NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.651
LogD:	2.076
LogS:	-2.903
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	4.703
Fsp3:	0.6
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:	-4.653
MDCK Permeability:	1.5474757674383e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.688

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	93.57262420654297%
Volume Distribution (VD):	0.95
Pgp-substrate:	5.037576198577881%

ADMET: Metabolism

CYP1A2-inhibitor:	0.413
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.297
CYP2C19-substrate:	0.634
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.274
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	9.735
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.446
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.937
Carcinogencity:	0.811
Eye Corrosion:	0.081
Eye Irritation:	0.639
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC155587

Natural Product ID:	NPC155587
*Common Name:**	Argolide
IUPAC Name:	(3aS,6E,10R,11aR)-6,10-dimethyl-3-methylidene-4,5,8,10,11,11a-hexahydro-3aH-cyclodeca[b]furan-2,9-dione
Synonyms:
Standard InCHIKey:	WBBCIKNHTYTDRA-YYYMEZEWSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-4-6-12-11(3)15(17)18-14(12)8-10(2)13(16)7-5-9/h5,10,12,14H,3-4,6-8H2,1-2H3/b9-5+/t10-,12+,14-/m1/s1
SMILES:	C/C/1=CCC(=O)[C@H](C)C[C@@H]2[C@@H](CC1)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380796
PubChem CID:	14466572
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:0001771] Germacranolides and derivatives

*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
NPO1438	Artemisia glabella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO1438	Artemisia glabella	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	23334.58	nM	PMID[515515]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[515515]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	23330.0	nM	PMID[515515]

☑ 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 NPC155587 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	181
0.1-0.2	1311
0.2-0.3	6549
0.3-0.4	16079
0.4-0.5	9354
0.5-0.6	6189
0.6-0.7	2382
0.7-0.8	483
0.8-0.85	108
0.85-0.9	46
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC235906
0.9437	High Similarity	NPC138408
0.9437	High Similarity	NPC193351
0.9437	High Similarity	NPC226669
0.9429	High Similarity	NPC295633
0.9429	High Similarity	NPC58956
0.9429	High Similarity	NPC269206
0.9178	High Similarity	NPC65603
0.9014	High Similarity	NPC163003
0.9014	High Similarity	NPC129665
0.8933	High Similarity	NPC264227
0.8933	High Similarity	NPC472965
0.8933	High Similarity	NPC63649
0.8933	High Similarity	NPC270126
0.8919	High Similarity	NPC476794
0.8919	High Similarity	NPC187568
0.8919	High Similarity	NPC141789
0.8919	High Similarity	NPC470240
0.8919	High Similarity	NPC476028
0.8919	High Similarity	NPC171204
0.8919	High Similarity	NPC41780
0.8846	High Similarity	NPC141193
0.8846	High Similarity	NPC96259
0.8816	High Similarity	NPC302426
0.88	High Similarity	NPC471465
0.88	High Similarity	NPC196653
0.8767	High Similarity	NPC476355
0.8767	High Similarity	NPC140287
0.8701	High Similarity	NPC301477
0.8701	High Similarity	NPC25684
0.8701	High Similarity	NPC281949
0.8684	High Similarity	NPC617
0.8684	High Similarity	NPC182550
0.8684	High Similarity	NPC470244
0.8684	High Similarity	NPC98557
0.8684	High Similarity	NPC167881
0.8684	High Similarity	NPC470239
0.8608	High Similarity	NPC191476
0.8608	High Similarity	NPC114979
0.859	High Similarity	NPC173609
0.8571	High Similarity	NPC74673
0.8571	High Similarity	NPC223904
0.8571	High Similarity	NPC69271
0.8571	High Similarity	NPC281132
0.8571	High Similarity	NPC276356
0.8553	High Similarity	NPC128276
0.8553	High Similarity	NPC472960
0.8533	High Similarity	NPC123360
0.85	High Similarity	NPC38468
0.85	High Similarity	NPC255307
0.85	High Similarity	NPC319795
0.85	High Similarity	NPC50362
0.8481	Intermediate Similarity	NPC318468
0.8481	Intermediate Similarity	NPC215294
0.8481	Intermediate Similarity	NPC39588
0.8481	Intermediate Similarity	NPC474703
0.8472	Intermediate Similarity	NPC144511
0.8472	Intermediate Similarity	NPC296522
0.8462	Intermediate Similarity	NPC141810
0.8462	Intermediate Similarity	NPC35089
0.8462	Intermediate Similarity	NPC24417
0.8462	Intermediate Similarity	NPC471325
0.8462	Intermediate Similarity	NPC10276
0.8442	Intermediate Similarity	NPC178277
0.8442	Intermediate Similarity	NPC89128
0.8421	Intermediate Similarity	NPC97516
0.8421	Intermediate Similarity	NPC57744
0.8421	Intermediate Similarity	NPC320630
0.8421	Intermediate Similarity	NPC7563
0.8421	Intermediate Similarity	NPC116177
0.8421	Intermediate Similarity	NPC474760
0.8395	Intermediate Similarity	NPC305475
0.8395	Intermediate Similarity	NPC50637
0.8395	Intermediate Similarity	NPC150755
0.8395	Intermediate Similarity	NPC475461
0.8378	Intermediate Similarity	NPC472956
0.8375	Intermediate Similarity	NPC476804
0.8375	Intermediate Similarity	NPC115786
0.8356	Intermediate Similarity	NPC472955
0.8354	Intermediate Similarity	NPC229825
0.8354	Intermediate Similarity	NPC178676
0.8333	Intermediate Similarity	NPC470256
0.8312	Intermediate Similarity	NPC108816
0.8312	Intermediate Similarity	NPC299235
0.8312	Intermediate Similarity	NPC93763
0.8312	Intermediate Similarity	NPC267231
0.8289	Intermediate Similarity	NPC266159
0.8289	Intermediate Similarity	NPC472967
0.8272	Intermediate Similarity	NPC161957
0.8272	Intermediate Similarity	NPC21471
0.8272	Intermediate Similarity	NPC165162
0.8272	Intermediate Similarity	NPC110405
0.8272	Intermediate Similarity	NPC33570
0.825	Intermediate Similarity	NPC59097
0.825	Intermediate Similarity	NPC272814
0.825	Intermediate Similarity	NPC40746
0.825	Intermediate Similarity	NPC131669
0.825	Intermediate Similarity	NPC473390
0.825	Intermediate Similarity	NPC169575
0.8228	Intermediate Similarity	NPC52861
0.8219	Intermediate Similarity	NPC199557
0.8214	Intermediate Similarity	NPC251385
0.8214	Intermediate Similarity	NPC49342
0.8194	Intermediate Similarity	NPC194871
0.8182	Intermediate Similarity	NPC195785
0.8182	Intermediate Similarity	NPC15975
0.8171	Intermediate Similarity	NPC107787
0.8148	Intermediate Similarity	NPC158756
0.8143	Intermediate Similarity	NPC474658
0.8125	Intermediate Similarity	NPC85772
0.8095	Intermediate Similarity	NPC151770
0.8095	Intermediate Similarity	NPC166919
0.8095	Intermediate Similarity	NPC474032
0.8052	Intermediate Similarity	NPC472959
0.8049	Intermediate Similarity	NPC470755
0.8049	Intermediate Similarity	NPC78089
0.8026	Intermediate Similarity	NPC143979
0.8026	Intermediate Similarity	NPC15499
0.8026	Intermediate Similarity	NPC117746
0.8026	Intermediate Similarity	NPC294434
0.8026	Intermediate Similarity	NPC320537
0.8026	Intermediate Similarity	NPC259599
0.8025	Intermediate Similarity	NPC250315
0.8025	Intermediate Similarity	NPC475947
0.8023	Intermediate Similarity	NPC475302
0.8	Intermediate Similarity	NPC179394
0.8	Intermediate Similarity	NPC469368
0.8	Intermediate Similarity	NPC42470
0.8	Intermediate Similarity	NPC144133
0.7976	Intermediate Similarity	NPC476803
0.7976	Intermediate Similarity	NPC215831
0.7976	Intermediate Similarity	NPC476805
0.7975	Intermediate Similarity	NPC469690
0.7952	Intermediate Similarity	NPC284902
0.7952	Intermediate Similarity	NPC279859
0.7952	Intermediate Similarity	NPC38576
0.7952	Intermediate Similarity	NPC469910
0.7949	Intermediate Similarity	NPC208223
0.7927	Intermediate Similarity	NPC156485
0.7927	Intermediate Similarity	NPC159635
0.7922	Intermediate Similarity	NPC324762
0.7922	Intermediate Similarity	NPC244166
0.7901	Intermediate Similarity	NPC89555
0.7882	Intermediate Similarity	NPC268298
0.7882	Intermediate Similarity	NPC73995
0.7875	Intermediate Similarity	NPC293418
0.7875	Intermediate Similarity	NPC6823
0.7875	Intermediate Similarity	NPC73052
0.7875	Intermediate Similarity	NPC290508
0.7857	Intermediate Similarity	NPC231889
0.7857	Intermediate Similarity	NPC475703
0.7857	Intermediate Similarity	NPC266957
0.7848	Intermediate Similarity	NPC471220
0.7838	Intermediate Similarity	NPC218477
0.7831	Intermediate Similarity	NPC261380
0.7831	Intermediate Similarity	NPC215364
0.7831	Intermediate Similarity	NPC235792
0.7831	Intermediate Similarity	NPC177932
0.7821	Intermediate Similarity	NPC68819
0.7821	Intermediate Similarity	NPC473223
0.7816	Intermediate Similarity	NPC228451
0.7816	Intermediate Similarity	NPC125674
0.7816	Intermediate Similarity	NPC273579
0.7816	Intermediate Similarity	NPC475838
0.7816	Intermediate Similarity	NPC295204
0.7816	Intermediate Similarity	NPC162205
0.7816	Intermediate Similarity	NPC288240
0.7805	Intermediate Similarity	NPC193198
0.7805	Intermediate Similarity	NPC128429
0.7805	Intermediate Similarity	NPC170286
0.7805	Intermediate Similarity	NPC22611
0.7792	Intermediate Similarity	NPC469643
0.7792	Intermediate Similarity	NPC469641
0.7792	Intermediate Similarity	NPC472966
0.7791	Intermediate Similarity	NPC152467
0.7791	Intermediate Similarity	NPC475855
0.7791	Intermediate Similarity	NPC469718
0.7791	Intermediate Similarity	NPC312042
0.7791	Intermediate Similarity	NPC129419
0.7791	Intermediate Similarity	NPC329857
0.7791	Intermediate Similarity	NPC62815
0.7778	Intermediate Similarity	NPC325031
0.7778	Intermediate Similarity	NPC38642
0.7778	Intermediate Similarity	NPC255580
0.7778	Intermediate Similarity	NPC39411
0.7765	Intermediate Similarity	NPC473715
0.7765	Intermediate Similarity	NPC475819
0.7765	Intermediate Similarity	NPC202672
0.7765	Intermediate Similarity	NPC91248
0.775	Intermediate Similarity	NPC19841
0.775	Intermediate Similarity	NPC469620
0.7738	Intermediate Similarity	NPC67493
0.7738	Intermediate Similarity	NPC261721
0.7733	Intermediate Similarity	NPC476591
0.7733	Intermediate Similarity	NPC88877
0.7727	Intermediate Similarity	NPC473316
0.7727	Intermediate Similarity	NPC473330
0.7727	Intermediate Similarity	NPC476596
0.7727	Intermediate Similarity	NPC303942
0.7727	Intermediate Similarity	NPC57405

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 NPC155587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1859
0.2-0.3	4081
0.3-0.4	2074
0.4-0.5	640
0.5-0.6	265
0.6-0.7	46
0.7-0.8	10
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
0.85	High Similarity	NPD1733	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD1694	Approved
0.7674	Intermediate Similarity	NPD1695	Approved
0.7444	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5785	Approved
0.7059	Intermediate Similarity	NPD5209	Approved
0.7037	Intermediate Similarity	NPD8039	Approved
0.7011	Intermediate Similarity	NPD5363	Approved
0.6977	Remote Similarity	NPD7154	Phase 3
0.6941	Remote Similarity	NPD5369	Approved
0.686	Remote Similarity	NPD4270	Approved
0.686	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD46	Approved
0.6813	Remote Similarity	NPD6698	Approved
0.6782	Remote Similarity	NPD5362	Discontinued
0.6742	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD7521	Approved
0.6742	Remote Similarity	NPD6409	Approved
0.6742	Remote Similarity	NPD5786	Approved
0.6742	Remote Similarity	NPD6684	Approved
0.6742	Remote Similarity	NPD5330	Approved
0.6742	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6629	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD6903	Approved
0.6593	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4225	Approved
0.6489	Remote Similarity	NPD6399	Phase 3
0.6437	Remote Similarity	NPD5368	Approved
0.6437	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5737	Approved
0.6413	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD5693	Phase 1
0.6346	Remote Similarity	NPD6371	Approved
0.6279	Remote Similarity	NPD4756	Discovery
0.6277	Remote Similarity	NPD5207	Approved
0.6277	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7331	Phase 2
0.625	Remote Similarity	NPD4819	Approved
0.6222	Remote Similarity	NPD5332	Approved
0.6222	Remote Similarity	NPD5331	Approved
0.6211	Remote Similarity	NPD7983	Approved
0.6207	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD4271	Approved
0.6196	Remote Similarity	NPD6422	Discontinued
0.6196	Remote Similarity	NPD4249	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4790	Discontinued
0.617	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6101	Approved
0.617	Remote Similarity	NPD5370	Suspended
0.6162	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5779	Approved
0.6146	Remote Similarity	NPD5778	Approved
0.6132	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3573	Approved
0.6129	Remote Similarity	NPD4250	Approved
0.6129	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD28	Approved
0.6111	Remote Similarity	NPD3667	Approved
0.6111	Remote Similarity	NPD29	Approved
0.6111	Remote Similarity	NPD6927	Phase 3
0.6082	Remote Similarity	NPD7748	Approved
0.6082	Remote Similarity	NPD6001	Approved
0.6081	Remote Similarity	NPD9298	Approved
0.6064	Remote Similarity	NPD5208	Approved
0.6061	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD6411	Approved
0.6042	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3618	Phase 1
0.6022	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3197	Phase 1
0.5981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3133	Approved
0.5978	Remote Similarity	NPD4786	Approved
0.5978	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3668	Phase 3
0.5978	Remote Similarity	NPD3666	Approved
0.5978	Remote Similarity	NPD3665	Phase 1
0.596	Remote Similarity	NPD7839	Suspended
0.596	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD3172	Approved
0.5941	Remote Similarity	NPD7639	Approved
0.5941	Remote Similarity	NPD7640	Approved
0.5938	Remote Similarity	NPD5692	Phase 3
0.5926	Remote Similarity	NPD7341	Phase 2
0.59	Remote Similarity	NPD6084	Phase 2
0.59	Remote Similarity	NPD6083	Phase 2
0.5889	Remote Similarity	NPD4695	Discontinued
0.5888	Remote Similarity	NPD2067	Discontinued
0.5876	Remote Similarity	NPD5694	Approved
0.5876	Remote Similarity	NPD6050	Approved
0.5876	Remote Similarity	NPD7515	Phase 2
0.5875	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD3194	Approved
0.5867	Remote Similarity	NPD3195	Phase 2
0.5867	Remote Similarity	NPD4266	Approved
0.5867	Remote Similarity	NPD3196	Approved
0.5851	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD6051	Approved
0.578	Remote Similarity	NPD6053	Discontinued
0.5765	Remote Similarity	NPD4691	Approved
0.5755	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD5284	Approved
0.5714	Remote Similarity	NPD6079	Approved
0.5714	Remote Similarity	NPD5281	Approved
0.5701	Remote Similarity	NPD6881	Approved
0.5701	Remote Similarity	NPD6899	Approved
0.5701	Remote Similarity	NPD6011	Approved
0.5694	Remote Similarity	NPD5343	Approved
0.5688	Remote Similarity	NPD6650	Approved
0.5688	Remote Similarity	NPD6649	Approved
0.567	Remote Similarity	NPD5328	Approved
0.5663	Remote Similarity	NPD3704	Approved
0.566	Remote Similarity	NPD7128	Approved
0.566	Remote Similarity	NPD6402	Approved
0.566	Remote Similarity	NPD5739	Approved
0.566	Remote Similarity	NPD6675	Approved
0.5652	Remote Similarity	NPD857	Phase 3
0.5648	Remote Similarity	NPD6014	Approved
0.5648	Remote Similarity	NPD6372	Approved
0.5648	Remote Similarity	NPD6012	Approved
0.5648	Remote Similarity	NPD6373	Approved
0.5648	Remote Similarity	NPD6013	Approved
0.5647	Remote Similarity	NPD4137	Phase 3
0.5634	Remote Similarity	NPD3174	Discontinued
0.5631	Remote Similarity	NPD6648	Approved
0.5625	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1145	Discontinued
0.5619	Remote Similarity	NPD6052	Approved
0.5619	Remote Similarity	NPD6647	Phase 2
0.5612	Remote Similarity	NPD3672	Approved
0.5612	Remote Similarity	NPD3673	Approved
0.5607	Remote Similarity	NPD5701	Approved
0.5607	Remote Similarity	NPD5954	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