NPASS Compound

Structure

NPC186861 OpenBabel07101718322D 23 26 0 0 1 0 0 0 0 0999 V2000 0.1658 -3.6528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6296 0.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1320 -2.2723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 0.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5283 -2.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -1.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5311 -2.7219 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6146 -0.2897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5811 -3.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0917 -1.8209 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1355 -2.1526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7969 -0.8653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1490 -1.9888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4148 -0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8944 -0.5527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0284 -4.0012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3703 -0.5948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5295 0.2197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5828 -3.0470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0915 -1.8359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 8 2 0 0 0 0 3 9 1 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 6 16 1 0 0 0 0 7 1 1 1 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 18 2 0 0 0 0 9 21 1 0 0 0 0 10 5 1 1 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 1 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 13 17 1 1 0 0 0 14 17 1 1 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 1 0 0 0 16 20 1 0 0 0 0 17 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.14
Volume:	313.194
LogP:	1.138
LogD:	1.743
LogS:	-3.281
# Rotatable Bonds:	2
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	5.432
Fsp3:	0.765
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:	-4.946
MDCK Permeability:	5.687007069354877e-05
Pgp-inhibitor:	0.317
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.538
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	27.479625701904297%
Volume Distribution (VD):	0.725
Pgp-substrate:	54.043983459472656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.108
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	5.877
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.682
Carcinogencity:	0.521
Eye Corrosion:	0.804
Eye Irritation:	0.809
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC186861

Natural Product ID:	NPC186861
*Common Name:**	ZYYHSYGMMLFTOT-MACYQYCFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZYYHSYGMMLFTOT-MACYQYCFSA-N
Standard InCHI:	InChI=1S/C17H22O6/c1-7-5-10-12(8(2)15(19)22-10)14-17(23-14)13(7)11(21-9(3)18)6-16(17,4)20/h7,10-14,20H,2,5-6H2,1,3-4H3/t7-,10+,11+,12-,13+,14+,16-,17-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@]([C@]23[C@H]1[C@H](C)C[C@H]1[C@H]([C@@H]3O2)C(=C)C(=O)O1)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165551
PubChem CID:	46849499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene 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
NPO33493	inula lineariifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515062]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	26180.0	nM	PMID[566532]

☑ 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 NPC186861 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	299
0.1-0.2	2113
0.2-0.3	7066
0.3-0.4	15076
0.4-0.5	9394
0.5-0.6	5907
0.6-0.7	2238
0.7-0.8	480
0.8-0.85	79
0.85-0.9	25
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC471381
0.957	High Similarity	NPC471150
0.9485	High Similarity	NPC54737
0.9468	High Similarity	NPC45125
0.9355	High Similarity	NPC476053
0.9355	High Similarity	NPC472873
0.9239	High Similarity	NPC155215
0.92	High Similarity	NPC139838
0.92	High Similarity	NPC59489
0.914	High Similarity	NPC258216
0.9022	High Similarity	NPC472872
0.8958	High Similarity	NPC181151
0.8947	High Similarity	NPC163228
0.8925	High Similarity	NPC216284
0.8913	High Similarity	NPC79549
0.89	High Similarity	NPC44004
0.8817	High Similarity	NPC215556
0.8804	High Similarity	NPC270270
0.8737	High Similarity	NPC472874
0.8713	High Similarity	NPC243998
0.8713	High Similarity	NPC223450
0.871	High Similarity	NPC178875
0.8679	High Similarity	NPC255450
0.8679	High Similarity	NPC170692
0.8632	High Similarity	NPC57304
0.8632	High Similarity	NPC293001
0.8632	High Similarity	NPC29821
0.8632	High Similarity	NPC133888
0.8632	High Similarity	NPC171360
0.8632	High Similarity	NPC63193
0.8632	High Similarity	NPC35959
0.8602	High Similarity	NPC190753
0.8602	High Similarity	NPC118601
0.8587	High Similarity	NPC300082
0.8587	High Similarity	NPC284534
0.8587	High Similarity	NPC204105
0.8571	High Similarity	NPC474313
0.8571	High Similarity	NPC311904
0.8526	High Similarity	NPC297474
0.8526	High Similarity	NPC54065
0.8526	High Similarity	NPC35809
0.8511	High Similarity	NPC207114
0.8511	High Similarity	NPC217983
0.8495	Intermediate Similarity	NPC470242
0.8485	Intermediate Similarity	NPC221615
0.8469	Intermediate Similarity	NPC91771
0.8469	Intermediate Similarity	NPC213078
0.8469	Intermediate Similarity	NPC142529
0.8462	Intermediate Similarity	NPC115352
0.8454	Intermediate Similarity	NPC127019
0.8438	Intermediate Similarity	NPC184063
0.8421	Intermediate Similarity	NPC155935
0.8411	Intermediate Similarity	NPC121816
0.8404	Intermediate Similarity	NPC24728
0.8404	Intermediate Similarity	NPC186148
0.8387	Intermediate Similarity	NPC304509
0.8387	Intermediate Similarity	NPC47958
0.8387	Intermediate Similarity	NPC149725
0.8384	Intermediate Similarity	NPC161493
0.8381	Intermediate Similarity	NPC193741
0.837	Intermediate Similarity	NPC245665
0.8367	Intermediate Similarity	NPC475900
0.8367	Intermediate Similarity	NPC213698
0.8367	Intermediate Similarity	NPC67584
0.8365	Intermediate Similarity	NPC117604
0.8365	Intermediate Similarity	NPC68248
0.8351	Intermediate Similarity	NPC153590
0.8351	Intermediate Similarity	NPC60386
0.8351	Intermediate Similarity	NPC212486
0.8351	Intermediate Similarity	NPC473273
0.8351	Intermediate Similarity	NPC473263
0.8351	Intermediate Similarity	NPC473234
0.8351	Intermediate Similarity	NPC308656
0.8333	Intermediate Similarity	NPC124881
0.8333	Intermediate Similarity	NPC19087
0.8318	Intermediate Similarity	NPC273242
0.8317	Intermediate Similarity	NPC150923
0.8316	Intermediate Similarity	NPC58219
0.8316	Intermediate Similarity	NPC471149
0.8316	Intermediate Similarity	NPC177629
0.8298	Intermediate Similarity	NPC187661
0.8298	Intermediate Similarity	NPC236692
0.8298	Intermediate Similarity	NPC309757
0.8283	Intermediate Similarity	NPC18019
0.8283	Intermediate Similarity	NPC24956
0.8283	Intermediate Similarity	NPC476009
0.8265	Intermediate Similarity	NPC198853
0.8261	Intermediate Similarity	NPC246076
0.8247	Intermediate Similarity	NPC133698
0.8247	Intermediate Similarity	NPC286341
0.8247	Intermediate Similarity	NPC191339
0.8247	Intermediate Similarity	NPC70251
0.8247	Intermediate Similarity	NPC475881
0.8235	Intermediate Similarity	NPC80144
0.8229	Intermediate Similarity	NPC283409
0.8229	Intermediate Similarity	NPC38392
0.8229	Intermediate Similarity	NPC92974
0.8224	Intermediate Similarity	NPC475851
0.8224	Intermediate Similarity	NPC475924
0.8218	Intermediate Similarity	NPC70865
0.8211	Intermediate Similarity	NPC5130
0.8182	Intermediate Similarity	NPC14961
0.8182	Intermediate Similarity	NPC170120
0.8182	Intermediate Similarity	NPC52044
0.8182	Intermediate Similarity	NPC270013
0.8172	Intermediate Similarity	NPC111409
0.8163	Intermediate Similarity	NPC475788
0.8163	Intermediate Similarity	NPC200237
0.8144	Intermediate Similarity	NPC246173
0.8137	Intermediate Similarity	NPC67296
0.8137	Intermediate Similarity	NPC171759
0.8125	Intermediate Similarity	NPC224652
0.8119	Intermediate Similarity	NPC249171
0.8119	Intermediate Similarity	NPC49833
0.8105	Intermediate Similarity	NPC304558
0.8105	Intermediate Similarity	NPC475019
0.8105	Intermediate Similarity	NPC476015
0.8105	Intermediate Similarity	NPC474949
0.8105	Intermediate Similarity	NPC56593
0.8105	Intermediate Similarity	NPC474762
0.8095	Intermediate Similarity	NPC148270
0.8095	Intermediate Similarity	NPC197813
0.8095	Intermediate Similarity	NPC80338
0.8085	Intermediate Similarity	NPC194859
0.8085	Intermediate Similarity	NPC224386
0.8081	Intermediate Similarity	NPC323008
0.8081	Intermediate Similarity	NPC81386
0.8081	Intermediate Similarity	NPC474035
0.8081	Intermediate Similarity	NPC262133
0.8081	Intermediate Similarity	NPC470013
0.8081	Intermediate Similarity	NPC470010
0.8081	Intermediate Similarity	NPC477131
0.8077	Intermediate Similarity	NPC474741
0.8061	Intermediate Similarity	NPC12172
0.8061	Intermediate Similarity	NPC208886
0.8061	Intermediate Similarity	NPC131209
0.8061	Intermediate Similarity	NPC475925
0.8061	Intermediate Similarity	NPC184463
0.8058	Intermediate Similarity	NPC86077
0.8043	Intermediate Similarity	NPC156658
0.8043	Intermediate Similarity	NPC258965
0.8041	Intermediate Similarity	NPC4986
0.8041	Intermediate Similarity	NPC307411
0.802	Intermediate Similarity	NPC108475
0.802	Intermediate Similarity	NPC304445
0.802	Intermediate Similarity	NPC213947
0.802	Intermediate Similarity	NPC236580
0.802	Intermediate Similarity	NPC170143
0.8	Intermediate Similarity	NPC224689
0.8	Intermediate Similarity	NPC170432
0.8	Intermediate Similarity	NPC329749
0.7981	Intermediate Similarity	NPC473148
0.798	Intermediate Similarity	NPC179746
0.798	Intermediate Similarity	NPC81419
0.798	Intermediate Similarity	NPC475912
0.798	Intermediate Similarity	NPC135776
0.798	Intermediate Similarity	NPC476300
0.7979	Intermediate Similarity	NPC474472
0.7979	Intermediate Similarity	NPC257358
0.7979	Intermediate Similarity	NPC128246
0.7961	Intermediate Similarity	NPC471767
0.7959	Intermediate Similarity	NPC206614
0.7959	Intermediate Similarity	NPC474323
0.7959	Intermediate Similarity	NPC51004
0.7959	Intermediate Similarity	NPC37607
0.7959	Intermediate Similarity	NPC301969
0.7941	Intermediate Similarity	NPC474213
0.7941	Intermediate Similarity	NPC473326
0.7938	Intermediate Similarity	NPC202672
0.7938	Intermediate Similarity	NPC91248
0.7925	Intermediate Similarity	NPC26617
0.7921	Intermediate Similarity	NPC476315
0.7917	Intermediate Similarity	NPC64153
0.7917	Intermediate Similarity	NPC67493
0.7905	Intermediate Similarity	NPC100487
0.79	Intermediate Similarity	NPC473331
0.79	Intermediate Similarity	NPC190294
0.7895	Intermediate Similarity	NPC474780
0.789	Intermediate Similarity	NPC189338
0.789	Intermediate Similarity	NPC258711
0.789	Intermediate Similarity	NPC35069
0.789	Intermediate Similarity	NPC95290
0.7885	Intermediate Similarity	NPC474747
0.7885	Intermediate Similarity	NPC250594
0.7879	Intermediate Similarity	NPC30515
0.787	Intermediate Similarity	NPC50223
0.787	Intermediate Similarity	NPC41551
0.7857	Intermediate Similarity	NPC151770
0.7857	Intermediate Similarity	NPC474951
0.7857	Intermediate Similarity	NPC168679
0.7857	Intermediate Similarity	NPC173926
0.7857	Intermediate Similarity	NPC475401
0.7857	Intermediate Similarity	NPC12872
0.7849	Intermediate Similarity	NPC476625
0.7843	Intermediate Similarity	NPC263674
0.7843	Intermediate Similarity	NPC261372
0.7843	Intermediate Similarity	NPC58267
0.7835	Intermediate Similarity	NPC231889
0.7835	Intermediate Similarity	NPC201658
0.783	Intermediate Similarity	NPC127235

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 NPC186861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	2826
0.2-0.3	3808
0.3-0.4	1501
0.4-0.5	423
0.5-0.6	203
0.6-0.7	33
0.7-0.8	5
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
0.8041	Intermediate Similarity	NPD1695	Approved
0.7925	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6371	Approved
0.7449	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD46	Approved
0.7087	Intermediate Similarity	NPD6698	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.6863	Remote Similarity	NPD4249	Approved
0.68	Remote Similarity	NPD6435	Approved
0.6796	Remote Similarity	NPD4250	Approved
0.6796	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD7838	Discovery
0.6602	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5368	Approved
0.6569	Remote Similarity	NPD5362	Discontinued
0.656	Remote Similarity	NPD7507	Approved
0.6557	Remote Similarity	NPD6319	Approved
0.6542	Remote Similarity	NPD7983	Approved
0.6518	Remote Similarity	NPD1700	Approved
0.6491	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD4632	Approved
0.6449	Remote Similarity	NPD5785	Approved
0.6446	Remote Similarity	NPD7115	Discovery
0.6436	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4819	Approved
0.6436	Remote Similarity	NPD4821	Approved
0.6436	Remote Similarity	NPD4822	Approved
0.6436	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD6616	Approved
0.6423	Remote Similarity	NPD6054	Approved
0.6406	Remote Similarity	NPD7319	Approved
0.6381	Remote Similarity	NPD5786	Approved
0.6378	Remote Similarity	NPD7078	Approved
0.6373	Remote Similarity	NPD5369	Approved
0.6372	Remote Similarity	NPD5344	Discontinued
0.6371	Remote Similarity	NPD6015	Approved
0.6371	Remote Similarity	NPD6016	Approved
0.6333	Remote Similarity	NPD8133	Approved
0.6328	Remote Similarity	NPD7736	Approved
0.6325	Remote Similarity	NPD6686	Approved
0.632	Remote Similarity	NPD6370	Approved
0.632	Remote Similarity	NPD5988	Approved
0.6303	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6059	Approved
0.6286	Remote Similarity	NPD5363	Approved
0.6273	Remote Similarity	NPD5282	Discontinued
0.6271	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD4271	Approved
0.6238	Remote Similarity	NPD4268	Approved
0.6218	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4225	Approved
0.6186	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7320	Approved
0.6186	Remote Similarity	NPD6881	Approved
0.6179	Remote Similarity	NPD6009	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.6167	Remote Similarity	NPD6650	Approved
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD4270	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD4269	Approved
0.6142	Remote Similarity	NPD7604	Phase 2
0.614	Remote Similarity	NPD6648	Approved
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6372	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6134	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD8515	Approved
0.6111	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD8517	Approved
0.6111	Remote Similarity	NPD8516	Approved
0.6111	Remote Similarity	NPD8513	Phase 3
0.6102	Remote Similarity	NPD6412	Phase 2
0.6102	Remote Similarity	NPD5701	Approved
0.6095	Remote Similarity	NPD5332	Approved
0.6095	Remote Similarity	NPD5331	Approved
0.6083	Remote Similarity	NPD7290	Approved
0.6083	Remote Similarity	NPD7102	Approved
0.6083	Remote Similarity	NPD4634	Approved
0.6083	Remote Similarity	NPD6883	Approved
0.6071	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD4790	Discontinued
0.6053	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7638	Approved
0.6053	Remote Similarity	NPD5696	Approved
0.605	Remote Similarity	NPD6011	Approved
0.6036	Remote Similarity	NPD6399	Phase 3
0.6036	Remote Similarity	NPD5778	Approved
0.6036	Remote Similarity	NPD5779	Approved
0.6033	Remote Similarity	NPD6847	Approved
0.6033	Remote Similarity	NPD6617	Approved
0.6033	Remote Similarity	NPD8130	Phase 1
0.6033	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7328	Approved
0.6	Remote Similarity	NPD7639	Approved
0.5984	Remote Similarity	NPD6882	Approved
0.5966	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6084	Phase 2
0.5965	Remote Similarity	NPD6083	Phase 2
0.5962	Remote Similarity	NPD4252	Approved
0.5952	Remote Similarity	NPD7516	Approved
0.5946	Remote Similarity	NPD8034	Phase 2
0.5946	Remote Similarity	NPD8035	Phase 2
0.5929	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6336	Discontinued
0.5906	Remote Similarity	NPD8377	Approved
0.5906	Remote Similarity	NPD8294	Approved
0.5897	Remote Similarity	NPD5211	Phase 2
0.5896	Remote Similarity	NPD6845	Suspended
0.5891	Remote Similarity	NPD7642	Approved
0.5878	Remote Similarity	NPD8074	Phase 3
0.5862	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD4696	Approved
0.5862	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD8268	Approved
0.5859	Remote Similarity	NPD8269	Approved
0.5859	Remote Similarity	NPD8380	Approved
0.5859	Remote Similarity	NPD7503	Approved
0.5859	Remote Similarity	NPD8378	Approved
0.5859	Remote Similarity	NPD8379	Approved
0.5859	Remote Similarity	NPD8266	Approved
0.5859	Remote Similarity	NPD8296	Approved
0.5859	Remote Similarity	NPD8267	Approved
0.5859	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8335	Approved
0.584	Remote Similarity	NPD6274	Approved
0.5833	Remote Similarity	NPD6033	Approved
0.5826	Remote Similarity	NPD4755	Approved
0.5821	Remote Similarity	NPD7260	Phase 2
0.5804	Remote Similarity	NPD5693	Phase 1
0.5804	Remote Similarity	NPD5281	Approved
0.5804	Remote Similarity	NPD5284	Approved
0.5802	Remote Similarity	NPD8273	Phase 1
0.5798	Remote Similarity	NPD5141	Approved
0.5794	Remote Similarity	NPD4788	Approved
0.5772	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7830	Approved
0.5769	Remote Similarity	NPD4802	Phase 2
0.5769	Remote Similarity	NPD7829	Approved
0.5769	Remote Similarity	NPD4238	Approved
0.5769	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6101	Approved
0.5763	Remote Similarity	NPD5225	Approved
0.5763	Remote Similarity	NPD4633	Approved
0.5763	Remote Similarity	NPD5224	Approved
0.5763	Remote Similarity	NPD5226	Approved
0.5746	Remote Similarity	NPD5956	Approved
0.5727	Remote Similarity	NPD7524	Approved
0.5726	Remote Similarity	NPD4700	Approved
0.5725	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5703	Remote Similarity	NPD7100	Approved
0.5703	Remote Similarity	NPD7101	Approved
0.5702	Remote Similarity	NPD6001	Approved
0.5701	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD1694	Approved
0.5678	Remote Similarity	NPD5223	Approved
0.5676	Remote Similarity	NPD6903	Approved
0.5669	Remote Similarity	NPD6317	Approved
0.5667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD7637	Suspended
0.5664	Remote Similarity	NPD6411	Approved
0.5652	Remote Similarity	NPD4629	Approved
0.5652	Remote Similarity	NPD5210	Approved
0.5645	Remote Similarity	NPD2204	Approved
0.5638	Remote Similarity	NPD3198	Approved
0.5636	Remote Similarity	NPD7334	Approved
0.5636	Remote Similarity	NPD5330	Approved
0.5636	Remote Similarity	NPD6409	Approved
0.5636	Remote Similarity	NPD7521	Approved
0.5636	Remote Similarity	NPD7146	Approved
0.5636	Remote Similarity	NPD6684	Approved
0.5631	Remote Similarity	NPD3702	Approved
0.563	Remote Similarity	NPD7632	Discontinued
0.5625	Remote Similarity	NPD6314	Approved
0.5625	Remote Similarity	NPD6313	Approved
0.5625	Remote Similarity	NPD6335	Approved
0.5625	Remote Similarity	NPD4753	Phase 2
0.5625	Remote Similarity	NPD7641	Discontinued
0.5615	Remote Similarity	NPD6921	Approved
0.5603	Remote Similarity	NPD7839	Suspended

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