NPASS Compound

Structure

NPC473068 OpenBabel07101718282D 28 30 0 0 1 0 0 0 0 0999 V2000 1.0951 3.6445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0205 -0.9844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1216 -0.0226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3258 -0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0075 1.9717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4807 1.1606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9198 -1.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5136 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 2.8334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6761 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6761 -0.9671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8385 -1.4507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0010 -0.9671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7781 -1.0489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0010 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2380 -0.4159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4883 -0.4836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9198 0.2989 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5136 1.4507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 2.8840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5136 -1.4507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8385 -2.4178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1634 -1.4507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1715 -1.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8385 0.4836 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 3.1634 0.4836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 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 9 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 7 1 6 0 0 0 10 15 1 0 0 0 0 10 27 1 0 0 0 0 11 8 1 6 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 1 0 0 0 13 14 1 0 0 0 0 13 23 1 6 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 26 1 0 0 0 0 16 28 1 6 0 0 0 17 19 1 0 0 0 0 18 19 1 6 0 0 0 18 28 1 0 0 0 0 19 6 1 1 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.19
Volume:	385.35
LogP:	-0.233
LogD:	-0.38
LogS:	-2.703
# Rotatable Bonds:	5
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	5.814
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.551
MDCK Permeability:	6.605174712603912e-05
Pgp-inhibitor:	0.223
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.623
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	25.342876434326172%
Volume Distribution (VD):	0.477
Pgp-substrate:	55.87527084350586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	1.561
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.746
Rat Oral Acute Toxicity:	0.512
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.894
Carcinogencity:	0.668
Eye Corrosion:	0.007
Eye Irritation:	0.066
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC473068

Natural Product ID:	NPC473068
*Common Name:**	PVZZOBJHAQCRIF-BUOSROCHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PVZZOBJHAQCRIF-BUOSROCHSA-N
Standard InCHI:	InChI=1S/C19H30O9/c1-9(21)5-6-19-17(2,3)15(25)10(27-19)7-18(19,4)28-16-14(24)13(23)12(22)11(8-20)26-16/h5-6,10-16,20,22-25H,7-8H2,1-4H3/b6-5+/t10-,11+,12+,13-,14+,15-,16-,18-,19-/m0/s1
SMILES:	CC(=O)C=CC12C(C(C(O1)CC2(C)OC3C(C(C(C(O3)CO)O)O)O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608832
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	=	98.5	%	PMID[513210]

☑ 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 NPC473068 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	207
0.1-0.2	1543
0.2-0.3	4995
0.3-0.4	9174
0.4-0.5	13431
0.5-0.6	8106
0.6-0.7	4566
0.7-0.8	650
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC473070
0.9697	High Similarity	NPC473069
0.92	High Similarity	NPC194941
0.8812	High Similarity	NPC150463
0.8812	High Similarity	NPC214277
0.8333	Intermediate Similarity	NPC312325
0.8208	Intermediate Similarity	NPC239961
0.8148	Intermediate Similarity	NPC206618
0.8091	Intermediate Similarity	NPC470025
0.8091	Intermediate Similarity	NPC328074
0.8091	Intermediate Similarity	NPC321272
0.8091	Intermediate Similarity	NPC317460
0.8087	Intermediate Similarity	NPC471082
0.8073	Intermediate Similarity	NPC46407
0.8073	Intermediate Similarity	NPC316708
0.8056	Intermediate Similarity	NPC38948
0.8018	Intermediate Similarity	NPC470027
0.8	Intermediate Similarity	NPC198992
0.8	Intermediate Similarity	NPC17791
0.8	Intermediate Similarity	NPC470026
0.7981	Intermediate Similarity	NPC475068
0.789	Intermediate Similarity	NPC128795
0.789	Intermediate Similarity	NPC217921
0.789	Intermediate Similarity	NPC181994
0.789	Intermediate Similarity	NPC135015
0.789	Intermediate Similarity	NPC48548
0.7885	Intermediate Similarity	NPC120446
0.7857	Intermediate Similarity	NPC264153
0.785	Intermediate Similarity	NPC120009
0.7818	Intermediate Similarity	NPC257853
0.7818	Intermediate Similarity	NPC28844
0.7818	Intermediate Similarity	NPC473318
0.7818	Intermediate Similarity	NPC473328
0.7818	Intermediate Similarity	NPC316974
0.7818	Intermediate Similarity	NPC40728
0.7798	Intermediate Similarity	NPC109376
0.7798	Intermediate Similarity	NPC122816
0.7798	Intermediate Similarity	NPC125423
0.7798	Intermediate Similarity	NPC88013
0.7778	Intermediate Similarity	NPC196130
0.7768	Intermediate Similarity	NPC473125
0.7759	Intermediate Similarity	NPC48692
0.7757	Intermediate Similarity	NPC472815
0.7757	Intermediate Similarity	NPC121423
0.7748	Intermediate Similarity	NPC170974
0.7748	Intermediate Similarity	NPC103627
0.7748	Intermediate Similarity	NPC191439
0.7748	Intermediate Similarity	NPC177047
0.7748	Intermediate Similarity	NPC65155
0.7739	Intermediate Similarity	NPC83287
0.7727	Intermediate Similarity	NPC38376
0.7727	Intermediate Similarity	NPC80210
0.7727	Intermediate Similarity	NPC470024
0.7727	Intermediate Similarity	NPC224660
0.7727	Intermediate Similarity	NPC311223
0.7719	Intermediate Similarity	NPC471816
0.7706	Intermediate Similarity	NPC82251
0.7706	Intermediate Similarity	NPC51719
0.7706	Intermediate Similarity	NPC218158
0.7706	Intermediate Similarity	NPC172867
0.7699	Intermediate Similarity	NPC290608
0.7699	Intermediate Similarity	NPC44298
0.7699	Intermediate Similarity	NPC40133
0.7699	Intermediate Similarity	NPC49413
0.7699	Intermediate Similarity	NPC473128
0.7692	Intermediate Similarity	NPC233500
0.7685	Intermediate Similarity	NPC474575
0.7677	Intermediate Similarity	NPC471267
0.7677	Intermediate Similarity	NPC34581
0.7672	Intermediate Similarity	NPC470914
0.7664	Intermediate Similarity	NPC154127
0.7664	Intermediate Similarity	NPC280991
0.7664	Intermediate Similarity	NPC472554
0.7658	Intermediate Similarity	NPC221110
0.7658	Intermediate Similarity	NPC180459
0.7658	Intermediate Similarity	NPC195116
0.7658	Intermediate Similarity	NPC285253
0.7653	Intermediate Similarity	NPC471987
0.7652	Intermediate Similarity	NPC84987
0.7652	Intermediate Similarity	NPC471355
0.7652	Intermediate Similarity	NPC471353
0.7652	Intermediate Similarity	NPC196429
0.7652	Intermediate Similarity	NPC99728
0.7652	Intermediate Similarity	NPC87250
0.7652	Intermediate Similarity	NPC50305
0.7652	Intermediate Similarity	NPC27507
0.7652	Intermediate Similarity	NPC471354
0.7652	Intermediate Similarity	NPC473852
0.7652	Intermediate Similarity	NPC158344
0.7652	Intermediate Similarity	NPC474418
0.7652	Intermediate Similarity	NPC243196
0.7652	Intermediate Similarity	NPC203862
0.7652	Intermediate Similarity	NPC142066
0.7652	Intermediate Similarity	NPC152615
0.7652	Intermediate Similarity	NPC309034
0.7652	Intermediate Similarity	NPC471351
0.7652	Intermediate Similarity	NPC34390
0.7652	Intermediate Similarity	NPC157376
0.7652	Intermediate Similarity	NPC77319
0.7652	Intermediate Similarity	NPC244402
0.7642	Intermediate Similarity	NPC61630
0.7642	Intermediate Similarity	NPC307517
0.7642	Intermediate Similarity	NPC81483
0.7642	Intermediate Similarity	NPC169468
0.7636	Intermediate Similarity	NPC471205
0.7611	Intermediate Similarity	NPC231797
0.7607	Intermediate Similarity	NPC475136
0.7607	Intermediate Similarity	NPC474466
0.7603	Intermediate Similarity	NPC270109
0.7593	Intermediate Similarity	NPC472552
0.7593	Intermediate Similarity	NPC223834
0.7593	Intermediate Similarity	NPC201191
0.7589	Intermediate Similarity	NPC119550
0.7586	Intermediate Similarity	NPC234522
0.757	Intermediate Similarity	NPC188968
0.7565	Intermediate Similarity	NPC193382
0.7565	Intermediate Similarity	NPC99620
0.7565	Intermediate Similarity	NPC310341
0.7565	Intermediate Similarity	NPC199428
0.7565	Intermediate Similarity	NPC5311
0.7547	Intermediate Similarity	NPC474194
0.7547	Intermediate Similarity	NPC26307
0.7545	Intermediate Similarity	NPC476592
0.7545	Intermediate Similarity	NPC85670
0.7544	Intermediate Similarity	NPC311592
0.7544	Intermediate Similarity	NPC75167
0.7544	Intermediate Similarity	NPC287075
0.7523	Intermediate Similarity	NPC127933
0.7523	Intermediate Similarity	NPC475889
0.7523	Intermediate Similarity	NPC281378
0.7523	Intermediate Similarity	NPC151516
0.7523	Intermediate Similarity	NPC7613
0.7523	Intermediate Similarity	NPC7644
0.7522	Intermediate Similarity	NPC208189
0.7522	Intermediate Similarity	NPC65034
0.7522	Intermediate Similarity	NPC110494
0.7522	Intermediate Similarity	NPC157474
0.7521	Intermediate Similarity	NPC219656
0.7521	Intermediate Similarity	NPC329905
0.7521	Intermediate Similarity	NPC5883
0.7521	Intermediate Similarity	NPC304260
0.7521	Intermediate Similarity	NPC29639
0.7521	Intermediate Similarity	NPC44899
0.75	Intermediate Similarity	NPC93883
0.75	Intermediate Similarity	NPC11974
0.75	Intermediate Similarity	NPC119467
0.75	Intermediate Similarity	NPC27999
0.75	Intermediate Similarity	NPC475767
0.75	Intermediate Similarity	NPC13713
0.75	Intermediate Similarity	NPC477116
0.7479	Intermediate Similarity	NPC264336
0.7478	Intermediate Similarity	NPC69576
0.7478	Intermediate Similarity	NPC181145
0.7478	Intermediate Similarity	NPC31354
0.7478	Intermediate Similarity	NPC106446
0.7478	Intermediate Similarity	NPC471633
0.7478	Intermediate Similarity	NPC475163
0.7478	Intermediate Similarity	NPC84949
0.7477	Intermediate Similarity	NPC33053
0.7477	Intermediate Similarity	NPC475074
0.7477	Intermediate Similarity	NPC472390
0.7476	Intermediate Similarity	NPC474249
0.7476	Intermediate Similarity	NPC261990
0.7475	Intermediate Similarity	NPC106912
0.7475	Intermediate Similarity	NPC2379
0.7475	Intermediate Similarity	NPC31019
0.7475	Intermediate Similarity	NPC263087
0.7475	Intermediate Similarity	NPC27314
0.7459	Intermediate Similarity	NPC470850
0.7458	Intermediate Similarity	NPC135369
0.7458	Intermediate Similarity	NPC475629
0.7458	Intermediate Similarity	NPC475556
0.7456	Intermediate Similarity	NPC476305
0.7455	Intermediate Similarity	NPC264867
0.7455	Intermediate Similarity	NPC470321
0.7455	Intermediate Similarity	NPC473207
0.7455	Intermediate Similarity	NPC81567
0.7455	Intermediate Similarity	NPC201880
0.7453	Intermediate Similarity	NPC90583
0.7453	Intermediate Similarity	NPC472995
0.7438	Intermediate Similarity	NPC222307
0.7436	Intermediate Similarity	NPC218093
0.7436	Intermediate Similarity	NPC473617
0.7436	Intermediate Similarity	NPC473828
0.7434	Intermediate Similarity	NPC235014
0.7431	Intermediate Similarity	NPC300399
0.7431	Intermediate Similarity	NPC11956
0.7431	Intermediate Similarity	NPC471482
0.7431	Intermediate Similarity	NPC238397
0.7431	Intermediate Similarity	NPC37207
0.7431	Intermediate Similarity	NPC471363
0.7429	Intermediate Similarity	NPC25701
0.7429	Intermediate Similarity	NPC2003
0.7429	Intermediate Similarity	NPC256368
0.7414	Intermediate Similarity	NPC207637
0.7411	Intermediate Similarity	NPC392
0.7411	Intermediate Similarity	NPC177524
0.7411	Intermediate Similarity	NPC219900
0.7407	Intermediate Similarity	NPC324841
0.7407	Intermediate Similarity	NPC38855

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 NPC473068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1940
0.2-0.3	4056
0.3-0.4	2049
0.4-0.5	579
0.5-0.6	286
0.6-0.7	53
0.7-0.8	13
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
0.7826	Intermediate Similarity	NPD7516	Approved
0.7739	Intermediate Similarity	NPD7328	Approved
0.7739	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD5344	Discontinued
0.7411	Intermediate Similarity	NPD6686	Approved
0.7395	Intermediate Similarity	NPD8296	Approved
0.7395	Intermediate Similarity	NPD8335	Approved
0.7395	Intermediate Similarity	NPD8380	Approved
0.7395	Intermediate Similarity	NPD8379	Approved
0.7395	Intermediate Similarity	NPD8378	Approved
0.7395	Intermediate Similarity	NPD8033	Approved
0.7311	Intermediate Similarity	NPD8377	Approved
0.7311	Intermediate Similarity	NPD8294	Approved
0.725	Intermediate Similarity	NPD7503	Approved
0.7091	Intermediate Similarity	NPD6648	Approved
0.7016	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6984	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6370	Approved
0.6724	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7838	Discovery
0.6613	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8515	Approved
0.656	Remote Similarity	NPD6016	Approved
0.656	Remote Similarity	NPD8517	Approved
0.656	Remote Similarity	NPD6015	Approved
0.656	Remote Similarity	NPD8513	Phase 3
0.656	Remote Similarity	NPD8516	Approved
0.6514	Remote Similarity	NPD6698	Approved
0.6514	Remote Similarity	NPD46	Approved
0.6512	Remote Similarity	NPD7736	Approved
0.6508	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7492	Approved
0.6404	Remote Similarity	NPD7638	Approved
0.6393	Remote Similarity	NPD8133	Approved
0.6371	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD3168	Discontinued
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD6059	Approved
0.6348	Remote Similarity	NPD7639	Approved
0.6348	Remote Similarity	NPD7640	Approved
0.6339	Remote Similarity	NPD5282	Discontinued
0.6328	Remote Similarity	NPD8328	Phase 3
0.6308	Remote Similarity	NPD7078	Approved
0.6308	Remote Similarity	NPD8293	Discontinued
0.6303	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6371	Approved
0.624	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD7524	Approved
0.622	Remote Similarity	NPD6319	Approved
0.6202	Remote Similarity	NPD6067	Discontinued
0.6202	Remote Similarity	NPD7642	Approved
0.6179	Remote Similarity	NPD6882	Approved
0.6172	Remote Similarity	NPD6921	Approved
0.614	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4632	Approved
0.6111	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7625	Phase 1
0.6061	Remote Similarity	NPD8074	Phase 3
0.6048	Remote Similarity	NPD8297	Approved
0.5966	Remote Similarity	NPD7632	Discontinued
0.5965	Remote Similarity	NPD8171	Discontinued
0.5963	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7829	Approved
0.5954	Remote Similarity	NPD7830	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5902	Remote Similarity	NPD5697	Approved
0.5896	Remote Similarity	NPD6033	Approved
0.5887	Remote Similarity	NPD4634	Approved
0.5882	Remote Similarity	NPD4159	Approved
0.5872	Remote Similarity	NPD6695	Phase 3
0.5868	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4249	Approved
0.5854	Remote Similarity	NPD6881	Approved
0.5854	Remote Similarity	NPD6899	Approved
0.584	Remote Similarity	NPD6649	Approved
0.584	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.582	Remote Similarity	NPD6008	Approved
0.582	Remote Similarity	NPD5357	Phase 1
0.5814	Remote Similarity	NPD7641	Discontinued
0.5809	Remote Similarity	NPD5956	Approved
0.5806	Remote Similarity	NPD6013	Approved
0.5806	Remote Similarity	NPD6014	Approved
0.5806	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD4250	Approved
0.5804	Remote Similarity	NPD4251	Approved
0.5802	Remote Similarity	NPD8444	Approved
0.5802	Remote Similarity	NPD5983	Phase 2
0.5798	Remote Similarity	NPD5286	Approved
0.5798	Remote Similarity	NPD4696	Approved
0.5798	Remote Similarity	NPD5285	Approved
0.5794	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD5785	Approved
0.5766	Remote Similarity	NPD7260	Phase 2
0.5766	Remote Similarity	NPD1696	Phase 3
0.576	Remote Similarity	NPD7102	Approved
0.576	Remote Similarity	NPD7290	Approved
0.576	Remote Similarity	NPD6883	Approved
0.5758	Remote Similarity	NPD5126	Approved
0.5758	Remote Similarity	NPD5125	Phase 3
0.5746	Remote Similarity	NPD8451	Approved
0.5739	Remote Similarity	NPD7637	Suspended
0.5739	Remote Similarity	NPD7983	Approved
0.5738	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD6011	Approved
0.5726	Remote Similarity	NPD7320	Approved
0.5725	Remote Similarity	NPD8338	Approved
0.5725	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD6617	Approved
0.5704	Remote Similarity	NPD8448	Approved
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5225	Approved
0.5702	Remote Similarity	NPD5226	Approved
0.5691	Remote Similarity	NPD5739	Approved
0.5691	Remote Similarity	NPD6402	Approved
0.5691	Remote Similarity	NPD6675	Approved
0.5691	Remote Similarity	NPD7128	Approved
0.568	Remote Similarity	NPD6372	Approved
0.568	Remote Similarity	NPD6373	Approved
0.5674	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD7750	Discontinued
0.5656	Remote Similarity	NPD5175	Approved
0.5656	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5701	Approved
0.5636	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.563	Remote Similarity	NPD4755	Approved
0.563	Remote Similarity	NPD6336	Discontinued
0.562	Remote Similarity	NPD5223	Approved
0.5619	Remote Similarity	NPD1811	Approved
0.5619	Remote Similarity	NPD1810	Approved
0.5612	Remote Similarity	NPD8449	Approved
0.5603	Remote Similarity	NPD6079	Approved
0.56	Remote Similarity	NPD4729	Approved
0.56	Remote Similarity	NPD4730	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