NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.936
LogD:	1.624
LogS:	-2.769
# 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:	0.675
Synthetic Accessibility Score:	4.506
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.584
MDCK Permeability:	2.8455262508941814e-05
Pgp-inhibitor:	0.605
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.169

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	53.019989013671875%
Volume Distribution (VD):	0.644
Pgp-substrate:	57.6977424621582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.679
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	10.784
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.471
Drug-inuced Liver Injury (DILI):	0.577
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.249
Skin Sensitization:	0.294
Carcinogencity:	0.578
Eye Corrosion:	0.126
Eye Irritation:	0.404
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC32922

Natural Product ID:	NPC32922
*Common Name:**	(11S)-10Alpha-Hydroxy-3-Oxoguaia-4-Eno-12,6Alpha-Lactone
IUPAC Name:	(3S,3aS,6R,6aR,9bS)-6-hydroxy-3,6,9-trimethyl-3a,4,5,6a,7,9b-hexahydro-3H-azuleno[4,5-b]furan-2,8-dione
Synonyms:
Standard InCHIKey:	FUKGETHUQZLZRJ-YIUCUBBLSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-9-4-5-15(3,18)10-6-11(16)8(2)12(10)13(9)19-14(7)17/h7,9-10,13,18H,4-6H2,1-3H3/t7-,9-,10+,13-,15+/m0/s1
SMILES:	C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@@]([C@H]1C2=C(C)C(=O)C1)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516875
PubChem CID:	14263690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15635221]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067155]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	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	15

Activity Type	# Activity
Cell Line	14
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[570907]
NPT1374	Cell Line	WI-38	Homo sapiens	IC50	=	25000.0	nM	PMID[570907]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	130000.0	nM	PMID[570907]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT403	Cell Line	UACC-257	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT381	Cell Line	OVCAR-8	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT2280	Cell Line	A704	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[570908]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	230000.0	nM	PMID[570907]

☑ 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 NPC32922 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	236
0.1-0.2	1512
0.2-0.3	5675
0.3-0.4	12040
0.4-0.5	12827
0.5-0.6	6518
0.6-0.7	3034
0.7-0.8	770
0.8-0.85	64
0.85-0.9	15
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC135776
0.8889	High Similarity	NPC477131
0.8851	High Similarity	NPC118601
0.875	High Similarity	NPC178875
0.8681	High Similarity	NPC470010
0.8681	High Similarity	NPC323008
0.8681	High Similarity	NPC470013
0.8681	High Similarity	NPC262133
0.8667	High Similarity	NPC131209
0.8667	High Similarity	NPC133698
0.8587	High Similarity	NPC304886
0.8556	High Similarity	NPC62815
0.8539	High Similarity	NPC91248
0.8478	Intermediate Similarity	NPC198853
0.8444	Intermediate Similarity	NPC268298
0.8427	Intermediate Similarity	NPC237540
0.837	Intermediate Similarity	NPC153590
0.8367	Intermediate Similarity	NPC243998
0.8367	Intermediate Similarity	NPC223450
0.8352	Intermediate Similarity	NPC71533
0.8352	Intermediate Similarity	NPC129419
0.8352	Intermediate Similarity	NPC106510
0.8315	Intermediate Similarity	NPC470242
0.8315	Intermediate Similarity	NPC67493
0.828	Intermediate Similarity	NPC127019
0.8265	Intermediate Similarity	NPC203659
0.8265	Intermediate Similarity	NPC100487
0.8261	Intermediate Similarity	NPC475925
0.8261	Intermediate Similarity	NPC111114
0.8261	Intermediate Similarity	NPC261607
0.8261	Intermediate Similarity	NPC300312
0.8256	Intermediate Similarity	NPC74673
0.8256	Intermediate Similarity	NPC69271
0.8247	Intermediate Similarity	NPC86077
0.8242	Intermediate Similarity	NPC295312
0.8211	Intermediate Similarity	NPC213947
0.8211	Intermediate Similarity	NPC170143
0.8211	Intermediate Similarity	NPC108475
0.8202	Intermediate Similarity	NPC78089
0.8191	Intermediate Similarity	NPC193645
0.8191	Intermediate Similarity	NPC48803
0.8191	Intermediate Similarity	NPC52044
0.8191	Intermediate Similarity	NPC163228
0.8191	Intermediate Similarity	NPC90121
0.8191	Intermediate Similarity	NPC213698
0.8191	Intermediate Similarity	NPC275960
0.8191	Intermediate Similarity	NPC170120
0.8191	Intermediate Similarity	NPC37408
0.8191	Intermediate Similarity	NPC67584
0.8182	Intermediate Similarity	NPC252234
0.8182	Intermediate Similarity	NPC39588
0.8172	Intermediate Similarity	NPC81419
0.8172	Intermediate Similarity	NPC179746
0.8163	Intermediate Similarity	NPC475945
0.8163	Intermediate Similarity	NPC110989
0.8163	Intermediate Similarity	NPC475871
0.8161	Intermediate Similarity	NPC35089
0.8161	Intermediate Similarity	NPC10276
0.8152	Intermediate Similarity	NPC37607
0.8152	Intermediate Similarity	NPC301969
0.8152	Intermediate Similarity	NPC51004
0.8144	Intermediate Similarity	NPC171759
0.8144	Intermediate Similarity	NPC474742
0.8132	Intermediate Similarity	NPC202672
0.8132	Intermediate Similarity	NPC79549
0.8125	Intermediate Similarity	NPC141191
0.8111	Intermediate Similarity	NPC284902
0.8111	Intermediate Similarity	NPC107787
0.8111	Intermediate Similarity	NPC64153
0.8111	Intermediate Similarity	NPC236692
0.8111	Intermediate Similarity	NPC309757
0.8105	Intermediate Similarity	NPC213078
0.809	Intermediate Similarity	NPC472957
0.809	Intermediate Similarity	NPC154893
0.809	Intermediate Similarity	NPC472958
0.809	Intermediate Similarity	NPC53011
0.809	Intermediate Similarity	NPC165287
0.809	Intermediate Similarity	NPC16887
0.809	Intermediate Similarity	NPC37005
0.8085	Intermediate Similarity	NPC167219
0.8081	Intermediate Similarity	NPC474741
0.8065	Intermediate Similarity	NPC12172
0.8065	Intermediate Similarity	NPC208886
0.8065	Intermediate Similarity	NPC30515
0.8061	Intermediate Similarity	NPC474747
0.8061	Intermediate Similarity	NPC225353
0.8043	Intermediate Similarity	NPC215556
0.8043	Intermediate Similarity	NPC4986
0.8043	Intermediate Similarity	NPC307411
0.8043	Intermediate Similarity	NPC212664
0.8022	Intermediate Similarity	NPC190753
0.8022	Intermediate Similarity	NPC160138
0.8022	Intermediate Similarity	NPC475703
0.8021	Intermediate Similarity	NPC161493
0.8021	Intermediate Similarity	NPC169205
0.8	Intermediate Similarity	NPC161957
0.8	Intermediate Similarity	NPC166115
0.8	Intermediate Similarity	NPC284534
0.8	Intermediate Similarity	NPC476053
0.8	Intermediate Similarity	NPC235792
0.8	Intermediate Similarity	NPC204105
0.8	Intermediate Similarity	NPC300082
0.7979	Intermediate Similarity	NPC473234
0.7979	Intermediate Similarity	NPC60386
0.7979	Intermediate Similarity	NPC475912
0.7979	Intermediate Similarity	NPC308656
0.7979	Intermediate Similarity	NPC473263
0.7979	Intermediate Similarity	NPC473273
0.7979	Intermediate Similarity	NPC476300
0.7979	Intermediate Similarity	NPC200237
0.7959	Intermediate Similarity	NPC150923
0.7957	Intermediate Similarity	NPC179394
0.7957	Intermediate Similarity	NPC216284
0.7957	Intermediate Similarity	NPC312042
0.7957	Intermediate Similarity	NPC144133
0.7941	Intermediate Similarity	NPC273433
0.7938	Intermediate Similarity	NPC473326
0.7938	Intermediate Similarity	NPC221615
0.7935	Intermediate Similarity	NPC207114
0.7935	Intermediate Similarity	NPC217983
0.7921	Intermediate Similarity	NPC26617
0.7917	Intermediate Similarity	NPC18019
0.7917	Intermediate Similarity	NPC91771
0.7917	Intermediate Similarity	NPC24956
0.7917	Intermediate Similarity	NPC185553
0.7917	Intermediate Similarity	NPC142529
0.7912	Intermediate Similarity	NPC187661
0.7895	Intermediate Similarity	NPC474035
0.7895	Intermediate Similarity	NPC474338
0.7895	Intermediate Similarity	NPC81386
0.7895	Intermediate Similarity	NPC473331
0.7889	Intermediate Similarity	NPC224386
0.7889	Intermediate Similarity	NPC194859
0.7889	Intermediate Similarity	NPC115786
0.7889	Intermediate Similarity	NPC156485
0.7885	Intermediate Similarity	NPC95290
0.7885	Intermediate Similarity	NPC35069
0.7885	Intermediate Similarity	NPC258711
0.7885	Intermediate Similarity	NPC189338
0.7872	Intermediate Similarity	NPC70595
0.7872	Intermediate Similarity	NPC74103
0.7872	Intermediate Similarity	NPC123177
0.7872	Intermediate Similarity	NPC150978
0.7872	Intermediate Similarity	NPC155215
0.7872	Intermediate Similarity	NPC284185
0.7872	Intermediate Similarity	NPC184463
0.7872	Intermediate Similarity	NPC184063
0.7865	Intermediate Similarity	NPC246076
0.7865	Intermediate Similarity	NPC89555
0.7857	Intermediate Similarity	NPC70865
0.7849	Intermediate Similarity	NPC12872
0.7849	Intermediate Similarity	NPC155935
0.7849	Intermediate Similarity	NPC166919
0.7849	Intermediate Similarity	NPC168679
0.7841	Intermediate Similarity	NPC223904
0.7841	Intermediate Similarity	NPC302426
0.7841	Intermediate Similarity	NPC51507
0.7841	Intermediate Similarity	NPC276356
0.7835	Intermediate Similarity	NPC471150
0.7835	Intermediate Similarity	NPC477949
0.7826	Intermediate Similarity	NPC186148
0.7826	Intermediate Similarity	NPC270270
0.7826	Intermediate Similarity	NPC231889
0.7822	Intermediate Similarity	NPC54737
0.7812	Intermediate Similarity	NPC475900
0.7812	Intermediate Similarity	NPC36954
0.7812	Intermediate Similarity	NPC469873
0.7812	Intermediate Similarity	NPC270013
0.7812	Intermediate Similarity	NPC14961
0.781	Intermediate Similarity	NPC209058
0.7802	Intermediate Similarity	NPC165162
0.7802	Intermediate Similarity	NPC215364
0.78	Intermediate Similarity	NPC475873
0.7789	Intermediate Similarity	NPC125674
0.7789	Intermediate Similarity	NPC258216
0.7789	Intermediate Similarity	NPC212486
0.7789	Intermediate Similarity	NPC228451
0.7789	Intermediate Similarity	NPC475838
0.7778	Intermediate Similarity	NPC128246
0.7778	Intermediate Similarity	NPC272814
0.7778	Intermediate Similarity	NPC477950
0.7778	Intermediate Similarity	NPC250315
0.7778	Intermediate Similarity	NPC54468
0.7766	Intermediate Similarity	NPC19087
0.7766	Intermediate Similarity	NPC253144
0.7766	Intermediate Similarity	NPC475855
0.7766	Intermediate Similarity	NPC474761
0.7766	Intermediate Similarity	NPC54065
0.7766	Intermediate Similarity	NPC476004
0.7766	Intermediate Similarity	NPC35809
0.7766	Intermediate Similarity	NPC297474
0.7765	Intermediate Similarity	NPC469641
0.7765	Intermediate Similarity	NPC215030
0.7765	Intermediate Similarity	NPC469643
0.7753	Intermediate Similarity	NPC39411
0.7753	Intermediate Similarity	NPC126248
0.7753	Intermediate Similarity	NPC255580
0.7742	Intermediate Similarity	NPC58219
0.7742	Intermediate Similarity	NPC177629
0.7742	Intermediate Similarity	NPC224652

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 NPC32922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	2244
0.2-0.3	3759
0.3-0.4	1993
0.4-0.5	566
0.5-0.6	290
0.6-0.7	41
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8191	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1695	Approved
0.7921	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6371	Approved
0.7234	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6053	Discontinued
0.7172	Intermediate Similarity	NPD5282	Discontinued
0.7041	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD1694	Approved
0.6869	Remote Similarity	NPD5785	Approved
0.6842	Remote Similarity	NPD5362	Discontinued
0.6822	Remote Similarity	NPD6008	Approved
0.6804	Remote Similarity	NPD4249	Approved
0.6804	Remote Similarity	NPD5786	Approved
0.6737	Remote Similarity	NPD6435	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6701	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6634	Remote Similarity	NPD7983	Approved
0.6632	Remote Similarity	NPD5369	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7638	Approved
0.6569	Remote Similarity	NPD5779	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6562	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4270	Approved
0.6562	Remote Similarity	NPD4269	Approved
0.6535	Remote Similarity	NPD7838	Discovery
0.6526	Remote Similarity	NPD5368	Approved
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6486	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7341	Phase 2
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD6686	Approved
0.6392	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7632	Discontinued
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4820	Approved
0.6354	Remote Similarity	NPD4822	Approved
0.6354	Remote Similarity	NPD4819	Approved
0.6354	Remote Similarity	NPD4252	Approved
0.6354	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6845	Suspended
0.6316	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7320	Approved
0.623	Remote Similarity	NPD7507	Approved
0.6224	Remote Similarity	NPD5209	Approved
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6162	Remote Similarity	NPD5331	Approved
0.6162	Remote Similarity	NPD5332	Approved
0.6161	Remote Similarity	NPD5697	Approved
0.6161	Remote Similarity	NPD5701	Approved
0.6147	Remote Similarity	NPD5344	Discontinued
0.6146	Remote Similarity	NPD4268	Approved
0.6146	Remote Similarity	NPD4271	Approved
0.6132	Remote Similarity	NPD5695	Phase 3
0.6122	Remote Similarity	NPD4790	Discontinued
0.6121	Remote Similarity	NPD4632	Approved
0.6117	Remote Similarity	NPD6101	Approved
0.6117	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD5696	Approved
0.6106	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD7115	Discovery
0.6087	Remote Similarity	NPD6649	Approved
0.6087	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD7319	Approved
0.6075	Remote Similarity	NPD7839	Suspended
0.6067	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD6903	Approved
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6084	Phase 2
0.6016	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7334	Approved
0.598	Remote Similarity	NPD5330	Approved
0.598	Remote Similarity	NPD6409	Approved
0.598	Remote Similarity	NPD6684	Approved
0.598	Remote Similarity	NPD7521	Approved
0.598	Remote Similarity	NPD7146	Approved
0.5968	Remote Similarity	NPD6616	Approved
0.5966	Remote Similarity	NPD6009	Approved
0.5965	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6319	Approved
0.595	Remote Similarity	NPD6054	Approved
0.595	Remote Similarity	NPD6059	Approved
0.5948	Remote Similarity	NPD6847	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD6617	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6869	Approved
0.5935	Remote Similarity	NPD7642	Approved
0.592	Remote Similarity	NPD8293	Discontinued
0.592	Remote Similarity	NPD7078	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5905	Remote Similarity	NPD5207	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD5983	Phase 2
0.5902	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5888	Remote Similarity	NPD7748	Approved
0.5877	Remote Similarity	NPD6412	Phase 2
0.5873	Remote Similarity	NPD7736	Approved
0.5872	Remote Similarity	NPD4755	Approved
0.5865	Remote Similarity	NPD6672	Approved
0.5865	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5737	Approved
0.5854	Remote Similarity	NPD5988	Approved
0.5854	Remote Similarity	NPD6370	Approved
0.5849	Remote Similarity	NPD7637	Suspended
0.5842	Remote Similarity	NPD6110	Phase 1
0.5825	Remote Similarity	NPD3618	Phase 1
0.5816	Remote Similarity	NPD4802	Phase 2
0.5816	Remote Similarity	NPD4238	Approved
0.581	Remote Similarity	NPD5328	Approved
0.5806	Remote Similarity	NPD7604	Phase 2
0.5804	Remote Similarity	NPD5211	Phase 2
0.5784	Remote Similarity	NPD3665	Phase 1
0.5784	Remote Similarity	NPD3666	Approved
0.5784	Remote Similarity	NPD3133	Approved
0.578	Remote Similarity	NPD4697	Phase 3
0.5766	Remote Similarity	NPD4700	Approved
0.5766	Remote Similarity	NPD5286	Approved
0.5766	Remote Similarity	NPD5285	Approved
0.5766	Remote Similarity	NPD4696	Approved
0.5758	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6274	Approved
0.5743	Remote Similarity	NPD3667	Approved
0.5741	Remote Similarity	NPD7900	Approved
0.5741	Remote Similarity	NPD6001	Approved
0.5741	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD1696	Phase 3
0.5726	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD5223	Approved
0.5714	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD4756	Discovery
0.5702	Remote Similarity	NPD5141	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5701	Remote Similarity	NPD7515	Phase 2
0.5701	Remote Similarity	NPD8034	Phase 2
0.5701	Remote Similarity	NPD8035	Phase 2
0.5701	Remote Similarity	NPD6079	Approved
0.5678	Remote Similarity	NPD2204	Approved
0.5673	Remote Similarity	NPD5279	Phase 3
0.5673	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6422	Discontinued
0.5673	Remote Similarity	NPD4623	Approved
0.5673	Remote Similarity	NPD4519	Discontinued
0.567	Remote Similarity	NPD8039	Approved
0.5664	Remote Similarity	NPD5225	Approved
0.5664	Remote Similarity	NPD4633	Approved
0.5664	Remote Similarity	NPD5224	Approved
0.5664	Remote Similarity	NPD5226	Approved
0.566	Remote Similarity	NPD6673	Approved
0.566	Remote Similarity	NPD5370	Suspended
0.566	Remote Similarity	NPD6080	Approved
0.566	Remote Similarity	NPD4753	Phase 2
0.566	Remote Similarity	NPD6904	Approved
0.5657	Remote Similarity	NPD3617	Approved
0.5656	Remote Similarity	NPD7328	Approved
0.5656	Remote Similarity	NPD7641	Discontinued
0.5656	Remote Similarity	NPD6314	Approved
0.5656	Remote Similarity	NPD7327	Approved
0.5656	Remote Similarity	NPD6335	Approved
0.5656	Remote Similarity	NPD6313	Approved
0.5652	Remote Similarity	NPD3704	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