NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.22
Volume:	320.999
LogP:	5.451
LogD:	4.907
LogS:	-5.502
# Rotatable Bonds:	9
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.4
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.551
MDCK Permeability:	2.2658705347566865e-05
Pgp-inhibitor:	0.167
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.858

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	97.73201751708984%
Volume Distribution (VD):	1.205
Pgp-substrate:	1.8251724243164062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.85
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.744
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.952
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	3.701
Half-life (T1/2):	0.19

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.951
Carcinogencity:	0.065
Eye Corrosion:	0.054
Eye Irritation:	0.464
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC265574

Natural Product ID:	NPC265574
*Common Name:**	Plakortone G
IUPAC Name:	(5S)-3,5-diethyl-5-[(E,4R)-4-ethyloct-5-enyl]furan-2-one
Synonyms:	Plakortone G
Standard InCHIKey:	ZOVPLJJDPDLGND-BQCDODHWSA-N
Standard InCHI:	InChI=1S/C18H30O2/c1-5-9-11-15(6-2)12-10-13-18(8-4)14-16(7-3)17(19)20-18/h9,11,14-15H,5-8,10,12-13H2,1-4H3/b11-9+/t15-,18-/m0/s1
SMILES:	CC/C=C/[C@@H](CCC[C@@]1(CC)C=C(C(=O)O1)CC)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450146
PubChem CID:	44576264
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[11720540]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738400]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam	n.a.	PMID[19618913]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20235550]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[23186727]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760075]
NPO32577	plakortis sp.	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722495]

☑ 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
EC50	1
IC50	5
Others	1

Activity Type	# Activity
Cell Line	3
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[572871]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[572871]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[572871]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.2	ug.mL-1	PMID[572871]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	4.76	ug.mL-1	PMID[572871]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	EC50	>	100.0	ug.mL-1	PMID[572871]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	4.0	%	PMID[572871]

☑ 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 NPC265574 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	190
0.1-0.2	1362
0.2-0.3	6897
0.3-0.4	17741
0.4-0.5	8806
0.5-0.6	5347
0.6-0.7	2050
0.7-0.8	283
0.8-0.85	18
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC470688
0.8551	High Similarity	NPC232812
0.8529	High Similarity	NPC472266
0.8429	Intermediate Similarity	NPC64234
0.8429	Intermediate Similarity	NPC37929
0.8406	Intermediate Similarity	NPC276290
0.8333	Intermediate Similarity	NPC474758
0.8289	Intermediate Similarity	NPC325031
0.8219	Intermediate Similarity	NPC329852
0.8169	Intermediate Similarity	NPC67183
0.8143	Intermediate Similarity	NPC218477
0.8133	Intermediate Similarity	NPC128276
0.8116	Intermediate Similarity	NPC191233
0.8082	Intermediate Similarity	NPC259599
0.8082	Intermediate Similarity	NPC15499
0.8082	Intermediate Similarity	NPC117746
0.8082	Intermediate Similarity	NPC294434
0.8052	Intermediate Similarity	NPC42470
0.8028	Intermediate Similarity	NPC470693
0.8026	Intermediate Similarity	NPC469617
0.8	Intermediate Similarity	NPC21998
0.8	Intermediate Similarity	NPC180290
0.8	Intermediate Similarity	NPC57744
0.7973	Intermediate Similarity	NPC244166
0.7971	Intermediate Similarity	NPC220766
0.7917	Intermediate Similarity	NPC469660
0.7895	Intermediate Similarity	NPC184737
0.7895	Intermediate Similarity	NPC471220
0.7875	Intermediate Similarity	NPC215364
0.7867	Intermediate Similarity	NPC123360
0.7867	Intermediate Similarity	NPC235906
0.7857	Intermediate Similarity	NPC116013
0.7838	Intermediate Similarity	NPC476355
0.7826	Intermediate Similarity	NPC34883
0.7821	Intermediate Similarity	NPC471325
0.7821	Intermediate Similarity	NPC59994
0.7821	Intermediate Similarity	NPC78677
0.7821	Intermediate Similarity	NPC141810
0.7808	Intermediate Similarity	NPC257618
0.7808	Intermediate Similarity	NPC163003
0.7792	Intermediate Similarity	NPC178277
0.7792	Intermediate Similarity	NPC617
0.7763	Intermediate Similarity	NPC54996
0.7763	Intermediate Similarity	NPC53581
0.7763	Intermediate Similarity	NPC41780
0.7763	Intermediate Similarity	NPC470240
0.7763	Intermediate Similarity	NPC187568
0.7763	Intermediate Similarity	NPC476794
0.7763	Intermediate Similarity	NPC103987
0.7763	Intermediate Similarity	NPC65603
0.7722	Intermediate Similarity	NPC35556
0.7722	Intermediate Similarity	NPC85772
0.7722	Intermediate Similarity	NPC474291
0.7722	Intermediate Similarity	NPC173609
0.7722	Intermediate Similarity	NPC200513
0.7703	Intermediate Similarity	NPC474705
0.7692	Intermediate Similarity	NPC47747
0.7683	Intermediate Similarity	NPC160138
0.7683	Intermediate Similarity	NPC475703
0.7681	Intermediate Similarity	NPC155849
0.7681	Intermediate Similarity	NPC217940
0.7671	Intermediate Similarity	NPC316029
0.7662	Intermediate Similarity	NPC63445
0.7662	Intermediate Similarity	NPC267231
0.7662	Intermediate Similarity	NPC299235
0.7662	Intermediate Similarity	NPC222210
0.7654	Intermediate Similarity	NPC261380
0.7654	Intermediate Similarity	NPC189311
0.7639	Intermediate Similarity	NPC470256
0.7632	Intermediate Similarity	NPC40353
0.7632	Intermediate Similarity	NPC473223
0.7632	Intermediate Similarity	NPC27205
0.7625	Intermediate Similarity	NPC193198
0.7625	Intermediate Similarity	NPC53867
0.7625	Intermediate Similarity	NPC250315
0.7625	Intermediate Similarity	NPC475947
0.7619	Intermediate Similarity	NPC473448
0.7606	Intermediate Similarity	NPC248125
0.76	Intermediate Similarity	NPC140287
0.7595	Intermediate Similarity	NPC112868
0.7595	Intermediate Similarity	NPC281949
0.7595	Intermediate Similarity	NPC301477
0.7595	Intermediate Similarity	NPC25684
0.759	Intermediate Similarity	NPC469631
0.759	Intermediate Similarity	NPC475906
0.759	Intermediate Similarity	NPC469653
0.759	Intermediate Similarity	NPC471047
0.759	Intermediate Similarity	NPC469628
0.7568	Intermediate Similarity	NPC84038
0.7568	Intermediate Similarity	NPC186531
0.7564	Intermediate Similarity	NPC264227
0.7564	Intermediate Similarity	NPC63649
0.7564	Intermediate Similarity	NPC472965
0.7561	Intermediate Similarity	NPC284902
0.7561	Intermediate Similarity	NPC261721
0.7561	Intermediate Similarity	NPC279859
0.7561	Intermediate Similarity	NPC38576
0.7534	Intermediate Similarity	NPC269841
0.7532	Intermediate Similarity	NPC122264
0.7532	Intermediate Similarity	NPC189206
0.7532	Intermediate Similarity	NPC476439
0.7532	Intermediate Similarity	NPC471225
0.7531	Intermediate Similarity	NPC82297
0.7531	Intermediate Similarity	NPC475100
0.7531	Intermediate Similarity	NPC196487
0.7531	Intermediate Similarity	NPC14575
0.7531	Intermediate Similarity	NPC30486
0.7531	Intermediate Similarity	NPC149869
0.75	Intermediate Similarity	NPC138408
0.75	Intermediate Similarity	NPC194871
0.75	Intermediate Similarity	NPC471326
0.75	Intermediate Similarity	NPC151919
0.75	Intermediate Similarity	NPC193351
0.75	Intermediate Similarity	NPC226669
0.75	Intermediate Similarity	NPC221231
0.75	Intermediate Similarity	NPC155587
0.747	Intermediate Similarity	NPC478145
0.747	Intermediate Similarity	NPC471657
0.747	Intermediate Similarity	NPC45957
0.7468	Intermediate Similarity	NPC302426
0.7468	Intermediate Similarity	NPC268827
0.7467	Intermediate Similarity	NPC287878
0.7467	Intermediate Similarity	NPC269206
0.7467	Intermediate Similarity	NPC58956
0.7467	Intermediate Similarity	NPC295633
0.7439	Intermediate Similarity	NPC106416
0.7439	Intermediate Similarity	NPC65661
0.7439	Intermediate Similarity	NPC474547
0.7439	Intermediate Similarity	NPC86316
0.7436	Intermediate Similarity	NPC253749
0.7436	Intermediate Similarity	NPC108816
0.7436	Intermediate Similarity	NPC474005
0.7436	Intermediate Similarity	NPC93763
0.7429	Intermediate Similarity	NPC179087
0.7429	Intermediate Similarity	NPC44343
0.7429	Intermediate Similarity	NPC210303
0.7407	Intermediate Similarity	NPC474193
0.7407	Intermediate Similarity	NPC474809
0.7407	Intermediate Similarity	NPC170286
0.7407	Intermediate Similarity	NPC39588
0.7407	Intermediate Similarity	NPC272814
0.7407	Intermediate Similarity	NPC170377
0.7407	Intermediate Similarity	NPC12283
0.7407	Intermediate Similarity	NPC30502
0.7403	Intermediate Similarity	NPC476317
0.7397	Intermediate Similarity	NPC313444
0.7397	Intermediate Similarity	NPC476614
0.7381	Intermediate Similarity	NPC260343
0.7381	Intermediate Similarity	NPC226863
0.7381	Intermediate Similarity	NPC475902
0.7368	Intermediate Similarity	NPC470686
0.7349	Intermediate Similarity	NPC234038
0.7349	Intermediate Similarity	NPC474045
0.7349	Intermediate Similarity	NPC50637
0.7349	Intermediate Similarity	NPC469483
0.7349	Intermediate Similarity	NPC261253
0.7349	Intermediate Similarity	NPC107787
0.7349	Intermediate Similarity	NPC204048
0.7349	Intermediate Similarity	NPC305475
0.7349	Intermediate Similarity	NPC475461
0.7344	Intermediate Similarity	NPC148056
0.7342	Intermediate Similarity	NPC470239
0.7342	Intermediate Similarity	NPC270126
0.7342	Intermediate Similarity	NPC150646
0.7342	Intermediate Similarity	NPC470244
0.7342	Intermediate Similarity	NPC182550
0.7342	Intermediate Similarity	NPC469690
0.7333	Intermediate Similarity	NPC477084
0.7333	Intermediate Similarity	NPC129665
0.7317	Intermediate Similarity	NPC474693
0.7317	Intermediate Similarity	NPC115786
0.7317	Intermediate Similarity	NPC238197
0.7317	Intermediate Similarity	NPC471301
0.7313	Intermediate Similarity	NPC96663
0.7308	Intermediate Similarity	NPC7563
0.7308	Intermediate Similarity	NPC473825
0.7308	Intermediate Similarity	NPC171204
0.7308	Intermediate Similarity	NPC320630
0.7308	Intermediate Similarity	NPC476028
0.7308	Intermediate Similarity	NPC97516
0.7308	Intermediate Similarity	NPC116177
0.7308	Intermediate Similarity	NPC141789
0.7308	Intermediate Similarity	NPC316324
0.7297	Intermediate Similarity	NPC475004
0.7297	Intermediate Similarity	NPC151481
0.7297	Intermediate Similarity	NPC101622
0.7294	Intermediate Similarity	NPC115179
0.7294	Intermediate Similarity	NPC64913
0.7294	Intermediate Similarity	NPC295312
0.7294	Intermediate Similarity	NPC166919
0.7294	Intermediate Similarity	NPC285982
0.7294	Intermediate Similarity	NPC242877
0.7294	Intermediate Similarity	NPC5509
0.7294	Intermediate Similarity	NPC212598
0.7294	Intermediate Similarity	NPC106040
0.7286	Intermediate Similarity	NPC151648
0.7284	Intermediate Similarity	NPC186276
0.7273	Intermediate Similarity	NPC329826
0.7273	Intermediate Similarity	NPC469414
0.7273	Intermediate Similarity	NPC68624

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 NPC265574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1882
0.2-0.3	4169
0.3-0.4	2098
0.4-0.5	575
0.5-0.6	212
0.6-0.7	29
0.7-0.8	3
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
0.7971	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5209	Approved
0.7229	Intermediate Similarity	NPD1694	Approved
0.7051	Intermediate Similarity	NPD8039	Approved
0.6824	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7838	Discovery
0.6742	Remote Similarity	NPD5693	Phase 1
0.6705	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6629	Remote Similarity	NPD5785	Approved
0.6628	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7154	Phase 3
0.6567	Remote Similarity	NPD6927	Phase 3
0.6522	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4225	Approved
0.6447	Remote Similarity	NPD7331	Phase 2
0.6444	Remote Similarity	NPD6698	Approved
0.6444	Remote Similarity	NPD46	Approved
0.6444	Remote Similarity	NPD5207	Approved
0.6437	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6404	Remote Similarity	NPD5208	Approved
0.6395	Remote Similarity	NPD5362	Discontinued
0.6374	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6351	Remote Similarity	NPD4193	Approved
0.6351	Remote Similarity	NPD4194	Approved
0.6351	Remote Similarity	NPD4192	Approved
0.6351	Remote Similarity	NPD4191	Approved
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6051	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.6324	Remote Similarity	NPD29	Approved
0.6324	Remote Similarity	NPD28	Approved
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7341	Phase 2
0.6316	Remote Similarity	NPD7638	Approved
0.6264	Remote Similarity	NPD5692	Phase 3
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6222	Remote Similarity	NPD5737	Approved
0.6222	Remote Similarity	NPD6903	Approved
0.6222	Remote Similarity	NPD6672	Approved
0.6222	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD5332	Approved
0.62	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6050	Approved
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD5344	Discontinued
0.618	Remote Similarity	NPD6098	Approved
0.618	Remote Similarity	NPD4519	Discontinued
0.618	Remote Similarity	NPD4623	Approved
0.6163	Remote Similarity	NPD4790	Discontinued
0.6163	Remote Similarity	NPD5369	Approved
0.6143	Remote Similarity	NPD3172	Approved
0.6139	Remote Similarity	NPD6686	Approved
0.6118	Remote Similarity	NPD4195	Approved
0.6092	Remote Similarity	NPD4270	Approved
0.6092	Remote Similarity	NPD6435	Approved
0.6092	Remote Similarity	NPD4269	Approved
0.6071	Remote Similarity	NPD4756	Discovery
0.6064	Remote Similarity	NPD6001	Approved
0.6061	Remote Similarity	NPD3174	Discontinued
0.6056	Remote Similarity	NPD3196	Approved
0.6056	Remote Similarity	NPD3194	Approved
0.6056	Remote Similarity	NPD3195	Phase 2
0.6056	Remote Similarity	NPD4266	Approved
0.6026	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5281	Approved
0.6022	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD6371	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5690	Phase 2
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5779	Approved
0.5957	Remote Similarity	NPD5778	Approved
0.5934	Remote Similarity	NPD4250	Approved
0.5934	Remote Similarity	NPD4251	Approved
0.5909	Remote Similarity	NPD4221	Approved
0.5909	Remote Similarity	NPD4223	Phase 3
0.5882	Remote Similarity	NPD5343	Approved
0.5876	Remote Similarity	NPD6083	Phase 2
0.5876	Remote Similarity	NPD6084	Phase 2
0.5862	Remote Similarity	NPD4695	Discontinued
0.5862	Remote Similarity	NPD5368	Approved
0.5862	Remote Similarity	NPD4252	Approved
0.5851	Remote Similarity	NPD7637	Suspended
0.5851	Remote Similarity	NPD7983	Approved
0.5842	Remote Similarity	NPD5909	Discontinued
0.5833	Remote Similarity	NPD5654	Approved
0.5833	Remote Similarity	NPD7115	Discovery
0.5816	Remote Similarity	NPD5696	Approved
0.5806	Remote Similarity	NPD6101	Approved
0.5806	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD3173	Approved
0.5797	Remote Similarity	NPD4220	Pre-registration
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1145	Discontinued
0.5778	Remote Similarity	NPD4197	Approved
0.5755	Remote Similarity	NPD6053	Discontinued
0.5743	Remote Similarity	NPD6647	Phase 2
0.5732	Remote Similarity	NPD4691	Approved
0.573	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7900	Approved
0.5729	Remote Similarity	NPD5282	Discontinued
0.5729	Remote Similarity	NPD7748	Approved
0.5729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5697	Approved
0.5728	Remote Similarity	NPD6614	Approved
0.5728	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2067	Discontinued
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD4058	Approved
0.5714	Remote Similarity	NPD5959	Approved
0.5699	Remote Similarity	NPD4518	Approved
0.5684	Remote Similarity	NPD6411	Approved
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.5673	Remote Similarity	NPD6011	Approved
0.5672	Remote Similarity	NPD6097	Approved
0.5672	Remote Similarity	NPD6096	Approved
0.566	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5926	Approved
0.5652	Remote Similarity	NPD5205	Approved
0.5652	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4688	Approved
0.5652	Remote Similarity	NPD4138	Approved
0.5652	Remote Similarity	NPD4694	Approved
0.5652	Remote Similarity	NPD4693	Phase 3
0.5652	Remote Similarity	NPD4689	Approved
0.5652	Remote Similarity	NPD4690	Approved
0.5652	Remote Similarity	NPD5280	Approved
0.5644	Remote Similarity	NPD7632	Discontinued
0.5641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5370	Suspended
0.5631	Remote Similarity	NPD4211	Phase 1
0.5625	Remote Similarity	NPD6399	Phase 3
0.5619	Remote Similarity	NPD6012	Approved
0.5619	Remote Similarity	NPD6014	Approved
0.5619	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6013	Approved
0.5618	Remote Similarity	NPD857	Phase 3
0.5612	Remote Similarity	NPD7839	Suspended
0.561	Remote Similarity	NPD4137	Phase 3
0.5604	Remote Similarity	NPD3666	Approved
0.5604	Remote Similarity	NPD3133	Approved
0.5604	Remote Similarity	NPD3665	Phase 1
0.56	Remote Similarity	NPD6404	Discontinued

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