Similarity	NPC198992
0.8317	Intermediate Similarity	NPC472554
0.8316	Intermediate Similarity	NPC291665
0.8316	Intermediate Similarity	NPC93411
0.8316	Intermediate Similarity	NPC106332
0.8302	Intermediate Similarity	NPC17791
0.83	Intermediate Similarity	NPC107806
0.83	Intermediate Similarity	NPC474440
0.83	Intermediate Similarity	NPC72647
0.83	Intermediate Similarity	NPC218107
0.8298	Intermediate Similarity	NPC471219
0.8286	Intermediate Similarity	NPC31522
0.8286	Intermediate Similarity	NPC475030
0.8283	Intermediate Similarity	NPC234993
0.8283	Intermediate Similarity	NPC8954
0.8283	Intermediate Similarity	NPC94905
0.8283	Intermediate Similarity	NPC134072
0.828	Intermediate Similarity	NPC32223
0.8269	Intermediate Similarity	NPC216636
0.8269	Intermediate Similarity	NPC187435
0.8269	Intermediate Similarity	NPC67321
0.8269	Intermediate Similarity	NPC319438
0.8265	Intermediate Similarity	NPC324078
0.8265	Intermediate Similarity	NPC189513
0.8265	Intermediate Similarity	NPC57117
0.8265	Intermediate Similarity	NPC477722
0.8261	Intermediate Similarity	NPC2524
0.8257	Intermediate Similarity	NPC471353
0.8257	Intermediate Similarity	NPC27507
0.8257	Intermediate Similarity	NPC142066
0.8257	Intermediate Similarity	NPC309034
0.8257	Intermediate Similarity	NPC34390
0.8257	Intermediate Similarity	NPC87250
0.8257	Intermediate Similarity	NPC158344
0.8257	Intermediate Similarity	NPC196429
0.8257	Intermediate Similarity	NPC77319
0.8257	Intermediate Similarity	NPC203862
0.8257	Intermediate Similarity	NPC474418
0.8257	Intermediate Similarity	NPC84987
0.8257	Intermediate Similarity	NPC290693
0.8257	Intermediate Similarity	NPC99728
0.8257	Intermediate Similarity	NPC50305
0.8257	Intermediate Similarity	NPC157376
0.8257	Intermediate Similarity	NPC471355
0.8257	Intermediate Similarity	NPC473852
0.8257	Intermediate Similarity	NPC93883
0.8257	Intermediate Similarity	NPC471354
0.8257	Intermediate Similarity	NPC244402
0.8257	Intermediate Similarity	NPC243196
0.8257	Intermediate Similarity	NPC471351
0.8257	Intermediate Similarity	NPC152615
0.8252	Intermediate Similarity	NPC201880
0.8252	Intermediate Similarity	NPC264867
0.8252	Intermediate Similarity	NPC470321
0.8252	Intermediate Similarity	NPC473207
0.8252	Intermediate Similarity	NPC81567
0.8247	Intermediate Similarity	NPC473675
0.8247	Intermediate Similarity	NPC477122
0.8235	Intermediate Similarity	NPC472552
0.8235	Intermediate Similarity	NPC470571
0.8229	Intermediate Similarity	NPC246028
0.8229	Intermediate Similarity	NPC470819
0.8224	Intermediate Similarity	NPC194951
0.8224	Intermediate Similarity	NPC317460
0.8224	Intermediate Similarity	NPC470025
0.8224	Intermediate Similarity	NPC328074
0.8224	Intermediate Similarity	NPC12046
0.8224	Intermediate Similarity	NPC321272
0.8211	Intermediate Similarity	NPC471796
0.8208	Intermediate Similarity	NPC316708
0.82	Intermediate Similarity	NPC97867

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 NPC324841 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	1607
0.2-0.3	3836
0.3-0.4	2324
0.4-0.5	765
0.5-0.6	252
0.6-0.7	173
0.7-0.8	23
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
0.84	Intermediate Similarity	NPD7639	Approved
0.84	Intermediate Similarity	NPD7640	Approved
0.8349	Intermediate Similarity	NPD7327	Approved
0.8349	Intermediate Similarity	NPD7328	Approved
0.83	Intermediate Similarity	NPD7638	Approved
0.8273	Intermediate Similarity	NPD7516	Approved
0.8036	Intermediate Similarity	NPD8377	Approved
0.8036	Intermediate Similarity	NPD8294	Approved
0.8019	Intermediate Similarity	NPD6686	Approved
0.7965	Intermediate Similarity	NPD8380	Approved
0.7965	Intermediate Similarity	NPD8379	Approved
0.7965	Intermediate Similarity	NPD8296	Approved
0.7965	Intermediate Similarity	NPD8378	Approved
0.7965	Intermediate Similarity	NPD8033	Approved
0.7965	Intermediate Similarity	NPD8335	Approved
0.7714	Intermediate Similarity	NPD7632	Discontinued
0.7708	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7507	Approved
0.7652	Intermediate Similarity	NPD7503	Approved
0.7619	Intermediate Similarity	NPD5344	Discontinued
0.7615	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7319	Approved
0.7387	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6412	Phase 2
0.7117	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7525	Registered
0.7048	Intermediate Similarity	NPD7748	Approved
0.7043	Intermediate Similarity	NPD8133	Approved
0.7027	Intermediate Similarity	NPD7128	Approved
0.7027	Intermediate Similarity	NPD5739	Approved
0.7027	Intermediate Similarity	NPD6675	Approved
0.7027	Intermediate Similarity	NPD6402	Approved
0.7019	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6051	Approved
0.6957	Remote Similarity	NPD6882	Approved
0.6944	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD6881	Approved
0.6903	Remote Similarity	NPD6899	Approved
0.6903	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD6695	Phase 3
0.6864	Remote Similarity	NPD6009	Approved
0.686	Remote Similarity	NPD6370	Approved
0.6857	Remote Similarity	NPD7637	Suspended
0.6855	Remote Similarity	NPD7736	Approved
0.6842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD6373	Approved
0.6814	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD5697	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.6792	Remote Similarity	NPD6399	Phase 3
0.6783	Remote Similarity	NPD7102	Approved
0.6783	Remote Similarity	NPD7290	Approved
0.6783	Remote Similarity	NPD6883	Approved
0.6754	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6011	Approved
0.6752	Remote Similarity	NPD4632	Approved
0.6748	Remote Similarity	NPD7492	Approved
0.6729	Remote Similarity	NPD7900	Approved
0.6729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD8130	Phase 1
0.6724	Remote Similarity	NPD6869	Approved
0.6724	Remote Similarity	NPD6649	Approved
0.6724	Remote Similarity	NPD6847	Approved
0.6724	Remote Similarity	NPD6617	Approved
0.6724	Remote Similarity	NPD6650	Approved
0.6724	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3618	Phase 1
0.6697	Remote Similarity	NPD6083	Phase 2
0.6697	Remote Similarity	NPD6084	Phase 2
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6059	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD8297	Approved
0.664	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6636	Remote Similarity	NPD4202	Approved
0.6635	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7524	Approved
0.6635	Remote Similarity	NPD7750	Discontinued
0.6618	Remote Similarity	NPD7625	Phase 1
0.6607	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD6698	Approved
0.6604	Remote Similarity	NPD7838	Discovery
0.6604	Remote Similarity	NPD46	Approved
0.6602	Remote Similarity	NPD1694	Approved
0.66	Remote Similarity	NPD6931	Approved
0.66	Remote Similarity	NPD6930	Phase 2
0.6557	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD4755	Approved
0.6542	Remote Similarity	NPD6079	Approved
0.6542	Remote Similarity	NPD8034	Phase 2
0.6542	Remote Similarity	NPD8035	Phase 2
0.6538	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD6409	Approved
0.6538	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD7521	Approved
0.6538	Remote Similarity	NPD5330	Approved
0.6532	Remote Similarity	NPD7604	Phase 2
0.6504	Remote Similarity	NPD6015	Approved
0.6504	Remote Similarity	NPD5983	Phase 2
0.6504	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6929	Approved
0.6496	Remote Similarity	NPD6371	Approved
0.6491	Remote Similarity	NPD5141	Approved
0.6481	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD5988	Approved
0.6446	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7332	Phase 2
0.6436	Remote Similarity	NPD7514	Phase 3
0.6429	Remote Similarity	NPD6942	Approved
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD7339	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.6429	Remote Similarity	NPD4696	Approved
0.6415	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD5737	Approved
0.6415	Remote Similarity	NPD6672	Approved
0.6415	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6335	Approved
0.6389	Remote Similarity	NPD7087	Discontinued
0.6389	Remote Similarity	NPD5693	Phase 1
0.6372	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD6274	Approved
0.6346	Remote Similarity	NPD3133	Approved
0.6346	Remote Similarity	NPD4786	Approved
0.6346	Remote Similarity	NPD3666	Approved
0.6346	Remote Similarity	NPD3665	Phase 1
0.6341	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD7101	Approved
0.6339	Remote Similarity	NPD5696	Approved
0.6328	Remote Similarity	NPD6033	Approved
0.6327	Remote Similarity	NPD6926	Approved
0.6327	Remote Similarity	NPD6924	Approved
0.6321	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5224	Approved
0.6316	Remote Similarity	NPD5226	Approved
0.6316	Remote Similarity	NPD4633	Approved
0.6311	Remote Similarity	NPD3667	Approved
0.6311	Remote Similarity	NPD6317	Approved
0.6306	Remote Similarity	NPD5222	Approved
0.6306	Remote Similarity	NPD4697	Phase 3
0.6306	Remote Similarity	NPD5221	Approved
0.6306	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6925	Approved
0.63	Remote Similarity	NPD5776	Phase 2
0.6296	Remote Similarity	NPD3168	Discontinued
0.6296	Remote Similarity	NPD5785	Approved
0.6286	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6893	Approved
0.6275	Remote Similarity	NPD7509	Discontinued
0.6263	Remote Similarity	NPD8264	Approved
0.6261	Remote Similarity	NPD5175	Approved
0.6261	Remote Similarity	NPD4754	Approved
0.6261	Remote Similarity	NPD5174	Approved
0.626	Remote Similarity	NPD6313	Approved
0.626	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD5173	Approved
0.624	Remote Similarity	NPD6908	Approved
0.624	Remote Similarity	NPD6909	Approved
0.6238	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7145	Approved
0.623	Remote Similarity	NPD6868	Approved
0.6226	Remote Similarity	NPD4519	Discontinued
0.6226	Remote Similarity	NPD4623	Approved
0.6218	Remote Similarity	NPD4634	Approved
0.6214	Remote Similarity	NPD6902	Approved
0.6214	Remote Similarity	NPD6898	Phase 1
0.6204	Remote Similarity	NPD4753	Phase 2
0.6204	Remote Similarity	NPD6080	Approved
0.6204	Remote Similarity	NPD6904	Approved
0.6204	Remote Similarity	NPD6673	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