NPASS Compound

Structure

CID35208 OpenBabel06191715362D 54 58 0 0 1 0 0 0 0 0999 V2000 -2.2235 1.6155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5281 2.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7399 1.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5071 -2.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2291 0.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7033 -3.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4902 -1.7573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3447 1.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6166 0.0216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1472 -0.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6166 0.5637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5391 -1.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3839 0.6176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4574 1.0588 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0546 1.4215 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5582 2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1694 -1.5526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8779 -1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2820 0.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 -2.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6778 0.0216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9007 -1.2397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6778 0.5637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5656 -1.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2583 0.5066 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4574 -0.4735 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8614 -0.4735 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4694 1.2613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8064 -0.0536 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5391 1.5890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4574 -0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9470 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7880 0.8228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5656 0.1409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9007 0.2927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1472 0.8347 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5545 2.9820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0868 -1.7876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8250 -1.2937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8085 1.1668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8758 -2.3196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1560 -1.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6380 2.5309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2235 -1.0302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7299 0.7238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3802 1.5646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0546 -0.8362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6591 0.2715 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4044 -0.4735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8085 -0.4735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2961 -1.8777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5324 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 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 9 34 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 22 1 0 0 0 0 12 37 2 0 0 0 0 13 33 1 0 0 0 0 13 48 1 0 0 0 0 14 35 1 0 0 0 0 14 47 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 31 1 0 0 0 0 17 38 2 0 0 0 0 17 47 1 0 0 0 0 18 39 2 0 0 0 0 18 49 1 0 0 0 0 19 40 2 0 0 0 0 19 50 1 0 0 0 0 20 41 2 0 0 0 0 20 51 1 0 0 0 0 21 42 2 0 0 0 0 21 52 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 1 0 0 0 24 37 1 0 0 0 0 25 28 1 0 0 0 0 25 43 2 0 0 0 0 26 29 1 0 0 0 0 26 30 1 0 0 0 0 26 49 1 1 0 0 0 27 36 1 6 0 0 0 27 50 1 0 0 0 0 28 35 1 6 0 0 0 28 51 1 0 0 0 0 29 34 1 6 0 0 0 29 53 1 0 0 0 0 30 35 1 1 0 0 0 30 52 1 0 0 0 0 31 44 2 0 0 0 0 31 53 1 0 0 0 0 32 45 2 0 0 0 0 32 48 1 0 0 0 0 33 8 1 1 0 0 0 33 54 1 0 0 0 0 34 36 1 1 0 0 0 34 46 1 0 0 0 0 35 36 1 6 0 0 0 36 54 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	761.25
Volume:	719.859
LogP:	1.508
LogD:	0.762
LogS:	-4.027
# Rotatable Bonds:	11
TPSA:	243.52
# H-Bond Aceptor:	18
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	7.532
Fsp3:	0.639
Lipinski Rule-of-5:	Rejected
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:	-5.361
MDCK Permeability:	0.00019601346866693348
Pgp-inhibitor:	0.999
Pgp-substrate:	0.379
Human Intestinal Absorption (HIA):	0.682
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.904

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	33.37688064575195%
Volume Distribution (VD):	1.265
Pgp-substrate:	40.03569793701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	2.864
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.1
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.129
Carcinogencity:	0.104
Eye Corrosion:	0.004
Eye Irritation:	0.048
Respiratory Toxicity:	0.153

Download Data

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

Natural Product: NPC35208

Natural Product ID:	NPC35208
*Common Name:**	Evonine
IUPAC Name:	n.a.
Synonyms:	Evonine
Standard InCHIKey:	IMIAGCONYJPMDY-RYQZUCOZSA-N
Standard InCHI:	InChI=1S/C36H43NO17/c1-15-16(2)31(44)53-29-26(49-18(4)39)30(52-21(7)42)35(14-47-17(3)38)28(51-20(6)41)25(43)23-27(50-19(5)40)36(35,34(29,9)46)54-33(23,8)13-48-32(45)22-11-10-12-37-24(15)22/h10-12,15-16,23,26-30,46H,13-14H2,1-9H3/t15?,16?,23-,26+,27-,28-,29+,30+,33+,34+,35-,36+/m1/s1
SMILES:	CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@H]3[C@]([C@@]42O[C@@]([C@H](C(=O)[C@H]1OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1c(C(C(C(=O)O3)C)C)nccc1)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449845
PubChem CID:	44583776
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29118	Euonymus alatus	Species	Celastraceae	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
IC50	1
Others	1

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
NPT759	Cell Line	H9	Homo sapiens	IC50	=	21.2	ug.mL-1	PMID[513085]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.503	ug.mL-1	PMID[513085]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	42.1	n.a.	PMID[513085]

☑ 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 NPC35208 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	363
0.1-0.2	1507
0.2-0.3	3380
0.3-0.4	11137
0.4-0.5	17122
0.5-0.6	7084
0.6-0.7	1780
0.7-0.8	145
0.8-0.85	36
0.85-0.9	78
0.9-0.95	56
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC253482
0.971	High Similarity	NPC475601
0.9621	High Similarity	NPC475426
0.9581	High Similarity	NPC475648
0.9565	High Similarity	NPC76565
0.9522	High Similarity	NPC146824
0.9519	High Similarity	NPC475137
0.9519	High Similarity	NPC475498
0.9479	High Similarity	NPC150698
0.9479	High Similarity	NPC96801
0.9476	High Similarity	NPC475362
0.9434	High Similarity	NPC320324
0.9434	High Similarity	NPC319880
0.9434	High Similarity	NPC469748
0.9434	High Similarity	NPC244839
0.9429	High Similarity	NPC87152
0.9429	High Similarity	NPC475631
0.9429	High Similarity	NPC476110
0.9429	High Similarity	NPC475600
0.939	High Similarity	NPC237702
0.9387	High Similarity	NPC473689
0.9387	High Similarity	NPC292416
0.9384	High Similarity	NPC475644
0.9384	High Similarity	NPC470486
0.9384	High Similarity	NPC471190
0.9384	High Similarity	NPC471977
0.9378	High Similarity	NPC57797
0.9378	High Similarity	NPC250807
0.9333	High Similarity	NPC473850
0.9333	High Similarity	NPC328154
0.9302	High Similarity	NPC38959
0.9302	High Similarity	NPC327904
0.9296	High Similarity	NPC475303
0.9296	High Similarity	NPC475596
0.9289	High Similarity	NPC473506
0.9275	High Similarity	NPC471016
0.9256	High Similarity	NPC475406
0.9252	High Similarity	NPC30456
0.9245	High Similarity	NPC328186
0.9245	High Similarity	NPC228377
0.9245	High Similarity	NPC122968
0.9245	High Similarity	NPC477787
0.9227	High Similarity	NPC470306
0.9183	High Similarity	NPC471014
0.9183	High Similarity	NPC475408
0.9167	High Similarity	NPC170751
0.9167	High Similarity	NPC327769
0.9155	High Similarity	NPC124029
0.9155	High Similarity	NPC211920
0.9119	High Similarity	NPC473833
0.9116	High Similarity	NPC316841
0.9095	High Similarity	NPC84815
0.9095	High Similarity	NPC301368
0.9061	High Similarity	NPC477902
0.9057	High Similarity	NPC477788
0.9009	High Similarity	NPC477912
0.9	High Similarity	NPC6981
0.8995	High Similarity	NPC319128
0.8995	High Similarity	NPC228331
0.8967	High Similarity	NPC127720
0.8967	High Similarity	NPC127026
0.8957	High Similarity	NPC294579
0.8957	High Similarity	NPC144779
0.8957	High Similarity	NPC62367
0.8945	High Similarity	NPC238278
0.8943	High Similarity	NPC475301
0.8943	High Similarity	NPC326930
0.894	High Similarity	NPC477906
0.893	High Similarity	NPC148860
0.8925	High Similarity	NPC471980
0.8915	High Similarity	NPC216428
0.8905	High Similarity	NPC264674
0.8905	High Similarity	NPC4421
0.89	High Similarity	NPC472553
0.8863	High Similarity	NPC42678
0.8863	High Similarity	NPC477910
0.8863	High Similarity	NPC477907
0.8863	High Similarity	NPC477909
0.8832	High Similarity	NPC477903
0.8821	High Similarity	NPC13603
0.8813	High Similarity	NPC213143
0.8796	High Similarity	NPC26881
0.8779	High Similarity	NPC158020
0.8779	High Similarity	NPC6576
0.8779	High Similarity	NPC75600
0.8779	High Similarity	NPC473089
0.8779	High Similarity	NPC473115
0.8779	High Similarity	NPC212768
0.8777	High Similarity	NPC53255
0.8777	High Similarity	NPC85879
0.8761	High Similarity	NPC311196
0.8761	High Similarity	NPC134384
0.8756	High Similarity	NPC304179
0.8756	High Similarity	NPC48042
0.8756	High Similarity	NPC472550
0.8716	High Similarity	NPC285411
0.8716	High Similarity	NPC14116
0.8712	High Similarity	NPC471978
0.8712	High Similarity	NPC328928
0.871	High Similarity	NPC477900
0.871	High Similarity	NPC477899
0.871	High Similarity	NPC233727
0.8704	High Similarity	NPC235364
0.8704	High Similarity	NPC477911
0.8678	High Similarity	NPC475315
0.8678	High Similarity	NPC324619
0.8651	High Similarity	NPC472555
0.8636	High Similarity	NPC91125
0.8634	High Similarity	NPC475533
0.8619	High Similarity	NPC63041
0.8611	High Similarity	NPC477901
0.8602	High Similarity	NPC471979
0.8578	High Similarity	NPC472752
0.8571	High Similarity	NPC471015
0.8558	High Similarity	NPC206343
0.8558	High Similarity	NPC477908
0.8519	High Similarity	NPC187494
0.8411	Intermediate Similarity	NPC470189
0.8411	Intermediate Similarity	NPC40919
0.8357	Intermediate Similarity	NPC470190
0.8348	Intermediate Similarity	NPC148896
0.8348	Intermediate Similarity	NPC180668
0.8348	Intermediate Similarity	NPC471013
0.8341	Intermediate Similarity	NPC193361
0.8341	Intermediate Similarity	NPC30570
0.8341	Intermediate Similarity	NPC62844
0.8287	Intermediate Similarity	NPC476467
0.8265	Intermediate Similarity	NPC319556
0.8205	Intermediate Similarity	NPC10904
0.8203	Intermediate Similarity	NPC292517
0.8174	Intermediate Similarity	NPC207531
0.8136	Intermediate Similarity	NPC162812
0.8119	Intermediate Similarity	NPC280473
0.8119	Intermediate Similarity	NPC323551
0.8082	Intermediate Similarity	NPC41724
0.8082	Intermediate Similarity	NPC51008
0.8028	Intermediate Similarity	NPC470279
0.7963	Intermediate Similarity	NPC289086
0.7957	Intermediate Similarity	NPC476090
0.7911	Intermediate Similarity	NPC253314
0.789	Intermediate Similarity	NPC475835
0.7838	Intermediate Similarity	NPC165837
0.7759	Intermediate Similarity	NPC471004
0.7757	Intermediate Similarity	NPC109922
0.7664	Intermediate Similarity	NPC103230
0.7652	Intermediate Similarity	NPC235885
0.7652	Intermediate Similarity	NPC141428
0.7625	Intermediate Similarity	NPC107123
0.7586	Intermediate Similarity	NPC57690
0.758	Intermediate Similarity	NPC328559
0.758	Intermediate Similarity	NPC32451
0.7531	Intermediate Similarity	NPC37473
0.7531	Intermediate Similarity	NPC476516
0.7523	Intermediate Similarity	NPC309498
0.7468	Intermediate Similarity	NPC267926
0.7465	Intermediate Similarity	NPC135950
0.7459	Intermediate Similarity	NPC134637
0.7446	Intermediate Similarity	NPC2395
0.7443	Intermediate Similarity	NPC324245
0.7443	Intermediate Similarity	NPC320748
0.7421	Intermediate Similarity	NPC155792
0.7409	Intermediate Similarity	NPC103361
0.7407	Intermediate Similarity	NPC114974
0.7401	Intermediate Similarity	NPC111732
0.7393	Intermediate Similarity	NPC471997
0.7389	Intermediate Similarity	NPC314834
0.7382	Intermediate Similarity	NPC266192
0.7376	Intermediate Similarity	NPC79223
0.7364	Intermediate Similarity	NPC317672
0.7333	Intermediate Similarity	NPC156044
0.7318	Intermediate Similarity	NPC329024
0.7316	Intermediate Similarity	NPC141385
0.7314	Intermediate Similarity	NPC119134
0.7304	Intermediate Similarity	NPC204491
0.7304	Intermediate Similarity	NPC203614
0.7295	Intermediate Similarity	NPC476517
0.7287	Intermediate Similarity	NPC183537
0.7285	Intermediate Similarity	NPC149708
0.728	Intermediate Similarity	NPC70155
0.7269	Intermediate Similarity	NPC290529
0.7269	Intermediate Similarity	NPC478045
0.7265	Intermediate Similarity	NPC176371
0.7265	Intermediate Similarity	NPC136573
0.7257	Intermediate Similarity	NPC315545
0.7257	Intermediate Similarity	NPC314297
0.7254	Intermediate Similarity	NPC15406
0.7248	Intermediate Similarity	NPC306001
0.7248	Intermediate Similarity	NPC471629
0.7248	Intermediate Similarity	NPC275170
0.7248	Intermediate Similarity	NPC324251
0.7248	Intermediate Similarity	NPC473400
0.7248	Intermediate Similarity	NPC206211
0.7244	Intermediate Similarity	NPC12944
0.7244	Intermediate Similarity	NPC25442
0.7244	Intermediate Similarity	NPC477043
0.7229	Intermediate Similarity	NPC473441
0.7229	Intermediate Similarity	NPC131273
0.7227	Intermediate Similarity	NPC24019
0.7224	Intermediate Similarity	NPC124313
0.7218	Intermediate Similarity	NPC77878

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 NPC35208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	530
0.2-0.3	701
0.3-0.4	1946
0.4-0.5	3234
0.5-0.6	1970
0.6-0.7	498
0.7-0.8	31
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
0.8312	Intermediate Similarity	NPD8468	Phase 2
0.7681	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD1483	Discontinued
0.7546	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD8325	Phase 3
0.7424	Intermediate Similarity	NPD8326	Phase 3
0.7368	Intermediate Similarity	NPD3795	Approved
0.7368	Intermediate Similarity	NPD3794	Approved
0.7321	Intermediate Similarity	NPD7396	Approved
0.7244	Intermediate Similarity	NPD6987	Phase 1
0.722	Intermediate Similarity	NPD5891	Approved
0.7168	Intermediate Similarity	NPD3947	Discontinued
0.7162	Intermediate Similarity	NPD8485	Approved
0.7156	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD3393	Approved
0.7155	Intermediate Similarity	NPD3389	Approved
0.7155	Intermediate Similarity	NPD3394	Approved
0.7154	Intermediate Similarity	NPD7708	Approved
0.7149	Intermediate Similarity	NPD2509	Approved
0.7149	Intermediate Similarity	NPD2510	Approved
0.713	Intermediate Similarity	NPD53	Approved
0.713	Intermediate Similarity	NPD7778	Approved
0.713	Intermediate Similarity	NPD7777	Approved
0.7109	Intermediate Similarity	NPD7803	Approved
0.7108	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7069	Discontinued
0.7094	Intermediate Similarity	NPD7878	Phase 2
0.7083	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4373	Phase 2
0.7048	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8435	Approved
0.7039	Intermediate Similarity	NPD7707	Approved
0.7034	Intermediate Similarity	NPD3280	Approved
0.7018	Intermediate Similarity	NPD8407	Phase 2
0.7005	Intermediate Similarity	NPD820	Phase 3
0.7	Intermediate Similarity	NPD7233	Approved
0.7	Intermediate Similarity	NPD7234	Approved
0.6992	Remote Similarity	NPD7886	Phase 2
0.6992	Remote Similarity	NPD7885	Phase 2
0.6983	Remote Similarity	NPD6962	Phase 2
0.6983	Remote Similarity	NPD4417	Approved
0.6978	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6642	Approved
0.6977	Remote Similarity	NPD6641	Approved
0.697	Remote Similarity	NPD4506	Discontinued
0.697	Remote Similarity	NPD6529	Discontinued
0.6968	Remote Similarity	NPD8360	Approved
0.6968	Remote Similarity	NPD8361	Approved
0.6962	Remote Similarity	NPD8479	Phase 2
0.6947	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4952	Phase 3
0.692	Remote Similarity	NPD6770	Approved
0.6917	Remote Similarity	NPD3925	Approved
0.6914	Remote Similarity	NPD7956	Approved
0.6914	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7955	Approved
0.6913	Remote Similarity	NPD7010	Phase 3
0.6881	Remote Similarity	NPD8368	Discontinued
0.688	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5088	Discontinued
0.6869	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2336	Approved
0.6844	Remote Similarity	NPD4427	Phase 2
0.684	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5475	Discontinued
0.6827	Remote Similarity	NPD6790	Phase 1
0.6802	Remote Similarity	NPD3006	Discontinued
0.6802	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4301	Approved
0.6792	Remote Similarity	NPD6635	Approved
0.679	Remote Similarity	NPD4086	Phase 1
0.6784	Remote Similarity	NPD5003	Discontinued
0.6783	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8409	Suspended
0.6767	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4989	Phase 2
0.6758	Remote Similarity	NPD8370	Discontinued
0.6749	Remote Similarity	NPD5640	Discontinued
0.6744	Remote Similarity	NPD8091	Phase 3
0.6742	Remote Similarity	NPD8467	Approved
0.6742	Remote Similarity	NPD8466	Approved
0.6742	Remote Similarity	NPD8465	Approved
0.6741	Remote Similarity	NPD8063	Discontinued
0.674	Remote Similarity	NPD2307	Discontinued
0.6731	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2831	Approved
0.6723	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8404	Phase 2
0.6694	Remote Similarity	NPD8356	Approved
0.6693	Remote Similarity	NPD7417	Discontinued
0.6667	Remote Similarity	NPD5866	Approved
0.6667	Remote Similarity	NPD5022	Discontinued
0.6667	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8462	Phase 1
0.6667	Remote Similarity	NPD9271	Approved
0.6652	Remote Similarity	NPD4948	Discontinued
0.6652	Remote Similarity	NPD4529	Approved
0.6652	Remote Similarity	NPD4526	Approved
0.6652	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5901	Discontinued
0.6652	Remote Similarity	NPD4528	Approved
0.6642	Remote Similarity	NPD8460	Approved
0.6642	Remote Similarity	NPD8425	Approved
0.6642	Remote Similarity	NPD8426	Approved
0.6642	Remote Similarity	NPD8459	Approved
0.6641	Remote Similarity	NPD5482	Discontinued
0.6639	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7470	Discontinued
0.6624	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8428	Approved
0.6617	Remote Similarity	NPD8427	Approved
0.6617	Remote Similarity	NPD8429	Approved
0.6612	Remote Similarity	NPD8289	Discontinued
0.6611	Remote Similarity	NPD4897	Phase 2
0.6608	Remote Similarity	NPD4376	Phase 3
0.6601	Remote Similarity	NPD6716	Phase 1
0.6599	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2565	Phase 2
0.6593	Remote Similarity	NPD2564	Approved
0.6585	Remote Similarity	NPD8430	Approved
0.6584	Remote Similarity	NPD5507	Approved
0.6584	Remote Similarity	NPD5506	Approved
0.6577	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7187	Phase 2
0.6565	Remote Similarity	NPD6206	Phase 1
0.6562	Remote Similarity	NPD4889	Approved
0.6561	Remote Similarity	NPD7576	Discontinued
0.656	Remote Similarity	NPD8329	Phase 3
0.656	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7001	Phase 3
0.6552	Remote Similarity	NPD4600	Approved
0.6552	Remote Similarity	NPD4601	Approved
0.6549	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.654	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3924	Approved
0.6535	Remote Similarity	NPD4950	Approved
0.6535	Remote Similarity	NPD3923	Approved
0.6535	Remote Similarity	NPD3922	Approved
0.6535	Remote Similarity	NPD3921	Approved
0.6518	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4328	Approved
0.6516	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8160	Phase 2
0.6514	Remote Similarity	NPD1575	Approved
0.6514	Remote Similarity	NPD1573	Approved
0.6513	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6511	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6999	Discontinued
0.6508	Remote Similarity	NPD5805	Approved
0.6506	Remote Similarity	NPD7688	Phase 1
0.6502	Remote Similarity	NPD6531	Approved
0.6502	Remote Similarity	NPD7404	Approved
0.6502	Remote Similarity	NPD6530	Approved
0.6502	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3178	Discontinued
0.6498	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6276	Discontinued
0.6494	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3217	Phase 2
0.6491	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.649	Remote Similarity	NPD9074	Approved
0.649	Remote Similarity	NPD6995	Phase 1
0.649	Remote Similarity	NPD9075	Approved
0.6483	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7957	Phase 1
0.6481	Remote Similarity	NPD1631	Approved
0.6479	Remote Similarity	NPD6026	Approved
0.6475	Remote Similarity	NPD6242	Discontinued
0.6473	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6176	Phase 1
0.6468	Remote Similarity	NPD5513	Phase 2
0.6466	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD2511	Approved
0.6463	Remote Similarity	NPD6665	Discontinued
0.6461	Remote Similarity	NPD7395	Discontinued
0.6461	Remote Similarity	NPD3354	Phase 2
0.6461	Remote Similarity	NPD1926	Approved
0.6461	Remote Similarity	NPD4429	Discontinued
0.6459	Remote Similarity	NPD5488	Discontinued
0.6457	Remote Similarity	NPD1643	Phase 3
0.6457	Remote Similarity	NPD5899	Approved
0.6457	Remote Similarity	NPD5897	Approved
0.6457	Remote Similarity	NPD5898	Approved
0.6455	Remote Similarity	NPD8364	Approved
0.6455	Remote Similarity	NPD8363	Approved
0.6452	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3259	Approved
0.6452	Remote Similarity	NPD4845	Discontinued
0.6452	Remote Similarity	NPD6292	Clinical (unspecified phase)

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