NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	404.26
Volume:	425.476
LogP:	4.205
LogD:	3.926
LogS:	-4.731
# Rotatable Bonds:	4
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	6.071
Fsp3:	0.833
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:	-4.783
MDCK Permeability:	4.0508293750463054e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.545
Plasma Protein Binding (PPB):	87.71633911132812%
Volume Distribution (VD):	1.243
Pgp-substrate:	14.642980575561523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.21
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	12.063
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.365
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.708
Skin Sensitization:	0.671
Carcinogencity:	0.113
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC476716

Natural Product ID:	NPC476716
*Common Name:**	[(2S,3R,4R,8R,11S,14Z)-4,8,11,15-tetramethyl-9-oxo-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-4-yl] butanoate
IUPAC Name:	[(2S,3R,4R,8R,11S,14Z)-4,8,11,15-tetramethyl-9-oxo-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-4-yl] butanoate
Synonyms:	Briarellin R
Standard InCHIKey:	WFKXCGWVYJNIRE-IFUPWAAUSA-N
Standard InCHI:	InChI=1S/C24H36O5/c1-6-8-18(25)28-23(4)12-10-16-15(3)22(26)29-24(5)11-7-9-14(2)13-17-20(23)19(16)21(24)27-17/h9,15-17,19-21H,6-8,10-13H2,1-5H3/b14-9-/t15-,16?,17?,19+,20+,21?,23-,24+/m1/s1
SMILES:	CCCC(=O)O[C@@]1(CCC2[C@H](C(=O)O[C@]3(CC/C=C(\CC4[C@H]1[C@H]2C3O4)/C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566422
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33599	Briareum polyanthes	Species	Briareidae	Eukaryota	n.a.	coral reef off Cabo Rojo, Puerto Rico, at a depth of 10-15 m	2000-OCT	PMID[17190449]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

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	=	8.9	ug/ml	PMID[17190449]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	15	ug/ml	PMID[17190449]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	91	%	PMID[17190449]

☑ 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 NPC476716 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	217
0.1-0.2	1366
0.2-0.3	5181
0.3-0.4	11813
0.4-0.5	11007
0.5-0.6	6993
0.6-0.7	5606
0.7-0.8	501
0.8-0.85	4
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC214315
0.8913	High Similarity	NPC476722
0.8804	High Similarity	NPC477615
0.8696	High Similarity	NPC165180
0.8247	Intermediate Similarity	NPC111348
0.8242	Intermediate Similarity	NPC476725
0.8229	Intermediate Similarity	NPC476720
0.8022	Intermediate Similarity	NPC476721
0.8022	Intermediate Similarity	NPC127917
0.7979	Intermediate Similarity	NPC476724
0.7979	Intermediate Similarity	NPC476723
0.7979	Intermediate Similarity	NPC92370
0.7979	Intermediate Similarity	NPC309656
0.7959	Intermediate Similarity	NPC8803
0.7925	Intermediate Similarity	NPC474516
0.79	Intermediate Similarity	NPC272223
0.7895	Intermediate Similarity	NPC291875
0.7864	Intermediate Similarity	NPC470975
0.7864	Intermediate Similarity	NPC103088
0.7864	Intermediate Similarity	NPC470979
0.7849	Intermediate Similarity	NPC476715
0.781	Intermediate Similarity	NPC469370
0.78	Intermediate Similarity	NPC471932
0.7788	Intermediate Similarity	NPC59530
0.7788	Intermediate Similarity	NPC180744
0.7778	Intermediate Similarity	NPC90472
0.7767	Intermediate Similarity	NPC471293
0.7766	Intermediate Similarity	NPC475684
0.7757	Intermediate Similarity	NPC152117
0.7757	Intermediate Similarity	NPC234042
0.7736	Intermediate Similarity	NPC253906
0.7732	Intermediate Similarity	NPC312805
0.7708	Intermediate Similarity	NPC471222
0.7692	Intermediate Similarity	NPC102352
0.7684	Intermediate Similarity	NPC44538
0.767	Intermediate Similarity	NPC254202
0.7653	Intermediate Similarity	NPC469315
0.7642	Intermediate Similarity	NPC471934
0.7642	Intermediate Similarity	NPC143706
0.7642	Intermediate Similarity	NPC472534
0.7634	Intermediate Similarity	NPC239308
0.7629	Intermediate Similarity	NPC312471
0.7629	Intermediate Similarity	NPC471378
0.7629	Intermediate Similarity	NPC475748
0.7619	Intermediate Similarity	NPC3316
0.7619	Intermediate Similarity	NPC144854
0.7619	Intermediate Similarity	NPC230541
0.7619	Intermediate Similarity	NPC475510
0.7619	Intermediate Similarity	NPC475587
0.7619	Intermediate Similarity	NPC293512
0.7615	Intermediate Similarity	NPC473798
0.7609	Intermediate Similarity	NPC207188
0.7604	Intermediate Similarity	NPC470260
0.7604	Intermediate Similarity	NPC75443
0.76	Intermediate Similarity	NPC256227
0.7596	Intermediate Similarity	NPC475036
0.7596	Intermediate Similarity	NPC258532
0.7593	Intermediate Similarity	NPC269530
0.7579	Intermediate Similarity	NPC476717
0.7576	Intermediate Similarity	NPC471446
0.7576	Intermediate Similarity	NPC474841
0.7576	Intermediate Similarity	NPC66581
0.7576	Intermediate Similarity	NPC473434
0.7573	Intermediate Similarity	NPC474709
0.7573	Intermediate Similarity	NPC162973
0.757	Intermediate Similarity	NPC250956
0.7551	Intermediate Similarity	NPC122057
0.7551	Intermediate Similarity	NPC208839
0.7551	Intermediate Similarity	NPC474631
0.7551	Intermediate Similarity	NPC184463
0.7549	Intermediate Similarity	NPC474718
0.7549	Intermediate Similarity	NPC471413
0.7547	Intermediate Similarity	NPC192813
0.7547	Intermediate Similarity	NPC94377
0.7547	Intermediate Similarity	NPC277017
0.7547	Intermediate Similarity	NPC473939
0.7547	Intermediate Similarity	NPC473595
0.7547	Intermediate Similarity	NPC258323
0.7547	Intermediate Similarity	NPC154608
0.7545	Intermediate Similarity	NPC152199
0.7545	Intermediate Similarity	NPC96312
0.7545	Intermediate Similarity	NPC235539
0.7545	Intermediate Similarity	NPC474734
0.7545	Intermediate Similarity	NPC474046
0.7545	Intermediate Similarity	NPC259306
0.7545	Intermediate Similarity	NPC470628
0.7545	Intermediate Similarity	NPC328374
0.7545	Intermediate Similarity	NPC251236
0.7545	Intermediate Similarity	NPC40632
0.7545	Intermediate Similarity	NPC134869
0.7526	Intermediate Similarity	NPC474679
0.7526	Intermediate Similarity	NPC161560
0.7526	Intermediate Similarity	NPC151770
0.7526	Intermediate Similarity	NPC307411
0.7525	Intermediate Similarity	NPC474921
0.7525	Intermediate Similarity	NPC272451
0.7524	Intermediate Similarity	NPC127609
0.7524	Intermediate Similarity	NPC472655
0.7523	Intermediate Similarity	NPC49451
0.7523	Intermediate Similarity	NPC472757
0.7523	Intermediate Similarity	NPC470120
0.75	Intermediate Similarity	NPC476718
0.75	Intermediate Similarity	NPC474775
0.75	Intermediate Similarity	NPC469380
0.75	Intermediate Similarity	NPC231889
0.75	Intermediate Similarity	NPC469655
0.75	Intermediate Similarity	NPC469656
0.75	Intermediate Similarity	NPC474846
0.75	Intermediate Similarity	NPC474981
0.75	Intermediate Similarity	NPC201992
0.7477	Intermediate Similarity	NPC473590
0.7477	Intermediate Similarity	NPC218853
0.7477	Intermediate Similarity	NPC42662
0.7477	Intermediate Similarity	NPC273433
0.7477	Intermediate Similarity	NPC474242
0.7477	Intermediate Similarity	NPC141350
0.7476	Intermediate Similarity	NPC471412
0.7475	Intermediate Similarity	NPC476300
0.7475	Intermediate Similarity	NPC147272
0.7474	Intermediate Similarity	NPC471379
0.7474	Intermediate Similarity	NPC196911
0.7473	Intermediate Similarity	NPC264610
0.7455	Intermediate Similarity	NPC472400
0.7455	Intermediate Similarity	NPC474906
0.7455	Intermediate Similarity	NPC117712
0.7455	Intermediate Similarity	NPC18547
0.7455	Intermediate Similarity	NPC469877
0.7455	Intermediate Similarity	NPC470919
0.7453	Intermediate Similarity	NPC67321
0.7453	Intermediate Similarity	NPC187435
0.7451	Intermediate Similarity	NPC470067
0.7451	Intermediate Similarity	NPC119036
0.7451	Intermediate Similarity	NPC260149
0.7451	Intermediate Similarity	NPC58942
0.7451	Intermediate Similarity	NPC470066
0.7451	Intermediate Similarity	NPC17183
0.7451	Intermediate Similarity	NPC216478
0.7449	Intermediate Similarity	NPC475776
0.7449	Intermediate Similarity	NPC153853
0.7449	Intermediate Similarity	NPC51004
0.7447	Intermediate Similarity	NPC5958
0.7447	Intermediate Similarity	NPC474472
0.7447	Intermediate Similarity	NPC257358
0.7434	Intermediate Similarity	NPC151616
0.7434	Intermediate Similarity	NPC4548
0.7431	Intermediate Similarity	NPC289312
0.7431	Intermediate Similarity	NPC471933
0.7431	Intermediate Similarity	NPC222834
0.7431	Intermediate Similarity	NPC472002
0.7431	Intermediate Similarity	NPC302146
0.7431	Intermediate Similarity	NPC11252
0.7429	Intermediate Similarity	NPC65523
0.7426	Intermediate Similarity	NPC471822
0.7426	Intermediate Similarity	NPC476327
0.7426	Intermediate Similarity	NPC476318
0.7423	Intermediate Similarity	NPC477128
0.7419	Intermediate Similarity	NPC118116
0.7411	Intermediate Similarity	NPC297179
0.7407	Intermediate Similarity	NPC5284
0.7407	Intermediate Similarity	NPC475134
0.7407	Intermediate Similarity	NPC474586
0.7407	Intermediate Similarity	NPC5103
0.7407	Intermediate Similarity	NPC470065
0.7407	Intermediate Similarity	NPC210005
0.7407	Intermediate Similarity	NPC475563
0.7407	Intermediate Similarity	NPC474567
0.7407	Intermediate Similarity	NPC473843
0.7407	Intermediate Similarity	NPC281624
0.7407	Intermediate Similarity	NPC473975
0.7407	Intermediate Similarity	NPC473594
0.7407	Intermediate Similarity	NPC101450
0.7404	Intermediate Similarity	NPC183571
0.7404	Intermediate Similarity	NPC22388
0.7404	Intermediate Similarity	NPC295791
0.7404	Intermediate Similarity	NPC476081
0.74	Intermediate Similarity	NPC250075
0.74	Intermediate Similarity	NPC240617
0.7396	Intermediate Similarity	NPC6979
0.7396	Intermediate Similarity	NPC475753
0.7387	Intermediate Similarity	NPC471127
0.7387	Intermediate Similarity	NPC207217
0.7387	Intermediate Similarity	NPC234858
0.7387	Intermediate Similarity	NPC476711
0.7387	Intermediate Similarity	NPC476710
0.7387	Intermediate Similarity	NPC477509
0.7387	Intermediate Similarity	NPC243981
0.7387	Intermediate Similarity	NPC179626
0.7387	Intermediate Similarity	NPC154363
0.7383	Intermediate Similarity	NPC472219
0.7383	Intermediate Similarity	NPC472218
0.7383	Intermediate Similarity	NPC275539
0.7383	Intermediate Similarity	NPC153587
0.7383	Intermediate Similarity	NPC189075
0.7383	Intermediate Similarity	NPC472217
0.7383	Intermediate Similarity	NPC293850
0.7379	Intermediate Similarity	NPC472972
0.7379	Intermediate Similarity	NPC167974
0.7379	Intermediate Similarity	NPC477656
0.7374	Intermediate Similarity	NPC91251
0.7374	Intermediate Similarity	NPC30515

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 NPC476716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1873
0.2-0.3	3993
0.3-0.4	2099
0.4-0.5	583
0.5-0.6	251
0.6-0.7	162
0.7-0.8	2
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
0.7524	Intermediate Similarity	NPD6008	Approved
0.7113	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5739	Approved
0.7037	Intermediate Similarity	NPD6402	Approved
0.7037	Intermediate Similarity	NPD7128	Approved
0.7037	Intermediate Similarity	NPD6675	Approved
0.6964	Remote Similarity	NPD6053	Discontinued
0.6964	Remote Similarity	NPD8297	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD6399	Phase 3
0.6961	Remote Similarity	NPD5778	Approved
0.6909	Remote Similarity	NPD6881	Approved
0.6909	Remote Similarity	NPD7320	Approved
0.6909	Remote Similarity	NPD6899	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7492	Approved
0.6863	Remote Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD6373	Approved
0.6847	Remote Similarity	NPD6372	Approved
0.6838	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6059	Approved
0.6838	Remote Similarity	NPD6319	Approved
0.6833	Remote Similarity	NPD6616	Approved
0.6832	Remote Similarity	NPD6101	Approved
0.6832	Remote Similarity	NPD1695	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5701	Approved
0.6818	Remote Similarity	NPD5697	Approved
0.6818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3573	Approved
0.6792	Remote Similarity	NPD7638	Approved
0.6786	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD6883	Approved
0.6786	Remote Similarity	NPD7102	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6777	Remote Similarity	NPD8293	Discontinued
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7748	Approved
0.6729	Remote Similarity	NPD6648	Approved
0.6729	Remote Similarity	NPD7639	Approved
0.6729	Remote Similarity	NPD7640	Approved
0.6726	Remote Similarity	NPD6847	Approved
0.6726	Remote Similarity	NPD8130	Phase 1
0.6726	Remote Similarity	NPD6869	Approved
0.6726	Remote Similarity	NPD6617	Approved
0.6726	Remote Similarity	NPD6649	Approved
0.6726	Remote Similarity	NPD6650	Approved
0.6724	Remote Similarity	NPD6009	Approved
0.6723	Remote Similarity	NPD6370	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.67	Remote Similarity	NPD7146	Approved
0.67	Remote Similarity	NPD6409	Approved
0.67	Remote Similarity	NPD7334	Approved
0.67	Remote Similarity	NPD6684	Approved
0.67	Remote Similarity	NPD7521	Approved
0.67	Remote Similarity	NPD5330	Approved
0.6699	Remote Similarity	NPD6411	Approved
0.6698	Remote Similarity	NPD7902	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6014	Approved
0.6696	Remote Similarity	NPD6013	Approved
0.6696	Remote Similarity	NPD6012	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6882	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4225	Approved
0.6633	Remote Similarity	NPD6435	Approved
0.6607	Remote Similarity	NPD6011	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6672	Approved
0.6569	Remote Similarity	NPD5737	Approved
0.6569	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6903	Approved
0.6557	Remote Similarity	NPD6336	Discontinued
0.6549	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4755	Approved
0.6538	Remote Similarity	NPD8035	Phase 2
0.6538	Remote Similarity	NPD7515	Phase 2
0.6538	Remote Similarity	NPD8034	Phase 2
0.6532	Remote Similarity	NPD7319	Approved
0.6531	Remote Similarity	NPD1780	Approved
0.6531	Remote Similarity	NPD1779	Approved
0.6529	Remote Similarity	NPD8328	Phase 3
0.6518	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD5328	Approved
0.6465	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3168	Discontinued
0.6441	Remote Similarity	NPD7115	Discovery
0.6436	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD5368	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6415	Remote Similarity	NPD5282	Discontinued
0.6389	Remote Similarity	NPD6083	Phase 2
0.6389	Remote Similarity	NPD6084	Phase 2
0.6381	Remote Similarity	NPD6079	Approved
0.6373	Remote Similarity	NPD6098	Approved
0.6373	Remote Similarity	NPD6422	Discontinued
0.6371	Remote Similarity	NPD8074	Phase 3
0.6356	Remote Similarity	NPD6274	Approved
0.6355	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5695	Phase 3
0.6348	Remote Similarity	NPD4634	Approved
0.6348	Remote Similarity	NPD6371	Approved
0.6346	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD6080	Approved
0.6346	Remote Similarity	NPD6673	Approved
0.6337	Remote Similarity	NPD4786	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD7100	Approved
0.6333	Remote Similarity	NPD7101	Approved
0.6325	Remote Similarity	NPD8133	Approved
0.632	Remote Similarity	NPD6033	Approved
0.6311	Remote Similarity	NPD4250	Approved
0.6311	Remote Similarity	NPD4251	Approved
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5224	Approved
0.6306	Remote Similarity	NPD5211	Phase 2
0.63	Remote Similarity	NPD3667	Approved
0.6293	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6001	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD5175	Approved
0.6238	Remote Similarity	NPD7154	Phase 3
0.623	Remote Similarity	NPD6909	Approved
0.623	Remote Similarity	NPD6908	Approved
0.6226	Remote Similarity	NPD6050	Approved
0.6216	Remote Similarity	NPD5223	Approved
0.6214	Remote Similarity	NPD4249	Approved
0.6214	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD5369	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.6182	Remote Similarity	NPD5696	Approved
0.6168	Remote Similarity	NPD4202	Approved
0.6167	Remote Similarity	NPD6317	Approved
0.6161	Remote Similarity	NPD7632	Discontinued
0.6161	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD5221	Approved
0.6147	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4697	Phase 3
0.6147	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7839	Suspended
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD4768	Approved
0.6132	Remote Similarity	NPD7838	Discovery
0.6132	Remote Similarity	NPD5207	Approved
0.6132	Remote Similarity	NPD5692	Phase 3
0.6129	Remote Similarity	NPD6067	Discontinued
0.6116	Remote Similarity	NPD7328	Approved
0.6116	Remote Similarity	NPD7327	Approved
0.6116	Remote Similarity	NPD6314	Approved
0.6116	Remote Similarity	NPD6313	Approved
0.6106	Remote Similarity	NPD4754	Approved
0.61	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4822	Approved
0.61	Remote Similarity	NPD4820	Approved
0.61	Remote Similarity	NPD4821	Approved
0.61	Remote Similarity	NPD7525	Registered
0.61	Remote Similarity	NPD4819	Approved
0.6098	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8033	Approved
0.6098	Remote Similarity	NPD6921	Approved
0.6095	Remote Similarity	NPD5208	Approved
0.6091	Remote Similarity	NPD5173	Approved
0.6083	Remote Similarity	NPD6868	Approved
0.6078	Remote Similarity	NPD5362	Discontinued
0.6075	Remote Similarity	NPD5693	Phase 1
0.6075	Remote Similarity	NPD7637	Suspended
0.6075	Remote Similarity	NPD5694	Approved
0.6071	Remote Similarity	NPD1700	Approved
0.6066	Remote Similarity	NPD7516	Approved
0.6058	Remote Similarity	NPD5786	Approved
0.6038	Remote Similarity	NPD6051	Approved
0.6034	Remote Similarity	NPD4729	Approved
0.6034	Remote Similarity	NPD5128	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data