NPASS Compound

Structure

NPC475498 OpenBabel07101718322D 54 58 0 0 1 0 0 0 0 0999 V2000 3.2334 2.3492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5136 2.9973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0651 -2.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1829 -1.6346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3795 2.7398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2356 -0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7585 -1.6673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7449 -1.2650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8581 1.4264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6402 0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1544 0.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6402 1.2606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 -0.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0205 -0.7020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4404 1.7731 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0236 2.1484 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8043 -2.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6430 -0.8166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5792 2.9436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9086 -0.2414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7998 -1.8711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6686 0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5083 0.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6686 1.2606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4195 1.7770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1463 -0.1158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9322 1.2830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4464 1.9827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6744 0.9242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4469 -0.2106 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4900 2.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4404 0.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9322 -0.3029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1166 1.5288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0633 0.2772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1544 1.5411 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6309 -2.7345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0814 0.0600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8821 3.8757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8622 -0.4679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4970 -2.8033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0925 2.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5925 3.2965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2334 -0.3889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4595 2.3218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8471 -1.2287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0236 -0.1882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6862 -0.9338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2350 2.2152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6279 0.6977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1440 -1.1427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9322 2.2631 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 26 1 0 0 0 0 23 27 1 0 0 0 0 23 33 1 6 0 0 0 24 37 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 25 43 1 1 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 34 1 6 0 0 0 28 53 1 0 0 0 0 29 35 1 1 0 0 0 29 51 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 1 0 0 0 36 54 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	763.27
Volume:	722.496
LogP:	1.215
LogD:	0.714
LogS:	-4.17
# Rotatable Bonds:	11
TPSA:	246.68
# H-Bond Aceptor:	18
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	7.563
Fsp3:	0.667
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:	-5.384
MDCK Permeability:	0.00018874628585763276
Pgp-inhibitor:	0.998
Pgp-substrate:	0.805
Human Intestinal Absorption (HIA):	0.887
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	32.066436767578125%
Volume Distribution (VD):	1.213
Pgp-substrate:	35.87998580932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.234
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	2.635
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.176
Carcinogencity:	0.096
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC475498

Natural Product ID:	NPC475498
*Common Name:**	VWRGSMDCPWKKRO-YMYBHSDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VWRGSMDCPWKKRO-YMYBHSDNSA-N
Standard InCHI:	InChI=1S/C36H45NO17/c1-15-16(2)31(44)53-28-25(43)29(51-20(6)41)35(14-47-17(3)38)30(52-21(7)42)26(49-18(4)39)23-27(50-19(5)40)36(35,34(28,9)46)54-33(23,8)13-48-32(45)22-11-10-12-37-24(15)22/h10-12,15-16,23,25-30,43,46H,13-14H2,1-9H3/t15?,16?,23-,25+,26-,27-,28+,29+,30-,33+,34+,35+,36+/m1/s1
SMILES:	CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506799
PubChem CID:	10876437
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
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	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
LD50	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	LD50	>	100.0	ug ml-1	PMID[464959]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	50.0	microg/cm2	PMID[464959]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	94.0	%	PMID[464959]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	101.0	%	PMID[464959]
NPT27	Others	Unspecified		LD50	=	57.54	ug ml-1	PMID[464959]

☑ 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 NPC475498 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	328
0.1-0.2	1373
0.2-0.3	3213
0.3-0.4	10437
0.4-0.5	19083
0.5-0.6	5847
0.6-0.7	2056
0.7-0.8	189
0.8-0.85	37
0.85-0.9	41
0.9-0.95	60
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475137
0.995	High Similarity	NPC76565
0.9851	High Similarity	NPC470486
0.9851	High Similarity	NPC475644
0.9851	High Similarity	NPC471190
0.9851	High Similarity	NPC471977
0.9802	High Similarity	NPC476110
0.9802	High Similarity	NPC475600
0.9802	High Similarity	NPC87152
0.9802	High Similarity	NPC475631
0.9801	High Similarity	NPC473850
0.9754	High Similarity	NPC475362
0.9752	High Similarity	NPC473506
0.9751	High Similarity	NPC250807
0.9751	High Similarity	NPC57797
0.9707	High Similarity	NPC30456
0.9704	High Similarity	NPC146824
0.9659	High Similarity	NPC475596
0.9659	High Similarity	NPC475303
0.9648	High Similarity	NPC471014
0.9648	High Similarity	NPC475408
0.9648	High Similarity	NPC471016
0.9614	High Similarity	NPC170751
0.9608	High Similarity	NPC122968
0.9608	High Similarity	NPC328186
0.9608	High Similarity	NPC228377
0.9608	High Similarity	NPC477787
0.9598	High Similarity	NPC470306
0.9565	High Similarity	NPC237702
0.9563	High Similarity	NPC473689
0.9563	High Similarity	NPC292416
0.9519	High Similarity	NPC475426
0.9519	High Similarity	NPC327769
0.9519	High Similarity	NPC35208
0.9517	High Similarity	NPC244839
0.9517	High Similarity	NPC319880
0.9517	High Similarity	NPC320324
0.9469	High Similarity	NPC316841
0.9455	High Similarity	NPC301368
0.9455	High Similarity	NPC84815
0.9426	High Similarity	NPC475406
0.9412	High Similarity	NPC477788
0.9406	High Similarity	NPC144779
0.9406	High Similarity	NPC294579
0.9381	High Similarity	NPC327904
0.9381	High Similarity	NPC38959
0.9366	High Similarity	NPC471980
0.9356	High Similarity	NPC6981
0.932	High Similarity	NPC328154
0.9317	High Similarity	NPC127026
0.9317	High Similarity	NPC127720
0.931	High Similarity	NPC62367
0.9265	High Similarity	NPC216428
0.9257	High Similarity	NPC4421
0.9254	High Similarity	NPC472553
0.9249	High Similarity	NPC253482
0.9231	High Similarity	NPC475601
0.9227	High Similarity	NPC477902
0.9212	High Similarity	NPC477909
0.9212	High Similarity	NPC477907
0.9212	High Similarity	NPC42678
0.9175	High Similarity	NPC477912
0.9147	High Similarity	NPC469748
0.9139	High Similarity	NPC124029
0.9139	High Similarity	NPC211920
0.9122	High Similarity	NPC212768
0.9122	High Similarity	NPC473115
0.9122	High Similarity	NPC75600
0.9122	High Similarity	NPC158020
0.9122	High Similarity	NPC473089
0.9122	High Similarity	NPC6576
0.912	High Similarity	NPC475648
0.9118	High Similarity	NPC477910
0.9104	High Similarity	NPC48042
0.9104	High Similarity	NPC472550
0.9104	High Similarity	NPC304179
0.91	High Similarity	NPC150698
0.91	High Similarity	NPC96801
0.9069	High Similarity	NPC319128
0.9055	High Similarity	NPC63041
0.9	High Similarity	NPC148860
0.8986	High Similarity	NPC472555
0.8976	High Similarity	NPC228331
0.8976	High Similarity	NPC264674
0.892	High Similarity	NPC477906
0.89	High Similarity	NPC477903
0.8889	High Similarity	NPC477908
0.8889	High Similarity	NPC206343
0.8857	High Similarity	NPC477911
0.8839	High Similarity	NPC475301
0.8839	High Similarity	NPC326930
0.8774	High Similarity	NPC477900
0.8774	High Similarity	NPC477899
0.8768	High Similarity	NPC235364
0.8717	High Similarity	NPC13603
0.8696	High Similarity	NPC476467
0.8685	High Similarity	NPC26881
0.8684	High Similarity	NPC473833
0.8673	High Similarity	NPC477901
0.8673	High Similarity	NPC85879
0.8673	High Similarity	NPC53255
0.8609	High Similarity	NPC471978
0.8609	High Similarity	NPC328928
0.8527	High Similarity	NPC475533
0.8525	High Similarity	NPC91125
0.8519	High Similarity	NPC14116
0.8519	High Similarity	NPC285411
0.8493	Intermediate Similarity	NPC238278
0.8489	Intermediate Similarity	NPC324619
0.8489	Intermediate Similarity	NPC475315
0.8479	Intermediate Similarity	NPC134384
0.8479	Intermediate Similarity	NPC311196
0.8462	Intermediate Similarity	NPC472752
0.8429	Intermediate Similarity	NPC280473
0.8429	Intermediate Similarity	NPC323551
0.8419	Intermediate Similarity	NPC471979
0.84	Intermediate Similarity	NPC180668
0.84	Intermediate Similarity	NPC471013
0.84	Intermediate Similarity	NPC148896
0.8389	Intermediate Similarity	NPC51008
0.8389	Intermediate Similarity	NPC41724
0.8384	Intermediate Similarity	NPC471015
0.8364	Intermediate Similarity	NPC213143
0.8319	Intermediate Similarity	NPC476090
0.831	Intermediate Similarity	NPC30570
0.8271	Intermediate Similarity	NPC162812
0.8269	Intermediate Similarity	NPC289086
0.8257	Intermediate Similarity	NPC233727
0.8255	Intermediate Similarity	NPC292517
0.8253	Intermediate Similarity	NPC10904
0.8252	Intermediate Similarity	NPC470279
0.814	Intermediate Similarity	NPC193361
0.814	Intermediate Similarity	NPC62844
0.8131	Intermediate Similarity	NPC165837
0.8122	Intermediate Similarity	NPC470189
0.8122	Intermediate Similarity	NPC40919
0.8104	Intermediate Similarity	NPC475835
0.8066	Intermediate Similarity	NPC470190
0.8065	Intermediate Similarity	NPC187494
0.7982	Intermediate Similarity	NPC319556
0.789	Intermediate Similarity	NPC207531
0.7887	Intermediate Similarity	NPC309498
0.7873	Intermediate Similarity	NPC253314
0.787	Intermediate Similarity	NPC37473
0.7867	Intermediate Similarity	NPC328559
0.7867	Intermediate Similarity	NPC32451
0.7788	Intermediate Similarity	NPC103230
0.7725	Intermediate Similarity	NPC324245
0.7725	Intermediate Similarity	NPC320748
0.7719	Intermediate Similarity	NPC471004
0.7671	Intermediate Similarity	NPC111732
0.7658	Intermediate Similarity	NPC141385
0.7653	Intermediate Similarity	NPC79223
0.7642	Intermediate Similarity	NPC317672
0.763	Intermediate Similarity	NPC109922
0.7604	Intermediate Similarity	NPC156044
0.7594	Intermediate Similarity	NPC329024
0.758	Intermediate Similarity	NPC314834
0.7512	Intermediate Similarity	NPC25442
0.7512	Intermediate Similarity	NPC12944
0.7512	Intermediate Similarity	NPC317010
0.75	Intermediate Similarity	NPC135950
0.749	Intermediate Similarity	NPC476516
0.7477	Intermediate Similarity	NPC59033
0.7457	Intermediate Similarity	NPC70155
0.7456	Intermediate Similarity	NPC235885
0.7443	Intermediate Similarity	NPC315545
0.7443	Intermediate Similarity	NPC314297
0.7442	Intermediate Similarity	NPC103361
0.7437	Intermediate Similarity	NPC107123
0.7427	Intermediate Similarity	NPC471997
0.7404	Intermediate Similarity	NPC207851
0.7397	Intermediate Similarity	NPC313345
0.7397	Intermediate Similarity	NPC314855
0.7397	Intermediate Similarity	NPC315638
0.7397	Intermediate Similarity	NPC313796
0.7395	Intermediate Similarity	NPC149708
0.7389	Intermediate Similarity	NPC249614
0.738	Intermediate Similarity	NPC141428
0.7373	Intermediate Similarity	NPC155792
0.7368	Intermediate Similarity	NPC282103
0.7366	Intermediate Similarity	NPC274842
0.7361	Intermediate Similarity	NPC123395
0.7357	Intermediate Similarity	NPC140311
0.7354	Intermediate Similarity	NPC244856
0.7352	Intermediate Similarity	NPC477043
0.7346	Intermediate Similarity	NPC44354
0.7333	Intermediate Similarity	NPC204491
0.733	Intermediate Similarity	NPC470280
0.7321	Intermediate Similarity	NPC236424
0.7321	Intermediate Similarity	NPC306644
0.7321	Intermediate Similarity	NPC317752
0.7316	Intermediate Similarity	NPC57690
0.7299	Intermediate Similarity	NPC325775
0.7293	Intermediate Similarity	NPC106593
0.7277	Intermediate Similarity	NPC318299
0.7277	Intermediate Similarity	NPC114974
0.7273	Intermediate Similarity	NPC314648
0.7273	Intermediate Similarity	NPC134637
0.7268	Intermediate Similarity	NPC191310

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 NPC475498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	515
0.2-0.3	632
0.3-0.4	1727
0.4-0.5	3200
0.5-0.6	2186
0.6-0.7	636
0.7-0.8	31
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
0.8527	High Similarity	NPD8468	Phase 2
0.799	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7837	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3795	Approved
0.7717	Intermediate Similarity	NPD3794	Approved
0.7593	Intermediate Similarity	NPD7396	Approved
0.7545	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5891	Approved
0.7409	Intermediate Similarity	NPD2509	Approved
0.7409	Intermediate Similarity	NPD2510	Approved
0.7384	Intermediate Similarity	NPD1483	Discontinued
0.7357	Intermediate Similarity	NPD3280	Approved
0.7354	Intermediate Similarity	NPD7069	Discontinued
0.7352	Intermediate Similarity	NPD3947	Discontinued
0.7333	Intermediate Similarity	NPD3393	Approved
0.7333	Intermediate Similarity	NPD3389	Approved
0.7333	Intermediate Similarity	NPD3394	Approved
0.7306	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8325	Phase 3
0.7301	Intermediate Similarity	NPD8326	Phase 3
0.7301	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD820	Phase 3
0.7273	Intermediate Similarity	NPD6987	Phase 1
0.7235	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4417	Approved
0.7202	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7233	Approved
0.7183	Intermediate Similarity	NPD7234	Approved
0.7162	Intermediate Similarity	NPD7010	Phase 3
0.7156	Intermediate Similarity	NPD7777	Approved
0.7156	Intermediate Similarity	NPD53	Approved
0.7156	Intermediate Similarity	NPD7778	Approved
0.7143	Intermediate Similarity	NPD6529	Discontinued
0.7143	Intermediate Similarity	NPD4506	Discontinued
0.7118	Intermediate Similarity	NPD7878	Phase 2
0.7106	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6770	Approved
0.7085	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5475	Discontinued
0.707	Intermediate Similarity	NPD8063	Discontinued
0.7059	Intermediate Similarity	NPD6635	Approved
0.7056	Intermediate Similarity	NPD8479	Phase 2
0.7053	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7708	Approved
0.7018	Intermediate Similarity	NPD4427	Phase 2
0.7	Intermediate Similarity	NPD6642	Approved
0.7	Intermediate Similarity	NPD6641	Approved
0.6996	Remote Similarity	NPD7803	Approved
0.6953	Remote Similarity	NPD4301	Approved
0.6942	Remote Similarity	NPD7886	Phase 2
0.6942	Remote Similarity	NPD7885	Phase 2
0.6935	Remote Similarity	NPD9271	Approved
0.6932	Remote Similarity	NPD7955	Approved
0.6932	Remote Similarity	NPD7956	Approved
0.6923	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7417	Discontinued
0.6913	Remote Similarity	NPD7707	Approved
0.6907	Remote Similarity	NPD8289	Discontinued
0.6898	Remote Similarity	NPD4948	Discontinued
0.6895	Remote Similarity	NPD4529	Approved
0.6895	Remote Similarity	NPD4526	Approved
0.6895	Remote Similarity	NPD4528	Approved
0.6891	Remote Similarity	NPD5022	Discontinued
0.6889	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5901	Discontinued
0.6888	Remote Similarity	NPD3006	Discontinued
0.6881	Remote Similarity	NPD2336	Approved
0.6878	Remote Similarity	NPD5003	Discontinued
0.687	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7470	Discontinued
0.6853	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4376	Phase 3
0.6844	Remote Similarity	NPD6790	Phase 1
0.6833	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5866	Approved
0.682	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6026	Approved
0.6812	Remote Similarity	NPD5088	Discontinued
0.6812	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4889	Approved
0.6805	Remote Similarity	NPD4373	Phase 2
0.6802	Remote Similarity	NPD8485	Approved
0.68	Remote Similarity	NPD7187	Phase 2
0.68	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6962	Phase 2
0.6792	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5482	Discontinued
0.6786	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7001	Phase 3
0.678	Remote Similarity	NPD6995	Phase 1
0.678	Remote Similarity	NPD8356	Approved
0.6774	Remote Similarity	NPD6276	Discontinued
0.6773	Remote Similarity	NPD3922	Approved
0.6773	Remote Similarity	NPD3924	Approved
0.6773	Remote Similarity	NPD3923	Approved
0.6773	Remote Similarity	NPD3921	Approved
0.6765	Remote Similarity	NPD5640	Discontinued
0.6759	Remote Similarity	NPD8091	Phase 3
0.6757	Remote Similarity	NPD2307	Discontinued
0.675	Remote Similarity	NPD9075	Approved
0.675	Remote Similarity	NPD9074	Approved
0.6745	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3178	Discontinued
0.6741	Remote Similarity	NPD6999	Discontinued
0.6741	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2831	Approved
0.6736	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4086	Phase 1
0.6725	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3925	Approved
0.6723	Remote Similarity	NPD7404	Approved
0.6722	Remote Similarity	NPD7688	Phase 1
0.6721	Remote Similarity	NPD5805	Approved
0.6711	Remote Similarity	NPD4600	Approved
0.6711	Remote Similarity	NPD4601	Approved
0.6711	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4989	Phase 2
0.6699	Remote Similarity	NPD2581	Approved
0.6699	Remote Similarity	NPD2582	Approved
0.6696	Remote Similarity	NPD6176	Phase 1
0.6695	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8435	Approved
0.6682	Remote Similarity	NPD6281	Approved
0.6682	Remote Similarity	NPD8361	Approved
0.6682	Remote Similarity	NPD1575	Approved
0.6682	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD1573	Approved
0.6682	Remote Similarity	NPD2565	Phase 2
0.6682	Remote Similarity	NPD8360	Approved
0.6682	Remote Similarity	NPD2564	Approved
0.6681	Remote Similarity	NPD3354	Phase 2
0.6681	Remote Similarity	NPD7395	Discontinued
0.668	Remote Similarity	NPD6716	Phase 1
0.668	Remote Similarity	NPD4952	Phase 3
0.6667	Remote Similarity	NPD6791	Phase 2
0.6667	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8160	Phase 2
0.6667	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8430	Approved
0.6667	Remote Similarity	NPD6361	Phase 2
0.6667	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8363	Approved
0.6654	Remote Similarity	NPD8364	Approved
0.6653	Remote Similarity	NPD8409	Suspended
0.6653	Remote Similarity	NPD8101	Phase 3
0.6652	Remote Similarity	NPD8399	Phase 1
0.6652	Remote Similarity	NPD8423	Phase 2
0.6651	Remote Similarity	NPD8407	Phase 2
0.6651	Remote Similarity	NPD1631	Approved
0.6651	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6228	Discontinued
0.664	Remote Similarity	NPD7576	Discontinued
0.664	Remote Similarity	NPD8370	Discontinued
0.6639	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7957	Phase 1
0.6638	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7944	Discontinued
0.6637	Remote Similarity	NPD6479	Discontinued
0.6635	Remote Similarity	NPD2511	Approved
0.6633	Remote Similarity	NPD107	Approved
0.6629	Remote Similarity	NPD8467	Approved
0.6629	Remote Similarity	NPD8466	Approved
0.6629	Remote Similarity	NPD8465	Approved
0.6625	Remote Similarity	NPD7426	Phase 1
0.6624	Remote Similarity	NPD1996	Discontinued
0.6624	Remote Similarity	NPD6242	Discontinued
0.6622	Remote Similarity	NPD6665	Discontinued
0.661	Remote Similarity	NPD4429	Discontinued
0.6609	Remote Similarity	NPD7562	Approved
0.6609	Remote Similarity	NPD3815	Phase 1
0.6609	Remote Similarity	NPD3816	Phase 1
0.6607	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3259	Approved
0.6597	Remote Similarity	NPD6298	Discontinued
0.6594	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7191	Phase 2
0.6573	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7967	Discontinued
0.6558	Remote Similarity	NPD5100	Phase 3
0.6555	Remote Similarity	NPD5827	Discontinued
0.6553	Remote Similarity	NPD4897	Phase 2
0.6553	Remote Similarity	NPD180	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5513	Phase 2
0.6546	Remote Similarity	NPD8412	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