NPASS Compound

Structure

NPC472553 OpenBabel07101718222D 42 45 0 0 1 0 0 0 0 0999 V2000 0.8472 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 3.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3835 -2.3617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1277 -1.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9783 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1430 0.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4386 1.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8482 0.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3284 -2.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0880 0.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8899 -0.4719 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4155 1.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2360 3.4239 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 -2.8003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0311 2.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4891 0.8472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6687 0.6434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5816 -1.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 6 31 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 19 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 33 2 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 22 2 0 0 0 0 16 33 1 0 0 0 0 17 21 1 0 0 0 0 17 39 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 34 2 0 0 0 0 20 40 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 14 1 1 0 0 0 24 31 1 0 0 0 0 24 40 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 27 1 0 0 0 0 26 30 1 6 0 0 0 26 41 1 0 0 0 0 27 32 1 1 0 0 0 27 42 1 0 0 0 0 28 36 2 0 0 0 0 28 42 1 0 0 0 0 29 37 2 0 0 0 0 29 41 1 0 0 0 0 30 5 1 6 0 0 0 31 32 1 6 0 0 0 32 7 1 6 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	583.28
Volume:	594.183
LogP:	3.83
LogD:	2.438
LogS:	-4.066
# Rotatable Bonds:	11
TPSA:	145.39
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	5.179
Fsp3:	0.562
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:	-5.188
MDCK Permeability:	2.3632355805602856e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.748
Plasma Protein Binding (PPB):	88.88599395751953%
Volume Distribution (VD):	1.158
Pgp-substrate:	13.539637565612793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.322
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.558
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	9.536
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.635
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.588
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.155
Carcinogencity:	0.143
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC472553

Natural Product ID:	NPC472553
*Common Name:**	OIKGYJRBMDIBAR-DWRAXSAJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OIKGYJRBMDIBAR-DWRAXSAJSA-N
Standard InCHI:	InChI=1S/C32H41NO9/c1-18(2)28(36)42-27-26(41-29(37)22-11-9-13-33-16-22)30(5)19(3)10-8-12-23(30)31(6,32(27,7)38)24(40-20(4)34)14-21-15-25(35)39-17-21/h9-11,13,15-16,18,23-24,26-27,38H,8,12,14,17H2,1-7H3/t23-,24-,26-,27-,30-,31-,32-/m0/s1
SMILES:	CC(=O)O[C@H]([C@]1(C)[C@H]2CCC=C([C@]2(C)[C@H]([C@@H]([C@]1(C)O)OC(=O)C(C)C)OC(=O)c1cccnc1)C)CC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577089
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	<	50.0	%	PMID[543840]

☑ 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 NPC472553 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	287
0.1-0.2	1299
0.2-0.3	3369
0.3-0.4	10298
0.4-0.5	18829
0.5-0.6	6796
0.6-0.7	1518
0.7-0.8	113
0.8-0.85	70
0.85-0.9	64
0.9-0.95	35
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.984	High Similarity	NPC304179
0.984	High Similarity	NPC48042
0.984	High Similarity	NPC472550
0.9791	High Similarity	NPC319128
0.9741	High Similarity	NPC62367
0.974	High Similarity	NPC477910
0.9691	High Similarity	NPC216428
0.9691	High Similarity	NPC472555
0.9688	High Similarity	NPC228331
0.9683	High Similarity	NPC63041
0.9637	High Similarity	NPC42678
0.9637	High Similarity	NPC470306
0.9637	High Similarity	NPC477909
0.9637	High Similarity	NPC477907
0.9592	High Similarity	NPC477912
0.9588	High Similarity	NPC477908
0.9588	High Similarity	NPC475408
0.9588	High Similarity	NPC471014
0.9588	High Similarity	NPC206343
0.9588	High Similarity	NPC6981
0.9588	High Similarity	NPC471016
0.9543	High Similarity	NPC477911
0.9538	High Similarity	NPC144779
0.9538	High Similarity	NPC294579
0.949	High Similarity	NPC301368
0.949	High Similarity	NPC84815
0.94	High Similarity	NPC148860
0.935	High Similarity	NPC477902
0.9347	High Similarity	NPC127026
0.9347	High Similarity	NPC127720
0.93	High Similarity	NPC250807
0.93	High Similarity	NPC471980
0.93	High Similarity	NPC57797
0.93	High Similarity	NPC76565
0.9286	High Similarity	NPC264674
0.9286	High Similarity	NPC4421
0.9257	High Similarity	NPC124029
0.9254	High Similarity	NPC475498
0.9254	High Similarity	NPC473850
0.9254	High Similarity	NPC328154
0.9254	High Similarity	NPC475137
0.9163	High Similarity	NPC477787
0.9163	High Similarity	NPC475631
0.9163	High Similarity	NPC475601
0.9163	High Similarity	NPC328186
0.9163	High Similarity	NPC211920
0.9163	High Similarity	NPC476110
0.9163	High Similarity	NPC146824
0.9163	High Similarity	NPC87152
0.9163	High Similarity	NPC228377
0.9163	High Similarity	NPC475600
0.9163	High Similarity	NPC122968
0.9146	High Similarity	NPC158020
0.9146	High Similarity	NPC6576
0.9146	High Similarity	NPC212768
0.9146	High Similarity	NPC473115
0.9146	High Similarity	NPC75600
0.9146	High Similarity	NPC473089
0.9122	High Similarity	NPC477906
0.9118	High Similarity	NPC471977
0.9118	High Similarity	NPC475644
0.9118	High Similarity	NPC470486
0.9118	High Similarity	NPC471190
0.9118	High Similarity	NPC475362
0.9104	High Similarity	NPC477903
0.9059	High Similarity	NPC235364
0.9029	High Similarity	NPC473689
0.9029	High Similarity	NPC475303
0.9029	High Similarity	NPC150698
0.9029	High Similarity	NPC96801
0.9029	High Similarity	NPC316841
0.9029	High Similarity	NPC475596
0.9029	High Similarity	NPC292416
0.902	High Similarity	NPC473506
0.8986	High Similarity	NPC469748
0.8986	High Similarity	NPC320324
0.8986	High Similarity	NPC30456
0.8986	High Similarity	NPC244839
0.8986	High Similarity	NPC319880
0.8971	High Similarity	NPC477900
0.8971	High Similarity	NPC26881
0.8971	High Similarity	NPC477899
0.8966	High Similarity	NPC477788
0.896	High Similarity	NPC477901
0.8942	High Similarity	NPC237702
0.89	High Similarity	NPC327769
0.89	High Similarity	NPC475426
0.89	High Similarity	NPC475406
0.89	High Similarity	NPC35208
0.89	High Similarity	NPC170751
0.8894	High Similarity	NPC476467
0.8857	High Similarity	NPC38959
0.8857	High Similarity	NPC327904
0.8798	High Similarity	NPC91125
0.8732	High Similarity	NPC253482
0.8731	High Similarity	NPC289086
0.8706	High Similarity	NPC323551
0.8706	High Similarity	NPC280473
0.8702	High Similarity	NPC285411
0.8702	High Similarity	NPC14116
0.8673	High Similarity	NPC238278
0.867	High Similarity	NPC30570
0.8663	High Similarity	NPC51008
0.8663	High Similarity	NPC41724
0.866	High Similarity	NPC134384
0.866	High Similarity	NPC311196
0.8627	High Similarity	NPC162812
0.8614	High Similarity	NPC292517
0.8611	High Similarity	NPC475648
0.8571	High Similarity	NPC180668
0.8571	High Similarity	NPC165837
0.8571	High Similarity	NPC148896
0.8571	High Similarity	NPC471013
0.8557	High Similarity	NPC472752
0.855	High Similarity	NPC475835
0.8532	High Similarity	NPC475533
0.8493	Intermediate Similarity	NPC475315
0.8493	Intermediate Similarity	NPC324619
0.8451	Intermediate Similarity	NPC213143
0.8429	Intermediate Similarity	NPC233727
0.8416	Intermediate Similarity	NPC10904
0.8398	Intermediate Similarity	NPC193361
0.8398	Intermediate Similarity	NPC62844
0.8382	Intermediate Similarity	NPC470189
0.8382	Intermediate Similarity	NPC40919
0.8325	Intermediate Similarity	NPC470190
0.8317	Intermediate Similarity	NPC187494
0.8304	Intermediate Similarity	NPC471015
0.8267	Intermediate Similarity	NPC326930
0.8267	Intermediate Similarity	NPC475301
0.8267	Intermediate Similarity	NPC85879
0.8267	Intermediate Similarity	NPC53255
0.823	Intermediate Similarity	NPC319556
0.823	Intermediate Similarity	NPC13603
0.8227	Intermediate Similarity	NPC309498
0.8159	Intermediate Similarity	NPC470279
0.8134	Intermediate Similarity	NPC207531
0.8131	Intermediate Similarity	NPC103230
0.8122	Intermediate Similarity	NPC473833
0.8072	Intermediate Similarity	NPC476090
0.806	Intermediate Similarity	NPC324245
0.806	Intermediate Similarity	NPC320748
0.8052	Intermediate Similarity	NPC328928
0.8052	Intermediate Similarity	NPC471978
0.803	Intermediate Similarity	NPC32451
0.798	Intermediate Similarity	NPC79223
0.7949	Intermediate Similarity	NPC471979
0.7941	Intermediate Similarity	NPC328559
0.7921	Intermediate Similarity	NPC329024
0.786	Intermediate Similarity	NPC253314
0.7837	Intermediate Similarity	NPC156044
0.7794	Intermediate Similarity	NPC317672
0.7794	Intermediate Similarity	NPC59033
0.774	Intermediate Similarity	NPC12944
0.774	Intermediate Similarity	NPC25442
0.7736	Intermediate Similarity	NPC111732
0.7703	Intermediate Similarity	NPC471004
0.7699	Intermediate Similarity	NPC37473
0.7665	Intermediate Similarity	NPC317010
0.7639	Intermediate Similarity	NPC141385
0.7574	Intermediate Similarity	NPC44354
0.7553	Intermediate Similarity	NPC107287
0.7524	Intermediate Similarity	NPC109922
0.7476	Intermediate Similarity	NPC135950
0.7438	Intermediate Similarity	NPC328798
0.7438	Intermediate Similarity	NPC325775
0.7429	Intermediate Similarity	NPC155792
0.7416	Intermediate Similarity	NPC103361
0.7416	Intermediate Similarity	NPC123395
0.7413	Intermediate Similarity	NPC327373
0.74	Intermediate Similarity	NPC471997
0.736	Intermediate Similarity	NPC249614
0.734	Intermediate Similarity	NPC112741
0.7319	Intermediate Similarity	NPC476516
0.7295	Intermediate Similarity	NPC471546
0.7265	Intermediate Similarity	NPC107123
0.726	Intermediate Similarity	NPC289786
0.7246	Intermediate Similarity	NPC127647
0.7241	Intermediate Similarity	NPC322043
0.7241	Intermediate Similarity	NPC325093
0.7225	Intermediate Similarity	NPC146724
0.7215	Intermediate Similarity	NPC317752
0.7206	Intermediate Similarity	NPC207851
0.7205	Intermediate Similarity	NPC70155
0.7188	Intermediate Similarity	NPC106593
0.7178	Intermediate Similarity	NPC164340
0.7175	Intermediate Similarity	NPC140311
0.7175	Intermediate Similarity	NPC54066
0.7171	Intermediate Similarity	NPC318020
0.717	Intermediate Similarity	NPC160127
0.717	Intermediate Similarity	NPC50997
0.7169	Intermediate Similarity	NPC318299
0.7157	Intermediate Similarity	NPC477975
0.7156	Intermediate Similarity	NPC473667
0.7156	Intermediate Similarity	NPC314834
0.715	Intermediate Similarity	NPC263455
0.715	Intermediate Similarity	NPC182814
0.715	Intermediate Similarity	NPC191310
0.7143	Intermediate Similarity	NPC167400
0.7143	Intermediate Similarity	NPC198205

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 NPC472553 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	529
0.2-0.3	666
0.3-0.4	1567
0.4-0.5	3479
0.5-0.6	2184
0.6-0.7	507
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8263	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD8468	Phase 2
0.7913	Intermediate Similarity	NPD7396	Approved
0.7713	Intermediate Similarity	NPD820	Phase 3
0.7647	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD6635	Approved
0.7454	Intermediate Similarity	NPD3795	Approved
0.7454	Intermediate Similarity	NPD3794	Approved
0.7361	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD9271	Approved
0.73	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5891	Approved
0.7273	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.721	Intermediate Similarity	NPD1483	Discontinued
0.7209	Intermediate Similarity	NPD7010	Phase 3
0.7202	Intermediate Similarity	NPD4417	Approved
0.7195	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8325	Phase 3
0.7195	Intermediate Similarity	NPD8326	Phase 3
0.7189	Intermediate Similarity	NPD6529	Discontinued
0.7169	Intermediate Similarity	NPD7069	Discontinued
0.715	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9074	Approved
0.7143	Intermediate Similarity	NPD9075	Approved
0.7113	Intermediate Similarity	NPD6026	Approved
0.7107	Intermediate Similarity	NPD5088	Discontinued
0.7098	Intermediate Similarity	NPD3280	Approved
0.7083	Intermediate Similarity	NPD2831	Approved
0.7064	Intermediate Similarity	NPD2509	Approved
0.7064	Intermediate Similarity	NPD2510	Approved
0.7051	Intermediate Similarity	NPD7886	Phase 2
0.7051	Intermediate Similarity	NPD7885	Phase 2
0.7021	Intermediate Similarity	NPD107	Approved
0.7014	Intermediate Similarity	NPD6361	Phase 2
0.7005	Intermediate Similarity	NPD3947	Discontinued
0.6996	Remote Similarity	NPD3389	Approved
0.6996	Remote Similarity	NPD3393	Approved
0.6996	Remote Similarity	NPD3394	Approved
0.6991	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4427	Phase 2
0.6959	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4506	Discontinued
0.6952	Remote Similarity	NPD8063	Discontinued
0.6947	Remote Similarity	NPD8479	Phase 2
0.6937	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2336	Approved
0.6905	Remote Similarity	NPD7234	Approved
0.6905	Remote Similarity	NPD7233	Approved
0.6878	Remote Similarity	NPD6642	Approved
0.6878	Remote Similarity	NPD6641	Approved
0.6857	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6987	Phase 1
0.6842	Remote Similarity	NPD4301	Approved
0.6828	Remote Similarity	NPD6770	Approved
0.682	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5475	Discontinued
0.6808	Remote Similarity	NPD4376	Phase 3
0.6806	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2307	Discontinued
0.6776	Remote Similarity	NPD4529	Approved
0.6776	Remote Similarity	NPD4528	Approved
0.6776	Remote Similarity	NPD4526	Approved
0.6769	Remote Similarity	NPD6298	Discontinued
0.6762	Remote Similarity	NPD4889	Approved
0.6759	Remote Similarity	NPD8485	Approved
0.6751	Remote Similarity	NPD8409	Suspended
0.675	Remote Similarity	NPD2511	Approved
0.674	Remote Similarity	NPD4989	Phase 2
0.6737	Remote Similarity	NPD2896	Discontinued
0.6734	Remote Similarity	NPD2581	Approved
0.6734	Remote Similarity	NPD2582	Approved
0.6734	Remote Similarity	NPD7708	Approved
0.6728	Remote Similarity	NPD7778	Approved
0.6728	Remote Similarity	NPD7777	Approved
0.6728	Remote Similarity	NPD53	Approved
0.6722	Remote Similarity	NPD7967	Discontinued
0.6713	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3371	Approved
0.6711	Remote Similarity	NPD7878	Phase 2
0.6709	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6791	Phase 2
0.6696	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5490	Discontinued
0.6693	Remote Similarity	NPD7803	Approved
0.668	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7707	Approved
0.6651	Remote Similarity	NPD4375	Approved
0.6651	Remote Similarity	NPD3922	Approved
0.6651	Remote Similarity	NPD3923	Approved
0.6651	Remote Similarity	NPD3921	Approved
0.6651	Remote Similarity	NPD3924	Approved
0.6649	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8361	Approved
0.6636	Remote Similarity	NPD8360	Approved
0.6636	Remote Similarity	NPD8435	Approved
0.6635	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1270	Approved
0.6627	Remote Similarity	NPD7955	Approved
0.6627	Remote Similarity	NPD7956	Approved
0.6622	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5901	Discontinued
0.662	Remote Similarity	NPD4948	Discontinued
0.662	Remote Similarity	NPD8020	Approved
0.662	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4551	Phase 2
0.662	Remote Similarity	NPD8021	Approved
0.6619	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3386	Phase 2
0.6618	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3925	Approved
0.6607	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7187	Phase 2
0.6603	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7470	Discontinued
0.6592	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5100	Phase 3
0.6585	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8289	Discontinued
0.6581	Remote Similarity	NPD5640	Discontinued
0.6574	Remote Similarity	NPD6665	Discontinued
0.6569	Remote Similarity	NPD3006	Discontinued
0.6568	Remote Similarity	NPD5022	Discontinued
0.6565	Remote Similarity	NPD1926	Approved
0.6564	Remote Similarity	NPD5866	Approved
0.6564	Remote Similarity	NPD3813	Approved
0.6562	Remote Similarity	NPD7562	Approved
0.6562	Remote Similarity	NPD203	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6226	Phase 3
0.6558	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6281	Approved
0.6552	Remote Similarity	NPD5147	Discontinued
0.655	Remote Similarity	NPD2809	Approved
0.6544	Remote Similarity	NPD1173	Approved
0.654	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3178	Discontinued
0.6537	Remote Similarity	NPD7404	Approved
0.6529	Remote Similarity	NPD6790	Phase 1
0.6529	Remote Similarity	NPD7417	Discontinued
0.652	Remote Similarity	NPD8091	Phase 3
0.6518	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7957	Phase 1
0.6516	Remote Similarity	NPD6219	Discontinued
0.6512	Remote Similarity	NPD4021	Phase 2
0.6502	Remote Similarity	NPD8412	Phase 1
0.6494	Remote Similarity	NPD7395	Discontinued
0.6483	Remote Similarity	NPD4086	Phase 1
0.6483	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5482	Discontinued
0.6473	Remote Similarity	NPD5805	Approved
0.6471	Remote Similarity	NPD6962	Phase 2
0.6463	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6276	Discontinued
0.646	Remote Similarity	NPD7467	Discontinued
0.6459	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6206	Phase 1
0.6455	Remote Similarity	NPD5003	Discontinued
0.6453	Remote Similarity	NPD5255	Approved
0.6453	Remote Similarity	NPD8356	Approved
0.645	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6241	Phase 1
0.6449	Remote Similarity	NPD8407	Phase 2
0.6444	Remote Similarity	NPD7001	Phase 3
0.6443	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6479	Discontinued
0.6439	Remote Similarity	NPD1631	Approved
0.6438	Remote Similarity	NPD1996	Discontinued
0.6438	Remote Similarity	NPD3396	Approved
0.6438	Remote Similarity	NPD3395	Approved
0.6437	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4897	Phase 2
0.6435	Remote Similarity	NPD4334	Discontinued
0.6432	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3238	Discontinued
0.6429	Remote Similarity	NPD5513	Phase 2
0.6429	Remote Similarity	NPD6176	Phase 1
0.6422	Remote Similarity	NPD6569	Phase 2
0.6419	Remote Similarity	NPD3816	Phase 1
0.6419	Remote Similarity	NPD3815	Phase 1
0.6417	Remote Similarity	NPD4373	Phase 2
0.6417	Remote Similarity	NPD6494	Phase 2
0.641	Remote Similarity	NPD5507	Approved
0.641	Remote Similarity	NPD5506	Approved
0.641	Remote Similarity	NPD4923	Phase 1
0.6407	Remote Similarity	NPD8160	Phase 2
0.6406	Remote Similarity	NPD3321	Discontinued
0.6404	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1096	Discontinued

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