NPASS Compound

Structure

NPC475597 OpenBabel07101718302D 47 54 0 0 1 0 0 0 0 0999 V2000 -1.1691 1.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6780 -3.5802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1231 -0.4369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1080 -2.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7621 0.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2320 1.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8382 -1.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9818 0.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6923 0.9576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1661 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9239 -3.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4399 0.2304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0540 -3.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2920 0.5959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4123 1.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3569 -2.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 -2.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7013 -0.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8017 -1.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5239 -0.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1585 0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1594 1.8336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8268 1.2881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9552 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8304 0.1758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9318 -2.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2662 0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3094 0.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 0.8520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8002 -2.0871 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6920 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0194 -0.7528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0199 -1.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5451 -0.7652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8096 -0.6076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0697 -1.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 -0.1008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0776 -0.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8081 -3.0870 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 0.9067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7746 2.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1259 -0.5116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5643 -1.6433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5580 0.0557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1631 0.8757 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 -3.3708 -1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 39 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 8 1 0 0 0 0 5 23 2 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 10 2 0 0 0 0 7 24 1 0 0 0 0 8 27 2 0 0 0 0 9 27 1 0 0 0 0 10 31 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 24 2 0 0 0 0 17 33 1 0 0 0 0 18 25 2 0 0 0 0 18 32 1 0 0 0 0 19 26 2 0 0 0 0 19 35 1 0 0 0 0 20 28 2 0 0 0 0 20 34 1 0 0 0 0 21 44 1 0 0 0 0 21 45 1 0 0 0 0 22 40 1 0 0 0 0 22 41 2 0 0 0 0 25 28 1 0 0 0 0 26 36 1 0 0 0 0 27 46 1 0 0 0 0 28 29 1 0 0 0 0 29 15 1 6 0 0 0 29 40 1 0 0 0 0 30 16 1 6 0 0 0 30 36 1 0 0 0 0 30 39 1 0 0 0 0 31 33 2 0 0 0 0 31 42 1 0 0 0 0 32 34 2 0 0 0 0 32 43 1 0 0 0 0 33 47 1 0 0 0 0 34 47 1 0 0 0 0 35 37 2 0 0 0 0 35 44 1 0 0 0 0 36 38 2 0 0 0 0 37 38 1 0 0 0 0 37 45 1 0 0 0 0 38 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.27
Volume:	646.603
LogP:	6.483
LogD:	3.784
LogS:	-7.268
# Rotatable Bonds:	3
TPSA:	78.93
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	9
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	5.862
Fsp3:	0.342
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:	-5.649
MDCK Permeability:	3.114382707281038e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.959
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.136
Plasma Protein Binding (PPB):	98.01170349121094%
Volume Distribution (VD):	0.569
Pgp-substrate:	1.5962166786193848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.682
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.228
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.948

ADMET: Excretion

Clearance (CL):	8.485
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.79
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.357
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.141
Carcinogencity:	0.638
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC475597

Natural Product ID:	NPC475597
*Common Name:**	FACPTWNXIVCGNY-XZWHSSHBSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Isocuricycleatjenine
Standard InCHIKey:	FACPTWNXIVCGNY-XZWHSSHBSA-N
Standard InCHI:	InChI=1S/C38H38N2O7/c1-22(41)40-14-12-25-18-32(43-4)34-20-28(25)29(40)15-23-5-8-27(9-6-23)46-38-36-26(19-35-37(38)45-21-44-35)11-13-39(2)30(36)16-24-7-10-31(42-3)33(17-24)47-34/h5-10,17-20,29-30H,11-16,21H2,1-4H3/t29-,30+/m0/s1
SMILES:	CC(=O)N1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)OC)O3)N(CCC6=CC8=C5OCO8)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508957
PubChem CID:	44559027
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	=	13600.0	nM	PMID[528501]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1910.0	nM	PMID[528501]
NPT2	Others	Unspecified		Selectivity Index	=	1.6	n.a.	PMID[528501]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1050.0	nM	PMID[528501]
NPT2	Others	Unspecified		Selectivity Index	=	13.0	n.a.	PMID[528501]

☑ 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 NPC475597 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	367
0.1-0.2	1926
0.2-0.3	9223
0.3-0.4	9127
0.4-0.5	6735
0.5-0.6	10374
0.6-0.7	4146
0.7-0.8	616
0.8-0.85	95
0.85-0.9	61
0.9-0.95	21
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473716
0.9647	High Similarity	NPC299990
0.9647	High Similarity	NPC73492
0.9605	High Similarity	NPC475654
0.9371	High Similarity	NPC281581
0.9266	High Similarity	NPC24260
0.9235	High Similarity	NPC317439
0.9235	High Similarity	NPC227060
0.9235	High Similarity	NPC63646
0.9235	High Similarity	NPC317145
0.9235	High Similarity	NPC76682
0.9235	High Similarity	NPC198498
0.9235	High Similarity	NPC10908
0.9235	High Similarity	NPC115284
0.9235	High Similarity	NPC276890
0.9181	High Similarity	NPC129518
0.9181	High Similarity	NPC251580
0.9181	High Similarity	NPC41376
0.9181	High Similarity	NPC12424
0.9075	High Similarity	NPC293093
0.8971	High Similarity	NPC475479
0.8971	High Similarity	NPC243454
0.892	High Similarity	NPC239584
0.887	High Similarity	NPC229373
0.887	High Similarity	NPC181796
0.887	High Similarity	NPC290005
0.887	High Similarity	NPC328155
0.887	High Similarity	NPC185639
0.887	High Similarity	NPC182052
0.887	High Similarity	NPC54654
0.887	High Similarity	NPC7715
0.887	High Similarity	NPC222661
0.887	High Similarity	NPC217748
0.887	High Similarity	NPC49075
0.887	High Similarity	NPC290582
0.887	High Similarity	NPC239824
0.887	High Similarity	NPC42663
0.887	High Similarity	NPC258657
0.887	High Similarity	NPC271013
0.887	High Similarity	NPC90998
0.887	High Similarity	NPC104196
0.887	High Similarity	NPC251735
0.887	High Similarity	NPC223690
0.887	High Similarity	NPC285931
0.887	High Similarity	NPC311973
0.887	High Similarity	NPC8836
0.887	High Similarity	NPC279228
0.887	High Similarity	NPC15414
0.882	High Similarity	NPC254441
0.882	High Similarity	NPC167116
0.882	High Similarity	NPC274716
0.8814	High Similarity	NPC286119
0.8771	High Similarity	NPC95426
0.8771	High Similarity	NPC302245
0.8771	High Similarity	NPC16357
0.8764	High Similarity	NPC30779
0.8722	High Similarity	NPC139783
0.8722	High Similarity	NPC116465
0.8722	High Similarity	NPC65312
0.8722	High Similarity	NPC212237
0.8715	High Similarity	NPC302275
0.8674	High Similarity	NPC275680
0.8674	High Similarity	NPC22115
0.8667	High Similarity	NPC249996
0.8626	High Similarity	NPC175890
0.8626	High Similarity	NPC48490
0.8626	High Similarity	NPC82457
0.8626	High Similarity	NPC274661
0.8626	High Similarity	NPC206900
0.8626	High Similarity	NPC11296
0.8603	High Similarity	NPC195538
0.8588	High Similarity	NPC247639
0.8588	High Similarity	NPC25084
0.8579	High Similarity	NPC60295
0.8579	High Similarity	NPC191132
0.8556	High Similarity	NPC476202
0.8529	High Similarity	NPC216459
0.8529	High Similarity	NPC41178
0.8529	High Similarity	NPC138487
0.8516	High Similarity	NPC14507
0.8516	High Similarity	NPC47077
0.8486	Intermediate Similarity	NPC256124
0.848	Intermediate Similarity	NPC146288
0.8475	Intermediate Similarity	NPC149090
0.8475	Intermediate Similarity	NPC19520
0.8432	Intermediate Similarity	NPC478093
0.8387	Intermediate Similarity	NPC473589
0.8387	Intermediate Similarity	NPC30182
0.8387	Intermediate Similarity	NPC478092
0.8387	Intermediate Similarity	NPC478091
0.8372	Intermediate Similarity	NPC234392
0.8372	Intermediate Similarity	NPC31311
0.8371	Intermediate Similarity	NPC10871
0.8362	Intermediate Similarity	NPC241055
0.8343	Intermediate Similarity	NPC475393
0.8324	Intermediate Similarity	NPC82763
0.8315	Intermediate Similarity	NPC75958
0.8289	Intermediate Similarity	NPC85381
0.828	Intermediate Similarity	NPC318805
0.828	Intermediate Similarity	NPC41122
0.827	Intermediate Similarity	NPC237579
0.8249	Intermediate Similarity	NPC268503
0.8249	Intermediate Similarity	NPC317272
0.8249	Intermediate Similarity	NPC256012
0.8249	Intermediate Similarity	NPC42549
0.8249	Intermediate Similarity	NPC264850
0.8249	Intermediate Similarity	NPC13916
0.8249	Intermediate Similarity	NPC250846
0.8249	Intermediate Similarity	NPC24264
0.8249	Intermediate Similarity	NPC240841
0.8249	Intermediate Similarity	NPC476432
0.8232	Intermediate Similarity	NPC38964
0.8222	Intermediate Similarity	NPC2314
0.8202	Intermediate Similarity	NPC247389
0.8201	Intermediate Similarity	NPC234318
0.8198	Intermediate Similarity	NPC233029
0.8198	Intermediate Similarity	NPC210148
0.8197	Intermediate Similarity	NPC32413
0.8197	Intermediate Similarity	NPC474506
0.8192	Intermediate Similarity	NPC16805
0.8192	Intermediate Similarity	NPC225774
0.8192	Intermediate Similarity	NPC232514
0.8192	Intermediate Similarity	NPC302527
0.8192	Intermediate Similarity	NPC167546
0.8192	Intermediate Similarity	NPC24465
0.8192	Intermediate Similarity	NPC276944
0.8192	Intermediate Similarity	NPC238530
0.8187	Intermediate Similarity	NPC23219
0.8176	Intermediate Similarity	NPC59907
0.8176	Intermediate Similarity	NPC475959
0.8176	Intermediate Similarity	NPC37144
0.8172	Intermediate Similarity	NPC208890
0.8156	Intermediate Similarity	NPC204908
0.8156	Intermediate Similarity	NPC83198
0.815	Intermediate Similarity	NPC82056
0.8148	Intermediate Similarity	NPC477258
0.8146	Intermediate Similarity	NPC219341
0.8142	Intermediate Similarity	NPC258695
0.8142	Intermediate Similarity	NPC470879
0.8135	Intermediate Similarity	NPC254581
0.8132	Intermediate Similarity	NPC112575
0.8118	Intermediate Similarity	NPC476144
0.8118	Intermediate Similarity	NPC477259
0.8118	Intermediate Similarity	NPC210437
0.8118	Intermediate Similarity	NPC169387
0.8118	Intermediate Similarity	NPC51957
0.8118	Intermediate Similarity	NPC106295
0.8118	Intermediate Similarity	NPC16107
0.8101	Intermediate Similarity	NPC210918
0.8095	Intermediate Similarity	NPC471113
0.809	Intermediate Similarity	NPC168409
0.807	Intermediate Similarity	NPC7467
0.8054	Intermediate Similarity	NPC116284
0.8043	Intermediate Similarity	NPC244554
0.8023	Intermediate Similarity	NPC306902
0.8023	Intermediate Similarity	NPC232924
0.8023	Intermediate Similarity	NPC266753
0.8023	Intermediate Similarity	NPC160298
0.8023	Intermediate Similarity	NPC477559
0.8022	Intermediate Similarity	NPC152680
0.8022	Intermediate Similarity	NPC190783
0.8022	Intermediate Similarity	NPC232386
0.8021	Intermediate Similarity	NPC214116
0.8	Intermediate Similarity	NPC123323
0.8	Intermediate Similarity	NPC93593
0.7989	Intermediate Similarity	NPC148693
0.7989	Intermediate Similarity	NPC180306
0.7989	Intermediate Similarity	NPC231198
0.7989	Intermediate Similarity	NPC294790
0.7989	Intermediate Similarity	NPC118633
0.7967	Intermediate Similarity	NPC65403
0.7967	Intermediate Similarity	NPC475215
0.7967	Intermediate Similarity	NPC108434
0.7966	Intermediate Similarity	NPC477080
0.7966	Intermediate Similarity	NPC111485
0.7946	Intermediate Similarity	NPC220961
0.7926	Intermediate Similarity	NPC57036
0.7912	Intermediate Similarity	NPC6152
0.7901	Intermediate Similarity	NPC474324
0.7901	Intermediate Similarity	NPC57812
0.7898	Intermediate Similarity	NPC244112
0.7892	Intermediate Similarity	NPC114364
0.7892	Intermediate Similarity	NPC320223
0.7884	Intermediate Similarity	NPC476576
0.7884	Intermediate Similarity	NPC186546
0.7882	Intermediate Similarity	NPC476567
0.7882	Intermediate Similarity	NPC128019
0.7882	Intermediate Similarity	NPC136860
0.788	Intermediate Similarity	NPC229166
0.788	Intermediate Similarity	NPC128560
0.788	Intermediate Similarity	NPC49353
0.788	Intermediate Similarity	NPC199465
0.7872	Intermediate Similarity	NPC9867
0.7865	Intermediate Similarity	NPC106786
0.7857	Intermediate Similarity	NPC475845
0.7838	Intermediate Similarity	NPC241704
0.7833	Intermediate Similarity	NPC59567
0.7824	Intermediate Similarity	NPC24228
0.7814	Intermediate Similarity	NPC474708
0.7809	Intermediate Similarity	NPC476572

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 NPC475597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	755
0.2-0.3	1182
0.3-0.4	2287
0.4-0.5	2557
0.5-0.6	1577
0.6-0.7	479
0.7-0.8	82
0.8-0.85	4
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9235	High Similarity	NPD8251	Approved
0.9235	High Similarity	NPD8099	Discontinued
0.9235	High Similarity	NPD8252	Approved
0.9181	High Similarity	NPD8156	Discontinued
0.887	High Similarity	NPD8053	Approved
0.887	High Similarity	NPD8054	Approved
0.8307	Intermediate Similarity	NPD8095	Phase 1
0.8148	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD4584	Approved
0.8068	Intermediate Similarity	NPD6788	Approved
0.7806	Intermediate Similarity	NPD5005	Approved
0.7806	Intermediate Similarity	NPD5006	Approved
0.7765	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7298	Approved
0.7663	Intermediate Similarity	NPD4481	Phase 3
0.766	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5312	Approved
0.7634	Intermediate Similarity	NPD5313	Approved
0.7627	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4420	Approved
0.7554	Intermediate Similarity	NPD6071	Discontinued
0.7554	Intermediate Similarity	NPD4166	Phase 2
0.7542	Intermediate Similarity	NPD4772	Phase 2
0.7542	Intermediate Similarity	NPD4773	Phase 2
0.7541	Intermediate Similarity	NPD5677	Discontinued
0.7526	Intermediate Similarity	NPD7281	Phase 3
0.7526	Intermediate Similarity	NPD7280	Phase 3
0.75	Intermediate Similarity	NPD6107	Approved
0.7486	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7906	Approved
0.7459	Intermediate Similarity	NPD3051	Approved
0.7429	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3640	Phase 3
0.7416	Intermediate Similarity	NPD3641	Approved
0.7416	Intermediate Similarity	NPD3639	Approved
0.7401	Intermediate Similarity	NPD1424	Approved
0.7384	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7549	Discontinued
0.7363	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7833	Phase 2
0.7337	Intermediate Similarity	NPD7831	Phase 2
0.7337	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2969	Approved
0.7326	Intermediate Similarity	NPD2970	Approved
0.7322	Intermediate Similarity	NPD2560	Approved
0.7322	Intermediate Similarity	NPD2563	Approved
0.7318	Intermediate Similarity	NPD6031	Approved
0.7318	Intermediate Similarity	NPD6030	Approved
0.7316	Intermediate Similarity	NPD3885	Approved
0.7306	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6853	Approved
0.7306	Intermediate Similarity	NPD6851	Approved
0.729	Intermediate Similarity	NPD7224	Discontinued
0.729	Intermediate Similarity	NPD7223	Discontinued
0.7288	Intermediate Similarity	NPD7124	Phase 2
0.7282	Intermediate Similarity	NPD7291	Discontinued
0.7277	Intermediate Similarity	NPD6297	Approved
0.7264	Intermediate Similarity	NPD5457	Discontinued
0.7258	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2971	Approved
0.7254	Intermediate Similarity	NPD7310	Approved
0.7254	Intermediate Similarity	NPD2968	Approved
0.7254	Intermediate Similarity	NPD7311	Approved
0.7254	Intermediate Similarity	NPD7312	Approved
0.7254	Intermediate Similarity	NPD7313	Approved
0.7247	Intermediate Similarity	NPD5297	Approved
0.7238	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4017	Approved
0.723	Intermediate Similarity	NPD6997	Phase 2
0.7219	Intermediate Similarity	NPD7802	Discontinued
0.7216	Intermediate Similarity	NPD7309	Approved
0.7213	Intermediate Similarity	NPD3382	Approved
0.7213	Intermediate Similarity	NPD3384	Approved
0.7213	Intermediate Similarity	NPD3383	Approved
0.7212	Intermediate Similarity	NPD8153	Approved
0.7212	Intermediate Similarity	NPD8152	Approved
0.7202	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2489	Approved
0.7196	Intermediate Similarity	NPD27	Approved
0.719	Intermediate Similarity	NPD7047	Phase 3
0.7182	Intermediate Similarity	NPD4210	Discontinued
0.7175	Intermediate Similarity	NPD7466	Approved
0.7171	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2492	Phase 1
0.7165	Intermediate Similarity	NPD4577	Approved
0.7165	Intermediate Similarity	NPD4578	Approved
0.7158	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7110	Phase 1
0.7151	Intermediate Similarity	NPD4055	Discovery
0.7143	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4663	Approved
0.7129	Intermediate Similarity	NPD7827	Phase 1
0.7129	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6618	Phase 2
0.7121	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2974	Approved
0.7114	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2975	Approved
0.7114	Intermediate Similarity	NPD2973	Approved
0.7111	Intermediate Similarity	NPD7447	Phase 1
0.7098	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4474	Approved
0.7093	Intermediate Similarity	NPD4475	Approved
0.7091	Intermediate Similarity	NPD6625	Approved
0.7081	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6748	Discontinued
0.7065	Intermediate Similarity	NPD5582	Discontinued
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7598	Phase 2
0.7035	Intermediate Similarity	NPD5718	Phase 2
0.7033	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2200	Suspended
0.702	Intermediate Similarity	NPD3349	Phase 2
0.7018	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2898	Approved
0.7015	Intermediate Similarity	NPD6493	Phase 3
0.701	Intermediate Similarity	NPD4580	Approved
0.6989	Remote Similarity	NPD4585	Approved
0.6983	Remote Similarity	NPD5754	Discontinued
0.6978	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2494	Approved
0.6976	Remote Similarity	NPD3452	Approved
0.6976	Remote Similarity	NPD2493	Approved
0.6976	Remote Similarity	NPD3450	Approved
0.6966	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7212	Phase 2
0.6961	Remote Similarity	NPD3124	Discontinued
0.6961	Remote Similarity	NPD7213	Phase 3
0.695	Remote Similarity	NPD2490	Approved
0.695	Remote Similarity	NPD2488	Approved
0.695	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6843	Phase 3
0.6935	Remote Similarity	NPD6841	Approved
0.6935	Remote Similarity	NPD6842	Approved
0.6923	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6876	Approved
0.6919	Remote Similarity	NPD4678	Approved
0.6919	Remote Similarity	NPD4675	Approved
0.6919	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6875	Approved
0.6908	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD42	Phase 2
0.6907	Remote Similarity	NPD6042	Phase 2
0.69	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5773	Approved
0.6898	Remote Similarity	NPD5772	Approved
0.6879	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5604	Discontinued
0.6875	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD4582	Approved
0.6875	Remote Similarity	NPD4583	Approved
0.6865	Remote Similarity	NPD4005	Discontinued
0.6863	Remote Similarity	NPD5564	Approved
0.6861	Remote Similarity	NPD6723	Discontinued
0.6859	Remote Similarity	NPD7199	Phase 2
0.6851	Remote Similarity	NPD5241	Discontinued
0.6848	Remote Similarity	NPD5976	Discontinued
0.6842	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7400	Phase 3
0.6836	Remote Similarity	NPD6895	Approved
0.6836	Remote Similarity	NPD6111	Discontinued
0.6836	Remote Similarity	NPD6896	Approved
0.6834	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4004	Approved
0.6827	Remote Similarity	NPD4002	Approved
0.6825	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4010	Discontinued
0.6809	Remote Similarity	NPD2978	Approved
0.6809	Remote Similarity	NPD2977	Approved
0.6808	Remote Similarity	NPD3816	Phase 1
0.6808	Remote Similarity	NPD3815	Phase 1
0.68	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5089	Approved
0.6791	Remote Similarity	NPD5090	Approved
0.6788	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5977	Approved
0.6772	Remote Similarity	NPD5978	Approved
0.6769	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7177	Discontinued
0.6751	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7296	Approved
0.6742	Remote Similarity	NPD7119	Phase 2
0.674	Remote Similarity	NPD4237	Approved
0.674	Remote Similarity	NPD4236	Phase 3
0.6734	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7584	Approved
0.6721	Remote Similarity	NPD6667	Approved
0.6721	Remote Similarity	NPD6666	Approved
0.6719	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2904	Discontinued
0.6718	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD8149	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data