NPASS Compound

Structure

CID215400 OpenBabel06191716002D 39 43 0 0 1 0 0 0 0 0999 V2000 4.5608 2.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7536 1.6165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8062 -2.8630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9088 -2.5714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3729 -2.0355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8011 -0.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0430 -0.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6763 0.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1601 -0.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7935 0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1526 0.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3945 0.1456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 1.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7363 1.7286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 -1.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5617 0.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1951 1.9265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8708 1.2508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0354 0.3617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5639 1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1951 -0.3804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1951 -2.0355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9088 1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5117 0.5113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5639 0.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 -0.3804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8708 0.2953 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2395 -2.0355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9088 0.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7363 -0.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7618 -1.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 -2.8630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3870 1.4587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7618 -2.8630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7363 -2.0936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8506 -1.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5461 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 5.7536 -0.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 37 1 0 0 0 0 16 38 1 0 0 0 0 17 1 1 1 0 0 0 17 18 1 0 0 0 0 18 2 1 1 0 0 0 18 27 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 29 2 0 0 0 0 23 37 1 0 0 0 0 24 33 2 0 0 0 0 24 39 1 0 0 0 0 25 26 1 0 0 0 0 25 30 2 0 0 0 0 26 31 2 0 0 0 0 27 39 1 1 0 0 0 28 31 1 0 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 29 38 1 0 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.21
Volume:	543.27
LogP:	5.403
LogD:	4.539
LogS:	-6.165
# Rotatable Bonds:	7
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	3.998
Fsp3:	0.323
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	1.375861120322952e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	95.41112518310547%
Volume Distribution (VD):	0.521
Pgp-substrate:	4.037883281707764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.166
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.978
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.958
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.565
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	4.46
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.38
Skin Sensitization:	0.622
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.702
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC215400

Natural Product ID:	NPC215400
*Common Name:**	Tiegusanin L
IUPAC Name:	n.a.
Synonyms:	Tiegusanin L
Standard InCHIKey:	ZUSDJUTXFWPDCB-UCZNXJLISA-N
Standard InCHI:	InChI=1S/C31H32O8/c1-17-13-20-14-23-29(38-16-37-23)30(35-4)25(20)26-21(15-22(32)28(34-3)31(26)36-5)27(18(17)2)39-24(33)12-11-19-9-7-6-8-10-19/h6-12,14-15,17-18,27,32H,13,16H2,1-5H3/b12-11+/t17-,18-,27-/m1/s1
SMILES:	C[C@@H]1Cc2cc3c(c(c2-c2c(cc(c(c2OC)OC)O)[C@@H]([C@@H]1C)OC(=O)/C=C/c1ccccc1)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564434
PubChem CID:	44179267
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	74100.0	nM	PMID[529765]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	7300.0	nM	PMID[529765]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	10.2	n.a.	PMID[529765]

☑ 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 NPC215400 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	357
0.1-0.2	1504
0.2-0.3	3610
0.3-0.4	8981
0.4-0.5	9523
0.5-0.6	3873
0.6-0.7	6566
0.7-0.8	6766
0.8-0.85	1243
0.85-0.9	203
0.9-0.95	61
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230531
0.9669	High Similarity	NPC476065
0.9542	High Similarity	NPC475592
0.9536	High Similarity	NPC475141
0.9474	High Similarity	NPC473736
0.947	High Similarity	NPC471154
0.947	High Similarity	NPC477378
0.947	High Similarity	NPC475229
0.943	High Similarity	NPC311912
0.9408	High Similarity	NPC217708
0.9408	High Similarity	NPC297271
0.9408	High Similarity	NPC16791
0.9408	High Similarity	NPC53669
0.9408	High Similarity	NPC77237
0.9408	High Similarity	NPC126405
0.9408	High Similarity	NPC477377
0.9408	High Similarity	NPC474606
0.9408	High Similarity	NPC308739
0.9408	High Similarity	NPC24562
0.9404	High Similarity	NPC475756
0.9404	High Similarity	NPC224472
0.9371	High Similarity	NPC88557
0.9286	High Similarity	NPC238834
0.9272	High Similarity	NPC474393
0.9272	High Similarity	NPC474347
0.9245	High Similarity	NPC83049
0.9245	High Similarity	NPC118162
0.9245	High Similarity	NPC320471
0.9226	High Similarity	NPC473323
0.9221	High Similarity	NPC312763
0.9221	High Similarity	NPC198461
0.9211	High Similarity	NPC470916
0.9211	High Similarity	NPC24425
0.9205	High Similarity	NPC252281
0.9205	High Similarity	NPC327352
0.9205	High Similarity	NPC102934
0.9205	High Similarity	NPC316676
0.9205	High Similarity	NPC477375
0.9205	High Similarity	NPC198129
0.9205	High Similarity	NPC252402
0.9205	High Similarity	NPC325720
0.9145	High Similarity	NPC322426
0.9145	High Similarity	NPC477374
0.9145	High Similarity	NPC477376
0.9085	High Similarity	NPC473989
0.9085	High Similarity	NPC316989
0.9073	High Similarity	NPC474054
0.9068	High Similarity	NPC79322
0.9067	High Similarity	NPC121661
0.9067	High Similarity	NPC73467
0.9067	High Similarity	NPC87883
0.9067	High Similarity	NPC326144
0.9057	High Similarity	NPC473445
0.9057	High Similarity	NPC42797
0.9032	High Similarity	NPC149735
0.902	High Similarity	NPC85141
0.9013	High Similarity	NPC295297
0.9007	High Similarity	NPC110763
0.9007	High Similarity	NPC189239
0.9007	High Similarity	NPC197352
0.9007	High Similarity	NPC318286
0.9007	High Similarity	NPC166506
0.9007	High Similarity	NPC327651
0.9	High Similarity	NPC291977
0.9	High Similarity	NPC218510
0.9	High Similarity	NPC469630
0.9	High Similarity	NPC76415
0.8994	High Similarity	NPC319749
0.8974	High Similarity	NPC473425
0.8968	High Similarity	NPC478268
0.8957	High Similarity	NPC477883
0.8947	High Similarity	NPC154971
0.8947	High Similarity	NPC321958
0.8947	High Similarity	NPC321696
0.8947	High Similarity	NPC252286
0.8933	High Similarity	NPC184684
0.8933	High Similarity	NPC67467
0.8933	High Similarity	NPC184641
0.8933	High Similarity	NPC133934
0.8924	High Similarity	NPC125495
0.8902	High Similarity	NPC469506
0.8882	High Similarity	NPC477702
0.8875	High Similarity	NPC258322
0.8875	High Similarity	NPC191352
0.8874	High Similarity	NPC324962
0.8868	High Similarity	NPC478269
0.8861	High Similarity	NPC29727
0.8848	High Similarity	NPC477881
0.8846	High Similarity	NPC472612
0.8846	High Similarity	NPC476434
0.8846	High Similarity	NPC289967
0.8846	High Similarity	NPC472611
0.8839	High Similarity	NPC477381
0.8827	High Similarity	NPC477884
0.8824	High Similarity	NPC212890
0.882	High Similarity	NPC280778
0.8808	High Similarity	NPC230538
0.8808	High Similarity	NPC103637
0.8808	High Similarity	NPC229172
0.8808	High Similarity	NPC36531
0.879	High Similarity	NPC470769
0.8782	High Similarity	NPC477379
0.8774	High Similarity	NPC90896
0.8774	High Similarity	NPC106138
0.8774	High Similarity	NPC283839
0.8773	High Similarity	NPC59516
0.8765	High Similarity	NPC469475
0.8765	High Similarity	NPC469518
0.8758	High Similarity	NPC478267
0.8758	High Similarity	NPC475868
0.8742	High Similarity	NPC11411
0.8742	High Similarity	NPC477380
0.8734	High Similarity	NPC348849
0.8734	High Similarity	NPC178195
0.8733	High Similarity	NPC471183
0.8726	High Similarity	NPC302610
0.8718	High Similarity	NPC469707
0.8718	High Similarity	NPC225815
0.8718	High Similarity	NPC145979
0.8718	High Similarity	NPC185955
0.8718	High Similarity	NPC218041
0.8718	High Similarity	NPC214326
0.8718	High Similarity	NPC9933
0.8718	High Similarity	NPC260781
0.8718	High Similarity	NPC469706
0.8718	High Similarity	NPC182368
0.8704	High Similarity	NPC249070
0.8704	High Similarity	NPC469512
0.8701	High Similarity	NPC40222
0.8701	High Similarity	NPC268515
0.8696	High Similarity	NPC268718
0.8696	High Similarity	NPC150943
0.8696	High Similarity	NPC91634
0.8693	High Similarity	NPC472712
0.8693	High Similarity	NPC172171
0.8693	High Similarity	NPC187774
0.8693	High Similarity	NPC297342
0.8693	High Similarity	NPC118385
0.8693	High Similarity	NPC239254
0.8693	High Similarity	NPC473046
0.8693	High Similarity	NPC472713
0.869	High Similarity	NPC477880
0.869	High Similarity	NPC477882
0.8688	High Similarity	NPC477885
0.8688	High Similarity	NPC163527
0.8688	High Similarity	NPC181168
0.8688	High Similarity	NPC115281
0.8684	High Similarity	NPC191231
0.8684	High Similarity	NPC41782
0.8671	High Similarity	NPC115203
0.8671	High Similarity	NPC150442
0.8667	High Similarity	NPC117911
0.8667	High Similarity	NPC865
0.8645	High Similarity	NPC39657
0.8645	High Similarity	NPC183083
0.8645	High Similarity	NPC137352
0.8634	High Similarity	NPC173726
0.8634	High Similarity	NPC241600
0.8625	High Similarity	NPC228357
0.8609	High Similarity	NPC201404
0.8609	High Similarity	NPC53722
0.8609	High Similarity	NPC290714
0.8608	High Similarity	NPC176186
0.8608	High Similarity	NPC169404
0.8608	High Similarity	NPC21902
0.8608	High Similarity	NPC53587
0.86	High Similarity	NPC143895
0.86	High Similarity	NPC133025
0.8599	High Similarity	NPC472709
0.8599	High Similarity	NPC472710
0.859	High Similarity	NPC261122
0.859	High Similarity	NPC477879
0.859	High Similarity	NPC201148
0.859	High Similarity	NPC80732
0.859	High Similarity	NPC300262
0.859	High Similarity	NPC199311
0.859	High Similarity	NPC93924
0.859	High Similarity	NPC210611
0.859	High Similarity	NPC215095
0.859	High Similarity	NPC192763
0.859	High Similarity	NPC28651
0.859	High Similarity	NPC3460
0.8581	High Similarity	NPC190714
0.8581	High Similarity	NPC317053
0.8581	High Similarity	NPC199928
0.8581	High Similarity	NPC260397
0.8581	High Similarity	NPC99515
0.8581	High Similarity	NPC324492
0.858	High Similarity	NPC63061
0.8571	High Similarity	NPC470827
0.8571	High Similarity	NPC110063
0.8571	High Similarity	NPC207584
0.8571	High Similarity	NPC19947
0.8563	High Similarity	NPC178737
0.8563	High Similarity	NPC471181
0.8562	High Similarity	NPC5262
0.8562	High Similarity	NPC287124
0.8562	High Similarity	NPC140502
0.8562	High Similarity	NPC472714
0.8553	High Similarity	NPC65591

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 NPC215400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	905
0.2-0.3	1748
0.3-0.4	2745
0.4-0.5	1815
0.5-0.6	968
0.6-0.7	554
0.7-0.8	108
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6234	Discontinued
0.8553	High Similarity	NPD37	Approved
0.8509	High Similarity	NPD4965	Approved
0.8509	High Similarity	NPD4966	Approved
0.8509	High Similarity	NPD4967	Phase 2
0.8494	Intermediate Similarity	NPD7228	Approved
0.8415	Intermediate Similarity	NPD7199	Phase 2
0.8313	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1653	Approved
0.8129	Intermediate Similarity	NPD7266	Discontinued
0.8061	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3818	Discontinued
0.8013	Intermediate Similarity	NPD3027	Phase 3
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD7240	Approved
0.7937	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6232	Discontinued
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7861	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7765	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7472	Approved
0.774	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1465	Phase 2
0.7712	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6674	Discontinued
0.7665	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD7680	Approved
0.7647	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6166	Phase 2
0.763	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3705	Approved
0.7597	Intermediate Similarity	NPD4908	Phase 1
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7516	Intermediate Similarity	NPD4060	Phase 1
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.743	Intermediate Similarity	NPD7549	Discontinued
0.7414	Intermediate Similarity	NPD7229	Phase 3
0.7412	Intermediate Similarity	NPD8455	Phase 2
0.7412	Intermediate Similarity	NPD7819	Suspended
0.7412	Intermediate Similarity	NPD2801	Approved
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7384	Intermediate Similarity	NPD7075	Discontinued
0.7378	Intermediate Similarity	NPD6190	Approved
0.7356	Intermediate Similarity	NPD8127	Discontinued
0.7326	Intermediate Similarity	NPD7768	Phase 2
0.7317	Intermediate Similarity	NPD3750	Approved
0.7299	Intermediate Similarity	NPD5494	Approved
0.7297	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3620	Phase 2
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1610	Phase 2
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7239	Intermediate Similarity	NPD5763	Approved
0.7239	Intermediate Similarity	NPD5762	Approved
0.7235	Intermediate Similarity	NPD4380	Phase 2
0.7228	Intermediate Similarity	NPD6841	Approved
0.7228	Intermediate Similarity	NPD6842	Approved
0.7228	Intermediate Similarity	NPD6843	Phase 3
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD3018	Phase 2
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1511	Approved
0.7184	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3749	Approved
0.7179	Intermediate Similarity	NPD8151	Discontinued
0.717	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6959	Discontinued
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7108	Intermediate Similarity	NPD8166	Discontinued
0.7101	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1512	Approved
0.7093	Intermediate Similarity	NPD7411	Suspended
0.7076	Intermediate Similarity	NPD7458	Discontinued
0.7076	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5402	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD1357	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7052	Intermediate Similarity	NPD6801	Discontinued
0.7051	Intermediate Similarity	NPD2982	Phase 2
0.7051	Intermediate Similarity	NPD2983	Phase 2
0.7039	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1091	Approved
0.7013	Intermediate Similarity	NPD4626	Approved
0.7012	Intermediate Similarity	NPD3748	Approved
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.6993	Remote Similarity	NPD1548	Phase 1
0.6989	Remote Similarity	NPD8434	Phase 2
0.6987	Remote Similarity	NPD2981	Phase 2
0.6983	Remote Similarity	NPD3926	Phase 2
0.6982	Remote Similarity	NPD4357	Discontinued
0.6982	Remote Similarity	NPD6799	Approved
0.6975	Remote Similarity	NPD4140	Approved
0.697	Remote Similarity	NPD2935	Discontinued
0.6959	Remote Similarity	NPD5403	Approved
0.6957	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD919	Approved
0.6948	Remote Similarity	NPD5691	Approved
0.6946	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4749	Approved
0.6941	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7028	Phase 2
0.6936	Remote Similarity	NPD6599	Discontinued
0.6928	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7435	Discontinued
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2977	Approved
0.6914	Remote Similarity	NPD2978	Approved
0.6914	Remote Similarity	NPD6233	Phase 2
0.6909	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7003	Approved
0.6905	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4110	Phase 3
0.69	Remote Similarity	NPD7827	Phase 1
0.6897	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1549	Phase 2
0.6882	Remote Similarity	NPD8054	Approved
0.6882	Remote Similarity	NPD8053	Approved
0.6872	Remote Similarity	NPD5006	Approved
0.6872	Remote Similarity	NPD5005	Approved
0.6867	Remote Similarity	NPD2438	Suspended
0.6867	Remote Similarity	NPD228	Approved
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD6100	Approved
0.6864	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7906	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.685	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7783	Phase 2
0.6848	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5401	Approved
0.6842	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1933	Approved
0.6829	Remote Similarity	NPD5735	Approved
0.6826	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5058	Phase 3
0.6818	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5536	Phase 2
0.6816	Remote Similarity	NPD6746	Phase 2
0.6807	Remote Similarity	NPD4108	Discontinued
0.6802	Remote Similarity	NPD6273	Approved
0.68	Remote Similarity	NPD5090	Approved
0.68	Remote Similarity	NPD5089	Approved
0.6796	Remote Similarity	NPD5242	Approved
0.6795	Remote Similarity	NPD5125	Phase 3
0.6795	Remote Similarity	NPD5126	Approved
0.6788	Remote Similarity	NPD6653	Approved
0.6786	Remote Similarity	NPD6823	Phase 2
0.6782	Remote Similarity	NPD3226	Approved
0.6782	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4005	Discontinued
0.678	Remote Similarity	NPD5353	Approved
0.678	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5736	Approved
0.6769	Remote Similarity	NPD6777	Approved
0.6769	Remote Similarity	NPD6776	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