NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.07
Volume:	235.634
LogP:	1.354
LogD:	1.149
LogS:	-1.886
# Rotatable Bonds:	4
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.843
Synthetic Accessibility Score:	3.112
Fsp3:	0.154
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:	-4.655
MDCK Permeability:	1.4504470527754165e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.521
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	85.87776184082031%
Volume Distribution (VD):	0.798
Pgp-substrate:	18.239046096801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.179
CYP2C9-inhibitor:	0.177
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	7.753
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.251
Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.148
Carcinogencity:	0.439
Eye Corrosion:	0.004
Eye Irritation:	0.157
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC82426

Natural Product ID:	NPC82426
*Common Name:**	(-)-Goniobutenolide B
IUPAC Name:	(5E)-5-[(2S,3R)-2,3-dihydroxy-3-phenylpropylidene]furan-2-one
Synonyms:
Standard InCHIKey:	XDLSRIVPCBODNQ-YRFMYUJQSA-N
Standard InCHI:	InChI=1S/C13H12O4/c14-11(8-10-6-7-12(15)17-10)13(16)9-4-2-1-3-5-9/h1-8,11,13-14,16H/b10-8+/t11-,13+/m0/s1
SMILES:	c1ccc(cc1)[C@H]([C@H](/C=C/1C=CC(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3775075
PubChem CID:	11770317
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
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713398]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17329877]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791473]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20329	Gymnacranthera paniculata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27877	Eliokarmos thyrsoides	Species	Hyacinthaceae	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	9
Others	6

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	28940.0	nM	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	3.87	%	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	3.99	%	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	20.65	%	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	44.23	%	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	32.11	%	PMID[511339]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	3.01	%	PMID[511339]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	100000.0	nM	PMID[511339]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[511339]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5340.0	nM	PMID[511339]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	8110.0	nM	PMID[511339]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4740.0	nM	PMID[511339]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	32740.0	nM	PMID[511339]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45780.0	nM	PMID[511339]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21010.0	nM	PMID[511339]

☑ 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 NPC82426 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	194
0.1-0.2	968
0.2-0.3	3475
0.3-0.4	9134
0.4-0.5	10552
0.5-0.6	13214
0.6-0.7	4592
0.7-0.8	512
0.8-0.85	37
0.85-0.9	14
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91820
0.91	High Similarity	NPC171831
0.91	High Similarity	NPC242913
0.91	High Similarity	NPC280616
0.8922	High Similarity	NPC136962
0.8922	High Similarity	NPC37115
0.8857	High Similarity	NPC474314
0.8835	High Similarity	NPC277788
0.8738	High Similarity	NPC474376
0.8738	High Similarity	NPC475203
0.8738	High Similarity	NPC472316
0.8738	High Similarity	NPC472315
0.8679	High Similarity	NPC185840
0.8641	High Similarity	NPC472919
0.8519	High Similarity	NPC87069
0.8505	High Similarity	NPC234376
0.8426	Intermediate Similarity	NPC265002
0.8367	Intermediate Similarity	NPC472319
0.8333	Intermediate Similarity	NPC158282
0.8302	Intermediate Similarity	NPC156648
0.8269	Intermediate Similarity	NPC234305
0.8247	Intermediate Similarity	NPC304760
0.8224	Intermediate Similarity	NPC474364
0.8224	Intermediate Similarity	NPC281604
0.8208	Intermediate Similarity	NPC477251
0.8163	Intermediate Similarity	NPC173443
0.8155	Intermediate Similarity	NPC472318
0.8155	Intermediate Similarity	NPC98911
0.8148	Intermediate Similarity	NPC79543
0.8131	Intermediate Similarity	NPC475465
0.8131	Intermediate Similarity	NPC472314
0.8095	Intermediate Similarity	NPC160382
0.8095	Intermediate Similarity	NPC304638
0.8091	Intermediate Similarity	NPC272524
0.8073	Intermediate Similarity	NPC183700
0.8058	Intermediate Similarity	NPC175852
0.8058	Intermediate Similarity	NPC210529
0.8058	Intermediate Similarity	NPC160548
0.8053	Intermediate Similarity	NPC65791
0.802	Intermediate Similarity	NPC23453
0.8019	Intermediate Similarity	NPC85977
0.8018	Intermediate Similarity	NPC474363
0.8	Intermediate Similarity	NPC119631
0.7982	Intermediate Similarity	NPC309434
0.7959	Intermediate Similarity	NPC96625
0.7946	Intermediate Similarity	NPC217472
0.7944	Intermediate Similarity	NPC127676
0.7938	Intermediate Similarity	NPC58616
0.7909	Intermediate Similarity	NPC477247
0.7909	Intermediate Similarity	NPC476003
0.7905	Intermediate Similarity	NPC253746
0.79	Intermediate Similarity	NPC240108
0.79	Intermediate Similarity	NPC213156
0.7895	Intermediate Similarity	NPC117180
0.789	Intermediate Similarity	NPC206341
0.7876	Intermediate Similarity	NPC233669
0.7876	Intermediate Similarity	NPC296526
0.7857	Intermediate Similarity	NPC95381
0.7838	Intermediate Similarity	NPC477250
0.7838	Intermediate Similarity	NPC139946
0.783	Intermediate Similarity	NPC94343
0.7826	Intermediate Similarity	NPC471033
0.7826	Intermediate Similarity	NPC203124
0.7826	Intermediate Similarity	NPC311091
0.7812	Intermediate Similarity	NPC103326
0.7812	Intermediate Similarity	NPC87299
0.7812	Intermediate Similarity	NPC99394
0.7812	Intermediate Similarity	NPC329319
0.781	Intermediate Similarity	NPC171843
0.7807	Intermediate Similarity	NPC281277
0.7807	Intermediate Similarity	NPC128249
0.7798	Intermediate Similarity	NPC260952
0.7788	Intermediate Similarity	NPC328593
0.7788	Intermediate Similarity	NPC33749
0.7788	Intermediate Similarity	NPC474685
0.7788	Intermediate Similarity	NPC261453
0.7778	Intermediate Similarity	NPC470849
0.7778	Intermediate Similarity	NPC227255
0.7778	Intermediate Similarity	NPC470848
0.7778	Intermediate Similarity	NPC169050
0.7778	Intermediate Similarity	NPC89377
0.7778	Intermediate Similarity	NPC286608
0.7768	Intermediate Similarity	NPC17693
0.7759	Intermediate Similarity	NPC141791
0.7759	Intermediate Similarity	NPC263386
0.7748	Intermediate Similarity	NPC323007
0.7748	Intermediate Similarity	NPC260818
0.7739	Intermediate Similarity	NPC122117
0.7732	Intermediate Similarity	NPC324835
0.7732	Intermediate Similarity	NPC308619
0.7732	Intermediate Similarity	NPC127491
0.7727	Intermediate Similarity	NPC182549
0.7727	Intermediate Similarity	NPC469511
0.7727	Intermediate Similarity	NPC114741
0.7719	Intermediate Similarity	NPC474967
0.7714	Intermediate Similarity	NPC135951
0.7714	Intermediate Similarity	NPC154517
0.7708	Intermediate Similarity	NPC89950
0.7706	Intermediate Similarity	NPC51174
0.7699	Intermediate Similarity	NPC172525
0.7692	Intermediate Similarity	NPC30361
0.7692	Intermediate Similarity	NPC246679
0.7685	Intermediate Similarity	NPC148060
0.7685	Intermediate Similarity	NPC2518
0.7685	Intermediate Similarity	NPC269644
0.7679	Intermediate Similarity	NPC321852
0.7679	Intermediate Similarity	NPC226250
0.7672	Intermediate Similarity	NPC275519
0.7667	Intermediate Similarity	NPC246166
0.7658	Intermediate Similarity	NPC75272
0.7658	Intermediate Similarity	NPC326187
0.7658	Intermediate Similarity	NPC471954
0.7653	Intermediate Similarity	NPC304538
0.7647	Intermediate Similarity	NPC477151
0.7647	Intermediate Similarity	NPC132518
0.7647	Intermediate Similarity	NPC317645
0.7642	Intermediate Similarity	NPC80115
0.7636	Intermediate Similarity	NPC20485
0.7632	Intermediate Similarity	NPC41851
0.7632	Intermediate Similarity	NPC469509
0.7632	Intermediate Similarity	NPC235250
0.7627	Intermediate Similarity	NPC476872
0.7627	Intermediate Similarity	NPC229600
0.7624	Intermediate Similarity	NPC220893
0.7623	Intermediate Similarity	NPC473993
0.7619	Intermediate Similarity	NPC276775
0.7619	Intermediate Similarity	NPC249912
0.7619	Intermediate Similarity	NPC325499
0.7619	Intermediate Similarity	NPC270654
0.7619	Intermediate Similarity	NPC92754
0.7615	Intermediate Similarity	NPC288760
0.7611	Intermediate Similarity	NPC131530
0.7603	Intermediate Similarity	NPC79608
0.7596	Intermediate Similarity	NPC81010
0.7596	Intermediate Similarity	NPC32977
0.7593	Intermediate Similarity	NPC474365
0.7593	Intermediate Similarity	NPC179686
0.7593	Intermediate Similarity	NPC301943
0.7589	Intermediate Similarity	NPC43584
0.7589	Intermediate Similarity	NPC63345
0.7589	Intermediate Similarity	NPC474157
0.7583	Intermediate Similarity	NPC474275
0.7583	Intermediate Similarity	NPC471466
0.7583	Intermediate Similarity	NPC224208
0.7579	Intermediate Similarity	NPC176228
0.757	Intermediate Similarity	NPC469481
0.757	Intermediate Similarity	NPC42211
0.7568	Intermediate Similarity	NPC184633
0.7568	Intermediate Similarity	NPC83628
0.7568	Intermediate Similarity	NPC469636
0.7568	Intermediate Similarity	NPC265407
0.7568	Intermediate Similarity	NPC85493
0.7565	Intermediate Similarity	NPC210531
0.7563	Intermediate Similarity	NPC11724
0.7563	Intermediate Similarity	NPC475328
0.7563	Intermediate Similarity	NPC147654
0.7549	Intermediate Similarity	NPC185501
0.7547	Intermediate Similarity	NPC78701
0.7547	Intermediate Similarity	NPC225060
0.7547	Intermediate Similarity	NPC35448
0.7545	Intermediate Similarity	NPC30594
0.7545	Intermediate Similarity	NPC37622
0.7544	Intermediate Similarity	NPC308744
0.7544	Intermediate Similarity	NPC153053
0.7544	Intermediate Similarity	NPC237366
0.7542	Intermediate Similarity	NPC202474
0.7541	Intermediate Similarity	NPC61181
0.7526	Intermediate Similarity	NPC71795
0.7524	Intermediate Similarity	NPC257182
0.7523	Intermediate Similarity	NPC114594
0.7521	Intermediate Similarity	NPC469568
0.7521	Intermediate Similarity	NPC288945
0.7521	Intermediate Similarity	NPC20443
0.7521	Intermediate Similarity	NPC60517
0.7521	Intermediate Similarity	NPC146886
0.75	Intermediate Similarity	NPC52097
0.75	Intermediate Similarity	NPC327070
0.75	Intermediate Similarity	NPC154905
0.75	Intermediate Similarity	NPC170484
0.75	Intermediate Similarity	NPC167577
0.75	Intermediate Similarity	NPC60373
0.75	Intermediate Similarity	NPC78517
0.748	Intermediate Similarity	NPC103533
0.748	Intermediate Similarity	NPC288416
0.7479	Intermediate Similarity	NPC204466
0.7478	Intermediate Similarity	NPC306740
0.7477	Intermediate Similarity	NPC118343
0.7477	Intermediate Similarity	NPC146351
0.7477	Intermediate Similarity	NPC251306
0.7474	Intermediate Similarity	NPC66655
0.7459	Intermediate Similarity	NPC476033
0.7456	Intermediate Similarity	NPC474176
0.7456	Intermediate Similarity	NPC477246
0.7456	Intermediate Similarity	NPC161611
0.7456	Intermediate Similarity	NPC48525
0.7456	Intermediate Similarity	NPC477245
0.7456	Intermediate Similarity	NPC199462
0.7455	Intermediate Similarity	NPC128730
0.7455	Intermediate Similarity	NPC152384
0.7455	Intermediate Similarity	NPC37714

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 NPC82426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	720
0.2-0.3	1545
0.3-0.4	2843
0.4-0.5	2229
0.5-0.6	1265
0.6-0.7	352
0.7-0.8	21
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8624	High Similarity	NPD694	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD969	Suspended
0.8108	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD9495	Approved
0.798	Intermediate Similarity	NPD689	Discontinued
0.7925	Intermediate Similarity	NPD6647	Phase 2
0.7818	Intermediate Similarity	NPD2067	Discontinued
0.7778	Intermediate Similarity	NPD1282	Approved
0.7636	Intermediate Similarity	NPD1358	Approved
0.7477	Intermediate Similarity	NPD1238	Approved
0.7474	Intermediate Similarity	NPD9294	Approved
0.7434	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3134	Approved
0.7379	Intermediate Similarity	NPD9256	Approved
0.7379	Intermediate Similarity	NPD9258	Approved
0.7364	Intermediate Similarity	NPD1237	Approved
0.7328	Intermediate Similarity	NPD2629	Approved
0.7321	Intermediate Similarity	NPD290	Approved
0.7273	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4198	Discontinued
0.7263	Intermediate Similarity	NPD9716	Approved
0.7258	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2182	Approved
0.7227	Intermediate Similarity	NPD9545	Approved
0.7207	Intermediate Similarity	NPD164	Approved
0.7207	Intermediate Similarity	NPD5909	Discontinued
0.719	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD9697	Approved
0.7105	Intermediate Similarity	NPD2684	Approved
0.7059	Intermediate Similarity	NPD9493	Approved
0.7043	Intermediate Similarity	NPD9713	Approved
0.703	Intermediate Similarity	NPD9491	Approved
0.7018	Intermediate Similarity	NPD9532	Phase 3
0.7009	Intermediate Similarity	NPD1202	Approved
0.7009	Intermediate Similarity	NPD7843	Approved
0.699	Remote Similarity	NPD9259	Approved
0.699	Remote Similarity	NPD9257	Approved
0.6984	Remote Similarity	NPD5647	Approved
0.6957	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6653	Approved
0.6942	Remote Similarity	NPD1894	Discontinued
0.6935	Remote Similarity	NPD9717	Approved
0.693	Remote Similarity	NPD968	Approved
0.6866	Remote Similarity	NPD7266	Discontinued
0.6855	Remote Similarity	NPD422	Phase 1
0.6855	Remote Similarity	NPD1091	Approved
0.6842	Remote Similarity	NPD5048	Discontinued
0.6838	Remote Similarity	NPD4628	Phase 3
0.6833	Remote Similarity	NPD7157	Approved
0.6832	Remote Similarity	NPD226	Approved
0.6829	Remote Similarity	NPD5126	Approved
0.6829	Remote Similarity	NPD4626	Approved
0.6829	Remote Similarity	NPD5125	Phase 3
0.6807	Remote Similarity	NPD1241	Discontinued
0.68	Remote Similarity	NPD1877	Discontinued
0.6783	Remote Similarity	NPD6685	Approved
0.678	Remote Similarity	NPD228	Approved
0.6772	Remote Similarity	NPD2159	Approved
0.6772	Remote Similarity	NPD1203	Approved
0.6772	Remote Similarity	NPD2625	Approved
0.6772	Remote Similarity	NPD2626	Approved
0.6772	Remote Similarity	NPD2628	Approved
0.6772	Remote Similarity	NPD6362	Approved
0.6772	Remote Similarity	NPD2160	Approved
0.6772	Remote Similarity	NPD2627	Approved
0.6769	Remote Similarity	NPD6798	Discontinued
0.6757	Remote Similarity	NPD9609	Approved
0.6757	Remote Similarity	NPD9611	Approved
0.6757	Remote Similarity	NPD5926	Approved
0.6757	Remote Similarity	NPD9612	Approved
0.6748	Remote Similarity	NPD5691	Approved
0.6742	Remote Similarity	NPD4340	Discontinued
0.6742	Remote Similarity	NPD6355	Discontinued
0.6724	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD9267	Approved
0.6724	Remote Similarity	NPD9264	Approved
0.6724	Remote Similarity	NPD9263	Approved
0.6723	Remote Similarity	NPD5535	Approved
0.672	Remote Similarity	NPD1535	Discovery
0.6719	Remote Similarity	NPD6085	Phase 2
0.6719	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4062	Phase 3
0.6718	Remote Similarity	NPD6233	Phase 2
0.6699	Remote Similarity	NPD3971	Phase 1
0.6697	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD2066	Phase 3
0.6696	Remote Similarity	NPD9712	Approved
0.6694	Remote Similarity	NPD5305	Approved
0.6694	Remote Similarity	NPD5306	Approved
0.6694	Remote Similarity	NPD1778	Approved
0.6693	Remote Similarity	NPD3225	Approved
0.6692	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9365	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD5765	Approved
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD9250	Approved
0.6667	Remote Similarity	NPD9266	Approved
0.6667	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD1481	Phase 2
0.6642	Remote Similarity	NPD1652	Phase 2
0.6641	Remote Similarity	NPD2797	Approved
0.6641	Remote Similarity	NPD1048	Approved
0.6641	Remote Similarity	NPD3764	Approved
0.664	Remote Similarity	NPD4135	Approved
0.664	Remote Similarity	NPD3847	Discontinued
0.664	Remote Similarity	NPD4136	Approved
0.664	Remote Similarity	NPD4106	Approved
0.6639	Remote Similarity	NPD5291	Approved
0.6639	Remote Similarity	NPD5292	Approved
0.6639	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1693	Approved
0.6636	Remote Similarity	NPD2934	Approved
0.6636	Remote Similarity	NPD2933	Approved
0.6636	Remote Similarity	NPD800	Approved
0.6634	Remote Similarity	NPD9490	Approved
0.6618	Remote Similarity	NPD5763	Approved
0.6618	Remote Similarity	NPD5762	Approved
0.6617	Remote Similarity	NPD230	Phase 1
0.6617	Remote Similarity	NPD5124	Phase 1
0.6617	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1357	Approved
0.6607	Remote Similarity	NPD9710	Approved
0.6607	Remote Similarity	NPD9711	Approved
0.6593	Remote Similarity	NPD7033	Discontinued
0.6587	Remote Similarity	NPD4806	Approved
0.6587	Remote Similarity	NPD4807	Approved
0.6585	Remote Similarity	NPD2347	Approved
0.6583	Remote Similarity	NPD821	Approved
0.6579	Remote Similarity	NPD854	Approved
0.6579	Remote Similarity	NPD291	Approved
0.6579	Remote Similarity	NPD855	Approved
0.6577	Remote Similarity	NPD2859	Approved
0.6577	Remote Similarity	NPD2860	Approved
0.6574	Remote Similarity	NPD1086	Approved
0.6574	Remote Similarity	NPD1090	Approved
0.6574	Remote Similarity	NPD1089	Approved
0.6571	Remote Similarity	NPD111	Approved
0.6571	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7008	Discontinued
0.6549	Remote Similarity	NPD7798	Approved
0.6547	Remote Similarity	NPD6190	Approved
0.6545	Remote Similarity	NPD845	Approved
0.6542	Remote Similarity	NPD531	Approved
0.6541	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4140	Approved
0.6538	Remote Similarity	NPD3664	Approved
0.6538	Remote Similarity	NPD3661	Approved
0.6538	Remote Similarity	NPD3662	Phase 3
0.6538	Remote Similarity	NPD3663	Approved
0.6538	Remote Similarity	NPD5204	Approved
0.6535	Remote Similarity	NPD225	Approved
0.6535	Remote Similarity	NPD227	Approved
0.6529	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6010	Discontinued
0.6522	Remote Similarity	NPD1930	Approved
0.6522	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1929	Approved
0.6515	Remote Similarity	NPD3268	Approved
0.6515	Remote Similarity	NPD2313	Discontinued
0.6514	Remote Similarity	NPD1239	Approved
0.6512	Remote Similarity	NPD987	Approved
0.65	Remote Similarity	NPD9508	Approved
0.65	Remote Similarity	NPD6912	Phase 3
0.6496	Remote Similarity	NPD6005	Phase 3
0.6496	Remote Similarity	NPD6002	Phase 3
0.6496	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6004	Phase 3
0.6496	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD447	Suspended
0.6491	Remote Similarity	NPD2549	Approved
0.6491	Remote Similarity	NPD2553	Approved
0.6491	Remote Similarity	NPD2550	Approved
0.6491	Remote Similarity	NPD2558	Approved
0.6491	Remote Similarity	NPD2552	Approved
0.6491	Remote Similarity	NPD2555	Approved
0.6489	Remote Similarity	NPD6832	Phase 2
0.6486	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD9260	Approved
0.6484	Remote Similarity	NPD3685	Discontinued
0.648	Remote Similarity	NPD4102	Approved
0.648	Remote Similarity	NPD4105	Approved
0.6475	Remote Similarity	NPD5951	Approved
0.6475	Remote Similarity	NPD8166	Discontinued
0.6475	Remote Similarity	NPD9281	Approved
0.6471	Remote Similarity	NPD5240	Approved
0.6471	Remote Similarity	NPD5237	Approved
0.6471	Remote Similarity	NPD5236	Approved
0.6471	Remote Similarity	NPD5239	Approved
0.6471	Remote Similarity	NPD5235	Approved
0.6471	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD309	Approved
0.6466	Remote Similarity	NPD310	Approved
0.6466	Remote Similarity	NPD314	Approved
0.6466	Remote Similarity	NPD10	Approved
0.6466	Remote Similarity	NPD311	Approved
0.6466	Remote Similarity	NPD315	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