NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	278.369
LogP:	1.438
LogD:	1.25
LogS:	-3.161
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	5.023
Fsp3:	0.733
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:	-4.936
MDCK Permeability:	1.908082776935771e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.633
Plasma Protein Binding (PPB):	38.87758255004883%
Volume Distribution (VD):	0.814
Pgp-substrate:	72.0941390991211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.493
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.237
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	8.46
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.921
Carcinogencity:	0.77
Eye Corrosion:	0.079
Eye Irritation:	0.267
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC190753

Natural Product ID:	NPC190753
*Common Name:**	Psilostachyin A
IUPAC Name:	(3aS,6S,7R,8S,8aR)-8-hydroxy-6,8-dimethyl-3-methylidenespiro[4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-7,5'-oxolane]-2,2'-dione
Synonyms:
Standard InCHIKey:	IRPFOXRBPHCCTG-JISBIHODSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-8-4-5-10-9(2)13(17)19-12(10)14(3,18)15(8)7-6-11(16)20-15/h8,10,12,18H,2,4-7H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@@](C)([C@]21CCC(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270060
PubChem CID:	5320767
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 [CHEMONTID:0002046] Ambrosanolides and secoambrosanolides

*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
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31009220]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10125	Ambrosia psilostachya	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10125	Ambrosia psilostachya	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30595	Ambrosia artemisllfolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10125	Ambrosia psilostachya	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10125	Ambrosia psilostachya	Species	Asteraceae	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	8
Others	5

Activity Type	# Activity
CELL-LINE	1
Individual Protein	3
NON-MOLECULAR	1
Organism	5
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	4600.0	nM	PMID[502110]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	44060.0	nM	PMID[502109]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1.22	ug.mL-1	PMID[502111]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	0.76	ug.mL-1	PMID[502111]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	IC50	=	0.12	ug.mL-1	PMID[502111]
NPT27	Others	Unspecified		CC50	=	25.7	ug.mL-1	PMID[502111]
NPT2	Others	Unspecified		Selectivity Index	=	33.8	n.a.	PMID[502111]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	100.0	%	PMID[502111]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	FC	=	1.5	n.a.	PMID[502111]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	39.45	%	PMID[502112]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[502113]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[502113]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[502113]

☑ 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 NPC190753 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	239
0.1-0.2	1597
0.2-0.3	6190
0.3-0.4	14437
0.4-0.5	10593
0.5-0.6	6856
0.6-0.7	2176
0.7-0.8	433
0.8-0.85	134
0.85-0.9	39
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC186148
0.8953	High Similarity	NPC58219
0.8953	High Similarity	NPC177629
0.8851	High Similarity	NPC92974
0.8837	High Similarity	NPC118601
0.8791	High Similarity	NPC471150
0.8778	High Similarity	NPC475900
0.8736	High Similarity	NPC178875
0.8721	High Similarity	NPC470242
0.8681	High Similarity	NPC476009
0.8652	High Similarity	NPC208886
0.8652	High Similarity	NPC12172
0.8605	High Similarity	NPC329749
0.8602	High Similarity	NPC471381
0.8602	High Similarity	NPC186861
0.8587	High Similarity	NPC181151
0.8556	High Similarity	NPC179746
0.8556	High Similarity	NPC81419
0.8539	High Similarity	NPC474323
0.8539	High Similarity	NPC206614
0.8523	High Similarity	NPC79549
0.8506	High Similarity	NPC476015
0.8506	High Similarity	NPC475019
0.8506	High Similarity	NPC474949
0.8506	High Similarity	NPC309757
0.8506	High Similarity	NPC236692
0.8506	High Similarity	NPC474762
0.8488	Intermediate Similarity	NPC474780
0.8444	Intermediate Similarity	NPC70251
0.8444	Intermediate Similarity	NPC475881
0.8444	Intermediate Similarity	NPC184463
0.8427	Intermediate Similarity	NPC474951
0.8427	Intermediate Similarity	NPC307411
0.8427	Intermediate Similarity	NPC215556
0.8427	Intermediate Similarity	NPC173926
0.8391	Intermediate Similarity	NPC304509
0.8391	Intermediate Similarity	NPC300082
0.8391	Intermediate Similarity	NPC284534
0.8391	Intermediate Similarity	NPC204105
0.8391	Intermediate Similarity	NPC47958
0.8391	Intermediate Similarity	NPC149725
0.8387	Intermediate Similarity	NPC474313
0.8372	Intermediate Similarity	NPC245665
0.837	Intermediate Similarity	NPC163228
0.837	Intermediate Similarity	NPC472873
0.837	Intermediate Similarity	NPC476053
0.8352	Intermediate Similarity	NPC153590
0.8352	Intermediate Similarity	NPC60386
0.8352	Intermediate Similarity	NPC473234
0.8352	Intermediate Similarity	NPC135776
0.8352	Intermediate Similarity	NPC476300
0.8352	Intermediate Similarity	NPC308656
0.8352	Intermediate Similarity	NPC212486
0.8352	Intermediate Similarity	NPC475912
0.8352	Intermediate Similarity	NPC473273
0.8352	Intermediate Similarity	NPC473263
0.8333	Intermediate Similarity	NPC51004
0.8333	Intermediate Similarity	NPC216284
0.8316	Intermediate Similarity	NPC474742
0.8315	Intermediate Similarity	NPC202672
0.8315	Intermediate Similarity	NPC207114
0.8315	Intermediate Similarity	NPC217983
0.8298	Intermediate Similarity	NPC45125
0.8295	Intermediate Similarity	NPC187661
0.8295	Intermediate Similarity	NPC162071
0.8261	Intermediate Similarity	NPC190294
0.8242	Intermediate Similarity	NPC155215
0.8242	Intermediate Similarity	NPC133698
0.8242	Intermediate Similarity	NPC184063
0.8242	Intermediate Similarity	NPC131209
0.8242	Intermediate Similarity	NPC30515
0.8235	Intermediate Similarity	NPC474981
0.8229	Intermediate Similarity	NPC474747
0.8229	Intermediate Similarity	NPC86077
0.8222	Intermediate Similarity	NPC473564
0.8222	Intermediate Similarity	NPC168679
0.8222	Intermediate Similarity	NPC12872
0.8222	Intermediate Similarity	NPC155935
0.8211	Intermediate Similarity	NPC70865
0.8202	Intermediate Similarity	NPC5130
0.8202	Intermediate Similarity	NPC201658
0.8191	Intermediate Similarity	NPC311904
0.8172	Intermediate Similarity	NPC14961
0.8172	Intermediate Similarity	NPC270013
0.8172	Intermediate Similarity	NPC36954
0.8163	Intermediate Similarity	NPC54737
0.8163	Intermediate Similarity	NPC243998
0.8163	Intermediate Similarity	NPC223450
0.8152	Intermediate Similarity	NPC258216
0.8152	Intermediate Similarity	NPC200237
0.8152	Intermediate Similarity	NPC472874
0.8144	Intermediate Similarity	NPC475873
0.8144	Intermediate Similarity	NPC475871
0.8144	Intermediate Similarity	NPC475945
0.814	Intermediate Similarity	NPC47635
0.8132	Intermediate Similarity	NPC297474
0.8132	Intermediate Similarity	NPC474761
0.8132	Intermediate Similarity	NPC54065
0.8132	Intermediate Similarity	NPC476004
0.8132	Intermediate Similarity	NPC19087
0.8132	Intermediate Similarity	NPC35809
0.8111	Intermediate Similarity	NPC53158
0.8111	Intermediate Similarity	NPC91248
0.8105	Intermediate Similarity	NPC473326
0.8095	Intermediate Similarity	NPC208223
0.809	Intermediate Similarity	NPC56593
0.809	Intermediate Similarity	NPC67493
0.8085	Intermediate Similarity	NPC158416
0.8085	Intermediate Similarity	NPC470883
0.8085	Intermediate Similarity	NPC76862
0.8085	Intermediate Similarity	NPC142529
0.8085	Intermediate Similarity	NPC31645
0.8085	Intermediate Similarity	NPC39859
0.8085	Intermediate Similarity	NPC91771
0.8068	Intermediate Similarity	NPC224386
0.8068	Intermediate Similarity	NPC156485
0.8068	Intermediate Similarity	NPC475963
0.8068	Intermediate Similarity	NPC194859
0.8068	Intermediate Similarity	NPC3464
0.8068	Intermediate Similarity	NPC151176
0.8065	Intermediate Similarity	NPC81386
0.8065	Intermediate Similarity	NPC477131
0.8065	Intermediate Similarity	NPC470010
0.8065	Intermediate Similarity	NPC470013
0.8065	Intermediate Similarity	NPC323008
0.8065	Intermediate Similarity	NPC262133
0.8065	Intermediate Similarity	NPC198853
0.8065	Intermediate Similarity	NPC474035
0.8061	Intermediate Similarity	NPC474741
0.8061	Intermediate Similarity	NPC203659
0.8046	Intermediate Similarity	NPC246076
0.8043	Intermediate Similarity	NPC133888
0.8043	Intermediate Similarity	NPC57304
0.8043	Intermediate Similarity	NPC171360
0.8043	Intermediate Similarity	NPC293001
0.8043	Intermediate Similarity	NPC35959
0.8043	Intermediate Similarity	NPC29821
0.8043	Intermediate Similarity	NPC63193
0.8041	Intermediate Similarity	NPC80144
0.8041	Intermediate Similarity	NPC225353
0.8023	Intermediate Similarity	NPC73052
0.8023	Intermediate Similarity	NPC290508
0.8023	Intermediate Similarity	NPC293418
0.8023	Intermediate Similarity	NPC51507
0.8022	Intermediate Similarity	NPC32922
0.8022	Intermediate Similarity	NPC38392
0.8	Intermediate Similarity	NPC213947
0.8	Intermediate Similarity	NPC248602
0.8	Intermediate Similarity	NPC323421
0.8	Intermediate Similarity	NPC270270
0.8	Intermediate Similarity	NPC108475
0.8	Intermediate Similarity	NPC170143
0.8	Intermediate Similarity	NPC328562
0.7979	Intermediate Similarity	NPC304886
0.7978	Intermediate Similarity	NPC21469
0.7959	Intermediate Similarity	NPC110989
0.7959	Intermediate Similarity	NPC124881
0.7957	Intermediate Similarity	NPC475788
0.7955	Intermediate Similarity	NPC257358
0.7955	Intermediate Similarity	NPC128246
0.7955	Intermediate Similarity	NPC474472
0.7955	Intermediate Similarity	NPC54468
0.7952	Intermediate Similarity	NPC143979
0.7952	Intermediate Similarity	NPC320537
0.7938	Intermediate Similarity	NPC67296
0.7921	Intermediate Similarity	NPC139838
0.7921	Intermediate Similarity	NPC59489
0.7917	Intermediate Similarity	NPC474213
0.7917	Intermediate Similarity	NPC249171
0.7917	Intermediate Similarity	NPC187268
0.7917	Intermediate Similarity	NPC49833
0.7912	Intermediate Similarity	NPC153805
0.7912	Intermediate Similarity	NPC281516
0.7895	Intermediate Similarity	NPC476315
0.7889	Intermediate Similarity	NPC304558
0.7889	Intermediate Similarity	NPC238593
0.7879	Intermediate Similarity	NPC100487
0.7872	Intermediate Similarity	NPC71589
0.7872	Intermediate Similarity	NPC473331
0.7872	Intermediate Similarity	NPC303942
0.7872	Intermediate Similarity	NPC127019
0.7872	Intermediate Similarity	NPC57405
0.7865	Intermediate Similarity	NPC138647
0.7865	Intermediate Similarity	NPC470238
0.7857	Intermediate Similarity	NPC471491
0.7849	Intermediate Similarity	NPC286341
0.7849	Intermediate Similarity	NPC470373
0.7849	Intermediate Similarity	NPC300312
0.7849	Intermediate Similarity	NPC470379
0.7849	Intermediate Similarity	NPC329952
0.7849	Intermediate Similarity	NPC475925
0.7849	Intermediate Similarity	NPC111114
0.7849	Intermediate Similarity	NPC191339
0.7849	Intermediate Similarity	NPC261607
0.7826	Intermediate Similarity	NPC472872
0.7826	Intermediate Similarity	NPC295312
0.7826	Intermediate Similarity	NPC151770
0.7826	Intermediate Similarity	NPC474032
0.7822	Intermediate Similarity	NPC255082
0.7816	Intermediate Similarity	NPC156658

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 NPC190753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	2407
0.2-0.3	3845
0.3-0.4	1818
0.4-0.5	549
0.5-0.6	220
0.6-0.7	22
0.7-0.8	6
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
0.7789	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1695	Approved
0.717	Intermediate Similarity	NPD6371	Approved
0.701	Intermediate Similarity	NPD46	Approved
0.701	Intermediate Similarity	NPD6698	Approved
0.6768	Remote Similarity	NPD7983	Approved
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6577	Remote Similarity	NPD6053	Discontinued
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.6486	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6435	Approved
0.6337	Remote Similarity	NPD5785	Approved
0.6327	Remote Similarity	NPD1694	Approved
0.6289	Remote Similarity	NPD7154	Phase 3
0.6289	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8516	Approved
0.6263	Remote Similarity	NPD4249	Approved
0.6263	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD5369	Approved
0.6238	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6101	Approved
0.6226	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7115	Discovery
0.62	Remote Similarity	NPD4251	Approved
0.62	Remote Similarity	NPD4250	Approved
0.6186	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5363	Approved
0.6161	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5368	Approved
0.6134	Remote Similarity	NPD8268	Approved
0.6134	Remote Similarity	NPD8269	Approved
0.6134	Remote Similarity	NPD8266	Approved
0.6134	Remote Similarity	NPD8267	Approved
0.6117	Remote Similarity	NPD6411	Approved
0.6106	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8133	Approved
0.6066	Remote Similarity	NPD7507	Approved
0.6038	Remote Similarity	NPD7839	Suspended
0.6036	Remote Similarity	NPD6008	Approved
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD4269	Approved
0.6019	Remote Similarity	NPD6648	Approved
0.6016	Remote Similarity	NPD8074	Phase 3
0.5979	Remote Similarity	NPD4821	Approved
0.5979	Remote Similarity	NPD4820	Approved
0.5979	Remote Similarity	NPD4822	Approved
0.5979	Remote Similarity	NPD4819	Approved
0.5979	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD4632	Approved
0.5926	Remote Similarity	NPD7638	Approved
0.592	Remote Similarity	NPD7319	Approved
0.5917	Remote Similarity	NPD6319	Approved
0.5909	Remote Similarity	NPD7909	Approved
0.5905	Remote Similarity	NPD6399	Phase 3
0.5872	Remote Similarity	NPD7639	Approved
0.5872	Remote Similarity	NPD7640	Approved
0.5862	Remote Similarity	NPD8297	Approved
0.5859	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7492	Approved
0.5846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5697	Approved
0.5841	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD1700	Approved
0.5816	Remote Similarity	NPD4252	Approved
0.581	Remote Similarity	NPD8034	Phase 2
0.581	Remote Similarity	NPD8035	Phase 2
0.5806	Remote Similarity	NPD6616	Approved
0.5804	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5332	Approved
0.58	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD6899	Approved
0.5785	Remote Similarity	NPD6054	Approved
0.5781	Remote Similarity	NPD6845	Suspended
0.578	Remote Similarity	NPD5696	Approved
0.5776	Remote Similarity	NPD6650	Approved
0.5776	Remote Similarity	NPD2204	Approved
0.5776	Remote Similarity	NPD6649	Approved
0.5773	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4268	Approved
0.5773	Remote Similarity	NPD4271	Approved
0.5772	Remote Similarity	NPD7642	Approved
0.576	Remote Similarity	NPD7078	Approved
0.5758	Remote Similarity	NPD4790	Discontinued
0.5752	Remote Similarity	NPD5739	Approved
0.5752	Remote Similarity	NPD6402	Approved
0.5752	Remote Similarity	NPD7128	Approved
0.5752	Remote Similarity	NPD6675	Approved
0.575	Remote Similarity	NPD7641	Discontinued
0.5739	Remote Similarity	NPD6013	Approved
0.5739	Remote Similarity	NPD6372	Approved
0.5739	Remote Similarity	NPD6014	Approved
0.5739	Remote Similarity	NPD6012	Approved
0.5739	Remote Similarity	NPD6373	Approved
0.5738	Remote Similarity	NPD6921	Approved
0.5738	Remote Similarity	NPD6015	Approved
0.5738	Remote Similarity	NPD6016	Approved
0.5728	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD7736	Approved
0.5703	Remote Similarity	NPD7260	Phase 2
0.5702	Remote Similarity	NPD6412	Phase 2
0.5702	Remote Similarity	NPD5701	Approved
0.57	Remote Similarity	NPD5209	Approved
0.5691	Remote Similarity	NPD6370	Approved
0.5691	Remote Similarity	NPD5988	Approved
0.569	Remote Similarity	NPD6883	Approved
0.569	Remote Similarity	NPD7102	Approved
0.569	Remote Similarity	NPD7290	Approved
0.5688	Remote Similarity	NPD6084	Phase 2
0.5688	Remote Similarity	NPD6083	Phase 2
0.568	Remote Similarity	NPD8451	Approved
0.568	Remote Similarity	NPD8273	Phase 1
0.5667	Remote Similarity	NPD6009	Approved
0.5667	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7341	Phase 2
0.566	Remote Similarity	NPD7637	Suspended
0.5656	Remote Similarity	NPD6059	Approved
0.5652	Remote Similarity	NPD229	Approved
0.5652	Remote Similarity	NPD6011	Approved
0.5645	Remote Similarity	NPD7830	Approved
0.5645	Remote Similarity	NPD7829	Approved
0.5644	Remote Similarity	NPD6110	Phase 1
0.5641	Remote Similarity	NPD6869	Approved
0.5641	Remote Similarity	NPD6617	Approved
0.5641	Remote Similarity	NPD6847	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5635	Remote Similarity	NPD8448	Approved
0.5635	Remote Similarity	NPD8293	Discontinued
0.5631	Remote Similarity	NPD6422	Discontinued
0.5612	Remote Similarity	NPD4238	Approved
0.5612	Remote Similarity	NPD4802	Phase 2
0.561	Remote Similarity	NPD5983	Phase 2
0.5604	Remote Similarity	NPD7331	Phase 2

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