NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	275.448
LogP:	2.487
LogD:	2.599
LogS:	-3.744
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	4.962
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.658
MDCK Permeability:	2.871787546609994e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.509

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	90.62450408935547%
Volume Distribution (VD):	1.304
Pgp-substrate:	9.442110061645508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.459
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.221
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	5.125
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.453
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.427
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.301
Carcinogencity:	0.955
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC474353

Natural Product ID:	NPC474353
*Common Name:**	Conidione
IUPAC Name:	3,3,6-trimethylspiro[3a,4,5,7a-tetrahydro-2-benzofuran-1,5'-cyclohex-2-ene]-1',4'-dione
Synonyms:	Conidione
Standard InCHIKey:	GZXIEHLFGFWNKB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-10-4-6-12-13(8-10)16(19-15(12,2)3)9-11(17)5-7-14(16)18/h5,7-8,12-13H,4,6,9H2,1-3H3
SMILES:	CC1=CC2C(CC1)C(OC12CC(=O)C=CC1=O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465568
PubChem CID:	22297512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO33101	aplidium aff. densum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180826]

☑ 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	1
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10000000.0	nM	PMID[571438]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	2000000.0	nM	PMID[571438]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	2000000.0	nM	PMID[571438]

☑ 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 NPC474353 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	210
0.1-0.2	1479
0.2-0.3	8026
0.3-0.4	15177
0.4-0.5	10239
0.5-0.6	5571
0.6-0.7	1928
0.7-0.8	66
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7841	Intermediate Similarity	NPC241507
0.7647	Intermediate Similarity	NPC474085
0.764	Intermediate Similarity	NPC269677
0.7527	Intermediate Similarity	NPC31021
0.75	Intermediate Similarity	NPC478246
0.75	Intermediate Similarity	NPC133652
0.75	Intermediate Similarity	NPC478247
0.7473	Intermediate Similarity	NPC223093
0.7444	Intermediate Similarity	NPC469653
0.7444	Intermediate Similarity	NPC469631
0.7444	Intermediate Similarity	NPC471047
0.7444	Intermediate Similarity	NPC469628
0.7444	Intermediate Similarity	NPC475906
0.7442	Intermediate Similarity	NPC286229
0.7412	Intermediate Similarity	NPC471740
0.7386	Intermediate Similarity	NPC469569
0.7375	Intermediate Similarity	NPC469914
0.7333	Intermediate Similarity	NPC471739
0.7326	Intermediate Similarity	NPC108955
0.7308	Intermediate Similarity	NPC251118
0.7303	Intermediate Similarity	NPC132228
0.7303	Intermediate Similarity	NPC8518
0.7303	Intermediate Similarity	NPC96621
0.7303	Intermediate Similarity	NPC263997
0.7294	Intermediate Similarity	NPC207772
0.7263	Intermediate Similarity	NPC318082
0.7241	Intermediate Similarity	NPC55869
0.7241	Intermediate Similarity	NPC475833
0.7222	Intermediate Similarity	NPC38576
0.7222	Intermediate Similarity	NPC279859
0.7215	Intermediate Similarity	NPC16119
0.7204	Intermediate Similarity	NPC193396
0.7204	Intermediate Similarity	NPC32944
0.7204	Intermediate Similarity	NPC166110
0.7179	Intermediate Similarity	NPC34622
0.7179	Intermediate Similarity	NPC474400
0.7176	Intermediate Similarity	NPC283087
0.7172	Intermediate Similarity	NPC271059
0.7172	Intermediate Similarity	NPC25666
0.716	Intermediate Similarity	NPC256846
0.716	Intermediate Similarity	NPC477449
0.716	Intermediate Similarity	NPC477448
0.7159	Intermediate Similarity	NPC70479
0.7143	Intermediate Similarity	NPC469851
0.7143	Intermediate Similarity	NPC30421
0.7143	Intermediate Similarity	NPC38885
0.7128	Intermediate Similarity	NPC248193
0.7125	Intermediate Similarity	NPC474619
0.7111	Intermediate Similarity	NPC290329
0.7111	Intermediate Similarity	NPC472686
0.7111	Intermediate Similarity	NPC241512
0.7111	Intermediate Similarity	NPC33663
0.7111	Intermediate Similarity	NPC6185
0.7093	Intermediate Similarity	NPC474056
0.7093	Intermediate Similarity	NPC478122
0.7089	Intermediate Similarity	NPC98897
0.7065	Intermediate Similarity	NPC478259
0.7065	Intermediate Similarity	NPC478261
0.7065	Intermediate Similarity	NPC475902
0.7065	Intermediate Similarity	NPC478260
0.7059	Intermediate Similarity	NPC239758
0.7059	Intermediate Similarity	NPC1254
0.7059	Intermediate Similarity	NPC40353
0.7053	Intermediate Similarity	NPC469632
0.7051	Intermediate Similarity	NPC57463
0.7051	Intermediate Similarity	NPC151728
0.7045	Intermediate Similarity	NPC116797
0.7045	Intermediate Similarity	NPC478262
0.7045	Intermediate Similarity	NPC225515
0.7037	Intermediate Similarity	NPC260474
0.7037	Intermediate Similarity	NPC87141
0.7037	Intermediate Similarity	NPC188292
0.7033	Intermediate Similarity	NPC472863
0.7033	Intermediate Similarity	NPC470345
0.7024	Intermediate Similarity	NPC264178
0.7021	Intermediate Similarity	NPC20713
0.7021	Intermediate Similarity	NPC26865
0.7011	Intermediate Similarity	NPC276647
0.7011	Intermediate Similarity	NPC27817
0.7011	Intermediate Similarity	NPC622
0.7	Intermediate Similarity	NPC197089
0.7	Intermediate Similarity	NPC474330
0.7	Intermediate Similarity	NPC32565
0.7	Intermediate Similarity	NPC475796
0.7	Intermediate Similarity	NPC120726
0.7	Intermediate Similarity	NPC90446
0.7	Intermediate Similarity	NPC474207
0.6989	Remote Similarity	NPC142159
0.6989	Remote Similarity	NPC95364
0.6989	Remote Similarity	NPC305039
0.6979	Remote Similarity	NPC279313
0.6977	Remote Similarity	NPC180290
0.6966	Remote Similarity	NPC186276
0.6966	Remote Similarity	NPC470813
0.6951	Remote Similarity	NPC261398
0.6951	Remote Similarity	NPC199557
0.6951	Remote Similarity	NPC474060
0.6951	Remote Similarity	NPC262673
0.6939	Remote Similarity	NPC54843
0.6932	Remote Similarity	NPC476809
0.6932	Remote Similarity	NPC223904
0.6932	Remote Similarity	NPC304795
0.6931	Remote Similarity	NPC13385
0.6923	Remote Similarity	NPC125290
0.6923	Remote Similarity	NPC70685
0.6923	Remote Similarity	NPC469993
0.6915	Remote Similarity	NPC152467
0.6915	Remote Similarity	NPC280592
0.6915	Remote Similarity	NPC253177
0.6915	Remote Similarity	NPC213636
0.6915	Remote Similarity	NPC129913
0.6907	Remote Similarity	NPC476275
0.6907	Remote Similarity	NPC272411
0.6907	Remote Similarity	NPC472733
0.6907	Remote Similarity	NPC472734
0.6905	Remote Similarity	NPC472956
0.69	Remote Similarity	NPC308351
0.69	Remote Similarity	NPC271266
0.6897	Remote Similarity	NPC189485
0.6897	Remote Similarity	NPC74410
0.6897	Remote Similarity	NPC23778
0.6897	Remote Similarity	NPC275494
0.6897	Remote Similarity	NPC471409
0.6897	Remote Similarity	NPC469996
0.6889	Remote Similarity	NPC39588
0.6882	Remote Similarity	NPC215831
0.6882	Remote Similarity	NPC58271
0.6875	Remote Similarity	NPC61473
0.6875	Remote Similarity	NPC148463
0.6869	Remote Similarity	NPC46761
0.6869	Remote Similarity	NPC174314
0.6867	Remote Similarity	NPC291062
0.6867	Remote Similarity	NPC94743
0.6863	Remote Similarity	NPC469852
0.6863	Remote Similarity	NPC470267
0.686	Remote Similarity	NPC76966
0.686	Remote Similarity	NPC472967
0.686	Remote Similarity	NPC110725
0.686	Remote Similarity	NPC26504
0.686	Remote Similarity	NPC470525
0.686	Remote Similarity	NPC186554
0.686	Remote Similarity	NPC472959
0.686	Remote Similarity	NPC266159
0.686	Remote Similarity	NPC92080
0.6854	Remote Similarity	NPC44963
0.6854	Remote Similarity	NPC99308
0.6854	Remote Similarity	NPC275766
0.6854	Remote Similarity	NPC189237
0.6854	Remote Similarity	NPC119229
0.6854	Remote Similarity	NPC149237
0.6854	Remote Similarity	NPC472684
0.6848	Remote Similarity	NPC220478
0.6848	Remote Similarity	NPC70555
0.6848	Remote Similarity	NPC194417
0.6848	Remote Similarity	NPC70422
0.6848	Remote Similarity	NPC104961
0.6848	Remote Similarity	NPC203795
0.6848	Remote Similarity	NPC470346
0.6848	Remote Similarity	NPC261721
0.6842	Remote Similarity	NPC74103
0.6842	Remote Similarity	NPC111114
0.6842	Remote Similarity	NPC45579
0.6842	Remote Similarity	NPC123177
0.6842	Remote Similarity	NPC218301
0.6842	Remote Similarity	NPC150978
0.6842	Remote Similarity	NPC144629
0.6842	Remote Similarity	NPC471329
0.6842	Remote Similarity	NPC300312
0.6842	Remote Similarity	NPC172101
0.6842	Remote Similarity	NPC261607
0.6842	Remote Similarity	NPC296114
0.6842	Remote Similarity	NPC70595
0.6837	Remote Similarity	NPC472731
0.6837	Remote Similarity	NPC472732
0.6837	Remote Similarity	NPC27105
0.6835	Remote Similarity	NPC477830
0.6835	Remote Similarity	NPC288253
0.6832	Remote Similarity	NPC475873
0.6832	Remote Similarity	NPC131366
0.6832	Remote Similarity	NPC230918
0.6832	Remote Similarity	NPC470954
0.6829	Remote Similarity	NPC476614
0.6829	Remote Similarity	NPC134385
0.6827	Remote Similarity	NPC250018
0.6827	Remote Similarity	NPC220705
0.6824	Remote Similarity	NPC167049
0.6824	Remote Similarity	NPC469691
0.6824	Remote Similarity	NPC122244
0.6818	Remote Similarity	NPC476177
0.6818	Remote Similarity	NPC469617
0.6813	Remote Similarity	NPC469884
0.6813	Remote Similarity	NPC144258
0.6809	Remote Similarity	NPC280833
0.6809	Remote Similarity	NPC473039
0.6809	Remote Similarity	NPC173042
0.6809	Remote Similarity	NPC73995
0.6804	Remote Similarity	NPC474490
0.6804	Remote Similarity	NPC91408
0.68	Remote Similarity	NPC270155
0.68	Remote Similarity	NPC128733

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 NPC474353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1979
0.2-0.3	4249
0.3-0.4	1932
0.4-0.5	483
0.5-0.6	170
0.6-0.7	137
0.7-0.8	4
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
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7215	Intermediate Similarity	NPD7331	Phase 2
0.7215	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7097	Intermediate Similarity	NPD5692	Phase 3
0.7021	Intermediate Similarity	NPD6050	Approved
0.6989	Remote Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6904	Approved
0.6989	Remote Similarity	NPD6673	Approved
0.6932	Remote Similarity	NPD4695	Discontinued
0.6915	Remote Similarity	NPD5207	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD5282	Discontinued
0.6875	Remote Similarity	NPD7341	Phase 2
0.6848	Remote Similarity	NPD6098	Approved
0.6848	Remote Similarity	NPD4694	Approved
0.6848	Remote Similarity	NPD5280	Approved
0.6842	Remote Similarity	NPD5693	Phase 1
0.6813	Remote Similarity	NPD4197	Approved
0.6804	Remote Similarity	NPD5695	Phase 3
0.6739	Remote Similarity	NPD1694	Approved
0.6739	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4691	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD5654	Approved
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.6628	Remote Similarity	NPD4687	Approved
0.6628	Remote Similarity	NPD4058	Approved
0.6625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4223	Phase 3
0.6593	Remote Similarity	NPD4221	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5221	Approved
0.6548	Remote Similarity	NPD4137	Phase 3
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6535	Remote Similarity	NPD4696	Approved
0.6535	Remote Similarity	NPD5286	Approved
0.6535	Remote Similarity	NPD5285	Approved
0.6526	Remote Similarity	NPD4518	Approved
0.6526	Remote Similarity	NPD5208	Approved
0.6517	Remote Similarity	NPD3617	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD5959	Approved
0.65	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD6079	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD5279	Phase 3
0.6489	Remote Similarity	NPD4519	Discontinued
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD7146	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD4623	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD4747	Approved
0.6465	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4629	Approved
0.6465	Remote Similarity	NPD5210	Approved
0.6458	Remote Similarity	NPD4753	Phase 2
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6437	Remote Similarity	NPD5733	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5224	Approved
0.6408	Remote Similarity	NPD4633	Approved
0.6408	Remote Similarity	NPD5211	Phase 2
0.6408	Remote Similarity	NPD5225	Approved
0.6408	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD4697	Phase 3
0.6395	Remote Similarity	NPD5276	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6617	Approved
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD6001	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6354	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6903	Approved
0.6346	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD4755	Approved
0.633	Remote Similarity	NPD8297	Approved
0.633	Remote Similarity	NPD6882	Approved
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD5281	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD6614	Approved
0.6316	Remote Similarity	NPD4688	Approved
0.6316	Remote Similarity	NPD6015	Approved
0.6316	Remote Similarity	NPD4693	Phase 3
0.6316	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD4690	Approved
0.6316	Remote Similarity	NPD5205	Approved
0.6316	Remote Similarity	NPD6016	Approved
0.6316	Remote Similarity	NPD4138	Approved
0.6316	Remote Similarity	NPD5786	Approved
0.6304	Remote Similarity	NPD5369	Approved
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4634	Approved
0.6289	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5328	Approved
0.6286	Remote Similarity	NPD5141	Approved
0.6277	Remote Similarity	NPD3133	Approved
0.6277	Remote Similarity	NPD3666	Approved
0.6277	Remote Similarity	NPD3665	Phase 1
0.6264	Remote Similarity	NPD4195	Approved
0.6263	Remote Similarity	NPD5133	Approved
0.6262	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD5988	Approved
0.6261	Remote Similarity	NPD6370	Approved
0.6237	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3667	Approved
0.6228	Remote Similarity	NPD6319	Approved
0.6226	Remote Similarity	NPD6008	Approved
0.6222	Remote Similarity	NPD4756	Discovery
0.6214	Remote Similarity	NPD4700	Approved
0.6211	Remote Similarity	NPD5363	Approved
0.6211	Remote Similarity	NPD1696	Phase 3
0.6211	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3704	Approved
0.617	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7492	Approved
0.6146	Remote Similarity	NPD3618	Phase 1
0.6111	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD4730	Approved
0.6106	Remote Similarity	NPD6317	Approved
0.6105	Remote Similarity	NPD4786	Approved
0.6105	Remote Similarity	NPD3668	Phase 3
0.6102	Remote Similarity	NPD6616	Approved
0.61	Remote Similarity	NPD6399	Phase 3
0.6095	Remote Similarity	NPD5091	Approved
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6059	Approved
0.6064	Remote Similarity	NPD6435	Approved
0.6064	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD4096	Approved
0.6061	Remote Similarity	NPD5785	Approved
0.6053	Remote Similarity	NPD6335	Approved
0.6053	Remote Similarity	NPD6314	Approved
0.6053	Remote Similarity	NPD6313	Approved
0.605	Remote Similarity	NPD7078	Approved
0.6047	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7900	Approved
0.604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4754	Approved
0.6018	Remote Similarity	NPD6274	Approved
0.6018	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD5169	Approved
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5247	Approved
0.5982	Remote Similarity	NPD4632	Approved
0.5965	Remote Similarity	NPD6009	Approved
0.5963	Remote Similarity	NPD5168	Approved
0.5963	Remote Similarity	NPD5128	Approved
0.5957	Remote Similarity	NPD4692	Approved
0.5957	Remote Similarity	NPD4139	Approved
0.5946	Remote Similarity	NPD5217	Approved
0.5946	Remote Similarity	NPD5215	Approved
0.5946	Remote Similarity	NPD5127	Approved
0.5946	Remote Similarity	NPD5216	Approved
0.5941	Remote Similarity	NPD4202	Approved
0.5926	Remote Similarity	NPD287	Approved
0.5926	Remote Similarity	NPD4768	Approved
0.5926	Remote Similarity	NPD4767	Approved
0.5922	Remote Similarity	NPD7732	Phase 3
0.5897	Remote Similarity	NPD6291	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