NPASS Compound

Structure

NPC96584 OpenBabel07101718192D 44 50 0 0 1 0 0 0 0 0999 V2000 2.3499 4.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0328 3.0786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 -1.6710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9631 0.3619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5577 0.6768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2738 -0.2275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0257 0.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3936 4.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0046 3.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1459 2.5447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2159 1.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4250 2.1601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2159 2.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1153 1.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2020 3.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1498 4.3695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7586 3.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 0.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4483 3.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6874 -0.1323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9320 1.2683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3832 -0.0561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7437 3.9989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3395 2.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 1.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8622 3.3050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0913 2.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4839 2.8290 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0443 3.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5269 4.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5569 3.7663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8863 4.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4839 -0.1710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4839 1.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6179 1.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6179 0.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8977 2.2094 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3499 3.3290 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3584 2.8542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2482 1.8290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5636 3.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4839 -1.1710 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 -1.2263 4.5202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 6 1 0 0 0 0 4 21 2 0 0 0 0 5 7 2 0 0 0 0 5 21 1 0 0 0 0 6 22 2 0 0 0 0 7 22 1 0 0 0 0 8 9 2 0 0 0 0 8 23 1 0 0 0 0 9 29 1 0 0 0 0 10 12 2 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 15 23 1 0 0 0 0 16 23 2 0 0 0 0 16 30 1 0 0 0 0 17 24 2 0 0 0 0 17 31 1 0 0 0 0 18 25 2 0 0 0 0 18 33 1 0 0 0 0 19 26 2 0 0 0 0 19 32 1 0 0 0 0 20 22 1 0 0 0 0 20 43 1 0 0 0 0 24 26 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 27 37 2 0 0 0 0 28 15 1 6 0 0 0 28 34 1 0 0 0 0 28 38 1 0 0 0 0 29 30 2 0 0 0 0 29 39 1 0 0 0 0 30 44 1 0 0 0 0 31 32 2 0 0 0 0 31 41 1 0 0 0 0 32 44 1 0 0 0 0 33 36 2 0 0 0 0 33 42 1 0 0 0 0 34 35 2 0 0 0 0 35 36 1 0 0 0 0 35 40 1 0 0 0 0 36 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.24
Volume:	609.141
LogP:	5.595
LogD:	3.84
LogS:	-4.107
# Rotatable Bonds:	2
TPSA:	93.51
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	5.802
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.555
MDCK Permeability:	1.812985101423692e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.54
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.82781219482422%
Volume Distribution (VD):	0.861
Pgp-substrate:	3.094512462615967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.438
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.942

ADMET: Excretion

Clearance (CL):	11.55
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.785
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.912
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.784

Download Data

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

Natural Product: NPC96584

Natural Product ID:	NPC96584
*Common Name:**	JDQUPOMQSBZZHW-NDEPHWFRSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Cycleatjehine
Standard InCHIKey:	JDQUPOMQSBZZHW-NDEPHWFRSA-N
Standard InCHI:	InChI=1S/C36H34N2O6/c1-38-13-11-25-18-33(42-3)36-35(40)34(25)28(38)15-23-8-9-29(39)30(16-23)44-32-19-26-24(17-31(32)41-2)10-12-37-27(26)14-21-4-6-22(7-5-21)20-43-36/h4-10,12,16-19,28,39-40H,11,13-15,20H2,1-3H3/t28-/m0/s1
SMILES:	COc1cc2ccnc3c2cc1Oc1cc(ccc1O)C[C@@H]1N(C)CCc2c1c(O)c(OCc1ccc(C3)cc1)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502592
PubChem CID:	44559030
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO14592	Cyclea atjehensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO14592	Cyclea atjehensis	Species	Menispermaceae	Eukaryota	leaves	Thai	n.a.	Database[Title]
NPO14592	Cyclea atjehensis	Species	Menispermaceae	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
ED50	1
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	33900.0	nM	PMID[541843]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	110.0	nM	PMID[541843]
NPT2	Others	Unspecified		Selectivity Index	>	310.0	n.a.	PMID[541843]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	59.0	nM	PMID[541843]
NPT2	Others	Unspecified		Selectivity Index	>	580.0	n.a.	PMID[541843]

☑ 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 NPC96584 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	563
0.1-0.2	2784
0.2-0.3	12312
0.3-0.4	5543
0.4-0.5	9319
0.5-0.6	9762
0.6-0.7	2028
0.7-0.8	331
0.8-0.85	41
0.85-0.9	9
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255800
0.9807	High Similarity	NPC201508
0.9091	High Similarity	NPC473822
0.892	High Similarity	NPC122463
0.8848	High Similarity	NPC469792
0.8846	High Similarity	NPC290689
0.8762	High Similarity	NPC112206
0.8762	High Similarity	NPC202605
0.863	High Similarity	NPC476997
0.8591	High Similarity	NPC476998
0.8591	High Similarity	NPC476996
0.8565	High Similarity	NPC174049
0.8545	High Similarity	NPC476994
0.8429	Intermediate Similarity	NPC476581
0.8429	Intermediate Similarity	NPC36229
0.8429	Intermediate Similarity	NPC16452
0.8363	Intermediate Similarity	NPC476995
0.8294	Intermediate Similarity	NPC469440
0.8286	Intermediate Similarity	NPC31930
0.8278	Intermediate Similarity	NPC4071
0.8278	Intermediate Similarity	NPC476582
0.8278	Intermediate Similarity	NPC476578
0.8269	Intermediate Similarity	NPC234318
0.8252	Intermediate Similarity	NPC133140
0.8252	Intermediate Similarity	NPC195268
0.8225	Intermediate Similarity	NPC284141
0.8182	Intermediate Similarity	NPC15406
0.8182	Intermediate Similarity	NPC224928
0.8174	Intermediate Similarity	NPC217554
0.8173	Intermediate Similarity	NPC85381
0.8169	Intermediate Similarity	NPC164374
0.8169	Intermediate Similarity	NPC137929
0.8157	Intermediate Similarity	NPC202768
0.8157	Intermediate Similarity	NPC296482
0.8157	Intermediate Similarity	NPC53069
0.8153	Intermediate Similarity	NPC118121
0.8142	Intermediate Similarity	NPC476999
0.8087	Intermediate Similarity	NPC11408
0.8077	Intermediate Similarity	NPC41122
0.8077	Intermediate Similarity	NPC318805
0.8054	Intermediate Similarity	NPC204446
0.8029	Intermediate Similarity	NPC469390
0.8009	Intermediate Similarity	NPC313189
0.7991	Intermediate Similarity	NPC96405
0.7991	Intermediate Similarity	NPC171409
0.799	Intermediate Similarity	NPC280964
0.799	Intermediate Similarity	NPC141915
0.799	Intermediate Similarity	NPC114335
0.7962	Intermediate Similarity	NPC473053
0.7961	Intermediate Similarity	NPC285931
0.7961	Intermediate Similarity	NPC290582
0.7961	Intermediate Similarity	NPC222661
0.7961	Intermediate Similarity	NPC328155
0.7961	Intermediate Similarity	NPC90998
0.7961	Intermediate Similarity	NPC217748
0.7961	Intermediate Similarity	NPC223690
0.7961	Intermediate Similarity	NPC290005
0.7961	Intermediate Similarity	NPC104196
0.7961	Intermediate Similarity	NPC311973
0.7961	Intermediate Similarity	NPC8836
0.7961	Intermediate Similarity	NPC15414
0.7961	Intermediate Similarity	NPC7715
0.7961	Intermediate Similarity	NPC181796
0.7961	Intermediate Similarity	NPC229373
0.7961	Intermediate Similarity	NPC251735
0.7961	Intermediate Similarity	NPC182052
0.7961	Intermediate Similarity	NPC258657
0.7961	Intermediate Similarity	NPC49075
0.7961	Intermediate Similarity	NPC42663
0.7961	Intermediate Similarity	NPC279228
0.7961	Intermediate Similarity	NPC185639
0.7961	Intermediate Similarity	NPC271013
0.7961	Intermediate Similarity	NPC239824
0.7961	Intermediate Similarity	NPC54654
0.7923	Intermediate Similarity	NPC254441
0.7923	Intermediate Similarity	NPC274716
0.7923	Intermediate Similarity	NPC167116
0.7922	Intermediate Similarity	NPC295228
0.7913	Intermediate Similarity	NPC286119
0.7909	Intermediate Similarity	NPC251160
0.7899	Intermediate Similarity	NPC77878
0.7897	Intermediate Similarity	NPC477019
0.7895	Intermediate Similarity	NPC22115
0.7895	Intermediate Similarity	NPC275680
0.7892	Intermediate Similarity	NPC23614
0.7892	Intermediate Similarity	NPC100079
0.7885	Intermediate Similarity	NPC249996
0.7879	Intermediate Similarity	NPC90875
0.7874	Intermediate Similarity	NPC30779
0.787	Intermediate Similarity	NPC233334
0.7857	Intermediate Similarity	NPC206900
0.7847	Intermediate Similarity	NPC212237
0.7847	Intermediate Similarity	NPC116465
0.7844	Intermediate Similarity	NPC135549
0.7838	Intermediate Similarity	NPC235076
0.7837	Intermediate Similarity	NPC61350
0.7824	Intermediate Similarity	NPC183537
0.7799	Intermediate Similarity	NPC16357
0.7799	Intermediate Similarity	NPC302245
0.7799	Intermediate Similarity	NPC95426
0.7793	Intermediate Similarity	NPC149471
0.7793	Intermediate Similarity	NPC271215
0.7788	Intermediate Similarity	NPC476202
0.7787	Intermediate Similarity	NPC119134
0.7783	Intermediate Similarity	NPC478093
0.7778	Intermediate Similarity	NPC46451
0.7773	Intermediate Similarity	NPC82457
0.7773	Intermediate Similarity	NPC11296
0.7773	Intermediate Similarity	NPC48490
0.7773	Intermediate Similarity	NPC274661
0.7773	Intermediate Similarity	NPC175890
0.7762	Intermediate Similarity	NPC139783
0.7762	Intermediate Similarity	NPC65312
0.7746	Intermediate Similarity	NPC478091
0.7746	Intermediate Similarity	NPC473589
0.7746	Intermediate Similarity	NPC478092
0.7746	Intermediate Similarity	NPC30182
0.774	Intermediate Similarity	NPC195538
0.7738	Intermediate Similarity	NPC188420
0.7736	Intermediate Similarity	NPC191132
0.7736	Intermediate Similarity	NPC60295
0.7733	Intermediate Similarity	NPC173080
0.7729	Intermediate Similarity	NPC214980
0.7713	Intermediate Similarity	NPC266931
0.7706	Intermediate Similarity	NPC24019
0.77	Intermediate Similarity	NPC289786
0.77	Intermediate Similarity	NPC24260
0.7675	Intermediate Similarity	NPC280272
0.7671	Intermediate Similarity	NPC274291
0.7671	Intermediate Similarity	NPC264166
0.7671	Intermediate Similarity	NPC47059
0.7671	Intermediate Similarity	NPC118832
0.7671	Intermediate Similarity	NPC165349
0.7671	Intermediate Similarity	NPC329708
0.7657	Intermediate Similarity	NPC107123
0.765	Intermediate Similarity	NPC234197
0.7637	Intermediate Similarity	NPC210296
0.7633	Intermediate Similarity	NPC129897
0.7621	Intermediate Similarity	NPC276890
0.7621	Intermediate Similarity	NPC115284
0.7621	Intermediate Similarity	NPC10908
0.7621	Intermediate Similarity	NPC76682
0.7621	Intermediate Similarity	NPC317145
0.7621	Intermediate Similarity	NPC227060
0.7621	Intermediate Similarity	NPC198498
0.7621	Intermediate Similarity	NPC317439
0.7621	Intermediate Similarity	NPC63646
0.7615	Intermediate Similarity	NPC124313
0.7605	Intermediate Similarity	NPC84164
0.7605	Intermediate Similarity	NPC207283
0.7585	Intermediate Similarity	NPC251580
0.7585	Intermediate Similarity	NPC41376
0.7585	Intermediate Similarity	NPC129518
0.7585	Intermediate Similarity	NPC12424
0.7581	Intermediate Similarity	NPC256124
0.7576	Intermediate Similarity	NPC200888
0.7562	Intermediate Similarity	NPC134637
0.7556	Intermediate Similarity	NPC236668
0.7556	Intermediate Similarity	NPC474594
0.7544	Intermediate Similarity	NPC148409
0.7531	Intermediate Similarity	NPC302807
0.7522	Intermediate Similarity	NPC146976
0.7522	Intermediate Similarity	NPC210434
0.7512	Intermediate Similarity	NPC293093
0.7511	Intermediate Similarity	NPC469439
0.7511	Intermediate Similarity	NPC210256
0.75	Intermediate Similarity	NPC277351
0.7489	Intermediate Similarity	NPC475654
0.7477	Intermediate Similarity	NPC304183
0.7477	Intermediate Similarity	NPC472111
0.7468	Intermediate Similarity	NPC108342
0.7443	Intermediate Similarity	NPC287437
0.7441	Intermediate Similarity	NPC475479
0.7441	Intermediate Similarity	NPC243454
0.7437	Intermediate Similarity	NPC189903
0.7437	Intermediate Similarity	NPC182907
0.7434	Intermediate Similarity	NPC316981
0.7427	Intermediate Similarity	NPC13916
0.7427	Intermediate Similarity	NPC250846
0.7427	Intermediate Similarity	NPC317272
0.7427	Intermediate Similarity	NPC240841
0.7427	Intermediate Similarity	NPC264850
0.7427	Intermediate Similarity	NPC256012
0.7427	Intermediate Similarity	NPC42549
0.7427	Intermediate Similarity	NPC268503
0.7419	Intermediate Similarity	NPC284685
0.7418	Intermediate Similarity	NPC302275
0.7411	Intermediate Similarity	NPC470931
0.7406	Intermediate Similarity	NPC166722
0.7406	Intermediate Similarity	NPC239584
0.7382	Intermediate Similarity	NPC473449
0.7379	Intermediate Similarity	NPC24465
0.7371	Intermediate Similarity	NPC299990
0.7371	Intermediate Similarity	NPC73492
0.7371	Intermediate Similarity	NPC132385
0.7366	Intermediate Similarity	NPC474595
0.7359	Intermediate Similarity	NPC54066
0.7356	Intermediate Similarity	NPC204908
0.7356	Intermediate Similarity	NPC83198
0.7349	Intermediate Similarity	NPC320088

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 NPC96584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	672
0.2-0.3	974
0.3-0.4	1606
0.4-0.5	2534
0.5-0.6	2213
0.6-0.7	752
0.7-0.8	95
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD3924	Approved
0.8252	Intermediate Similarity	NPD3922	Approved
0.8252	Intermediate Similarity	NPD3921	Approved
0.8252	Intermediate Similarity	NPD3923	Approved
0.823	Intermediate Similarity	NPD6494	Phase 2
0.8186	Intermediate Similarity	NPD7169	Suspended
0.8157	Intermediate Similarity	NPD3816	Phase 1
0.8157	Intermediate Similarity	NPD3815	Phase 1
0.8038	Intermediate Similarity	NPD6361	Phase 2
0.799	Intermediate Similarity	NPD6569	Phase 2
0.7961	Intermediate Similarity	NPD8054	Approved
0.7961	Intermediate Similarity	NPD8053	Approved
0.7824	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7675	Phase 3
0.7807	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7674	Phase 3
0.7792	Intermediate Similarity	NPD7859	Phase 2
0.7783	Intermediate Similarity	NPD4551	Phase 2
0.7778	Intermediate Similarity	NPD3763	Approved
0.7763	Intermediate Similarity	NPD7222	Phase 2
0.7759	Intermediate Similarity	NPD7558	Phase 2
0.7748	Intermediate Similarity	NPD7069	Discontinued
0.7718	Intermediate Similarity	NPD3920	Phase 2
0.7714	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4034	Approved
0.7671	Intermediate Similarity	NPD32	Approved
0.7671	Intermediate Similarity	NPD4035	Approved
0.7671	Intermediate Similarity	NPD4122	Approved
0.7671	Intermediate Similarity	NPD4033	Approved
0.7671	Intermediate Similarity	NPD4036	Approved
0.7671	Intermediate Similarity	NPD4038	Approved
0.7671	Intermediate Similarity	NPD4039	Approved
0.7671	Intermediate Similarity	NPD31	Approved
0.7671	Intermediate Similarity	NPD4037	Approved
0.767	Intermediate Similarity	NPD8156	Discontinued
0.7661	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3386	Phase 2
0.7635	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD8251	Approved
0.7621	Intermediate Similarity	NPD8099	Discontinued
0.7621	Intermediate Similarity	NPD8252	Approved
0.7592	Intermediate Similarity	NPD8091	Phase 3
0.7583	Intermediate Similarity	NPD4375	Approved
0.7569	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD5612	Discontinued
0.7553	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1483	Discontinued
0.7523	Intermediate Similarity	NPD7452	Approved
0.7523	Intermediate Similarity	NPD7453	Approved
0.75	Intermediate Similarity	NPD6964	Approved
0.75	Intermediate Similarity	NPD7426	Phase 1
0.75	Intermediate Similarity	NPD6963	Approved
0.7489	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5530	Phase 1
0.7468	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4131	Phase 3
0.745	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7885	Phase 2
0.7448	Intermediate Similarity	NPD7886	Phase 2
0.7439	Intermediate Similarity	NPD8442	Discontinued
0.7419	Intermediate Similarity	NPD7955	Approved
0.7419	Intermediate Similarity	NPD7956	Approved
0.7404	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6230	Discontinued
0.7385	Intermediate Similarity	NPD3477	Phase 2
0.7385	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4437	Phase 3
0.7377	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4889	Approved
0.7344	Intermediate Similarity	NPD7417	Discontinued
0.7339	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6219	Discontinued
0.732	Intermediate Similarity	NPD7708	Approved
0.7318	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5903	Approved
0.7293	Intermediate Similarity	NPD5902	Approved
0.7284	Intermediate Similarity	NPD5930	Phase 3
0.7273	Intermediate Similarity	NPD7803	Approved
0.7273	Intermediate Similarity	NPD6568	Discontinued
0.7269	Intermediate Similarity	NPD4021	Phase 2
0.7244	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4875	Phase 3
0.7243	Intermediate Similarity	NPD4876	Phase 3
0.7237	Intermediate Similarity	NPD4502	Phase 2
0.7222	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7395	Discontinued
0.7182	Intermediate Similarity	NPD3395	Approved
0.7182	Intermediate Similarity	NPD3396	Approved
0.7181	Intermediate Similarity	NPD5658	Approved
0.7181	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5147	Discontinued
0.7161	Intermediate Similarity	NPD7719	Discontinued
0.7156	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8063	Discontinued
0.715	Intermediate Similarity	NPD4203	Approved
0.715	Intermediate Similarity	NPD4204	Approved
0.7143	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7555	Discontinued
0.7137	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8101	Phase 3
0.7137	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2952	Discontinued
0.7114	Intermediate Similarity	NPD4349	Approved
0.7114	Intermediate Similarity	NPD4350	Approved
0.7113	Intermediate Similarity	NPD7567	Approved
0.7111	Intermediate Similarity	NPD6975	Discontinued
0.7105	Intermediate Similarity	NPD7672	Approved
0.7105	Intermediate Similarity	NPD7671	Approved
0.7104	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6501	Approved
0.7094	Intermediate Similarity	NPD6500	Approved
0.709	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD4989	Phase 2
0.7082	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1856	Discontinued
0.7071	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8244	Phase 2
0.7061	Intermediate Similarity	NPD5429	Discontinued
0.7061	Intermediate Similarity	NPD1392	Approved
0.7059	Intermediate Similarity	NPD5640	Discontinued
0.7045	Intermediate Similarity	NPD2334	Discontinued
0.7043	Intermediate Similarity	NPD7673	Phase 3
0.704	Intermediate Similarity	NPD7948	Phase 1
0.7037	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7123	Suspended
0.7027	Intermediate Similarity	NPD4418	Discontinued
0.7026	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5945	Phase 1
0.7026	Intermediate Similarity	NPD5944	Phase 1
0.7021	Intermediate Similarity	NPD7194	Discontinued
0.7018	Intermediate Similarity	NPD3003	Approved
0.7016	Intermediate Similarity	NPD8100	Phase 3
0.7014	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5066	Phase 2
0.7013	Intermediate Similarity	NPD5067	Phase 2
0.7005	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4044	Discontinued
0.6995	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6856	Discontinued
0.6986	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1034	Phase 3
0.6978	Remote Similarity	NPD8095	Phase 1
0.6974	Remote Similarity	NPD4795	Phase 2
0.6974	Remote Similarity	NPD3397	Phase 2
0.6951	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8016	Phase 3
0.6943	Remote Similarity	NPD5601	Phase 2
0.6941	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4919	Phase 3
0.6941	Remote Similarity	NPD4921	Phase 3
0.6937	Remote Similarity	NPD4372	Phase 1
0.6935	Remote Similarity	NPD7620	Phase 2
0.6933	Remote Similarity	NPD1954	Phase 1
0.692	Remote Similarity	NPD6550	Discontinued
0.6916	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7682	Approved
0.6908	Remote Similarity	NPD7684	Approved
0.6907	Remote Similarity	NPD6985	Discontinued
0.6906	Remote Similarity	NPD1038	Approved
0.6895	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6298	Discontinued
0.6889	Remote Similarity	NPD1622	Discontinued
0.6889	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6327	Phase 1
0.6885	Remote Similarity	NPD4080	Discontinued
0.6883	Remote Similarity	NPD5905	Phase 1
0.6875	Remote Similarity	NPD6590	Discontinued
0.6865	Remote Similarity	NPD6244	Phase 3
0.6865	Remote Similarity	NPD6243	Phase 3
0.6864	Remote Similarity	NPD5256	Discontinued
0.6856	Remote Similarity	NPD6991	Approved
0.6852	Remote Similarity	NPD6159	Phase 2
0.6852	Remote Similarity	NPD1032	Phase 2
0.6851	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD8479	Phase 2
0.6844	Remote Similarity	NPD7797	Approved
0.6844	Remote Similarity	NPD7796	Approved
0.6844	Remote Similarity	NPD4885	Approved
0.6842	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7967	Discontinued
0.684	Remote Similarity	NPD7263	Phase 2
0.6831	Remote Similarity	NPD8512	Phase 3
0.6828	Remote Similarity	NPD3825	Phase 3
0.6827	Remote Similarity	NPD6473	Phase 1
0.6826	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8247	Approved
0.6824	Remote Similarity	NPD8246	Approved
0.6822	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1078	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