NPASS Compound

Structure

CID80210 OpenBabel06191715422D 44 50 0 0 1 0 0 0 0 0999 V2000 7.9611 -3.1587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2188 -4.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2260 -4.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2705 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0504 -0.7523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -3.0187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6310 -1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0074 -1.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -2.6587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1365 -0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 -2.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -1.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 -2.6044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0501 -2.0275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5074 -3.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0951 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3838 -2.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7601 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1450 -1.6115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7521 -1.8673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6310 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0951 -1.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2291 -1.1587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3630 -1.6587 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3630 -2.6587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8258 -3.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -1.9386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0074 -3.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1365 -1.9386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -1.5785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 -0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0074 -4.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 -2.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9611 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2291 -0.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -1.1587 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 6.2291 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4970 -3.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 12 1 0 0 0 0 8 21 1 0 0 0 0 9 13 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 31 1 0 0 0 0 12 33 1 0 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 16 23 1 0 0 0 0 16 30 1 0 0 0 0 17 24 1 0 0 0 0 17 34 1 0 0 0 0 18 32 1 0 0 0 0 18 37 1 0 0 0 0 19 35 1 0 0 0 0 19 42 1 0 0 0 0 20 1 1 1 0 0 0 20 26 1 0 0 0 0 20 43 1 0 0 0 0 21 31 1 6 0 0 0 21 32 1 0 0 0 0 22 31 1 6 0 0 0 22 33 1 0 0 0 0 23 35 1 6 0 0 0 23 36 1 0 0 0 0 24 35 1 6 0 0 0 24 38 1 0 0 0 0 25 32 1 6 0 0 0 25 44 1 0 0 0 0 26 27 1 0 0 0 0 26 39 1 1 0 0 0 27 28 1 0 0 0 0 27 40 1 1 0 0 0 28 29 1 0 0 0 0 28 41 1 6 0 0 0 29 43 1 0 0 0 0 29 44 1 1 0 0 0 31 4 1 6 0 0 0 32 5 1 6 0 0 0 33 34 1 1 0 0 0 34 36 1 6 0 0 0 35 15 1 1 0 0 0 36 13 1 1 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.41
Volume:	639.002
LogP:	4.104
LogD:	3.506
LogS:	-4.953
# Rotatable Bonds:	3
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	6.827
Fsp3:	0.944
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.377
MDCK Permeability:	6.890997610753402e-06
Pgp-inhibitor:	0.06
Pgp-substrate:	0.294
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	81.41307830810547%
Volume Distribution (VD):	0.916
Pgp-substrate:	7.134934425354004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.682
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.72
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.666
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	1.73
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.54
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.282
Maximum Recommended Daily Dose:	0.731
Skin Sensitization:	0.101
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC80210

Natural Product ID:	NPC80210
*Common Name:**	WSSVJIGMYVWUJL-WMYDXDAXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WSSVJIGMYVWUJL-WMYDXDAXSA-N
Standard InCHI:	InChI=1S/C36H58O8/c1-20-26(39)27(40)28(41)29(43-20)44-25-10-11-31(4)21(32(25,5)18-37)8-12-33(6)22(31)9-13-36-23-16-30(2,3)14-15-35(23,19-42-36)24(38)17-34(33,36)7/h9,13,20-29,37-41H,8,10-12,14-19H2,1-7H3/t20-,21-,22-,23-,24+,25+,26+,27+,28-,29+,31+,32+,33-,34+,35-,36+/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2C=C[C@]24[C@@H]5CC(C)(C)CC[C@]5(CO4)[C@H](C[C@@]32C)O)[C@]1(C)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3542195
PubChem CID:	21637633
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20248	Bupleurum marginatum	Species	Apiaceae	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	5
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[466439]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	13270.0	nM	PMID[466439]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	=	17280.0	nM	PMID[466439]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	43280.0	nM	PMID[466439]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Retention_time	=	45.5	min	PMID[466438]
NPT27	Others	Unspecified		Drug recovery	>	50.0	%	PMID[466438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19780.0	nM	PMID[466439]

☑ 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 NPC80210 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	272
0.1-0.2	1938
0.2-0.3	5634
0.3-0.4	12787
0.4-0.5	10040
0.5-0.6	5996
0.6-0.7	3430
0.7-0.8	1686
0.8-0.85	660
0.85-0.9	182
0.9-0.95	57
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38376
0.99	High Similarity	NPC221110
0.99	High Similarity	NPC195116
0.99	High Similarity	NPC180459
0.99	High Similarity	NPC285253
0.9706	High Similarity	NPC157474
0.9706	High Similarity	NPC110494
0.9612	High Similarity	NPC476305
0.9612	High Similarity	NPC473125
0.9519	High Similarity	NPC290608
0.9519	High Similarity	NPC49413
0.9519	High Similarity	NPC40133
0.9519	High Similarity	NPC473128
0.9519	High Similarity	NPC44298
0.94	High Similarity	NPC473124
0.94	High Similarity	NPC473123
0.9307	High Similarity	NPC473127
0.9307	High Similarity	NPC203354
0.9307	High Similarity	NPC110656
0.9135	High Similarity	NPC473328
0.9135	High Similarity	NPC473318
0.9135	High Similarity	NPC28844
0.9126	High Similarity	NPC281939
0.9048	High Similarity	NPC65155
0.9048	High Similarity	NPC170974
0.9048	High Similarity	NPC191439
0.9048	High Similarity	NPC103627
0.902	High Similarity	NPC162354
0.8952	High Similarity	NPC250089
0.8952	High Similarity	NPC14630
0.8952	High Similarity	NPC157530
0.8942	High Similarity	NPC33053
0.8879	High Similarity	NPC231797
0.8857	High Similarity	NPC472896
0.8857	High Similarity	NPC472897
0.8829	High Similarity	NPC473130
0.8824	High Similarity	NPC263756
0.8824	High Similarity	NPC117714
0.8785	High Similarity	NPC473021
0.8785	High Similarity	NPC208189
0.8785	High Similarity	NPC472987
0.8785	High Similarity	NPC65034
0.8774	High Similarity	NPC472901
0.8762	High Similarity	NPC231340
0.875	High Similarity	NPC93352
0.8738	High Similarity	NPC213674
0.8738	High Similarity	NPC30289
0.8738	High Similarity	NPC256133
0.8738	High Similarity	NPC76497
0.8725	High Similarity	NPC473790
0.8713	High Similarity	NPC240372
0.8704	High Similarity	NPC216595
0.8704	High Similarity	NPC473567
0.8704	High Similarity	NPC475354
0.8692	High Similarity	NPC472717
0.8679	High Similarity	NPC235824
0.8667	High Similarity	NPC472898
0.8667	High Similarity	NPC472899
0.8667	High Similarity	NPC472900
0.8654	High Similarity	NPC286969
0.8654	High Similarity	NPC120123
0.8654	High Similarity	NPC131479
0.8654	High Similarity	NPC123796
0.8654	High Similarity	NPC31907
0.8654	High Similarity	NPC8039
0.8654	High Similarity	NPC211879
0.8654	High Similarity	NPC155010
0.8654	High Similarity	NPC472252
0.8654	High Similarity	NPC473020
0.8654	High Similarity	NPC157659
0.8654	High Similarity	NPC473129
0.8654	High Similarity	NPC245280
0.8654	High Similarity	NPC16520
0.8654	High Similarity	NPC213190
0.8654	High Similarity	NPC189852
0.8654	High Similarity	NPC99627
0.8654	High Similarity	NPC114874
0.8641	High Similarity	NPC4831
0.8641	High Similarity	NPC160734
0.8641	High Similarity	NPC129372
0.8641	High Similarity	NPC285231
0.8641	High Similarity	NPC472023
0.8641	High Similarity	NPC21568
0.8641	High Similarity	NPC47566
0.8641	High Similarity	NPC309425
0.8641	High Similarity	NPC88000
0.8614	High Similarity	NPC90583
0.8611	High Similarity	NPC472715
0.86	High Similarity	NPC305160
0.8571	High Similarity	NPC470914
0.8571	High Similarity	NPC165033
0.8571	High Similarity	NPC54521
0.8571	High Similarity	NPC57065
0.8571	High Similarity	NPC471434
0.8571	High Similarity	NPC273879
0.8571	High Similarity	NPC187400
0.8571	High Similarity	NPC470885
0.8571	High Similarity	NPC471435
0.8571	High Similarity	NPC75608
0.8571	High Similarity	NPC148603
0.8571	High Similarity	NPC230948
0.8571	High Similarity	NPC109792
0.8571	High Similarity	NPC473734
0.8571	High Similarity	NPC173583
0.8571	High Similarity	NPC221562
0.8571	High Similarity	NPC475365
0.8559	High Similarity	NPC476690
0.8559	High Similarity	NPC100048
0.8559	High Similarity	NPC20979
0.8558	High Similarity	NPC288694
0.8558	High Similarity	NPC37207
0.8558	High Similarity	NPC159036
0.8558	High Similarity	NPC136816
0.8558	High Similarity	NPC312553
0.8544	High Similarity	NPC473200
0.8544	High Similarity	NPC7341
0.8544	High Similarity	NPC64348
0.8532	High Similarity	NPC472716
0.8515	High Similarity	NPC100892
0.8515	High Similarity	NPC477969
0.8515	High Similarity	NPC477970
0.8515	High Similarity	NPC135224
0.8505	High Similarity	NPC220427
0.85	High Similarity	NPC67398
0.85	High Similarity	NPC91654
0.85	High Similarity	NPC474792
0.8491	Intermediate Similarity	NPC269627
0.8491	Intermediate Similarity	NPC470512
0.8491	Intermediate Similarity	NPC127801
0.8491	Intermediate Similarity	NPC152584
0.8491	Intermediate Similarity	NPC208477
0.8491	Intermediate Similarity	NPC173859
0.8491	Intermediate Similarity	NPC194842
0.8491	Intermediate Similarity	NPC160816
0.8491	Intermediate Similarity	NPC208594
0.8491	Intermediate Similarity	NPC69737
0.8491	Intermediate Similarity	NPC138057
0.8485	Intermediate Similarity	NPC92885
0.8485	Intermediate Similarity	NPC476226
0.8485	Intermediate Similarity	NPC77796
0.8485	Intermediate Similarity	NPC261990
0.8485	Intermediate Similarity	NPC474249
0.8482	Intermediate Similarity	NPC10366
0.8476	Intermediate Similarity	NPC471886
0.8476	Intermediate Similarity	NPC471888
0.8476	Intermediate Similarity	NPC471885
0.8476	Intermediate Similarity	NPC16573
0.8476	Intermediate Similarity	NPC473198
0.8476	Intermediate Similarity	NPC471887
0.8455	Intermediate Similarity	NPC473159
0.8447	Intermediate Similarity	NPC234287
0.8447	Intermediate Similarity	NPC280825
0.8447	Intermediate Similarity	NPC312325
0.844	Intermediate Similarity	NPC13190
0.8416	Intermediate Similarity	NPC189513
0.8416	Intermediate Similarity	NPC72817
0.8416	Intermediate Similarity	NPC477927
0.8411	Intermediate Similarity	NPC181467
0.8411	Intermediate Similarity	NPC78034
0.8411	Intermediate Similarity	NPC63368
0.8411	Intermediate Similarity	NPC190395
0.8411	Intermediate Similarity	NPC14946
0.8411	Intermediate Similarity	NPC257964
0.8411	Intermediate Similarity	NPC208650
0.84	Intermediate Similarity	NPC289361
0.8396	Intermediate Similarity	NPC312774
0.8393	Intermediate Similarity	NPC473405
0.8381	Intermediate Similarity	NPC272015
0.8381	Intermediate Similarity	NPC300399
0.8381	Intermediate Similarity	NPC471482
0.8365	Intermediate Similarity	NPC282669
0.8364	Intermediate Similarity	NPC112274
0.8333	Intermediate Similarity	NPC135369
0.8333	Intermediate Similarity	NPC472988
0.8333	Intermediate Similarity	NPC246124
0.8333	Intermediate Similarity	NPC180183
0.8333	Intermediate Similarity	NPC159005
0.8333	Intermediate Similarity	NPC38217
0.8333	Intermediate Similarity	NPC126147
0.8333	Intermediate Similarity	NPC6931
0.8319	Intermediate Similarity	NPC470515
0.8319	Intermediate Similarity	NPC471548
0.8318	Intermediate Similarity	NPC473199
0.8318	Intermediate Similarity	NPC242748
0.8318	Intermediate Similarity	NPC26798
0.8318	Intermediate Similarity	NPC470767
0.8318	Intermediate Similarity	NPC470763
0.8318	Intermediate Similarity	NPC309448
0.8305	Intermediate Similarity	NPC220838
0.8305	Intermediate Similarity	NPC45606
0.8288	Intermediate Similarity	NPC51154
0.8288	Intermediate Similarity	NPC469347
0.8288	Intermediate Similarity	NPC469348
0.8286	Intermediate Similarity	NPC470434
0.8286	Intermediate Similarity	NPC280991
0.8273	Intermediate Similarity	NPC197231
0.8269	Intermediate Similarity	NPC158088
0.8269	Intermediate Similarity	NPC216260
0.8269	Intermediate Similarity	NPC5358
0.8257	Intermediate Similarity	NPC296761

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 NPC80210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	2068
0.2-0.3	4126
0.3-0.4	1839
0.4-0.5	526
0.5-0.6	285
0.6-0.7	54
0.7-0.8	16
0.8-0.85	4
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8174	Intermediate Similarity	NPD8377	Approved
0.8174	Intermediate Similarity	NPD8294	Approved
0.8158	Intermediate Similarity	NPD7327	Approved
0.8158	Intermediate Similarity	NPD7328	Approved
0.8103	Intermediate Similarity	NPD8378	Approved
0.8103	Intermediate Similarity	NPD8033	Approved
0.8103	Intermediate Similarity	NPD8380	Approved
0.8103	Intermediate Similarity	NPD8379	Approved
0.8103	Intermediate Similarity	NPD8335	Approved
0.8103	Intermediate Similarity	NPD8296	Approved
0.8087	Intermediate Similarity	NPD7516	Approved
0.7949	Intermediate Similarity	NPD7503	Approved
0.7652	Intermediate Similarity	NPD8133	Approved
0.7541	Intermediate Similarity	NPD7507	Approved
0.7522	Intermediate Similarity	NPD6686	Approved
0.7456	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8328	Phase 3
0.736	Intermediate Similarity	NPD7319	Approved
0.7355	Intermediate Similarity	NPD8513	Phase 3
0.7355	Intermediate Similarity	NPD8516	Approved
0.7355	Intermediate Similarity	NPD8515	Approved
0.7355	Intermediate Similarity	NPD8517	Approved
0.7311	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8171	Discontinued
0.7281	Intermediate Similarity	NPD6412	Phase 2
0.72	Intermediate Similarity	NPD7645	Phase 2
0.7008	Intermediate Similarity	NPD7736	Approved
0.6964	Remote Similarity	NPD7638	Approved
0.6903	Remote Similarity	NPD7639	Approved
0.6903	Remote Similarity	NPD7640	Approved
0.6891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6370	Approved
0.6864	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7525	Registered
0.678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6054	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8449	Approved
0.6617	Remote Similarity	NPD8450	Suspended
0.6613	Remote Similarity	NPD7115	Discovery
0.6607	Remote Similarity	NPD7748	Approved
0.6587	Remote Similarity	NPD6059	Approved
0.6579	Remote Similarity	NPD7902	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.6525	Remote Similarity	NPD7625	Phase 1
0.6514	Remote Similarity	NPD7524	Approved
0.6512	Remote Similarity	NPD7492	Approved
0.6484	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD6928	Phase 2
0.6462	Remote Similarity	NPD6616	Approved
0.6434	Remote Similarity	NPD6067	Discontinued
0.6429	Remote Similarity	NPD7515	Phase 2
0.6423	Remote Similarity	NPD8297	Approved
0.6423	Remote Similarity	NPD6882	Approved
0.6417	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7078	Approved
0.6389	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7632	Discontinued
0.6349	Remote Similarity	NPD6009	Approved
0.6328	Remote Similarity	NPD6319	Approved
0.6325	Remote Similarity	NPD6648	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD6695	Phase 3
0.6279	Remote Similarity	NPD6921	Approved
0.6271	Remote Similarity	NPD4159	Approved
0.624	Remote Similarity	NPD4632	Approved
0.6231	Remote Similarity	NPD5125	Phase 3
0.6231	Remote Similarity	NPD5126	Approved
0.6216	Remote Similarity	NPD7750	Discontinued
0.6216	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1810	Approved
0.6214	Remote Similarity	NPD1811	Approved
0.6195	Remote Similarity	NPD7838	Discovery
0.6195	Remote Similarity	NPD3168	Discontinued
0.6154	Remote Similarity	NPD6942	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.614	Remote Similarity	NPD8034	Phase 2
0.614	Remote Similarity	NPD8035	Phase 2
0.6119	Remote Similarity	NPD6033	Approved
0.6106	Remote Similarity	NPD6051	Approved
0.6098	Remote Similarity	NPD6881	Approved
0.6098	Remote Similarity	NPD6899	Approved
0.6095	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD8130	Phase 1
0.608	Remote Similarity	NPD6649	Approved
0.6066	Remote Similarity	NPD5739	Approved
0.6066	Remote Similarity	NPD6675	Approved
0.6066	Remote Similarity	NPD7128	Approved
0.6066	Remote Similarity	NPD6402	Approved
0.6053	Remote Similarity	NPD6698	Approved
0.6053	Remote Similarity	NPD46	Approved
0.6048	Remote Similarity	NPD6372	Approved
0.6048	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD7332	Phase 2
0.6019	Remote Similarity	NPD6931	Approved
0.6019	Remote Similarity	NPD6930	Phase 2
0.6019	Remote Similarity	NPD7514	Phase 3
0.6016	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD8264	Approved
0.598	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7320	Approved
0.5952	Remote Similarity	NPD6847	Approved
0.5952	Remote Similarity	NPD6869	Approved
0.5952	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD5211	Phase 2
0.5948	Remote Similarity	NPD6399	Phase 3
0.5943	Remote Similarity	NPD6933	Approved
0.594	Remote Similarity	NPD7604	Phase 2
0.5926	Remote Similarity	NPD6929	Approved
0.5922	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD2687	Approved
0.5922	Remote Similarity	NPD2686	Approved
0.5922	Remote Similarity	NPD2254	Approved
0.592	Remote Similarity	NPD6012	Approved
0.592	Remote Similarity	NPD6014	Approved
0.592	Remote Similarity	NPD6013	Approved
0.5917	Remote Similarity	NPD5286	Approved
0.5917	Remote Similarity	NPD4696	Approved
0.5917	Remote Similarity	NPD5285	Approved
0.5913	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5983	Phase 2
0.5893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6674	Discontinued
0.5888	Remote Similarity	NPD6932	Approved
0.5887	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD4755	Approved
0.5862	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD6079	Approved
0.5862	Remote Similarity	NPD7087	Discontinued
0.5856	Remote Similarity	NPD3669	Approved
0.5856	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5141	Approved
0.5852	Remote Similarity	NPD8451	Approved
0.5852	Remote Similarity	NPD6336	Discontinued
0.5847	Remote Similarity	NPD7991	Discontinued
0.5841	Remote Similarity	NPD3618	Phase 1
0.584	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD7145	Approved
0.5833	Remote Similarity	NPD7741	Discontinued
0.5826	Remote Similarity	NPD5328	Approved
0.582	Remote Similarity	NPD5225	Approved
0.582	Remote Similarity	NPD4633	Approved
0.582	Remote Similarity	NPD5226	Approved
0.582	Remote Similarity	NPD5224	Approved
0.5818	Remote Similarity	NPD6902	Approved
0.5812	Remote Similarity	NPD4202	Approved
0.5809	Remote Similarity	NPD8448	Approved
0.5806	Remote Similarity	NPD6008	Approved
0.5806	Remote Similarity	NPD6640	Phase 3
0.5806	Remote Similarity	NPD5357	Phase 1
0.5804	Remote Similarity	NPD4786	Approved
0.5802	Remote Similarity	NPD7799	Discontinued
0.5797	Remote Similarity	NPD8392	Approved
0.5797	Remote Similarity	NPD5956	Approved
0.5797	Remote Similarity	NPD8391	Approved
0.5797	Remote Similarity	NPD8390	Approved
0.5785	Remote Similarity	NPD4700	Approved
0.5781	Remote Similarity	NPD6053	Discontinued
0.5772	Remote Similarity	NPD5174	Approved
0.5772	Remote Similarity	NPD5175	Approved
0.5767	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD3667	Approved
0.576	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4785	Approved
0.5755	Remote Similarity	NPD4784	Approved
0.5755	Remote Similarity	NPD6924	Approved
0.5755	Remote Similarity	NPD6926	Approved
0.5752	Remote Similarity	NPD6893	Approved
0.575	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6925	Approved
0.5741	Remote Similarity	NPD5776	Phase 2
0.5738	Remote Similarity	NPD5223	Approved
0.5727	Remote Similarity	NPD7509	Discontinued
0.5726	Remote Similarity	NPD6411	Approved
0.5726	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD4243	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.5704	Remote Similarity	NPD7830	Approved
0.5704	Remote Similarity	NPD7829	Approved
0.5703	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.568	Remote Similarity	NPD4768	Approved
0.568	Remote Similarity	NPD4767	Approved
0.5678	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