NPASS Compound

Structure

NPC473070 OpenBabel07101719242D 27 29 0 0 1 0 0 0 0 0999 V2000 0.7074 3.7347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4114 -0.7179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3104 0.2428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1010 2.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7949 2.0638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3564 1.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0459 -1.1616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2898 -0.2839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4088 -2.0221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2688 2.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1010 -0.9607 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4088 -1.0561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2454 -0.5731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2454 0.3929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4088 0.8759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5722 0.3929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5289 -0.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1010 0.3929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8825 0.3929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5722 -2.5051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6959 2.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0820 -1.0561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0820 0.8759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4088 1.8419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5722 -0.5731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7356 0.8759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 7 1 1 0 0 0 11 26 1 0 0 0 0 12 9 1 6 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 1 0 0 0 14 15 1 0 0 0 0 14 23 1 6 0 0 0 15 16 1 0 0 0 0 15 24 1 1 0 0 0 16 25 1 0 0 0 0 16 27 1 6 0 0 0 17 19 1 0 0 0 0 18 19 1 1 0 0 0 18 27 1 0 0 0 0 19 6 1 6 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.19
Volume:	376.56
LogP:	0.371
LogD:	-0.119
LogS:	-2.563
# Rotatable Bonds:	5
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	5.671
Fsp3:	0.842
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:	-5.327
MDCK Permeability:	5.5880598665680736e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.828
Human Intestinal Absorption (HIA):	0.658
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	32.61854934692383%
Volume Distribution (VD):	0.732
Pgp-substrate:	49.26143264770508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	1.782
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.792
Carcinogencity:	0.757
Eye Corrosion:	0.029
Eye Irritation:	0.498
Respiratory Toxicity:	0.633

Download Data

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

Natural Product: NPC473070

Natural Product ID:	NPC473070
*Common Name:**	UWVPTDQDFQAEIW-OIDWXNETSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UWVPTDQDFQAEIW-OIDWXNETSA-N
Standard InCHI:	InChI=1S/C19H30O8/c1-10(21)5-6-19-17(2,3)7-11(26-19)8-18(19,4)27-16-15(24)14(23)13(22)12(9-20)25-16/h5-6,11-16,20,22-24H,7-9H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16-,18+,19+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@]2(C)C[C@H]3O[C@]2(/C=C/C(=O)C)C(C3)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608834
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	84.8	%	PMID[458397]

☑ 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 NPC473070 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	204
0.1-0.2	1494
0.2-0.3	4943
0.3-0.4	9094
0.4-0.5	13293
0.5-0.6	8092
0.6-0.7	4816
0.7-0.8	732
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC473068
0.9596	High Similarity	NPC473069
0.91	High Similarity	NPC194941
0.8713	High Similarity	NPC150463
0.8713	High Similarity	NPC214277
0.8286	Intermediate Similarity	NPC239961
0.8235	Intermediate Similarity	NPC312325
0.8224	Intermediate Similarity	NPC206618
0.8165	Intermediate Similarity	NPC328074
0.8165	Intermediate Similarity	NPC317460
0.8165	Intermediate Similarity	NPC470025
0.8165	Intermediate Similarity	NPC321272
0.8148	Intermediate Similarity	NPC316708
0.8148	Intermediate Similarity	NPC46407
0.8131	Intermediate Similarity	NPC38948
0.8091	Intermediate Similarity	NPC470027
0.8077	Intermediate Similarity	NPC198992
0.8073	Intermediate Similarity	NPC470026
0.8073	Intermediate Similarity	NPC17791
0.8058	Intermediate Similarity	NPC475068
0.8	Intermediate Similarity	NPC471082
0.7963	Intermediate Similarity	NPC128795
0.7963	Intermediate Similarity	NPC217921
0.7963	Intermediate Similarity	NPC135015
0.7963	Intermediate Similarity	NPC48548
0.7928	Intermediate Similarity	NPC264153
0.7925	Intermediate Similarity	NPC120009
0.789	Intermediate Similarity	NPC28844
0.789	Intermediate Similarity	NPC257853
0.789	Intermediate Similarity	NPC316974
0.789	Intermediate Similarity	NPC40728
0.789	Intermediate Similarity	NPC473318
0.789	Intermediate Similarity	NPC473328
0.787	Intermediate Similarity	NPC88013
0.787	Intermediate Similarity	NPC109376
0.787	Intermediate Similarity	NPC125423
0.783	Intermediate Similarity	NPC121423
0.783	Intermediate Similarity	NPC472815
0.7818	Intermediate Similarity	NPC191439
0.7818	Intermediate Similarity	NPC170974
0.7818	Intermediate Similarity	NPC177047
0.7818	Intermediate Similarity	NPC103627
0.7818	Intermediate Similarity	NPC65155
0.7798	Intermediate Similarity	NPC224660
0.7798	Intermediate Similarity	NPC470024
0.7798	Intermediate Similarity	NPC181994
0.7798	Intermediate Similarity	NPC311223
0.7788	Intermediate Similarity	NPC120446
0.7778	Intermediate Similarity	NPC82251
0.7778	Intermediate Similarity	NPC172867
0.7778	Intermediate Similarity	NPC218158
0.7759	Intermediate Similarity	NPC233500
0.7757	Intermediate Similarity	NPC474575
0.7755	Intermediate Similarity	NPC34581
0.7739	Intermediate Similarity	NPC470914
0.7736	Intermediate Similarity	NPC472554
0.7736	Intermediate Similarity	NPC280991
0.7736	Intermediate Similarity	NPC154127
0.7719	Intermediate Similarity	NPC50305
0.7719	Intermediate Similarity	NPC471353
0.7719	Intermediate Similarity	NPC84987
0.7719	Intermediate Similarity	NPC158344
0.7719	Intermediate Similarity	NPC27507
0.7719	Intermediate Similarity	NPC473852
0.7719	Intermediate Similarity	NPC243196
0.7719	Intermediate Similarity	NPC203862
0.7719	Intermediate Similarity	NPC142066
0.7719	Intermediate Similarity	NPC471351
0.7719	Intermediate Similarity	NPC309034
0.7719	Intermediate Similarity	NPC471354
0.7719	Intermediate Similarity	NPC474418
0.7719	Intermediate Similarity	NPC34390
0.7719	Intermediate Similarity	NPC157376
0.7719	Intermediate Similarity	NPC196429
0.7719	Intermediate Similarity	NPC244402
0.7719	Intermediate Similarity	NPC152615
0.7719	Intermediate Similarity	NPC77319
0.7719	Intermediate Similarity	NPC471355
0.7719	Intermediate Similarity	NPC99728
0.7719	Intermediate Similarity	NPC87250
0.7714	Intermediate Similarity	NPC169468
0.7714	Intermediate Similarity	NPC61630
0.7714	Intermediate Similarity	NPC81483
0.7714	Intermediate Similarity	NPC307517
0.7706	Intermediate Similarity	NPC122816
0.7692	Intermediate Similarity	NPC196130
0.7679	Intermediate Similarity	NPC231797
0.7679	Intermediate Similarity	NPC473125
0.7672	Intermediate Similarity	NPC48692
0.7672	Intermediate Similarity	NPC475136
0.7672	Intermediate Similarity	NPC474466
0.7664	Intermediate Similarity	NPC223834
0.7664	Intermediate Similarity	NPC201191
0.7664	Intermediate Similarity	NPC472552
0.7658	Intermediate Similarity	NPC119550
0.7652	Intermediate Similarity	NPC83287
0.7636	Intermediate Similarity	NPC38376
0.7636	Intermediate Similarity	NPC80210
0.7632	Intermediate Similarity	NPC310341
0.7632	Intermediate Similarity	NPC471816
0.7632	Intermediate Similarity	NPC99620
0.7632	Intermediate Similarity	NPC199428
0.7632	Intermediate Similarity	NPC193382
0.7632	Intermediate Similarity	NPC5311
0.7619	Intermediate Similarity	NPC26307
0.7619	Intermediate Similarity	NPC474194
0.7615	Intermediate Similarity	NPC51719
0.7615	Intermediate Similarity	NPC476592
0.7615	Intermediate Similarity	NPC85670
0.7611	Intermediate Similarity	NPC290608
0.7611	Intermediate Similarity	NPC40133
0.7611	Intermediate Similarity	NPC49413
0.7611	Intermediate Similarity	NPC44298
0.7611	Intermediate Similarity	NPC287075
0.7611	Intermediate Similarity	NPC473128
0.7593	Intermediate Similarity	NPC151516
0.7593	Intermediate Similarity	NPC7613
0.7593	Intermediate Similarity	NPC475889
0.7593	Intermediate Similarity	NPC7644
0.7593	Intermediate Similarity	NPC127933
0.7593	Intermediate Similarity	NPC281378
0.7589	Intermediate Similarity	NPC208189
0.7589	Intermediate Similarity	NPC65034
0.7586	Intermediate Similarity	NPC29639
0.7586	Intermediate Similarity	NPC44899
0.7586	Intermediate Similarity	NPC219656
0.7586	Intermediate Similarity	NPC329905
0.7586	Intermediate Similarity	NPC5883
0.7586	Intermediate Similarity	NPC304260
0.7576	Intermediate Similarity	NPC471267
0.757	Intermediate Similarity	NPC475767
0.757	Intermediate Similarity	NPC119467
0.7568	Intermediate Similarity	NPC221110
0.7568	Intermediate Similarity	NPC195116
0.7568	Intermediate Similarity	NPC285253
0.7568	Intermediate Similarity	NPC180459
0.7565	Intermediate Similarity	NPC13713
0.7565	Intermediate Similarity	NPC93883
0.7551	Intermediate Similarity	NPC31019
0.7551	Intermediate Similarity	NPC2379
0.7551	Intermediate Similarity	NPC106912
0.7551	Intermediate Similarity	NPC263087
0.7551	Intermediate Similarity	NPC27314
0.7551	Intermediate Similarity	NPC471987
0.7549	Intermediate Similarity	NPC261990
0.7549	Intermediate Similarity	NPC474249
0.7545	Intermediate Similarity	NPC33053
0.7545	Intermediate Similarity	NPC472390
0.7545	Intermediate Similarity	NPC475074
0.7545	Intermediate Similarity	NPC471205
0.7544	Intermediate Similarity	NPC471633
0.7544	Intermediate Similarity	NPC475163
0.7544	Intermediate Similarity	NPC84949
0.7544	Intermediate Similarity	NPC69576
0.7544	Intermediate Similarity	NPC106446
0.7544	Intermediate Similarity	NPC31354
0.7524	Intermediate Similarity	NPC90583
0.7523	Intermediate Similarity	NPC473207
0.7523	Intermediate Similarity	NPC81567
0.7523	Intermediate Similarity	NPC201880
0.7523	Intermediate Similarity	NPC264867
0.7523	Intermediate Similarity	NPC470321
0.7521	Intermediate Similarity	NPC475629
0.7521	Intermediate Similarity	NPC270109
0.7521	Intermediate Similarity	NPC135369
0.7521	Intermediate Similarity	NPC475556
0.75	Intermediate Similarity	NPC11956
0.75	Intermediate Similarity	NPC238397
0.75	Intermediate Similarity	NPC471482
0.75	Intermediate Similarity	NPC234522
0.75	Intermediate Similarity	NPC235014
0.75	Intermediate Similarity	NPC473828
0.75	Intermediate Similarity	NPC256368
0.75	Intermediate Similarity	NPC473617
0.75	Intermediate Similarity	NPC2003
0.75	Intermediate Similarity	NPC37207
0.75	Intermediate Similarity	NPC471363
0.75	Intermediate Similarity	NPC300399
0.75	Intermediate Similarity	NPC25701
0.75	Intermediate Similarity	NPC218093
0.7478	Intermediate Similarity	NPC207637
0.7477	Intermediate Similarity	NPC38855
0.7477	Intermediate Similarity	NPC392
0.7477	Intermediate Similarity	NPC177524
0.7477	Intermediate Similarity	NPC188968
0.7477	Intermediate Similarity	NPC219900
0.7459	Intermediate Similarity	NPC476966
0.7459	Intermediate Similarity	NPC471407
0.7458	Intermediate Similarity	NPC475219
0.7458	Intermediate Similarity	NPC173555
0.7458	Intermediate Similarity	NPC314535
0.7458	Intermediate Similarity	NPC231518
0.7456	Intermediate Similarity	NPC311592
0.7456	Intermediate Similarity	NPC473159
0.7456	Intermediate Similarity	NPC474410
0.7456	Intermediate Similarity	NPC75167
0.7456	Intermediate Similarity	NPC293658
0.7455	Intermediate Similarity	NPC470767
0.7455	Intermediate Similarity	NPC470763
0.7453	Intermediate Similarity	NPC266842

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 NPC473070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1899
0.2-0.3	4043
0.3-0.4	2073
0.4-0.5	591
0.5-0.6	306
0.6-0.7	54
0.7-0.8	14
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
0.7739	Intermediate Similarity	NPD7516	Approved
0.7652	Intermediate Similarity	NPD7327	Approved
0.7652	Intermediate Similarity	NPD7328	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7458	Intermediate Similarity	NPD8033	Approved
0.7458	Intermediate Similarity	NPD8378	Approved
0.7458	Intermediate Similarity	NPD8380	Approved
0.7458	Intermediate Similarity	NPD8379	Approved
0.7458	Intermediate Similarity	NPD8335	Approved
0.7458	Intermediate Similarity	NPD8296	Approved
0.7407	Intermediate Similarity	NPD5344	Discontinued
0.7373	Intermediate Similarity	NPD8294	Approved
0.7373	Intermediate Similarity	NPD8377	Approved
0.7311	Intermediate Similarity	NPD7503	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.7064	Intermediate Similarity	NPD4225	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.6829	Remote Similarity	NPD6370	Approved
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD8515	Approved
0.6613	Remote Similarity	NPD8516	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD8517	Approved
0.6613	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD46	Approved
0.6574	Remote Similarity	NPD6698	Approved
0.6562	Remote Similarity	NPD7736	Approved
0.656	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7638	Approved
0.6457	Remote Similarity	NPD7492	Approved
0.6446	Remote Similarity	NPD8133	Approved
0.6423	Remote Similarity	NPD7115	Discovery
0.6417	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6616	Approved
0.6404	Remote Similarity	NPD7640	Approved
0.6404	Remote Similarity	NPD7639	Approved
0.64	Remote Similarity	NPD6059	Approved
0.6396	Remote Similarity	NPD5282	Discontinued
0.6378	Remote Similarity	NPD8328	Phase 3
0.6357	Remote Similarity	NPD7078	Approved
0.6357	Remote Similarity	NPD8293	Discontinued
0.6356	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6371	Approved
0.6296	Remote Similarity	NPD7524	Approved
0.629	Remote Similarity	NPD6009	Approved
0.6273	Remote Similarity	NPD3168	Discontinued
0.627	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD6067	Discontinued
0.625	Remote Similarity	NPD7642	Approved
0.623	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD4632	Approved
0.616	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD7625	Phase 1
0.6107	Remote Similarity	NPD8074	Phase 3
0.6098	Remote Similarity	NPD8297	Approved
0.6094	Remote Similarity	NPD6921	Approved
0.6019	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8171	Discontinued
0.6017	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7830	Approved
0.5963	Remote Similarity	NPD1694	Approved
0.595	Remote Similarity	NPD5697	Approved
0.594	Remote Similarity	NPD6033	Approved
0.5935	Remote Similarity	NPD4634	Approved
0.5932	Remote Similarity	NPD4159	Approved
0.5926	Remote Similarity	NPD6695	Phase 3
0.5917	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4249	Approved
0.5902	Remote Similarity	NPD6881	Approved
0.5902	Remote Similarity	NPD6899	Approved
0.5887	Remote Similarity	NPD6649	Approved
0.5887	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD5211	Phase 2
0.5868	Remote Similarity	NPD6008	Approved
0.5859	Remote Similarity	NPD7641	Discontinued
0.5856	Remote Similarity	NPD4251	Approved
0.5856	Remote Similarity	NPD4250	Approved
0.5854	Remote Similarity	NPD6012	Approved
0.5854	Remote Similarity	NPD6014	Approved
0.5854	Remote Similarity	NPD6013	Approved
0.5852	Remote Similarity	NPD5956	Approved
0.5847	Remote Similarity	NPD5286	Approved
0.5847	Remote Similarity	NPD4696	Approved
0.5847	Remote Similarity	NPD5285	Approved
0.5846	Remote Similarity	NPD5983	Phase 2
0.5846	Remote Similarity	NPD8444	Approved
0.5841	Remote Similarity	NPD5785	Approved
0.584	Remote Similarity	NPD6053	Discontinued
0.5818	Remote Similarity	NPD1696	Phase 3
0.5809	Remote Similarity	NPD7260	Phase 2
0.5806	Remote Similarity	NPD7102	Approved
0.5806	Remote Similarity	NPD7290	Approved
0.5806	Remote Similarity	NPD6883	Approved
0.5802	Remote Similarity	NPD5126	Approved
0.5802	Remote Similarity	NPD5125	Phase 3
0.5789	Remote Similarity	NPD8451	Approved
0.5789	Remote Similarity	NPD7983	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.5785	Remote Similarity	NPD5141	Approved
0.5772	Remote Similarity	NPD7320	Approved
0.5772	Remote Similarity	NPD6011	Approved
0.5766	Remote Similarity	NPD6845	Suspended
0.576	Remote Similarity	NPD6869	Approved
0.576	Remote Similarity	NPD8130	Phase 1
0.576	Remote Similarity	NPD6847	Approved
0.576	Remote Similarity	NPD6617	Approved
0.5758	Remote Similarity	NPD7604	Phase 2
0.575	Remote Similarity	NPD5224	Approved
0.575	Remote Similarity	NPD5225	Approved
0.575	Remote Similarity	NPD5226	Approved
0.575	Remote Similarity	NPD4633	Approved
0.5746	Remote Similarity	NPD8448	Approved
0.5738	Remote Similarity	NPD6675	Approved
0.5738	Remote Similarity	NPD5739	Approved
0.5738	Remote Similarity	NPD7128	Approved
0.5738	Remote Similarity	NPD6402	Approved
0.5738	Remote Similarity	NPD5357	Phase 1
0.5726	Remote Similarity	NPD6372	Approved
0.5726	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5174	Approved
0.5702	Remote Similarity	NPD5175	Approved
0.5702	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5701	Approved
0.5688	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4755	Approved
0.5673	Remote Similarity	NPD1810	Approved
0.5673	Remote Similarity	NPD1811	Approved
0.5672	Remote Similarity	NPD6336	Discontinued
0.5667	Remote Similarity	NPD5223	Approved
0.5652	Remote Similarity	NPD8338	Approved
0.5652	Remote Similarity	NPD6079	Approved
0.5652	Remote Similarity	NPD8449	Approved
0.5648	Remote Similarity	NPD6931	Approved
0.5648	Remote Similarity	NPD7514	Phase 3
0.5648	Remote Similarity	NPD6930	Phase 2
0.5648	Remote Similarity	NPD7525	Registered
0.5648	Remote Similarity	NPD7332	Phase 2
0.5645	Remote Similarity	NPD4729	Approved
0.5645	Remote Similarity	NPD4730	Approved
0.5636	Remote Similarity	NPD3669	Approved
0.5636	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3618	Phase 1
0.562	Remote Similarity	NPD8392	Approved
0.562	Remote Similarity	NPD8390	Approved
0.562	Remote Similarity	NPD8391	Approved
0.562	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD1695	Approved
0.5612	Remote Similarity	NPD8450	Suspended
0.5603	Remote Similarity	NPD4202	Approved
0.5603	Remote Similarity	NPD5779	Approved
0.5603	Remote Similarity	NPD5778	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