NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.614
LogD:	2.81
LogS:	-2.368
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.398
Fsp3:	0.8
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:	-4.702
MDCK Permeability:	4.223697760608047e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.432
30% Bioavailability (F30%):	0.811

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.221
Plasma Protein Binding (PPB):	77.15762329101562%
Volume Distribution (VD):	0.844
Pgp-substrate:	20.201602935791016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	16.051
Half-life (T1/2):	0.634

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.261
Skin Sensitization:	0.94
Carcinogencity:	0.837
Eye Corrosion:	0.911
Eye Irritation:	0.879
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC56593

Natural Product ID:	NPC56593
*Common Name:**	Pseudoguaianolide
IUPAC Name:	(3aS,5R,5aS,8S,8aS,9aR)-8-hydroxy-5,8a-dimethyl-1-methylidene-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:	Pseudoguaianolide
Standard InCHIKey:	BOPADYWRUULRBD-MBICNOSFSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8-6-12-10(9(2)14(17)18-12)7-15(3)11(8)4-5-13(15)16/h8,10-13,16H,2,4-7H2,1,3H3/t8-,10-,11+,12+,13+,15+/m1/s1
SMILES:	C=C1C(=O)O[C@@H]2[C@@H]1C[C@]1(C)[C@@H](O)CC[C@H]1[C@@H](C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165514
PubChem CID:	10399864
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
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO33493	inula lineariifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515062]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26316467]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4637	Inula anatolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26335	Carpesium abrotanoides	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	21
MIC	1
Others	4

Activity Type	# Activity
Cell Line	16
Individual Protein	1
NON-MOLECULAR	1
Organism	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	100.0	nM	PMID[469483]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9.8	ug.mL-1	PMID[469484]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9890.0	nM	PMID[469485]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14900.0	nM	PMID[469486]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	17000.0	nM	PMID[469487]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11000.0	nM	PMID[469487]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6000.0	nM	PMID[469487]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	3100.0	nM	PMID[469487]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	2200.0	nM	PMID[469487]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	=	13000.0	nM	PMID[469487]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6200.0	nM	PMID[469487]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	5500.0	nM	PMID[469487]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2400.0	nM	PMID[469487]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	47.5	%	PMID[469488]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	4430.0	nM	PMID[469488]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3370.0	nM	PMID[469488]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2500.0	nM	PMID[469489]
NPT2	Others	Unspecified		Inhibition	=	17.01	%	PMID[469486]
NPT2	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[469486]
NPT2	Others	Unspecified		Inhibition	=	46.86	%	PMID[469486]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22000.0	nM	PMID[469487]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	29300.0	nM	PMID[469487]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	47300.0	nM	PMID[469487]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	7600.0	nM	PMID[469487]
NPT35	Others	n.a.		Solubility	=	200.0	ug.mL-1	PMID[469488]

☑ 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 NPC56593 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	237
0.1-0.2	1742
0.2-0.3	6806
0.3-0.4	15836
0.4-0.5	8435
0.5-0.6	6881
0.6-0.7	2327
0.7-0.8	321
0.8-0.85	32
0.85-0.9	46
0.9-0.95	29
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC155935
0.9524	High Similarity	NPC54065
0.9524	High Similarity	NPC297474
0.9524	High Similarity	NPC35809
0.9412	High Similarity	NPC35959
0.9412	High Similarity	NPC293001
0.9412	High Similarity	NPC133888
0.9412	High Similarity	NPC57304
0.9412	High Similarity	NPC63193
0.9412	High Similarity	NPC29821
0.9412	High Similarity	NPC171360
0.939	High Similarity	NPC204105
0.939	High Similarity	NPC284534
0.939	High Similarity	NPC300082
0.9302	High Similarity	NPC200237
0.9268	High Similarity	NPC224386
0.9268	High Similarity	NPC194859
0.9176	High Similarity	NPC215556
0.907	High Similarity	NPC216284
0.9059	High Similarity	NPC217983
0.9059	High Similarity	NPC79549
0.9059	High Similarity	NPC207114
0.9048	High Similarity	NPC187661
0.8989	High Similarity	NPC142529
0.8989	High Similarity	NPC24956
0.8989	High Similarity	NPC18019
0.8989	High Similarity	NPC91771
0.8977	High Similarity	NPC473331
0.8941	High Similarity	NPC24728
0.8916	High Similarity	NPC245665
0.8902	High Similarity	NPC126248
0.8889	High Similarity	NPC311904
0.8864	High Similarity	NPC473263
0.8864	High Similarity	NPC473273
0.8864	High Similarity	NPC473234
0.8864	High Similarity	NPC60386
0.8864	High Similarity	NPC153590
0.8864	High Similarity	NPC308656
0.8851	High Similarity	NPC19087
0.8837	High Similarity	NPC471149
0.8824	High Similarity	NPC67493
0.8795	High Similarity	NPC246076
0.878	High Similarity	NPC258965
0.878	High Similarity	NPC156658
0.875	High Similarity	NPC184063
0.875	High Similarity	NPC155215
0.8736	High Similarity	NPC38392
0.8736	High Similarity	NPC283409
0.8721	High Similarity	NPC201658
0.8721	High Similarity	NPC118601
0.869	High Similarity	NPC111409
0.869	High Similarity	NPC128246
0.8667	High Similarity	NPC472873
0.8652	High Similarity	NPC258216
0.8636	High Similarity	NPC37607
0.8636	High Similarity	NPC301969
0.8621	High Similarity	NPC91248
0.8621	High Similarity	NPC178875
0.8602	High Similarity	NPC171759
0.8554	High Similarity	NPC6823
0.8554	High Similarity	NPC293418
0.8554	High Similarity	NPC73052
0.8554	High Similarity	NPC290508
0.8539	High Similarity	NPC286341
0.8539	High Similarity	NPC191339
0.8539	High Similarity	NPC475925
0.8523	High Similarity	NPC168679
0.8523	High Similarity	NPC12872
0.8506	High Similarity	NPC270270
0.85	High Similarity	NPC320537
0.85	High Similarity	NPC143979
0.8478	Intermediate Similarity	NPC108475
0.8478	Intermediate Similarity	NPC170143
0.8478	Intermediate Similarity	NPC471150
0.8478	Intermediate Similarity	NPC213947
0.8462	Intermediate Similarity	NPC476053
0.8462	Intermediate Similarity	NPC52044
0.8462	Intermediate Similarity	NPC170120
0.8462	Intermediate Similarity	NPC213698
0.8462	Intermediate Similarity	NPC163228
0.8452	Intermediate Similarity	NPC47635
0.8391	Intermediate Similarity	NPC236692
0.8391	Intermediate Similarity	NPC470242
0.8391	Intermediate Similarity	NPC304558
0.8391	Intermediate Similarity	NPC64153
0.8391	Intermediate Similarity	NPC309757
0.8372	Intermediate Similarity	NPC156485
0.8352	Intermediate Similarity	NPC127019
0.8333	Intermediate Similarity	NPC131209
0.8315	Intermediate Similarity	NPC472872
0.8298	Intermediate Similarity	NPC471381
0.828	Intermediate Similarity	NPC161493
0.828	Intermediate Similarity	NPC474313
0.8276	Intermediate Similarity	NPC235792
0.8261	Intermediate Similarity	NPC67584
0.8256	Intermediate Similarity	NPC54468
0.8202	Intermediate Similarity	NPC224652
0.8193	Intermediate Similarity	NPC208223
0.8191	Intermediate Similarity	NPC45125
0.8172	Intermediate Similarity	NPC213078
0.8172	Intermediate Similarity	NPC126156
0.8152	Intermediate Similarity	NPC323008
0.8152	Intermediate Similarity	NPC470010
0.8152	Intermediate Similarity	NPC470013
0.8152	Intermediate Similarity	NPC262133
0.8152	Intermediate Similarity	NPC198853
0.8132	Intermediate Similarity	NPC133698
0.8111	Intermediate Similarity	NPC116620
0.8105	Intermediate Similarity	NPC186861
0.809	Intermediate Similarity	NPC190753
0.8085	Intermediate Similarity	NPC181151
0.8043	Intermediate Similarity	NPC135776
0.8041	Intermediate Similarity	NPC221421
0.8021	Intermediate Similarity	NPC150923
0.8	Intermediate Similarity	NPC249171
0.8	Intermediate Similarity	NPC470239
0.8	Intermediate Similarity	NPC49833
0.8	Intermediate Similarity	NPC470244
0.8	Intermediate Similarity	NPC5714
0.8	Intermediate Similarity	NPC182550
0.8	Intermediate Similarity	NPC221615
0.7978	Intermediate Similarity	NPC238593
0.7957	Intermediate Similarity	NPC477131
0.7917	Intermediate Similarity	NPC70865
0.7912	Intermediate Similarity	NPC4986
0.7907	Intermediate Similarity	NPC51507
0.7907	Intermediate Similarity	NPC74673
0.7907	Intermediate Similarity	NPC276356
0.7907	Intermediate Similarity	NPC69271
0.7895	Intermediate Similarity	NPC304445
0.7895	Intermediate Similarity	NPC236580
0.7895	Intermediate Similarity	NPC477949
0.7889	Intermediate Similarity	NPC186148
0.7879	Intermediate Similarity	NPC44004
0.7879	Intermediate Similarity	NPC54737
0.7872	Intermediate Similarity	NPC304886
0.7857	Intermediate Similarity	NPC473148
0.7849	Intermediate Similarity	NPC475788
0.7849	Intermediate Similarity	NPC472874
0.7841	Intermediate Similarity	NPC215294
0.7826	Intermediate Similarity	NPC158488
0.7802	Intermediate Similarity	NPC177629
0.7802	Intermediate Similarity	NPC58219
0.7778	Intermediate Similarity	NPC85698
0.7778	Intermediate Similarity	NPC477920
0.7778	Intermediate Similarity	NPC162071
0.7766	Intermediate Similarity	NPC469596
0.7766	Intermediate Similarity	NPC225474
0.7766	Intermediate Similarity	NPC148000
0.7755	Intermediate Similarity	NPC80144
0.7723	Intermediate Similarity	NPC68248
0.7717	Intermediate Similarity	NPC295312
0.7717	Intermediate Similarity	NPC32922
0.7717	Intermediate Similarity	NPC92974
0.7692	Intermediate Similarity	NPC305029
0.7692	Intermediate Similarity	NPC470012
0.7692	Intermediate Similarity	NPC181103
0.7684	Intermediate Similarity	NPC469873
0.7684	Intermediate Similarity	NPC37408
0.7684	Intermediate Similarity	NPC157686
0.7684	Intermediate Similarity	NPC259042
0.7684	Intermediate Similarity	NPC48803
0.7684	Intermediate Similarity	NPC167893
0.7684	Intermediate Similarity	NPC193645
0.7684	Intermediate Similarity	NPC90121
0.7684	Intermediate Similarity	NPC275960
0.7683	Intermediate Similarity	NPC18543
0.7677	Intermediate Similarity	NPC474775
0.7667	Intermediate Similarity	NPC21471
0.7667	Intermediate Similarity	NPC33570
0.7667	Intermediate Similarity	NPC161957
0.7667	Intermediate Similarity	NPC329749
0.7653	Intermediate Similarity	NPC67296
0.7647	Intermediate Similarity	NPC139838
0.7647	Intermediate Similarity	NPC59489
0.764	Intermediate Similarity	NPC250315
0.7634	Intermediate Similarity	NPC71533
0.7634	Intermediate Similarity	NPC106510
0.7634	Intermediate Similarity	NPC474323
0.7634	Intermediate Similarity	NPC206614
0.7619	Intermediate Similarity	NPC471380
0.7619	Intermediate Similarity	NPC123117
0.7619	Intermediate Similarity	NPC471382
0.7609	Intermediate Similarity	NPC202672
0.7604	Intermediate Similarity	NPC93245
0.7604	Intermediate Similarity	NPC476009
0.7604	Intermediate Similarity	NPC474297
0.7604	Intermediate Similarity	NPC284518
0.76	Intermediate Similarity	NPC203659
0.7582	Intermediate Similarity	NPC475019
0.7582	Intermediate Similarity	NPC9231
0.7582	Intermediate Similarity	NPC474949
0.7579	Intermediate Similarity	NPC90453
0.7579	Intermediate Similarity	NPC24861
0.7579	Intermediate Similarity	NPC167219
0.7576	Intermediate Similarity	NPC225353
0.7576	Intermediate Similarity	NPC86077
0.7556	Intermediate Similarity	NPC97505
0.7556	Intermediate Similarity	NPC474780
0.7553	Intermediate Similarity	NPC221282

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 NPC56593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	2518
0.2-0.3	3990
0.3-0.4	1635
0.4-0.5	407
0.5-0.6	271
0.6-0.7	39
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
0.7912	Intermediate Similarity	NPD1695	Approved
0.7684	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5785	Approved
0.7238	Intermediate Similarity	NPD6371	Approved
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7021	Intermediate Similarity	NPD4249	Approved
0.6947	Remote Similarity	NPD4251	Approved
0.6947	Remote Similarity	NPD4250	Approved
0.6931	Remote Similarity	NPD7638	Approved
0.6915	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5363	Approved
0.6863	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD7640	Approved
0.6848	Remote Similarity	NPD5369	Approved
0.6789	Remote Similarity	NPD6053	Discontinued
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6737	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6596	Remote Similarity	NPD6435	Approved
0.6566	Remote Similarity	NPD6698	Approved
0.6566	Remote Similarity	NPD46	Approved
0.6559	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4252	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD5282	Discontinued
0.6531	Remote Similarity	NPD6903	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD7154	Phase 3
0.6526	Remote Similarity	NPD5331	Approved
0.6526	Remote Similarity	NPD4788	Approved
0.6522	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD4790	Discontinued
0.6463	Remote Similarity	NPD3198	Approved
0.6458	Remote Similarity	NPD3665	Phase 1
0.6458	Remote Similarity	NPD3666	Approved
0.6458	Remote Similarity	NPD3133	Approved
0.6442	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6422	Remote Similarity	NPD6686	Approved
0.6421	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7632	Discontinued
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5368	Approved
0.6383	Remote Similarity	NPD4820	Approved
0.6383	Remote Similarity	NPD4821	Approved
0.6383	Remote Similarity	NPD4819	Approved
0.6383	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6344	Remote Similarity	NPD4268	Approved
0.6344	Remote Similarity	NPD4271	Approved
0.6337	Remote Similarity	NPD8034	Phase 2
0.6337	Remote Similarity	NPD8035	Phase 2
0.6311	Remote Similarity	NPD5695	Phase 3
0.6286	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6238	Remote Similarity	NPD7838	Discovery
0.6238	Remote Similarity	NPD5207	Approved
0.6182	Remote Similarity	NPD5697	Approved
0.6182	Remote Similarity	NPD6412	Phase 2
0.6176	Remote Similarity	NPD5693	Phase 1
0.6176	Remote Similarity	NPD7637	Suspended
0.617	Remote Similarity	NPD4238	Approved
0.617	Remote Similarity	NPD4802	Phase 2
0.6162	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4632	Approved
0.614	Remote Similarity	NPD8133	Approved
0.6126	Remote Similarity	NPD6881	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6126	Remote Similarity	NPD6899	Approved
0.6126	Remote Similarity	NPD6011	Approved
0.6122	Remote Similarity	NPD4786	Approved
0.6121	Remote Similarity	NPD7115	Discovery
0.6117	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD5778	Approved
0.6116	Remote Similarity	NPD7507	Approved
0.6106	Remote Similarity	NPD6649	Approved
0.6106	Remote Similarity	NPD6650	Approved
0.6091	Remote Similarity	NPD6402	Approved
0.6091	Remote Similarity	NPD6675	Approved
0.6091	Remote Similarity	NPD5739	Approved
0.6091	Remote Similarity	NPD7128	Approved
0.6082	Remote Similarity	NPD5209	Approved
0.6071	Remote Similarity	NPD6013	Approved
0.6071	Remote Similarity	NPD6012	Approved
0.6071	Remote Similarity	NPD6373	Approved
0.6071	Remote Similarity	NPD6014	Approved
0.6071	Remote Similarity	NPD6372	Approved
0.6058	Remote Similarity	NPD6001	Approved
0.6036	Remote Similarity	NPD5701	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.6022	Remote Similarity	NPD3702	Approved
0.6019	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD7983	Approved
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD5281	Approved
0.6018	Remote Similarity	NPD7102	Approved
0.6018	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4629	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD6009	Approved
0.5981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4753	Phase 2
0.5968	Remote Similarity	NPD7319	Approved
0.5966	Remote Similarity	NPD6054	Approved
0.5966	Remote Similarity	NPD6319	Approved
0.5965	Remote Similarity	NPD6617	Approved
0.5965	Remote Similarity	NPD6869	Approved
0.5965	Remote Similarity	NPD6847	Approved
0.5965	Remote Similarity	NPD8130	Phase 1
0.5965	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4202	Approved
0.5935	Remote Similarity	NPD7078	Approved
0.5929	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4223	Phase 3
0.5918	Remote Similarity	NPD4221	Approved
0.5917	Remote Similarity	NPD6015	Approved
0.5917	Remote Similarity	NPD6016	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8297	Approved
0.5913	Remote Similarity	NPD6882	Approved
0.5887	Remote Similarity	NPD7736	Approved
0.5882	Remote Similarity	NPD5737	Approved
0.5882	Remote Similarity	NPD6672	Approved
0.5882	Remote Similarity	NPD5208	Approved
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5777	Approved
0.5868	Remote Similarity	NPD5988	Approved
0.5868	Remote Similarity	NPD6370	Approved
0.5865	Remote Similarity	NPD6079	Approved
0.5859	Remote Similarity	NPD6695	Phase 3
0.5851	Remote Similarity	NPD8039	Approved
0.5842	Remote Similarity	NPD5690	Phase 2
0.5842	Remote Similarity	NPD6098	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6115	Approved
0.5833	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD6118	Approved
0.5833	Remote Similarity	NPD6697	Approved
0.5833	Remote Similarity	NPD6114	Approved
0.5827	Remote Similarity	NPD6845	Suspended
0.5826	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6080	Approved
0.5825	Remote Similarity	NPD6673	Approved
0.5825	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD5328	Approved
0.5825	Remote Similarity	NPD6904	Approved
0.5825	Remote Similarity	NPD6051	Approved
0.5825	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3698	Phase 2
0.582	Remote Similarity	NPD7604	Phase 2
0.5818	Remote Similarity	NPD5211	Phase 2
0.5806	Remote Similarity	NPD8293	Discontinued
0.58	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4197	Approved
0.5798	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD7327	Approved
0.5789	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8033	Approved
0.578	Remote Similarity	NPD4696	Approved
0.578	Remote Similarity	NPD5285	Approved
0.578	Remote Similarity	NPD5286	Approved
0.5773	Remote Similarity	NPD6929	Approved
0.5769	Remote Similarity	NPD5692	Phase 3
0.5763	Remote Similarity	NPD6274	Approved
0.5761	Remote Similarity	NPD4245	Approved
0.5761	Remote Similarity	NPD4244	Approved
0.5755	Remote Similarity	NPD7748	Approved
0.575	Remote Similarity	NPD7516	Approved
0.5748	Remote Similarity	NPD7260	Phase 2
0.5745	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5329	Approved
0.5741	Remote Similarity	NPD4755	Approved
0.5741	Remote Similarity	NPD7902	Approved
0.5728	Remote Similarity	NPD4518	Approved
0.5727	Remote Similarity	NPD5223	Approved
0.5727	Remote Similarity	NPD1700	Approved
0.5727	Remote Similarity	NPD5344	Discontinued
0.5726	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD6930	Phase 2
0.5714	Remote Similarity	NPD6050	Approved
0.5714	Remote Similarity	NPD5694	Approved
0.5714	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5141	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data