NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	0.907
LogD:	0.913
LogS:	-2.288
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	4.651
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:	-4.689
MDCK Permeability:	2.1282048692228273e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.351
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	66.34593200683594%
Volume Distribution (VD):	0.993
Pgp-substrate:	48.70212173461914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	6.353
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.131
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.616
Carcinogencity:	0.896
Eye Corrosion:	0.109
Eye Irritation:	0.519
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC153590

Natural Product ID:	NPC153590
*Common Name:**	Peruvin
IUPAC Name:	(3aR,5S,5aR,8aS,9aR)-5a-hydroxy-5,8a-dimethyl-1-methylidene-4,5,6,7,9,9a-hexahydro-3aH-azuleno[6,7-b]furan-2,8-dione
Synonyms:	Peruvin
Standard InCHIKey:	JPWMRQZYTCWJHW-SAPLOEGBSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(17)19-11)7-14(3)12(16)4-5-15(8,14)18/h8,10-11,18H,2,4-7H2,1,3H3/t8-,10+,11+,14+,15+/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@H](C[C@]3(C)C(=O)CC[C@@]13O)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1276311
PubChem CID:	52944698
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]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21040	Ambrosia artemisiifolia	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	6
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1.65	ug.mL-1	PMID[497362]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	52.8	ug.mL-1	PMID[497362]
NPT842	Organism	Leishmania mexicana	Leishmania mexicana	IC50	=	0.39	ug.mL-1	PMID[497362]
NPT27	Others	Unspecified		CC50	=	35.0	ug.mL-1	PMID[497362]
NPT2	Others	Unspecified		Selectivity Index	=	0.7	n.a.	PMID[497362]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[497363]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[497363]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[497363]

☑ 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 NPC153590 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	256
0.1-0.2	1914
0.2-0.3	6805
0.3-0.4	13431
0.4-0.5	10328
0.5-0.6	6580
0.6-0.7	2831
0.7-0.8	426
0.8-0.85	59
0.85-0.9	44
0.9-0.95	16
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC473234
0.9545	High Similarity	NPC60386
0.9545	High Similarity	NPC473263
0.9545	High Similarity	NPC200237
0.9545	High Similarity	NPC473273
0.9545	High Similarity	NPC308656
0.9444	High Similarity	NPC142529
0.9444	High Similarity	NPC91771
0.9419	High Similarity	NPC118601
0.931	High Similarity	NPC178875
0.9222	High Similarity	NPC473331
0.9213	High Similarity	NPC286341
0.9213	High Similarity	NPC191339
0.9205	High Similarity	NPC12872
0.9205	High Similarity	NPC168679
0.9195	High Similarity	NPC201658
0.913	High Similarity	NPC108475
0.913	High Similarity	NPC311904
0.913	High Similarity	NPC170143
0.913	High Similarity	NPC213947
0.9043	High Similarity	NPC171759
0.8989	High Similarity	NPC155935
0.8913	High Similarity	NPC163228
0.8889	High Similarity	NPC297474
0.8889	High Similarity	NPC35809
0.8889	High Similarity	NPC54065
0.8876	High Similarity	NPC79549
0.8864	High Similarity	NPC238593
0.8864	High Similarity	NPC56593
0.8791	High Similarity	NPC57304
0.8791	High Similarity	NPC171360
0.8791	High Similarity	NPC133888
0.8791	High Similarity	NPC184063
0.8791	High Similarity	NPC29821
0.8791	High Similarity	NPC35959
0.8791	High Similarity	NPC63193
0.8791	High Similarity	NPC293001
0.8778	High Similarity	NPC215556
0.875	High Similarity	NPC204105
0.875	High Similarity	NPC284534
0.875	High Similarity	NPC300082
0.8736	High Similarity	NPC54468
0.871	High Similarity	NPC476053
0.8696	High Similarity	NPC135776
0.8681	High Similarity	NPC19087
0.8681	High Similarity	NPC216284
0.8652	High Similarity	NPC236692
0.8652	High Similarity	NPC470242
0.8652	High Similarity	NPC309757
0.8617	High Similarity	NPC126156
0.8605	High Similarity	NPC290508
0.8605	High Similarity	NPC73052
0.8605	High Similarity	NPC293418
0.8605	High Similarity	NPC6823
0.8587	High Similarity	NPC155215
0.8571	High Similarity	NPC38392
0.8556	High Similarity	NPC24728
0.8556	High Similarity	NPC270270
0.8526	High Similarity	NPC471150
0.8511	High Similarity	NPC475900
0.8495	Intermediate Similarity	NPC258216
0.8462	Intermediate Similarity	NPC207114
0.8462	Intermediate Similarity	NPC471149
0.8462	Intermediate Similarity	NPC217983
0.8444	Intermediate Similarity	NPC187661
0.8444	Intermediate Similarity	NPC67493
0.8444	Intermediate Similarity	NPC304558
0.8427	Intermediate Similarity	NPC194859
0.8427	Intermediate Similarity	NPC224386
0.8421	Intermediate Similarity	NPC476009
0.8421	Intermediate Similarity	NPC18019
0.8421	Intermediate Similarity	NPC24956
0.8409	Intermediate Similarity	NPC246076
0.837	Intermediate Similarity	NPC283409
0.837	Intermediate Similarity	NPC32922
0.8352	Intermediate Similarity	NPC190753
0.8351	Intermediate Similarity	NPC186861
0.8351	Intermediate Similarity	NPC471381
0.8333	Intermediate Similarity	NPC474313
0.8316	Intermediate Similarity	NPC472873
0.8316	Intermediate Similarity	NPC48803
0.8316	Intermediate Similarity	NPC90121
0.8316	Intermediate Similarity	NPC275960
0.8316	Intermediate Similarity	NPC193645
0.8315	Intermediate Similarity	NPC245665
0.8295	Intermediate Similarity	NPC47635
0.8256	Intermediate Similarity	NPC208223
0.8211	Intermediate Similarity	NPC127019
0.82	Intermediate Similarity	NPC203659
0.8191	Intermediate Similarity	NPC133698
0.8191	Intermediate Similarity	NPC131209
0.8182	Intermediate Similarity	NPC156658
0.8182	Intermediate Similarity	NPC258965
0.8182	Intermediate Similarity	NPC51507
0.8182	Intermediate Similarity	NPC225353
0.8172	Intermediate Similarity	NPC472872
0.8152	Intermediate Similarity	NPC186148
0.8144	Intermediate Similarity	NPC477949
0.8144	Intermediate Similarity	NPC169205
0.8132	Intermediate Similarity	NPC235792
0.8125	Intermediate Similarity	NPC170120
0.8125	Intermediate Similarity	NPC67584
0.8125	Intermediate Similarity	NPC52044
0.8125	Intermediate Similarity	NPC213698
0.8111	Intermediate Similarity	NPC111409
0.8111	Intermediate Similarity	NPC128246
0.81	Intermediate Similarity	NPC110989
0.809	Intermediate Similarity	NPC126248
0.8085	Intermediate Similarity	NPC301969
0.8085	Intermediate Similarity	NPC71533
0.8085	Intermediate Similarity	NPC106510
0.8085	Intermediate Similarity	NPC37607
0.8081	Intermediate Similarity	NPC477950
0.8065	Intermediate Similarity	NPC58219
0.8065	Intermediate Similarity	NPC177629
0.8065	Intermediate Similarity	NPC91248
0.8061	Intermediate Similarity	NPC45125
0.8061	Intermediate Similarity	NPC141191
0.8043	Intermediate Similarity	NPC64153
0.8041	Intermediate Similarity	NPC185553
0.8041	Intermediate Similarity	NPC213078
0.8022	Intermediate Similarity	NPC156485
0.8021	Intermediate Similarity	NPC262133
0.8021	Intermediate Similarity	NPC198853
0.8021	Intermediate Similarity	NPC470013
0.8021	Intermediate Similarity	NPC470010
0.8021	Intermediate Similarity	NPC477131
0.8021	Intermediate Similarity	NPC323008
0.8021	Intermediate Similarity	NPC167219
0.802	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC150978
0.8	Intermediate Similarity	NPC474747
0.8	Intermediate Similarity	NPC123177
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC74103
0.8	Intermediate Similarity	NPC70595
0.798	Intermediate Similarity	NPC280963
0.7979	Intermediate Similarity	NPC92974
0.7959	Intermediate Similarity	NPC181151
0.7959	Intermediate Similarity	NPC161493
0.7941	Intermediate Similarity	NPC54737
0.7941	Intermediate Similarity	NPC44004
0.7921	Intermediate Similarity	NPC475945
0.7921	Intermediate Similarity	NPC475871
0.7917	Intermediate Similarity	NPC475788
0.7912	Intermediate Similarity	NPC215294
0.7907	Intermediate Similarity	NPC320537
0.7907	Intermediate Similarity	NPC143979
0.79	Intermediate Similarity	NPC474742
0.79	Intermediate Similarity	NPC475099
0.7895	Intermediate Similarity	NPC62815
0.7895	Intermediate Similarity	NPC246173
0.7895	Intermediate Similarity	NPC253144
0.7879	Intermediate Similarity	NPC221615
0.7872	Intermediate Similarity	NPC53158
0.7872	Intermediate Similarity	NPC224652
0.7872	Intermediate Similarity	NPC202672
0.7857	Intermediate Similarity	NPC39859
0.7857	Intermediate Similarity	NPC470883
0.7857	Intermediate Similarity	NPC76862
0.7857	Intermediate Similarity	NPC158416
0.7849	Intermediate Similarity	NPC474762
0.7849	Intermediate Similarity	NPC474949
0.7849	Intermediate Similarity	NPC476015
0.7849	Intermediate Similarity	NPC162071
0.7849	Intermediate Similarity	NPC475019
0.7843	Intermediate Similarity	NPC474741
0.7812	Intermediate Similarity	NPC12172
0.7812	Intermediate Similarity	NPC208886
0.7812	Intermediate Similarity	NPC284185
0.7812	Intermediate Similarity	NPC300312
0.7812	Intermediate Similarity	NPC221282
0.7812	Intermediate Similarity	NPC111114
0.7812	Intermediate Similarity	NPC261607
0.781	Intermediate Similarity	NPC471884
0.7789	Intermediate Similarity	NPC173926
0.7789	Intermediate Similarity	NPC117405
0.7789	Intermediate Similarity	NPC307411
0.7789	Intermediate Similarity	NPC52198
0.7789	Intermediate Similarity	NPC474951
0.7767	Intermediate Similarity	NPC223450
0.7767	Intermediate Similarity	NPC243998
0.7757	Intermediate Similarity	NPC209058
0.7755	Intermediate Similarity	NPC37408
0.7755	Intermediate Similarity	NPC90014
0.7755	Intermediate Similarity	NPC304886
0.7755	Intermediate Similarity	NPC469873
0.7745	Intermediate Similarity	NPC221421
0.7745	Intermediate Similarity	NPC474775
0.7745	Intermediate Similarity	NPC475873
0.7742	Intermediate Similarity	NPC21471
0.7742	Intermediate Similarity	NPC149725
0.7742	Intermediate Similarity	NPC304509
0.7742	Intermediate Similarity	NPC161957
0.7742	Intermediate Similarity	NPC329749
0.7742	Intermediate Similarity	NPC33570
0.7742	Intermediate Similarity	NPC47958
0.7732	Intermediate Similarity	NPC475488
0.7732	Intermediate Similarity	NPC81419
0.7732	Intermediate Similarity	NPC179746

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 NPC153590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	2615
0.2-0.3	3858
0.3-0.4	1625
0.4-0.5	429
0.5-0.6	265
0.6-0.7	41
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD1695	Approved
0.7477	Intermediate Similarity	NPD6371	Approved
0.7347	Intermediate Similarity	NPD5785	Approved
0.7129	Intermediate Similarity	NPD5282	Discontinued
0.701	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5369	Approved
0.6944	Remote Similarity	NPD6008	Approved
0.6939	Remote Similarity	NPD5786	Approved
0.6875	Remote Similarity	NPD6053	Discontinued
0.6837	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD4269	Approved
0.6701	Remote Similarity	NPD6435	Approved
0.6701	Remote Similarity	NPD4270	Approved
0.66	Remote Similarity	NPD4249	Approved
0.6538	Remote Similarity	NPD6399	Phase 3
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1694	Approved
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5368	Approved
0.6495	Remote Similarity	NPD4252	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6465	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6417	Remote Similarity	NPD6016	Approved
0.6417	Remote Similarity	NPD6015	Approved
0.6389	Remote Similarity	NPD4225	Approved
0.6389	Remote Similarity	NPD7638	Approved
0.6381	Remote Similarity	NPD5779	Approved
0.6381	Remote Similarity	NPD5778	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6372	Remote Similarity	NPD6011	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6881	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD5209	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6348	Remote Similarity	NPD6649	Approved
0.6348	Remote Similarity	NPD6650	Approved
0.6346	Remote Similarity	NPD46	Approved
0.6346	Remote Similarity	NPD6698	Approved
0.6339	Remote Similarity	NPD6675	Approved
0.6339	Remote Similarity	NPD6402	Approved
0.6339	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD7128	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.633	Remote Similarity	NPD7639	Approved
0.633	Remote Similarity	NPD7640	Approved
0.632	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.629	Remote Similarity	NPD8293	Discontinued
0.6289	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4238	Approved
0.6289	Remote Similarity	NPD4802	Phase 2
0.6286	Remote Similarity	NPD8034	Phase 2
0.6286	Remote Similarity	NPD6411	Approved
0.6286	Remote Similarity	NPD8035	Phase 2
0.6283	Remote Similarity	NPD5701	Approved
0.6273	Remote Similarity	NPD1700	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.6228	Remote Similarity	NPD6686	Approved
0.6218	Remote Similarity	NPD6009	Approved
0.621	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6617	Approved
0.62	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6845	Suspended
0.6162	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4821	Approved
0.6162	Remote Similarity	NPD4822	Approved
0.6162	Remote Similarity	NPD4820	Approved
0.6162	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD6882	Approved
0.6148	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5983	Phase 2
0.6147	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD6083	Phase 2
0.6139	Remote Similarity	NPD4788	Approved
0.6132	Remote Similarity	NPD7637	Suspended
0.6132	Remote Similarity	NPD5284	Approved
0.6132	Remote Similarity	NPD5693	Phase 1
0.6132	Remote Similarity	NPD5281	Approved
0.6121	Remote Similarity	NPD4634	Approved
0.6117	Remote Similarity	NPD6409	Approved
0.6117	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7334	Approved
0.6117	Remote Similarity	NPD5330	Approved
0.6117	Remote Similarity	NPD7146	Approved
0.6117	Remote Similarity	NPD6684	Approved
0.6117	Remote Similarity	NPD7521	Approved
0.6111	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6101	Approved
0.6095	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7260	Phase 2
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7604	Phase 2
0.6038	Remote Similarity	NPD7838	Discovery
0.6038	Remote Similarity	NPD5207	Approved
0.6036	Remote Similarity	NPD4696	Approved
0.6036	Remote Similarity	NPD5285	Approved
0.6036	Remote Similarity	NPD5286	Approved
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8516	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4755	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5223	Approved
0.598	Remote Similarity	NPD7154	Phase 3
0.598	Remote Similarity	NPD5332	Approved
0.598	Remote Similarity	NPD5331	Approved
0.5966	Remote Similarity	NPD8133	Approved
0.5965	Remote Similarity	NPD5141	Approved
0.596	Remote Similarity	NPD4271	Approved
0.596	Remote Similarity	NPD4268	Approved
0.5952	Remote Similarity	NPD6336	Discontinued
0.595	Remote Similarity	NPD6317	Approved
0.5946	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4790	Discontinued
0.5932	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5226	Approved
0.5929	Remote Similarity	NPD7632	Discontinued
0.5929	Remote Similarity	NPD5224	Approved
0.5929	Remote Similarity	NPD5225	Approved
0.5929	Remote Similarity	NPD4633	Approved
0.5922	Remote Similarity	NPD3666	Approved
0.5922	Remote Similarity	NPD3665	Phase 1
0.5922	Remote Similarity	NPD3133	Approved
0.5909	Remote Similarity	NPD7839	Suspended
0.5902	Remote Similarity	NPD6314	Approved
0.5902	Remote Similarity	NPD6335	Approved
0.5902	Remote Similarity	NPD6313	Approved
0.5897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4700	Approved
0.5887	Remote Similarity	NPD6921	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5877	Remote Similarity	NPD5175	Approved
0.5877	Remote Similarity	NPD5174	Approved
0.5872	Remote Similarity	NPD6001	Approved
0.5865	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7902	Approved
0.5854	Remote Similarity	NPD7100	Approved
0.5854	Remote Similarity	NPD7101	Approved
0.5851	Remote Similarity	NPD229	Approved
0.5849	Remote Similarity	NPD5737	Approved
0.5849	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD6079	Approved
0.5818	Remote Similarity	NPD5210	Approved
0.5818	Remote Similarity	NPD4629	Approved
0.5816	Remote Similarity	NPD3702	Approved
0.581	Remote Similarity	NPD3618	Phase 1
0.5794	Remote Similarity	NPD6080	Approved
0.5794	Remote Similarity	NPD6673	Approved
0.5794	Remote Similarity	NPD4753	Phase 2
0.5794	Remote Similarity	NPD5328	Approved
0.5794	Remote Similarity	NPD6904	Approved
0.5794	Remote Similarity	NPD5370	Suspended
0.5781	Remote Similarity	NPD8074	Phase 3
0.578	Remote Similarity	NPD4202	Approved
0.5769	Remote Similarity	NPD4786	Approved
0.5769	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5956	Approved
0.5766	Remote Similarity	NPD5222	Approved
0.5766	Remote Similarity	NPD4697	Phase 3
0.5766	Remote Similarity	NPD5221	Approved
0.5766	Remote Similarity	NPD5220	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