NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.326
LogD:	1.694
LogS:	-2.664
# 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:	0.531
Synthetic Accessibility Score:	4.496
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:	-4.647
MDCK Permeability:	2.9434509997372515e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.928
Plasma Protein Binding (PPB):	40.968963623046875%
Volume Distribution (VD):	0.578
Pgp-substrate:	52.88484191894531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.193
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	11.197
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.426
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.395
Skin Sensitization:	0.841
Carcinogencity:	0.793
Eye Corrosion:	0.754
Eye Irritation:	0.77
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC168679

Natural Product ID:	NPC168679
*Common Name:**	Carpesiolin
IUPAC Name:	(3aS,5R,5aS,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,7-b]furan-2,8-dione
Synonyms:	Carpesiolin
Standard InCHIKey:	IOUNDPHKKPZPKB-GSNHZRAGSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h7,9-10,12-13,17H,2,4-6H2,1,3H3/t7-,9+,10+,12-,13+,15+/m1/s1
SMILES:	C[C@@H]1C[C@H]2[C@@H](C(=C)C(=O)O2)[C@@H]([C@@]2(C)[C@H]1CCC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644106
PubChem CID:	10015663
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO24524	Gutierrezia gymnospermoides	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]
NPO25058	Mayetiola destructor	Species	Cecidomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23330	Guatteria dumetorum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25374	Crotalaria sericea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24701	Schizonepeta annua	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24797	Chuquiraga ulicina	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8400.0	nM	PMID[551616]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2180.0	nM	PMID[551617]

☑ 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 NPC168679 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	243
0.1-0.2	1757
0.2-0.3	6755
0.3-0.4	14205
0.4-0.5	9793
0.5-0.6	6637
0.6-0.7	2806
0.7-0.8	387
0.8-0.85	51
0.85-0.9	45
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12872
0.9405	High Similarity	NPC236692
0.9405	High Similarity	NPC238593
0.9405	High Similarity	NPC309757
0.9326	High Similarity	NPC142529
0.9326	High Similarity	NPC91771
0.9294	High Similarity	NPC201658
0.9205	High Similarity	NPC200237
0.9205	High Similarity	NPC153590
0.9101	High Similarity	NPC473331
0.9048	High Similarity	NPC54468
0.9	High Similarity	NPC275960
0.9	High Similarity	NPC90121
0.9	High Similarity	NPC193645
0.9	High Similarity	NPC48803
0.8989	High Similarity	NPC473273
0.8989	High Similarity	NPC473234
0.8989	High Similarity	NPC60386
0.8989	High Similarity	NPC473263
0.8989	High Similarity	NPC308656
0.8925	High Similarity	NPC171759
0.8916	High Similarity	NPC73052
0.8916	High Similarity	NPC51507
0.8916	High Similarity	NPC290508
0.8916	High Similarity	NPC293418
0.8916	High Similarity	NPC6823
0.8876	High Similarity	NPC286341
0.8876	High Similarity	NPC191339
0.8864	High Similarity	NPC155935
0.8851	High Similarity	NPC118601
0.8804	High Similarity	NPC169205
0.8804	High Similarity	NPC311904
0.8764	High Similarity	NPC19087
0.8764	High Similarity	NPC297474
0.8764	High Similarity	NPC54065
0.8764	High Similarity	NPC35809
0.875	High Similarity	NPC178875
0.871	High Similarity	NPC141191
0.8696	High Similarity	NPC185553
0.8667	High Similarity	NPC133888
0.8667	High Similarity	NPC184063
0.8667	High Similarity	NPC293001
0.8667	High Similarity	NPC171360
0.8667	High Similarity	NPC63193
0.8667	High Similarity	NPC57304
0.8667	High Similarity	NPC35959
0.8667	High Similarity	NPC29821
0.8652	High Similarity	NPC38392
0.8602	High Similarity	NPC213947
0.8602	High Similarity	NPC108475
0.8602	High Similarity	NPC170143
0.8554	High Similarity	NPC208223
0.8539	High Similarity	NPC207114
0.8539	High Similarity	NPC217983
0.8523	High Similarity	NPC187661
0.8523	High Similarity	NPC56593
0.8495	Intermediate Similarity	NPC126156
0.8462	Intermediate Similarity	NPC123177
0.8462	Intermediate Similarity	NPC150978
0.8462	Intermediate Similarity	NPC74103
0.8462	Intermediate Similarity	NPC70595
0.8444	Intermediate Similarity	NPC52198
0.8444	Intermediate Similarity	NPC215556
0.8444	Intermediate Similarity	NPC117405
0.8391	Intermediate Similarity	NPC245665
0.8387	Intermediate Similarity	NPC163228
0.8352	Intermediate Similarity	NPC216284
0.8352	Intermediate Similarity	NPC253144
0.8333	Intermediate Similarity	NPC79549
0.8333	Intermediate Similarity	NPC477950
0.8315	Intermediate Similarity	NPC304558
0.8315	Intermediate Similarity	NPC470242
0.8313	Intermediate Similarity	NPC179922
0.8298	Intermediate Similarity	NPC24956
0.8298	Intermediate Similarity	NPC476009
0.8298	Intermediate Similarity	NPC18019
0.8295	Intermediate Similarity	NPC224386
0.8295	Intermediate Similarity	NPC194859
0.828	Intermediate Similarity	NPC167219
0.8265	Intermediate Similarity	NPC203659
0.8261	Intermediate Similarity	NPC284185
0.8247	Intermediate Similarity	NPC225353
0.8222	Intermediate Similarity	NPC190753
0.8222	Intermediate Similarity	NPC24728
0.8211	Intermediate Similarity	NPC471150
0.8211	Intermediate Similarity	NPC474313
0.8193	Intermediate Similarity	NPC143979
0.8193	Intermediate Similarity	NPC320537
0.8191	Intermediate Similarity	NPC476053
0.8191	Intermediate Similarity	NPC475900
0.8182	Intermediate Similarity	NPC215294
0.8182	Intermediate Similarity	NPC128246
0.8172	Intermediate Similarity	NPC135776
0.8163	Intermediate Similarity	NPC110989
0.8152	Intermediate Similarity	NPC129419
0.814	Intermediate Similarity	NPC19841
0.8132	Intermediate Similarity	NPC53158
0.8132	Intermediate Similarity	NPC471149
0.809	Intermediate Similarity	NPC156485
0.8068	Intermediate Similarity	NPC246076
0.8065	Intermediate Similarity	NPC300312
0.8065	Intermediate Similarity	NPC155215
0.8065	Intermediate Similarity	NPC131209
0.8065	Intermediate Similarity	NPC475925
0.8065	Intermediate Similarity	NPC261607
0.8065	Intermediate Similarity	NPC111114
0.8043	Intermediate Similarity	NPC283409
0.8043	Intermediate Similarity	NPC268298
0.8041	Intermediate Similarity	NPC471381
0.8	Intermediate Similarity	NPC161957
0.8	Intermediate Similarity	NPC165162
0.8	Intermediate Similarity	NPC21471
0.8	Intermediate Similarity	NPC284534
0.8	Intermediate Similarity	NPC204105
0.8	Intermediate Similarity	NPC472873
0.8	Intermediate Similarity	NPC33570
0.8	Intermediate Similarity	NPC300082
0.7979	Intermediate Similarity	NPC258216
0.7978	Intermediate Similarity	NPC111409
0.7976	Intermediate Similarity	NPC48641
0.7955	Intermediate Similarity	NPC126248
0.7955	Intermediate Similarity	NPC47635
0.7938	Intermediate Similarity	NPC54843
0.7912	Intermediate Similarity	NPC104961
0.7912	Intermediate Similarity	NPC70555
0.7912	Intermediate Similarity	NPC70422
0.79	Intermediate Similarity	NPC309190
0.7895	Intermediate Similarity	NPC289004
0.7889	Intermediate Similarity	NPC165287
0.7879	Intermediate Similarity	NPC474747
0.7872	Intermediate Similarity	NPC133698
0.7865	Intermediate Similarity	NPC89555
0.7857	Intermediate Similarity	NPC186861
0.7849	Intermediate Similarity	NPC32922
0.7849	Intermediate Similarity	NPC212664
0.7841	Intermediate Similarity	NPC69271
0.7841	Intermediate Similarity	NPC74673
0.7841	Intermediate Similarity	NPC223904
0.7835	Intermediate Similarity	NPC477949
0.7826	Intermediate Similarity	NPC186148
0.7826	Intermediate Similarity	NPC237540
0.7826	Intermediate Similarity	NPC270270
0.7812	Intermediate Similarity	NPC213698
0.7812	Intermediate Similarity	NPC170120
0.7812	Intermediate Similarity	NPC52044
0.78	Intermediate Similarity	NPC475871
0.78	Intermediate Similarity	NPC475945
0.7789	Intermediate Similarity	NPC475788
0.7789	Intermediate Similarity	NPC475302
0.7778	Intermediate Similarity	NPC39588
0.7766	Intermediate Similarity	NPC469368
0.7766	Intermediate Similarity	NPC71533
0.7766	Intermediate Similarity	NPC106510
0.7753	Intermediate Similarity	NPC10276
0.7753	Intermediate Similarity	NPC35089
0.7742	Intermediate Similarity	NPC58219
0.7742	Intermediate Similarity	NPC177629
0.7738	Intermediate Similarity	NPC470243
0.7732	Intermediate Similarity	NPC39859
0.7732	Intermediate Similarity	NPC158416
0.7732	Intermediate Similarity	NPC470883
0.7732	Intermediate Similarity	NPC76862
0.7727	Intermediate Similarity	NPC470239
0.7727	Intermediate Similarity	NPC470244
0.7727	Intermediate Similarity	NPC182550
0.7723	Intermediate Similarity	NPC100487
0.7717	Intermediate Similarity	NPC67493
0.7717	Intermediate Similarity	NPC107787
0.7717	Intermediate Similarity	NPC64153
0.7717	Intermediate Similarity	NPC85698
0.7711	Intermediate Similarity	NPC5714
0.7708	Intermediate Similarity	NPC198853
0.7708	Intermediate Similarity	NPC470013
0.7708	Intermediate Similarity	NPC470010
0.7708	Intermediate Similarity	NPC323008
0.7708	Intermediate Similarity	NPC262133
0.7708	Intermediate Similarity	NPC127019
0.7708	Intermediate Similarity	NPC477131
0.77	Intermediate Similarity	NPC80144
0.7692	Intermediate Similarity	NPC96259
0.7692	Intermediate Similarity	NPC115786
0.7692	Intermediate Similarity	NPC141193
0.7692	Intermediate Similarity	NPC114979
0.7692	Intermediate Similarity	NPC191476
0.766	Intermediate Similarity	NPC472872
0.766	Intermediate Similarity	NPC92974
0.7653	Intermediate Similarity	NPC161493
0.7647	Intermediate Similarity	NPC54737
0.7647	Intermediate Similarity	NPC44004
0.7642	Intermediate Similarity	NPC209058
0.764	Intermediate Similarity	NPC276356
0.7634	Intermediate Similarity	NPC305029
0.7629	Intermediate Similarity	NPC469873
0.7629	Intermediate Similarity	NPC67584
0.7629	Intermediate Similarity	NPC304886
0.7619	Intermediate Similarity	NPC18543
0.7609	Intermediate Similarity	NPC78089
0.7609	Intermediate Similarity	NPC255307
0.76	Intermediate Similarity	NPC474742
0.76	Intermediate Similarity	NPC67296

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 NPC168679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	2498
0.2-0.3	3860
0.3-0.4	1733
0.4-0.5	465
0.5-0.6	236
0.6-0.7	60
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD1698	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5785	Approved
0.7292	Intermediate Similarity	NPD1695	Approved
0.7238	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6371	Approved
0.7158	Intermediate Similarity	NPD5786	Approved
0.7097	Intermediate Similarity	NPD6435	Approved
0.7053	Intermediate Similarity	NPD5363	Approved
0.6989	Remote Similarity	NPD5369	Approved
0.6915	Remote Similarity	NPD4269	Approved
0.6915	Remote Similarity	NPD4270	Approved
0.6893	Remote Similarity	NPD4225	Approved
0.6882	Remote Similarity	NPD5368	Approved
0.6832	Remote Similarity	NPD5282	Discontinued
0.68	Remote Similarity	NPD6411	Approved
0.6733	Remote Similarity	NPD6399	Phase 3
0.6702	Remote Similarity	NPD4252	Approved
0.6701	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1694	Approved
0.6701	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD5697	Approved
0.66	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5779	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6545	Remote Similarity	NPD6899	Approved
0.6545	Remote Similarity	NPD7320	Approved
0.6545	Remote Similarity	NPD6881	Approved
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD6675	Approved
0.6514	Remote Similarity	NPD6402	Approved
0.6514	Remote Similarity	NPD7128	Approved
0.6514	Remote Similarity	NPD5739	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6486	Remote Similarity	NPD6013	Approved
0.6486	Remote Similarity	NPD6373	Approved
0.6486	Remote Similarity	NPD6012	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6372	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD8035	Phase 2
0.6465	Remote Similarity	NPD4249	Approved
0.6455	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD6883	Approved
0.6429	Remote Similarity	NPD7290	Approved
0.6429	Remote Similarity	NPD7102	Approved
0.64	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD4250	Approved
0.6396	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6011	Approved
0.6392	Remote Similarity	NPD5209	Approved
0.6392	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6698	Approved
0.6373	Remote Similarity	NPD46	Approved
0.6372	Remote Similarity	NPD6869	Approved
0.6372	Remote Similarity	NPD6847	Approved
0.6372	Remote Similarity	NPD6617	Approved
0.6372	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD4820	Approved
0.6354	Remote Similarity	NPD4822	Approved
0.6354	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD4819	Approved
0.6321	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD6083	Phase 2
0.6316	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD6882	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD7637	Suspended
0.6286	Remote Similarity	NPD5695	Phase 3
0.6281	Remote Similarity	NPD7492	Approved
0.6262	Remote Similarity	NPD5696	Approved
0.6262	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6686	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.623	Remote Similarity	NPD6616	Approved
0.6224	Remote Similarity	NPD3667	Approved
0.6222	Remote Similarity	NPD229	Approved
0.6218	Remote Similarity	NPD6319	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD7639	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD7640	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7078	Approved
0.6176	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD4755	Approved
0.6167	Remote Similarity	NPD6015	Approved
0.6167	Remote Similarity	NPD6016	Approved
0.6167	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5331	Approved
0.6162	Remote Similarity	NPD5332	Approved
0.6162	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD6274	Approved
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6139	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD7736	Approved
0.6126	Remote Similarity	NPD5141	Approved
0.6122	Remote Similarity	NPD4790	Discontinued
0.6117	Remote Similarity	NPD5328	Approved
0.6116	Remote Similarity	NPD6370	Approved
0.6116	Remote Similarity	NPD5988	Approved
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD4786	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD3133	Approved
0.6091	Remote Similarity	NPD5226	Approved
0.6091	Remote Similarity	NPD5225	Approved
0.6091	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD7319	Approved
0.6075	Remote Similarity	NPD7839	Suspended
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6075	Remote Similarity	NPD4697	Phase 3
0.6058	Remote Similarity	NPD7838	Discovery
0.6055	Remote Similarity	NPD4700	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.6036	Remote Similarity	NPD5175	Approved
0.6036	Remote Similarity	NPD5174	Approved
0.6033	Remote Similarity	NPD8268	Approved
0.6033	Remote Similarity	NPD8269	Approved
0.6033	Remote Similarity	NPD8266	Approved
0.6033	Remote Similarity	NPD8267	Approved
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7902	Approved
0.6019	Remote Similarity	NPD5173	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD5281	Approved
0.5983	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5210	Approved
0.5981	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5279	Phase 3
0.5979	Remote Similarity	NPD4802	Phase 2
0.5979	Remote Similarity	NPD4238	Approved
0.5968	Remote Similarity	NPD7507	Approved
0.5966	Remote Similarity	NPD6317	Approved
0.5962	Remote Similarity	NPD5370	Suspended
0.5962	Remote Similarity	NPD4753	Phase 2
0.5938	Remote Similarity	NPD6845	Suspended
0.5917	Remote Similarity	NPD6314	Approved
0.5917	Remote Similarity	NPD6313	Approved
0.5917	Remote Similarity	NPD6335	Approved
0.5905	Remote Similarity	NPD5207	Approved
0.5902	Remote Similarity	NPD8517	Approved
0.5902	Remote Similarity	NPD8516	Approved
0.5902	Remote Similarity	NPD8515	Approved
0.5902	Remote Similarity	NPD8513	Phase 3
0.5889	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD6868	Approved
0.5877	Remote Similarity	NPD6412	Phase 2
0.5868	Remote Similarity	NPD7517	Approved
0.5868	Remote Similarity	NPD7518	Approved
0.5868	Remote Similarity	NPD7519	Approved
0.5862	Remote Similarity	NPD3198	Approved
0.5859	Remote Similarity	NPD7260	Phase 2
0.5856	Remote Similarity	NPD1700	Approved
0.5849	Remote Similarity	NPD7515	Phase 2
0.5849	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8133	Approved
0.5841	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6009	Approved
0.5826	Remote Similarity	NPD5128	Approved
0.5826	Remote Similarity	NPD4730	Approved
0.5826	Remote Similarity	NPD4729	Approved
0.5812	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD4202	Approved
0.5789	Remote Similarity	NPD4767	Approved
0.5789	Remote Similarity	NPD4768	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