NPASS Compound

Structure

CID319128 OpenBabel06191716142D 43 46 0 0 1 0 0 0 0 0999 V2000 -3.3904 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7199 0.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4894 0.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4850 -0.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7930 -0.7427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7812 -1.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1910 0.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4304 -0.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7585 -1.1664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 1.4681 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.9574 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 -5.0856 -1.9574 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 3.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3745 -1.9270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9787 1.6952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0118 -0.2210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 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 15 1 0 0 0 0 10 20 2 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 31 1 0 0 0 0 15 34 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 23 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 18 40 1 0 0 0 0 19 26 1 0 0 0 0 20 32 1 0 0 0 0 21 35 2 0 0 0 0 21 41 1 0 0 0 0 23 29 1 0 0 0 0 24 31 1 1 0 0 0 24 32 1 0 0 0 0 25 36 2 0 0 0 0 25 40 1 0 0 0 0 26 30 1 0 0 0 0 26 41 1 0 0 0 0 27 28 1 0 0 0 0 27 32 1 1 0 0 0 27 42 1 0 0 0 0 28 33 1 6 0 0 0 28 43 1 0 0 0 0 29 37 2 0 0 0 0 29 42 1 0 0 0 0 30 38 2 0 0 0 0 30 43 1 0 0 0 0 31 33 1 6 0 0 0 32 6 1 1 0 0 0 33 7 1 1 0 0 0 33 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	595.28
Volume:	608.842
LogP:	3.3
LogD:	1.804
LogS:	-3.952
# 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:	0.236
Synthetic Accessibility Score:	5.276
Fsp3:	0.515
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:	-5.152
MDCK Permeability:	1.7319540347671136e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.101
20% Bioavailability (F20%):	0.586
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.705
Plasma Protein Binding (PPB):	93.17115783691406%
Volume Distribution (VD):	1.328
Pgp-substrate:	10.499428749084473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.275
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	8.191
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.324
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.403
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC319128

Natural Product ID:	NPC319128
*Common Name:**	Scutebarbatine L
IUPAC Name:	[(1R,2S,3R,4R,4aS,8aR)-2-(2-acetyloxy-3-methylbutanoyl)oxy-3-hydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	QLQRVRCHRRIMMB-ZDYHSNSLSA-N
Standard InCHI:	InChI=1S/C33H41NO9/c1-19(2)26(41-21(4)35)30(38)43-28-27(42-29(37)23-11-9-15-34-17-23)32(6)20(3)10-8-12-24(32)31(5,33(28,7)39)14-13-22-16-25(36)40-18-22/h9-11,13-17,19,24,26-28,39H,8,12,18H2,1-7H3/b14-13+/t24-,26?,27+,28+,31-,32+,33+/m1/s1
SMILES:	CC(=O)OC(C(=O)O[C@H]1[C@H](OC(=O)c2cccnc2)[C@@]2(C)C(=CCC[C@@H]2[C@@]([C@@]1(C)O)(C)/C=C/C1=CC(=O)OC1)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577080
PubChem CID:	24809974
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
EC50	1
Others	4

Activity Type	# Activity
NON-MOLECULAR	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	=	307400.0	nM	PMID[544335]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	18700.0	nM	PMID[544335]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	16.4	n.a.	PMID[544335]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	>	50.0	%	PMID[544335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	23.8	%	PMID[544336]

☑ 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 NPC319128 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	292
0.1-0.2	1332
0.2-0.3	3549
0.3-0.4	10719
0.4-0.5	18808
0.5-0.6	6331
0.6-0.7	1385
0.7-0.8	102
0.8-0.85	65
0.85-0.9	82
0.9-0.95	19
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC228331
0.9791	High Similarity	NPC472553
0.9741	High Similarity	NPC477910
0.9737	High Similarity	NPC304179
0.9737	High Similarity	NPC48042
0.9737	High Similarity	NPC472550
0.9594	High Similarity	NPC477912
0.9581	High Similarity	NPC63041
0.9545	High Similarity	NPC477911
0.9541	High Similarity	NPC62367
0.9538	High Similarity	NPC477907
0.9538	High Similarity	NPC42678
0.9538	High Similarity	NPC477909
0.95	High Similarity	NPC148860
0.9492	High Similarity	NPC472555
0.9492	High Similarity	NPC216428
0.949	High Similarity	NPC477908
0.949	High Similarity	NPC206343
0.9439	High Similarity	NPC470306
0.9391	High Similarity	NPC471014
0.9391	High Similarity	NPC6981
0.9391	High Similarity	NPC471016
0.9391	High Similarity	NPC475408
0.9343	High Similarity	NPC294579
0.9343	High Similarity	NPC144779
0.9296	High Similarity	NPC301368
0.9296	High Similarity	NPC84815
0.9261	High Similarity	NPC475601
0.9257	High Similarity	NPC328154
0.9167	High Similarity	NPC146824
0.9163	High Similarity	NPC477902
0.9158	High Similarity	NPC127720
0.9158	High Similarity	NPC127026
0.9126	High Similarity	NPC150698
0.9126	High Similarity	NPC96801
0.9122	High Similarity	NPC475362
0.9113	High Similarity	NPC76565
0.9113	High Similarity	NPC471980
0.9113	High Similarity	NPC57797
0.9113	High Similarity	NPC250807
0.9095	High Similarity	NPC264674
0.9095	High Similarity	NPC4421
0.9082	High Similarity	NPC319880
0.9082	High Similarity	NPC244839
0.9082	High Similarity	NPC320324
0.9073	High Similarity	NPC124029
0.9069	High Similarity	NPC475137
0.9069	High Similarity	NPC473850
0.9069	High Similarity	NPC475498
0.9038	High Similarity	NPC237702
0.9034	High Similarity	NPC292416
0.9034	High Similarity	NPC473689
0.8995	High Similarity	NPC35208
0.899	High Similarity	NPC469748
0.8981	High Similarity	NPC122968
0.8981	High Similarity	NPC228377
0.8981	High Similarity	NPC211920
0.8981	High Similarity	NPC476110
0.8981	High Similarity	NPC477787
0.8981	High Similarity	NPC475600
0.8981	High Similarity	NPC87152
0.8981	High Similarity	NPC475631
0.8981	High Similarity	NPC328186
0.896	High Similarity	NPC473089
0.896	High Similarity	NPC212768
0.896	High Similarity	NPC473115
0.896	High Similarity	NPC75600
0.896	High Similarity	NPC6576
0.896	High Similarity	NPC158020
0.8952	High Similarity	NPC38959
0.8952	High Similarity	NPC327904
0.8942	High Similarity	NPC477906
0.8937	High Similarity	NPC471190
0.8937	High Similarity	NPC470486
0.8937	High Similarity	NPC471977
0.8937	High Similarity	NPC475644
0.8922	High Similarity	NPC477903
0.8905	High Similarity	NPC475406
0.8878	High Similarity	NPC235364
0.8852	High Similarity	NPC475303
0.8852	High Similarity	NPC316841
0.8852	High Similarity	NPC475596
0.8841	High Similarity	NPC473506
0.8826	High Similarity	NPC253482
0.881	High Similarity	NPC30456
0.8792	High Similarity	NPC477900
0.8792	High Similarity	NPC26881
0.8792	High Similarity	NPC477899
0.8786	High Similarity	NPC477788
0.878	High Similarity	NPC477901
0.8768	High Similarity	NPC238278
0.8756	High Similarity	NPC311196
0.8756	High Similarity	NPC134384
0.8726	High Similarity	NPC475426
0.8726	High Similarity	NPC170751
0.8726	High Similarity	NPC327769
0.8713	High Similarity	NPC476467
0.8708	High Similarity	NPC14116
0.8708	High Similarity	NPC285411
0.8704	High Similarity	NPC475648
0.8657	High Similarity	NPC472752
0.8643	High Similarity	NPC289086
0.8626	High Similarity	NPC91125
0.8624	High Similarity	NPC475533
0.8584	High Similarity	NPC324619
0.8584	High Similarity	NPC475315
0.8545	High Similarity	NPC213143
0.8529	High Similarity	NPC323551
0.8529	High Similarity	NPC280473
0.8524	High Similarity	NPC233727
0.8495	Intermediate Similarity	NPC30570
0.8488	Intermediate Similarity	NPC51008
0.8488	Intermediate Similarity	NPC41724
0.848	Intermediate Similarity	NPC470189
0.848	Intermediate Similarity	NPC40919
0.8454	Intermediate Similarity	NPC162812
0.8439	Intermediate Similarity	NPC292517
0.8424	Intermediate Similarity	NPC470190
0.8413	Intermediate Similarity	NPC187494
0.8409	Intermediate Similarity	NPC180668
0.8409	Intermediate Similarity	NPC471013
0.8409	Intermediate Similarity	NPC148896
0.8398	Intermediate Similarity	NPC165837
0.8374	Intermediate Similarity	NPC475835
0.8356	Intermediate Similarity	NPC85879
0.8356	Intermediate Similarity	NPC475301
0.8356	Intermediate Similarity	NPC53255
0.8356	Intermediate Similarity	NPC326930
0.8325	Intermediate Similarity	NPC319556
0.8319	Intermediate Similarity	NPC13603
0.8311	Intermediate Similarity	NPC471015
0.8259	Intermediate Similarity	NPC10904
0.823	Intermediate Similarity	NPC207531
0.823	Intermediate Similarity	NPC193361
0.823	Intermediate Similarity	NPC62844
0.821	Intermediate Similarity	NPC473833
0.8139	Intermediate Similarity	NPC471978
0.8139	Intermediate Similarity	NPC328928
0.8079	Intermediate Similarity	NPC470279
0.8058	Intermediate Similarity	NPC309498
0.8034	Intermediate Similarity	NPC471979
0.796	Intermediate Similarity	NPC103230
0.792	Intermediate Similarity	NPC476090
0.7892	Intermediate Similarity	NPC324245
0.7892	Intermediate Similarity	NPC320748
0.7864	Intermediate Similarity	NPC32451
0.7816	Intermediate Similarity	NPC79223
0.7778	Intermediate Similarity	NPC328559
0.7756	Intermediate Similarity	NPC329024
0.7706	Intermediate Similarity	NPC253314
0.7678	Intermediate Similarity	NPC156044
0.7634	Intermediate Similarity	NPC471004
0.7633	Intermediate Similarity	NPC317672
0.7633	Intermediate Similarity	NPC59033
0.7621	Intermediate Similarity	NPC109922
0.7583	Intermediate Similarity	NPC12944
0.7583	Intermediate Similarity	NPC25442
0.7581	Intermediate Similarity	NPC111732
0.7555	Intermediate Similarity	NPC37473
0.75	Intermediate Similarity	NPC44354
0.75	Intermediate Similarity	NPC471997
0.75	Intermediate Similarity	NPC317010
0.7489	Intermediate Similarity	NPC141385
0.7474	Intermediate Similarity	NPC107287
0.7404	Intermediate Similarity	NPC135950
0.7346	Intermediate Similarity	NPC123395
0.7346	Intermediate Similarity	NPC103361
0.7286	Intermediate Similarity	NPC249614
0.7282	Intermediate Similarity	NPC328798
0.7282	Intermediate Similarity	NPC325775
0.7277	Intermediate Similarity	NPC155792
0.7263	Intermediate Similarity	NPC112741
0.726	Intermediate Similarity	NPC114974
0.7257	Intermediate Similarity	NPC476516
0.7255	Intermediate Similarity	NPC327373
0.719	Intermediate Similarity	NPC289786
0.7176	Intermediate Similarity	NPC477043
0.7149	Intermediate Similarity	NPC317752
0.7143	Intermediate Similarity	NPC471546
0.7137	Intermediate Similarity	NPC235885
0.7136	Intermediate Similarity	NPC207851
0.7131	Intermediate Similarity	NPC107123
0.7111	Intermediate Similarity	NPC54066
0.7108	Intermediate Similarity	NPC164340
0.7104	Intermediate Similarity	NPC318299
0.7095	Intermediate Similarity	NPC127647
0.7091	Intermediate Similarity	NPC314834
0.7087	Intermediate Similarity	NPC322043
0.7087	Intermediate Similarity	NPC325093
0.7085	Intermediate Similarity	NPC477975
0.708	Intermediate Similarity	NPC2395
0.7079	Intermediate Similarity	NPC191310
0.7077	Intermediate Similarity	NPC263455
0.7075	Intermediate Similarity	NPC146724
0.7069	Intermediate Similarity	NPC70155
0.7068	Intermediate Similarity	NPC167400
0.7048	Intermediate Similarity	NPC106593
0.7035	Intermediate Similarity	NPC140311
0.7023	Intermediate Similarity	NPC50997
0.7023	Intermediate Similarity	NPC160127

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 NPC319128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	529
0.2-0.3	688
0.3-0.4	1619
0.4-0.5	3521
0.5-0.6	2121
0.6-0.7	449
0.7-0.8	19
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
0.8177	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8468	Phase 2
0.7751	Intermediate Similarity	NPD7396	Approved
0.7632	Intermediate Similarity	NPD820	Phase 3
0.7573	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3795	Approved
0.7385	Intermediate Similarity	NPD3794	Approved
0.7385	Intermediate Similarity	NPD6635	Approved
0.7296	Intermediate Similarity	NPD5088	Discontinued
0.7294	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD9271	Approved
0.7256	Intermediate Similarity	NPD2831	Approved
0.7228	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5891	Approved
0.7143	Intermediate Similarity	NPD7010	Phase 3
0.7136	Intermediate Similarity	NPD4417	Approved
0.7123	Intermediate Similarity	NPD6529	Discontinued
0.7104	Intermediate Similarity	NPD7069	Discontinued
0.7083	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1483	Discontinued
0.7068	Intermediate Similarity	NPD9075	Approved
0.7068	Intermediate Similarity	NPD9074	Approved
0.7054	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8325	Phase 3
0.7054	Intermediate Similarity	NPD8326	Phase 3
0.7041	Intermediate Similarity	NPD6026	Approved
0.7035	Intermediate Similarity	NPD3280	Approved
0.7	Intermediate Similarity	NPD2510	Approved
0.7	Intermediate Similarity	NPD2509	Approved
0.6992	Remote Similarity	NPD7886	Phase 2
0.6992	Remote Similarity	NPD7885	Phase 2
0.6948	Remote Similarity	NPD6361	Phase 2
0.6947	Remote Similarity	NPD107	Approved
0.6941	Remote Similarity	NPD6987	Phase 1
0.6941	Remote Similarity	NPD3947	Discontinued
0.6933	Remote Similarity	NPD3393	Approved
0.6933	Remote Similarity	NPD3394	Approved
0.6933	Remote Similarity	NPD3389	Approved
0.6895	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4506	Discontinued
0.6887	Remote Similarity	NPD8063	Discontinued
0.6886	Remote Similarity	NPD8479	Phase 2
0.6875	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2336	Approved
0.6852	Remote Similarity	NPD8485	Approved
0.684	Remote Similarity	NPD7234	Approved
0.684	Remote Similarity	NPD7233	Approved
0.6837	Remote Similarity	NPD4427	Phase 2
0.6828	Remote Similarity	NPD4989	Phase 2
0.6828	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6642	Approved
0.6812	Remote Similarity	NPD6641	Approved
0.6795	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6770	Approved
0.6767	Remote Similarity	NPD3925	Approved
0.6758	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD5475	Discontinued
0.6744	Remote Similarity	NPD4376	Phase 3
0.6743	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7707	Approved
0.6729	Remote Similarity	NPD8435	Approved
0.6728	Remote Similarity	NPD2307	Discontinued
0.6714	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4526	Approved
0.6713	Remote Similarity	NPD4529	Approved
0.6713	Remote Similarity	NPD4528	Approved
0.6712	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6298	Discontinued
0.671	Remote Similarity	NPD4301	Approved
0.6698	Remote Similarity	NPD4889	Approved
0.6683	Remote Similarity	NPD2511	Approved
0.6667	Remote Similarity	NPD53	Approved
0.6667	Remote Similarity	NPD2581	Approved
0.6667	Remote Similarity	NPD2582	Approved
0.6667	Remote Similarity	NPD2896	Discontinued
0.6667	Remote Similarity	NPD7778	Approved
0.6667	Remote Similarity	NPD7777	Approved
0.6667	Remote Similarity	NPD5640	Discontinued
0.6652	Remote Similarity	NPD7878	Phase 2
0.6652	Remote Similarity	NPD3371	Approved
0.6651	Remote Similarity	NPD8361	Approved
0.6651	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8360	Approved
0.6638	Remote Similarity	NPD5490	Discontinued
0.6636	Remote Similarity	NPD6791	Phase 2
0.6625	Remote Similarity	NPD8409	Suspended
0.6624	Remote Similarity	NPD6962	Phase 2
0.6614	Remote Similarity	NPD7708	Approved
0.6607	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7967	Discontinued
0.659	Remote Similarity	NPD3922	Approved
0.659	Remote Similarity	NPD3923	Approved
0.659	Remote Similarity	NPD3921	Approved
0.659	Remote Similarity	NPD3924	Approved
0.6589	Remote Similarity	NPD4375	Approved
0.6582	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7803	Approved
0.6569	Remote Similarity	NPD4373	Phase 2
0.6566	Remote Similarity	NPD1270	Approved
0.6562	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5901	Discontinued
0.6562	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4551	Phase 2
0.6559	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4948	Discontinued
0.6557	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3386	Phase 2
0.6553	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7187	Phase 2
0.6545	Remote Similarity	NPD6206	Phase 1
0.6542	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8407	Phase 2
0.654	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7470	Discontinued
0.6533	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5100	Phase 3
0.6522	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4897	Phase 2
0.6515	Remote Similarity	NPD3006	Discontinued
0.6514	Remote Similarity	NPD6665	Discontinued
0.6513	Remote Similarity	NPD5022	Discontinued
0.6509	Remote Similarity	NPD1926	Approved
0.6508	Remote Similarity	NPD7955	Approved
0.6508	Remote Similarity	NPD7956	Approved
0.6507	Remote Similarity	NPD5866	Approved
0.6504	Remote Similarity	NPD7562	Approved
0.65	Remote Similarity	NPD6226	Phase 3
0.6498	Remote Similarity	NPD6281	Approved
0.6497	Remote Similarity	NPD3813	Approved
0.6496	Remote Similarity	NPD5147	Discontinued
0.6496	Remote Similarity	NPD5506	Approved
0.6496	Remote Similarity	NPD5507	Approved
0.6495	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2809	Approved
0.6484	Remote Similarity	NPD1173	Approved
0.6481	Remote Similarity	NPD8020	Approved
0.6481	Remote Similarity	NPD7404	Approved
0.6481	Remote Similarity	NPD8021	Approved
0.6479	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD8368	Discontinued
0.6479	Remote Similarity	NPD3178	Discontinued
0.6475	Remote Similarity	NPD7417	Discontinued
0.6475	Remote Similarity	NPD6790	Phase 1
0.6468	Remote Similarity	NPD8091	Phase 3
0.6468	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6825	Phase 1
0.6457	Remote Similarity	NPD6219	Discontinued
0.6456	Remote Similarity	NPD8289	Discontinued
0.6452	Remote Similarity	NPD4021	Phase 2
0.645	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8412	Phase 1
0.6444	Remote Similarity	NPD4952	Phase 3
0.6438	Remote Similarity	NPD7395	Discontinued
0.6422	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5805	Approved
0.6417	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6276	Discontinued
0.6407	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7467	Discontinued
0.6398	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8356	Approved
0.6396	Remote Similarity	NPD5003	Discontinued
0.639	Remote Similarity	NPD5255	Approved
0.6389	Remote Similarity	NPD6241	Phase 1
0.6388	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7957	Phase 1
0.6388	Remote Similarity	NPD7001	Phase 3
0.6386	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6479	Discontinued
0.6383	Remote Similarity	NPD1996	Discontinued
0.6381	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3395	Approved
0.638	Remote Similarity	NPD3396	Approved
0.6379	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1631	Approved
0.6376	Remote Similarity	NPD4334	Discontinued
0.6376	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5487	Phase 1
0.6372	Remote Similarity	NPD6176	Phase 1
0.6372	Remote Similarity	NPD5513	Phase 2
0.6368	Remote Similarity	NPD3238	Discontinued
0.6368	Remote Similarity	NPD6261	Phase 3
0.6364	Remote Similarity	NPD6569	Phase 2
0.6364	Remote Similarity	NPD4950	Approved
0.6364	Remote Similarity	NPD3816	Phase 1
0.6364	Remote Similarity	NPD3815	Phase 1

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