NPASS Compound

Structure

NPC294263 OpenBabel07101718272D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 0.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 1.0801 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 3.3709 0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4689 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 24 2 0 0 0 0 13 27 1 0 0 0 0 14 9 1 1 0 0 0 15 18 1 0 0 0 0 15 25 1 6 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 21 1 6 0 0 0 17 27 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 26 2 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	390.884
LogP:	1.678
LogD:	1.915
LogS:	-3.291
# Rotatable Bonds:	3
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	5.843
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.721
MDCK Permeability:	3.0371398679562844e-05
Pgp-inhibitor:	0.259
Pgp-substrate:	0.807
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.592

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.697
Plasma Protein Binding (PPB):	43.40338134765625%
Volume Distribution (VD):	0.585
Pgp-substrate:	50.25007247924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.543
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.564
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	4.167
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.925
Carcinogencity:	0.734
Eye Corrosion:	0.111
Eye Irritation:	0.137
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC294263

Natural Product ID:	NPC294263
*Common Name:**	Excisusin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NSAONOIMMKIRAT-KRGOTXCRSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-12-14-9-15(25)18-20(3)7-6-17(27-13(2)24)21(4,11-23)16(20)5-8-22(18,10-14)19(12)26/h14-18,23,25H,1,5-11H2,2-4H3/t14-,15+,16+,17+,18+,20-,21+,22-/m1/s1
SMILES:	C=C1[C@@H]2C[C@@H]([C@H]3[C@]4(C)CC[C@@H]([C@@](C)(CO)[C@H]4CC[C@]3(C2)C1=O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223544
PubChem CID:	16215553
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
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10896056]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374970]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17338565]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21273070]
NPO26913	Isodon excisus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22066578]
NPO26913	Isodon excisus	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	900.0	nM	PMID[558260]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	670.0	nM	PMID[558260]

☑ 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 NPC294263 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	200
0.1-0.2	1544
0.2-0.3	5656
0.3-0.4	12286
0.4-0.5	8767
0.5-0.6	5804
0.6-0.7	5266
0.7-0.8	2692
0.8-0.85	303
0.85-0.9	119
0.9-0.95	56
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9551	High Similarity	NPC98639
0.9451	High Similarity	NPC38471
0.9451	High Similarity	NPC20479
0.9451	High Similarity	NPC98837
0.9451	High Similarity	NPC162459
0.9451	High Similarity	NPC28864
0.9451	High Similarity	NPC38296
0.9444	High Similarity	NPC13949
0.9444	High Similarity	NPC29410
0.9444	High Similarity	NPC200054
0.9432	High Similarity	NPC250753
0.9348	High Similarity	NPC293866
0.9341	High Similarity	NPC10864
0.9333	High Similarity	NPC210214
0.9302	High Similarity	NPC471042
0.9247	High Similarity	NPC46848
0.9247	High Similarity	NPC289148
0.9247	High Similarity	NPC163963
0.9247	High Similarity	NPC52899
0.9239	High Similarity	NPC89099
0.9239	High Similarity	NPC471038
0.9231	High Similarity	NPC329910
0.9231	High Similarity	NPC104568
0.9195	High Similarity	NPC174619
0.9149	High Similarity	NPC88203
0.9149	High Similarity	NPC76866
0.9149	High Similarity	NPC304832
0.9149	High Similarity	NPC148628
0.9149	High Similarity	NPC214946
0.9149	High Similarity	NPC246736
0.9149	High Similarity	NPC286519
0.9149	High Similarity	NPC275990
0.914	High Similarity	NPC287676
0.9121	High Similarity	NPC470229
0.9121	High Similarity	NPC470232
0.907	High Similarity	NPC146683
0.9053	High Similarity	NPC87927
0.9053	High Similarity	NPC470310
0.9043	High Similarity	NPC252614
0.9032	High Similarity	NPC474793
0.9032	High Similarity	NPC16911
0.9032	High Similarity	NPC78427
0.9011	High Similarity	NPC169751
0.9011	High Similarity	NPC470386
0.9011	High Similarity	NPC47853
0.9011	High Similarity	NPC272635
0.9011	High Similarity	NPC470385
0.9011	High Similarity	NPC475118
0.9	High Similarity	NPC198242
0.9	High Similarity	NPC211403
0.8977	High Similarity	NPC153604
0.8958	High Similarity	NPC301787
0.8958	High Similarity	NPC98603
0.8953	High Similarity	NPC471037
0.8953	High Similarity	NPC118800
0.8901	High Similarity	NPC224060
0.8901	High Similarity	NPC244356
0.8889	High Similarity	NPC180849
0.8876	High Similarity	NPC474719
0.8866	High Similarity	NPC200957
0.8866	High Similarity	NPC222833
0.8866	High Similarity	NPC138908
0.8854	High Similarity	NPC139347
0.8854	High Similarity	NPC216114
0.8854	High Similarity	NPC277074
0.8854	High Similarity	NPC209298
0.8854	High Similarity	NPC122811
0.8842	High Similarity	NPC121218
0.8842	High Similarity	NPC253886
0.8842	High Similarity	NPC236585
0.8842	High Similarity	NPC148279
0.8817	High Similarity	NPC470387
0.8804	High Similarity	NPC303863
0.8791	High Similarity	NPC470230
0.8776	High Similarity	NPC176949
0.8776	High Similarity	NPC201908
0.8776	High Similarity	NPC166993
0.8764	High Similarity	NPC33768
0.8764	High Similarity	NPC269360
0.8764	High Similarity	NPC264005
0.8763	High Similarity	NPC84928
0.875	High Similarity	NPC170615
0.875	High Similarity	NPC136289
0.8737	High Similarity	NPC470388
0.871	High Similarity	NPC266431
0.8696	High Similarity	NPC471902
0.8696	High Similarity	NPC59350
0.8696	High Similarity	NPC144739
0.8696	High Similarity	NPC287118
0.8696	High Similarity	NPC59170
0.8696	High Similarity	NPC473690
0.8696	High Similarity	NPC181594
0.8687	High Similarity	NPC231278
0.8687	High Similarity	NPC112895
0.8687	High Similarity	NPC218123
0.8687	High Similarity	NPC273155
0.8681	High Similarity	NPC80401
0.8673	High Similarity	NPC265127
0.8667	High Similarity	NPC4309
0.866	High Similarity	NPC96217
0.8652	High Similarity	NPC2783
0.8652	High Similarity	NPC12774
0.8646	High Similarity	NPC295276
0.8646	High Similarity	NPC71706
0.8646	High Similarity	NPC471790
0.8646	High Similarity	NPC81530
0.8632	High Similarity	NPC26270
0.8617	High Similarity	NPC219353
0.8602	High Similarity	NPC129004
0.8602	High Similarity	NPC111524
0.8602	High Similarity	NPC104371
0.8602	High Similarity	NPC101233
0.8602	High Similarity	NPC289539
0.8602	High Similarity	NPC153775
0.8602	High Similarity	NPC261333
0.8602	High Similarity	NPC91772
0.8602	High Similarity	NPC215271
0.8602	High Similarity	NPC29247
0.8602	High Similarity	NPC292374
0.8587	High Similarity	NPC471901
0.8587	High Similarity	NPC475416
0.8587	High Similarity	NPC476168
0.8587	High Similarity	NPC160506
0.8587	High Similarity	NPC299185
0.8571	High Similarity	NPC474558
0.8571	High Similarity	NPC202793
0.8571	High Similarity	NPC57954
0.8571	High Similarity	NPC213832
0.8571	High Similarity	NPC47281
0.8571	High Similarity	NPC471043
0.8557	High Similarity	NPC475803
0.8557	High Similarity	NPC309388
0.8556	High Similarity	NPC472497
0.8556	High Similarity	NPC165895
0.8556	High Similarity	NPC259009
0.8542	High Similarity	NPC267921
0.8542	High Similarity	NPC94906
0.8542	High Similarity	NPC293890
0.8539	High Similarity	NPC294438
0.8539	High Similarity	NPC76518
0.8539	High Similarity	NPC264317
0.8523	High Similarity	NPC291320
0.8523	High Similarity	NPC471036
0.8511	High Similarity	NPC317586
0.8511	High Similarity	NPC288906
0.8511	High Similarity	NPC205173
0.8511	High Similarity	NPC263135
0.8511	High Similarity	NPC138245
0.8511	High Similarity	NPC29112
0.8511	High Similarity	NPC470016
0.8511	High Similarity	NPC84018
0.8511	High Similarity	NPC231060
0.85	High Similarity	NPC63841
0.85	High Similarity	NPC211224
0.8488	Intermediate Similarity	NPC471475
0.8485	Intermediate Similarity	NPC28791
0.8485	Intermediate Similarity	NPC37600
0.8485	Intermediate Similarity	NPC295366
0.8485	Intermediate Similarity	NPC50535
0.8485	Intermediate Similarity	NPC4115
0.8478	Intermediate Similarity	NPC470378
0.8478	Intermediate Similarity	NPC149761
0.8478	Intermediate Similarity	NPC261994
0.8462	Intermediate Similarity	NPC146937
0.8462	Intermediate Similarity	NPC472739
0.8462	Intermediate Similarity	NPC56413
0.8462	Intermediate Similarity	NPC16377
0.8462	Intermediate Similarity	NPC471900
0.8454	Intermediate Similarity	NPC14634
0.8454	Intermediate Similarity	NPC75941
0.8438	Intermediate Similarity	NPC288
0.8438	Intermediate Similarity	NPC109059
0.8438	Intermediate Similarity	NPC472028
0.8431	Intermediate Similarity	NPC329953
0.8427	Intermediate Similarity	NPC475745
0.8427	Intermediate Similarity	NPC474482
0.8427	Intermediate Similarity	NPC299963
0.8421	Intermediate Similarity	NPC471039
0.8421	Intermediate Similarity	NPC264979
0.8421	Intermediate Similarity	NPC135548
0.8421	Intermediate Similarity	NPC234564
0.8421	Intermediate Similarity	NPC140242
0.8404	Intermediate Similarity	NPC302008
0.8404	Intermediate Similarity	NPC191094
0.8404	Intermediate Similarity	NPC166906
0.84	Intermediate Similarity	NPC186054
0.84	Intermediate Similarity	NPC88833
0.84	Intermediate Similarity	NPC86852
0.84	Intermediate Similarity	NPC96333
0.84	Intermediate Similarity	NPC251824
0.84	Intermediate Similarity	NPC470952
0.8391	Intermediate Similarity	NPC164999
0.8387	Intermediate Similarity	NPC278106
0.8387	Intermediate Similarity	NPC198054
0.8387	Intermediate Similarity	NPC297265
0.8384	Intermediate Similarity	NPC96268
0.8384	Intermediate Similarity	NPC13149
0.8384	Intermediate Similarity	NPC101842
0.837	Intermediate Similarity	NPC474704
0.837	Intermediate Similarity	NPC220498

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 NPC294263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1919
0.2-0.3	3968
0.3-0.4	2038
0.4-0.5	558
0.5-0.6	199
0.6-0.7	133
0.7-0.8	130
0.8-0.85	25
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD8034	Phase 2
0.8587	High Similarity	NPD8035	Phase 2
0.8539	High Similarity	NPD7520	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD6899	Approved
0.8317	Intermediate Similarity	NPD6881	Approved
0.83	Intermediate Similarity	NPD5739	Approved
0.83	Intermediate Similarity	NPD6675	Approved
0.83	Intermediate Similarity	NPD6402	Approved
0.83	Intermediate Similarity	NPD7128	Approved
0.8252	Intermediate Similarity	NPD6649	Approved
0.8252	Intermediate Similarity	NPD6650	Approved
0.8235	Intermediate Similarity	NPD6372	Approved
0.8235	Intermediate Similarity	NPD6373	Approved
0.8218	Intermediate Similarity	NPD5697	Approved
0.8191	Intermediate Similarity	NPD6079	Approved
0.8172	Intermediate Similarity	NPD5328	Approved
0.8155	Intermediate Similarity	NPD7102	Approved
0.8155	Intermediate Similarity	NPD7290	Approved
0.8155	Intermediate Similarity	NPD6883	Approved
0.8137	Intermediate Similarity	NPD7320	Approved
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8077	Intermediate Similarity	NPD6869	Approved
0.8077	Intermediate Similarity	NPD6847	Approved
0.8077	Intermediate Similarity	NPD8130	Phase 1
0.8077	Intermediate Similarity	NPD6617	Approved
0.8058	Intermediate Similarity	NPD6013	Approved
0.8058	Intermediate Similarity	NPD6014	Approved
0.8058	Intermediate Similarity	NPD6012	Approved
0.8039	Intermediate Similarity	NPD5701	Approved
0.8021	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD7515	Phase 2
0.7961	Intermediate Similarity	NPD6011	Approved
0.7959	Intermediate Similarity	NPD7902	Approved
0.7931	Intermediate Similarity	NPD6117	Approved
0.7912	Intermediate Similarity	NPD4788	Approved
0.7857	Intermediate Similarity	NPD5221	Approved
0.7857	Intermediate Similarity	NPD4697	Phase 3
0.7857	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5222	Approved
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7841	Intermediate Similarity	NPD6116	Phase 1
0.78	Intermediate Similarity	NPD5286	Approved
0.78	Intermediate Similarity	NPD4696	Approved
0.78	Intermediate Similarity	NPD5285	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7778	Intermediate Similarity	NPD4755	Approved
0.7778	Intermediate Similarity	NPD5173	Approved
0.7753	Intermediate Similarity	NPD6697	Approved
0.7753	Intermediate Similarity	NPD6115	Approved
0.7753	Intermediate Similarity	NPD6114	Approved
0.7753	Intermediate Similarity	NPD6118	Approved
0.7736	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD7900	Approved
0.7653	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4633	Approved
0.7647	Intermediate Similarity	NPD5226	Approved
0.7647	Intermediate Similarity	NPD5224	Approved
0.7647	Intermediate Similarity	NPD5225	Approved
0.7647	Intermediate Similarity	NPD5211	Phase 2
0.7634	Intermediate Similarity	NPD4786	Approved
0.7624	Intermediate Similarity	NPD4700	Approved
0.7624	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7639	Approved
0.7615	Intermediate Similarity	NPD6868	Approved
0.7615	Intermediate Similarity	NPD6274	Approved
0.7573	Intermediate Similarity	NPD5174	Approved
0.7573	Intermediate Similarity	NPD5175	Approved
0.7568	Intermediate Similarity	NPD7101	Approved
0.7568	Intermediate Similarity	NPD7100	Approved
0.7549	Intermediate Similarity	NPD5223	Approved
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7525	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6335	Approved
0.7474	Intermediate Similarity	NPD7146	Approved
0.7474	Intermediate Similarity	NPD7521	Approved
0.7474	Intermediate Similarity	NPD7334	Approved
0.7474	Intermediate Similarity	NPD6409	Approved
0.7474	Intermediate Similarity	NPD6684	Approved
0.7474	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4632	Approved
0.7429	Intermediate Similarity	NPD6008	Approved
0.7419	Intermediate Similarity	NPD3667	Approved
0.7416	Intermediate Similarity	NPD3703	Phase 2
0.74	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5695	Phase 3
0.7396	Intermediate Similarity	NPD3573	Approved
0.7387	Intermediate Similarity	NPD6317	Approved
0.7374	Intermediate Similarity	NPD4202	Approved
0.7345	Intermediate Similarity	NPD6319	Approved
0.7321	Intermediate Similarity	NPD6313	Approved
0.7321	Intermediate Similarity	NPD6314	Approved
0.732	Intermediate Similarity	NPD6903	Approved
0.729	Intermediate Similarity	NPD4729	Approved
0.729	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4730	Approved
0.729	Intermediate Similarity	NPD5128	Approved
0.7281	Intermediate Similarity	NPD6908	Approved
0.7281	Intermediate Similarity	NPD6909	Approved
0.7281	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6411	Approved
0.7264	Intermediate Similarity	NPD4768	Approved
0.7264	Intermediate Similarity	NPD4767	Approved
0.7263	Intermediate Similarity	NPD3133	Approved
0.7263	Intermediate Similarity	NPD3665	Phase 1
0.7263	Intermediate Similarity	NPD3666	Approved
0.7245	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7492	Approved
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4754	Approved
0.7232	Intermediate Similarity	NPD6009	Approved
0.7228	Intermediate Similarity	NPD5210	Approved
0.7228	Intermediate Similarity	NPD4629	Approved
0.7204	Intermediate Similarity	NPD7525	Registered
0.7203	Intermediate Similarity	NPD7736	Approved
0.7193	Intermediate Similarity	NPD6054	Approved
0.7184	Intermediate Similarity	NPD4225	Approved
0.7179	Intermediate Similarity	NPD6616	Approved
0.7156	Intermediate Similarity	NPD5249	Phase 3
0.7156	Intermediate Similarity	NPD5251	Approved
0.7156	Intermediate Similarity	NPD5250	Approved
0.7156	Intermediate Similarity	NPD4634	Approved
0.7156	Intermediate Similarity	NPD5248	Approved
0.7156	Intermediate Similarity	NPD5247	Approved
0.7155	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD5983	Phase 2
0.713	Intermediate Similarity	NPD5168	Approved
0.7119	Intermediate Similarity	NPD7078	Approved
0.7117	Intermediate Similarity	NPD8133	Approved
0.7113	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4224	Phase 2
0.7091	Intermediate Similarity	NPD5215	Approved
0.7091	Intermediate Similarity	NPD5217	Approved
0.7091	Intermediate Similarity	NPD5216	Approved
0.7079	Intermediate Similarity	NPD5777	Approved
0.7079	Intermediate Similarity	NPD6081	Approved
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD6904	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6673	Approved
0.7071	Intermediate Similarity	NPD6080	Approved
0.7069	Intermediate Similarity	NPD6370	Approved
0.7043	Intermediate Similarity	NPD6059	Approved
0.7034	Intermediate Similarity	NPD6336	Discontinued
0.7034	Intermediate Similarity	NPD7507	Approved
0.7033	Intermediate Similarity	NPD3702	Approved
0.7009	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD5135	Approved
0.7	Intermediate Similarity	NPD5169	Approved
0.7	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6015	Approved
0.6983	Remote Similarity	NPD6016	Approved
0.6975	Remote Similarity	NPD8293	Discontinued
0.6966	Remote Similarity	NPD4245	Approved
0.6966	Remote Similarity	NPD4244	Approved
0.6966	Remote Similarity	NPD4789	Approved
0.6961	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.6939	Remote Similarity	NPD6098	Approved
0.6937	Remote Similarity	NPD5127	Approved
0.6932	Remote Similarity	NPD5360	Phase 3
0.6932	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.6923	Remote Similarity	NPD5988	Approved
0.6915	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3668	Phase 3
0.6881	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4221	Approved
0.6875	Remote Similarity	NPD4223	Phase 3
0.6875	Remote Similarity	NPD6435	Approved
0.686	Remote Similarity	NPD7319	Approved
0.6854	Remote Similarity	NPD3698	Phase 2
0.6837	Remote Similarity	NPD1694	Approved
0.6837	Remote Similarity	NPD5329	Approved
0.6818	Remote Similarity	NPD6686	Approved
0.68	Remote Similarity	NPD5208	Approved
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6050	Approved
0.6765	Remote Similarity	NPD5693	Phase 1
0.6757	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5167	Approved
0.6735	Remote Similarity	NPD4197	Approved
0.6733	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1698	Clinical (unspecified phase)

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