NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	2.424
LogD:	2.491
LogS:	-3.221
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.461
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.64
MDCK Permeability:	4.400328180054203e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.847
Plasma Protein Binding (PPB):	51.868011474609375%
Volume Distribution (VD):	1.015
Pgp-substrate:	59.62814712524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.427

ADMET: Excretion

Clearance (CL):	7.582
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.969
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.732
Carcinogencity:	0.968
Eye Corrosion:	0.204
Eye Irritation:	0.181
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC258532

Natural Product ID:	NPC258532
*Common Name:**	Strobilactone A
IUPAC Name:	(5R,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-3,5,5a,7,8,9-hexahydrobenzo[g][2]benzofuran-1-one
Synonyms:	Strobilactone A
Standard InCHIKey:	ITJIJDWFGMAIKB-PKIAMQTDSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-8-19-12(17)15(9,14)18/h7,10-11,16,18H,4-6,8H2,1-3H3/t10-,11+,14+,15+/m1/s1
SMILES:	O[C@@H]1C=C2COC(=O)[C@@]2([C@@]2([C@@H]1C(C)(C)CCC2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915268
PubChem CID:	23955806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719247]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	Mediterranean sponge Psammocinia sp.	coast of Israel	n.a.	PMID[21676619]
NPO11252	Jacobaea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6436	Euryops virgineus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11252	Jacobaea alpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20001	Aspergillus insuetus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9796	Helipterum sterilescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1342	Premna japonica	Species	Lamiaceae	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	1
MIC	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3644	Organism	Neurospora crassa	Neurospora crassa	MIC	=	242000.0	nM	PMID[475878]
NPT2	Others	Unspecified		IC50	=	19800.0	nM	PMID[475879]

☑ 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 NPC258532 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	1088
0.2-0.3	3831
0.3-0.4	6943
0.4-0.5	13594
0.5-0.6	7209
0.6-0.7	6728
0.7-0.8	2927
0.8-0.85	155
0.85-0.9	22
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC5103
0.9231	High Similarity	NPC469454
0.9231	High Similarity	NPC469496
0.9231	High Similarity	NPC469463
0.9223	High Similarity	NPC304180
0.9223	High Similarity	NPC179798
0.9048	High Similarity	NPC56448
0.901	High Similarity	NPC296950
0.8846	High Similarity	NPC141350
0.8824	High Similarity	NPC146731
0.8796	High Similarity	NPC23046
0.8796	High Similarity	NPC473590
0.8774	High Similarity	NPC126691
0.8704	High Similarity	NPC474734
0.8704	High Similarity	NPC179626
0.87	High Similarity	NPC23364
0.8673	High Similarity	NPC250075
0.8654	High Similarity	NPC230541
0.8627	High Similarity	NPC295791
0.8624	High Similarity	NPC470775
0.8624	High Similarity	NPC176513
0.8598	High Similarity	NPC269530
0.8598	High Similarity	NPC302146
0.8585	High Similarity	NPC235014
0.8558	High Similarity	NPC477125
0.8545	High Similarity	NPC470776
0.8544	High Similarity	NPC474775
0.8532	High Similarity	NPC474046
0.8532	High Similarity	NPC259306
0.8532	High Similarity	NPC470628
0.8515	High Similarity	NPC216478
0.8505	High Similarity	NPC475668
0.8505	High Similarity	NPC475480
0.8505	High Similarity	NPC473921
0.8496	Intermediate Similarity	NPC67251
0.8491	Intermediate Similarity	NPC472534
0.8491	Intermediate Similarity	NPC42662
0.8491	Intermediate Similarity	NPC143706
0.8476	Intermediate Similarity	NPC67321
0.8476	Intermediate Similarity	NPC187435
0.8476	Intermediate Similarity	NPC112780
0.8476	Intermediate Similarity	NPC3316
0.8476	Intermediate Similarity	NPC144854
0.8462	Intermediate Similarity	NPC220964
0.8462	Intermediate Similarity	NPC475676
0.8455	Intermediate Similarity	NPC469684
0.844	Intermediate Similarity	NPC469877
0.844	Intermediate Similarity	NPC470919
0.844	Intermediate Similarity	NPC117712
0.8426	Intermediate Similarity	NPC472002
0.8411	Intermediate Similarity	NPC161816
0.8411	Intermediate Similarity	NPC475563
0.8411	Intermediate Similarity	NPC475134
0.8411	Intermediate Similarity	NPC115257
0.8407	Intermediate Similarity	NPC473231
0.8396	Intermediate Similarity	NPC476479
0.8396	Intermediate Similarity	NPC277017
0.8396	Intermediate Similarity	NPC154608
0.8396	Intermediate Similarity	NPC192813
0.8384	Intermediate Similarity	NPC475912
0.8381	Intermediate Similarity	NPC127609
0.8381	Intermediate Similarity	NPC469607
0.8365	Intermediate Similarity	NPC474165
0.8365	Intermediate Similarity	NPC4620
0.8365	Intermediate Similarity	NPC159533
0.8365	Intermediate Similarity	NPC475321
0.8365	Intermediate Similarity	NPC69171
0.8349	Intermediate Similarity	NPC51978
0.8349	Intermediate Similarity	NPC49451
0.8333	Intermediate Similarity	NPC469656
0.8333	Intermediate Similarity	NPC222303
0.8333	Intermediate Similarity	NPC188738
0.8333	Intermediate Similarity	NPC317107
0.8333	Intermediate Similarity	NPC469655
0.8333	Intermediate Similarity	NPC474846
0.8319	Intermediate Similarity	NPC473250
0.8318	Intermediate Similarity	NPC475922
0.8304	Intermediate Similarity	NPC476529
0.8304	Intermediate Similarity	NPC475775
0.8302	Intermediate Similarity	NPC475176
0.8302	Intermediate Similarity	NPC59530
0.8288	Intermediate Similarity	NPC53396
0.8288	Intermediate Similarity	NPC98249
0.8288	Intermediate Similarity	NPC473968
0.8288	Intermediate Similarity	NPC476713
0.8288	Intermediate Similarity	NPC476712
0.8286	Intermediate Similarity	NPC470104
0.8269	Intermediate Similarity	NPC183571
0.8261	Intermediate Similarity	NPC476729
0.8261	Intermediate Similarity	NPC470922
0.8261	Intermediate Similarity	NPC24651
0.8257	Intermediate Similarity	NPC317687
0.8257	Intermediate Similarity	NPC474516
0.8257	Intermediate Similarity	NPC473877
0.8246	Intermediate Similarity	NPC312833
0.8241	Intermediate Similarity	NPC210005
0.8241	Intermediate Similarity	NPC478211
0.823	Intermediate Similarity	NPC109607
0.823	Intermediate Similarity	NPC107338
0.8224	Intermediate Similarity	NPC474664
0.8224	Intermediate Similarity	NPC306265
0.8224	Intermediate Similarity	NPC233379
0.8224	Intermediate Similarity	NPC14862
0.8224	Intermediate Similarity	NPC275539
0.8224	Intermediate Similarity	NPC189075
0.8218	Intermediate Similarity	NPC270013
0.8218	Intermediate Similarity	NPC14961
0.8218	Intermediate Similarity	NPC36954
0.8214	Intermediate Similarity	NPC284707
0.8214	Intermediate Similarity	NPC251310
0.8208	Intermediate Similarity	NPC284365
0.8208	Intermediate Similarity	NPC173172
0.8208	Intermediate Similarity	NPC475414
0.8208	Intermediate Similarity	NPC123726
0.8208	Intermediate Similarity	NPC102352
0.82	Intermediate Similarity	NPC147272
0.8198	Intermediate Similarity	NPC478216
0.8198	Intermediate Similarity	NPC328374
0.8198	Intermediate Similarity	NPC270478
0.8198	Intermediate Similarity	NPC476711
0.8198	Intermediate Similarity	NPC207217
0.8198	Intermediate Similarity	NPC251236
0.8198	Intermediate Similarity	NPC96312
0.8198	Intermediate Similarity	NPC476710
0.8198	Intermediate Similarity	NPC40632
0.819	Intermediate Similarity	NPC99266
0.8182	Intermediate Similarity	NPC15059
0.8182	Intermediate Similarity	NPC471204
0.8182	Intermediate Similarity	NPC25909
0.8182	Intermediate Similarity	NPC472307
0.8174	Intermediate Similarity	NPC91693
0.8174	Intermediate Similarity	NPC265557
0.8174	Intermediate Similarity	NPC105926
0.8174	Intermediate Similarity	NPC18945
0.8165	Intermediate Similarity	NPC247031
0.8165	Intermediate Similarity	NPC97939
0.8165	Intermediate Similarity	NPC201992
0.8165	Intermediate Similarity	NPC132790
0.8165	Intermediate Similarity	NPC100329
0.8155	Intermediate Similarity	NPC212465
0.8155	Intermediate Similarity	NPC177232
0.8148	Intermediate Similarity	NPC173905
0.8148	Intermediate Similarity	NPC469370
0.8148	Intermediate Similarity	NPC5475
0.8148	Intermediate Similarity	NPC15218
0.8148	Intermediate Similarity	NPC472216
0.8148	Intermediate Similarity	NPC284828
0.8142	Intermediate Similarity	NPC122971
0.8142	Intermediate Similarity	NPC475041
0.8137	Intermediate Similarity	NPC469528
0.8137	Intermediate Similarity	NPC469369
0.8131	Intermediate Similarity	NPC324327
0.8131	Intermediate Similarity	NPC326994
0.8131	Intermediate Similarity	NPC72813
0.8131	Intermediate Similarity	NPC131665
0.8131	Intermediate Similarity	NPC255387
0.8131	Intermediate Similarity	NPC194620
0.8131	Intermediate Similarity	NPC110496
0.8131	Intermediate Similarity	NPC143609
0.8131	Intermediate Similarity	NPC474421
0.8125	Intermediate Similarity	NPC470854
0.8125	Intermediate Similarity	NPC58662
0.8125	Intermediate Similarity	NPC13713
0.8125	Intermediate Similarity	NPC287343
0.8125	Intermediate Similarity	NPC97908
0.8125	Intermediate Similarity	NPC122033
0.8125	Intermediate Similarity	NPC474654
0.812	Intermediate Similarity	NPC470780
0.8119	Intermediate Similarity	NPC81386
0.8119	Intermediate Similarity	NPC474035
0.8119	Intermediate Similarity	NPC196227
0.8113	Intermediate Similarity	NPC471293
0.8108	Intermediate Similarity	NPC474181
0.8108	Intermediate Similarity	NPC178289
0.8108	Intermediate Similarity	NPC473798
0.8108	Intermediate Similarity	NPC181145
0.81	Intermediate Similarity	NPC30515
0.81	Intermediate Similarity	NPC184463
0.81	Intermediate Similarity	NPC186363
0.81	Intermediate Similarity	NPC208839
0.81	Intermediate Similarity	NPC233345
0.8095	Intermediate Similarity	NPC469606
0.8095	Intermediate Similarity	NPC235369
0.8095	Intermediate Similarity	NPC137430
0.8095	Intermediate Similarity	NPC273005
0.8095	Intermediate Similarity	NPC476081
0.8095	Intermediate Similarity	NPC31058
0.8091	Intermediate Similarity	NPC236217
0.8091	Intermediate Similarity	NPC289312
0.8091	Intermediate Similarity	NPC11252
0.8087	Intermediate Similarity	NPC222688
0.8077	Intermediate Similarity	NPC472644
0.8077	Intermediate Similarity	NPC47024
0.8073	Intermediate Similarity	NPC83005
0.8073	Intermediate Similarity	NPC253906
0.807	Intermediate Similarity	NPC112038
0.8058	Intermediate Similarity	NPC91695
0.8058	Intermediate Similarity	NPC70145
0.8058	Intermediate Similarity	NPC254496
0.8056	Intermediate Similarity	NPC322903

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 NPC258532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1403
0.2-0.3	3591
0.3-0.4	2506
0.4-0.5	883
0.5-0.6	333
0.6-0.7	223
0.7-0.8	55
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
0.781	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD4632	Approved
0.7522	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD6319	Approved
0.7434	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7395	Intermediate Similarity	NPD8513	Phase 3
0.7395	Intermediate Similarity	NPD8516	Approved
0.7395	Intermediate Similarity	NPD8517	Approved
0.7395	Intermediate Similarity	NPD8515	Approved
0.7387	Intermediate Similarity	NPD7128	Approved
0.7387	Intermediate Similarity	NPD6675	Approved
0.7387	Intermediate Similarity	NPD6402	Approved
0.7387	Intermediate Similarity	NPD5739	Approved
0.7345	Intermediate Similarity	NPD6373	Approved
0.7345	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD5778	Approved
0.7333	Intermediate Similarity	NPD5779	Approved
0.7321	Intermediate Similarity	NPD5701	Approved
0.7321	Intermediate Similarity	NPD5697	Approved
0.7321	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7638	Approved
0.7308	Intermediate Similarity	NPD46	Approved
0.7308	Intermediate Similarity	NPD6698	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7304	Intermediate Similarity	NPD8297	Approved
0.7295	Intermediate Similarity	NPD7507	Approved
0.7281	Intermediate Similarity	NPD6371	Approved
0.7257	Intermediate Similarity	NPD7320	Approved
0.7257	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD6881	Approved
0.7238	Intermediate Similarity	NPD7983	Approved
0.7232	Intermediate Similarity	NPD6008	Approved
0.7217	Intermediate Similarity	NPD6649	Approved
0.7217	Intermediate Similarity	NPD6650	Approved
0.7213	Intermediate Similarity	NPD7492	Approved
0.7203	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6009	Approved
0.7196	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6014	Approved
0.7193	Intermediate Similarity	NPD6012	Approved
0.7193	Intermediate Similarity	NPD6013	Approved
0.717	Intermediate Similarity	NPD6399	Phase 3
0.7168	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6054	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7157	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7117	Intermediate Similarity	NPD5211	Phase 2
0.7107	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD6015	Approved
0.7105	Intermediate Similarity	NPD6011	Approved
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7097	Intermediate Similarity	NPD8074	Phase 3
0.7097	Intermediate Similarity	NPD7078	Approved
0.7069	Intermediate Similarity	NPD8130	Phase 1
0.7069	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD6617	Approved
0.7069	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7064	Intermediate Similarity	NPD4755	Approved
0.7049	Intermediate Similarity	NPD5988	Approved
0.7049	Intermediate Similarity	NPD6370	Approved
0.704	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD5695	Phase 3
0.7027	Intermediate Similarity	NPD5344	Discontinued
0.7018	Intermediate Similarity	NPD6412	Phase 2
0.7009	Intermediate Similarity	NPD6882	Approved
0.7008	Intermediate Similarity	NPD7260	Phase 2
0.7	Intermediate Similarity	NPD5696	Approved
0.6992	Remote Similarity	NPD7604	Phase 2
0.6991	Remote Similarity	NPD5141	Approved
0.6983	Remote Similarity	NPD4634	Approved
0.6967	Remote Similarity	NPD6921	Approved
0.6944	Remote Similarity	NPD5282	Discontinued
0.6937	Remote Similarity	NPD5286	Approved
0.6937	Remote Similarity	NPD4700	Approved
0.6937	Remote Similarity	NPD4696	Approved
0.6937	Remote Similarity	NPD5285	Approved
0.6923	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6411	Approved
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6336	Discontinued
0.6863	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6274	Approved
0.6822	Remote Similarity	NPD6845	Suspended
0.6818	Remote Similarity	NPD4697	Phase 3
0.6814	Remote Similarity	NPD5224	Approved
0.6814	Remote Similarity	NPD7632	Discontinued
0.6814	Remote Similarity	NPD5225	Approved
0.6814	Remote Similarity	NPD5226	Approved
0.6814	Remote Similarity	NPD4633	Approved
0.6807	Remote Similarity	NPD8133	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6759	Remote Similarity	NPD5693	Phase 1
0.6757	Remote Similarity	NPD7902	Approved
0.6754	Remote Similarity	NPD5174	Approved
0.6754	Remote Similarity	NPD5175	Approved
0.6729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6101	Approved
0.6729	Remote Similarity	NPD4753	Phase 2
0.6729	Remote Similarity	NPD1695	Approved
0.6726	Remote Similarity	NPD5223	Approved
0.6721	Remote Similarity	NPD7328	Approved
0.6721	Remote Similarity	NPD7327	Approved
0.6699	Remote Similarity	NPD3667	Approved
0.6698	Remote Similarity	NPD7524	Approved
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD8033	Approved
0.6694	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6641	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD6317	Approved
0.6638	Remote Similarity	NPD4767	Approved
0.6638	Remote Similarity	NPD4768	Approved
0.6637	Remote Similarity	NPD6648	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6672	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6613	Remote Similarity	NPD8377	Approved
0.6613	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD4754	Approved
0.6607	Remote Similarity	NPD5173	Approved
0.6606	Remote Similarity	NPD7515	Phase 2
0.6604	Remote Similarity	NPD4249	Approved
0.6604	Remote Similarity	NPD3618	Phase 1
0.6585	Remote Similarity	NPD6335	Approved
0.6585	Remote Similarity	NPD6314	Approved
0.6585	Remote Similarity	NPD6313	Approved
0.6577	Remote Similarity	NPD5210	Approved
0.6577	Remote Similarity	NPD4629	Approved
0.6574	Remote Similarity	NPD5328	Approved
0.6571	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4786	Approved
0.656	Remote Similarity	NPD8380	Approved
0.656	Remote Similarity	NPD8379	Approved
0.656	Remote Similarity	NPD6908	Approved
0.656	Remote Similarity	NPD8335	Approved
0.656	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD8296	Approved
0.656	Remote Similarity	NPD8378	Approved
0.6542	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD4250	Approved
0.6525	Remote Similarity	NPD4730	Approved
0.6525	Remote Similarity	NPD5128	Approved
0.6525	Remote Similarity	NPD4729	Approved
0.6514	Remote Similarity	NPD5785	Approved
0.6493	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7900	Approved
0.6486	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7154	Phase 3
0.6476	Remote Similarity	NPD6695	Phase 3
0.6476	Remote Similarity	NPD6110	Phase 1
0.6455	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD8034	Phase 2
0.6455	Remote Similarity	NPD5281	Approved
0.6455	Remote Similarity	NPD5284	Approved
0.6455	Remote Similarity	NPD6079	Approved
0.6449	Remote Similarity	NPD5330	Approved
0.6449	Remote Similarity	NPD5786	Approved
0.6449	Remote Similarity	NPD7334	Approved
0.6449	Remote Similarity	NPD6098	Approved
0.6449	Remote Similarity	NPD5279	Phase 3
0.6449	Remote Similarity	NPD6409	Approved
0.6449	Remote Similarity	NPD6684	Approved
0.6449	Remote Similarity	NPD7146	Approved
0.6449	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD1700	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6868	Approved
0.6422	Remote Similarity	NPD6904	Approved
0.6422	Remote Similarity	NPD6673	Approved
0.6422	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD6080	Approved
0.6417	Remote Similarity	NPD5249	Phase 3
0.6417	Remote Similarity	NPD5250	Approved
0.6417	Remote Similarity	NPD5248	Approved
0.6417	Remote Similarity	NPD5251	Approved
0.6417	Remote Similarity	NPD5247	Approved
0.6415	Remote Similarity	NPD6400	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