NPASS Compound

Structure

NPC254441 OpenBabel07101719152D 42 49 0 0 1 0 0 0 0 0999 V2000 2.3821 4.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3739 -0.6172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2450 2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7880 2.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6463 2.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2094 4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4894 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4142 3.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9449 3.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3515 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 2.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5215 0.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4199 1.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1804 3.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0116 4.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 1.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 1.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6601 3.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4988 0.7640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9772 3.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 2.7830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9860 0.5088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4087 1.2074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0072 3.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6948 4.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5161 -0.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3936 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0341 0.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 -0.0566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 3.2830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8387 0.2275 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 2.0795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2763 2.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3826 4.0641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9551 0.6009 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 39 1 0 0 0 0 4 7 1 0 0 0 0 4 20 2 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 21 1 0 0 0 0 7 24 2 0 0 0 0 8 24 1 0 0 0 0 9 29 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 16 30 1 0 0 0 0 17 23 2 0 0 0 0 17 28 1 0 0 0 0 18 22 2 0 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 32 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 0 0 0 0 24 40 1 0 0 0 0 25 26 1 0 0 0 0 26 15 1 6 0 0 0 26 36 1 0 0 0 0 27 14 1 1 0 0 0 27 33 1 0 0 0 0 27 37 1 0 0 0 0 28 34 2 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 40 1 0 0 0 0 31 32 2 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.25
Volume:	579.771
LogP:	6.668
LogD:	3.866
LogS:	-7.899
# Rotatable Bonds:	1
TPSA:	63.63
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	5.927
Fsp3:	0.314
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.796
MDCK Permeability:	2.3702803446212783e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.918
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	60.26959991455078%
Volume Distribution (VD):	0.948
Pgp-substrate:	19.293989181518555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.957
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.952
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	12.31
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.961
Human Hepatotoxicity (H-HT):	0.013
Drug-inuced Liver Injury (DILI):	0.548
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.896
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.433

Download Data

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

Natural Product: NPC254441

Natural Product ID:	NPC254441
*Common Name:**	DMJTVGRMFGITRL-SVBPBHIXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DMJTVGRMFGITRL-SVBPBHIXSA-N
Standard InCHI:	InChI=1S/C35H34N2O5/c1-36-12-10-22-18-31-32-19-25(22)26(36)15-21-6-9-29(39-3)30(16-21)40-24-7-4-20(5-8-24)14-27-33-23(11-13-37(27)2)17-28(38)34(41-31)35(33)42-32/h4-9,16-19,26-27,38H,10-15H2,1-3H3/t26-,27-/m0/s1
SMILES:	CN1CCc2cc3c4cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2c(CCN1C)cc(c(c2O4)O3)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505269
PubChem CID:	10257281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	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	5
Others	2

Activity Type	# Activity
Cell Line	2
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.4	ug.mL-1	PMID[465003]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6000.0	nM	PMID[465004]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0171	ug.mL-1	PMID[465003]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.063	ug.mL-1	PMID[465003]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	30.0	nM	PMID[465004]
NPT2	Others	Unspecified		Selectivity Index	=	200.0	n.a.	PMID[465004]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	112.0	nM	PMID[465004]
NPT2	Others	Unspecified		Selectivity Index	=	54.0	n.a.	PMID[465004]

☑ 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 NPC254441 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	365
0.1-0.2	1776
0.2-0.3	8970
0.3-0.4	9442
0.4-0.5	5495
0.5-0.6	8583
0.6-0.7	6506
0.7-0.8	1271
0.8-0.85	138
0.85-0.9	45
0.9-0.95	42
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC274716
1.0	High Similarity	NPC167116
0.9939	High Similarity	NPC42663
0.9939	High Similarity	NPC279228
0.9939	High Similarity	NPC271013
0.9939	High Similarity	NPC54654
0.9939	High Similarity	NPC285931
0.9939	High Similarity	NPC290582
0.9939	High Similarity	NPC222661
0.9939	High Similarity	NPC7715
0.9939	High Similarity	NPC104196
0.9939	High Similarity	NPC217748
0.9939	High Similarity	NPC239824
0.9939	High Similarity	NPC8836
0.9939	High Similarity	NPC229373
0.9939	High Similarity	NPC185639
0.9939	High Similarity	NPC182052
0.9939	High Similarity	NPC290005
0.9939	High Similarity	NPC258657
0.9939	High Similarity	NPC90998
0.9939	High Similarity	NPC15414
0.9939	High Similarity	NPC223690
0.9939	High Similarity	NPC49075
0.9939	High Similarity	NPC328155
0.9939	High Similarity	NPC251735
0.9939	High Similarity	NPC311973
0.9939	High Similarity	NPC181796
0.9879	High Similarity	NPC286119
0.9819	High Similarity	NPC30779
0.9762	High Similarity	NPC212237
0.9762	High Similarity	NPC116465
0.9706	High Similarity	NPC60295
0.9706	High Similarity	NPC191132
0.9704	High Similarity	NPC275680
0.9704	High Similarity	NPC22115
0.9647	High Similarity	NPC11296
0.9647	High Similarity	NPC82457
0.9647	High Similarity	NPC274661
0.9647	High Similarity	NPC175890
0.9647	High Similarity	NPC206900
0.9647	High Similarity	NPC48490
0.9645	High Similarity	NPC65312
0.9645	High Similarity	NPC139783
0.9586	High Similarity	NPC95426
0.9586	High Similarity	NPC302245
0.9586	High Similarity	NPC16357
0.9576	High Similarity	NPC129518
0.9576	High Similarity	NPC41376
0.9576	High Similarity	NPC12424
0.9576	High Similarity	NPC251580
0.9535	High Similarity	NPC24260
0.9515	High Similarity	NPC276890
0.9515	High Similarity	NPC63646
0.9515	High Similarity	NPC115284
0.9515	High Similarity	NPC198498
0.9515	High Similarity	NPC227060
0.9515	High Similarity	NPC317145
0.9515	High Similarity	NPC76682
0.9515	High Similarity	NPC10908
0.9515	High Similarity	NPC317439
0.9422	High Similarity	NPC478093
0.9368	High Similarity	NPC478091
0.9368	High Similarity	NPC30182
0.9368	High Similarity	NPC478092
0.9368	High Similarity	NPC473589
0.9368	High Similarity	NPC256124
0.9345	High Similarity	NPC293093
0.9294	High Similarity	NPC239584
0.9273	High Similarity	NPC13916
0.9273	High Similarity	NPC264850
0.9273	High Similarity	NPC268503
0.9273	High Similarity	NPC250846
0.9273	High Similarity	NPC317272
0.9273	High Similarity	NPC256012
0.9273	High Similarity	NPC240841
0.9273	High Similarity	NPC42549
0.9257	High Similarity	NPC85381
0.9253	High Similarity	NPC41122
0.9253	High Similarity	NPC318805
0.9235	High Similarity	NPC475479
0.9235	High Similarity	NPC243454
0.9213	High Similarity	NPC475654
0.9212	High Similarity	NPC24465
0.9162	High Similarity	NPC204908
0.9162	High Similarity	NPC83198
0.9153	High Similarity	NPC234318
0.9128	High Similarity	NPC73492
0.9128	High Similarity	NPC299990
0.9	High Similarity	NPC152680
0.9	High Similarity	NPC232386
0.9	High Similarity	NPC190783
0.8966	High Similarity	NPC302275
0.8956	High Similarity	NPC254581
0.8941	High Similarity	NPC475215
0.8941	High Similarity	NPC108434
0.8914	High Similarity	NPC249996
0.887	High Similarity	NPC281581
0.8851	High Similarity	NPC195538
0.8848	High Similarity	NPC247639
0.8848	High Similarity	NPC25084
0.882	High Similarity	NPC475597
0.882	High Similarity	NPC473716
0.88	High Similarity	NPC476202
0.8788	High Similarity	NPC39701
0.8788	High Similarity	NPC204828
0.8788	High Similarity	NPC127674
0.8788	High Similarity	NPC189266
0.8788	High Similarity	NPC276588
0.8788	High Similarity	NPC2413
0.8788	High Similarity	NPC249797
0.8788	High Similarity	NPC207757
0.8788	High Similarity	NPC295691
0.8788	High Similarity	NPC184026
0.8788	High Similarity	NPC469817
0.8788	High Similarity	NPC278799
0.8788	High Similarity	NPC54379
0.8788	High Similarity	NPC193949
0.8788	High Similarity	NPC172765
0.8788	High Similarity	NPC110416
0.8788	High Similarity	NPC5238
0.8757	High Similarity	NPC14507
0.8757	High Similarity	NPC47077
0.8721	High Similarity	NPC239775
0.8663	High Similarity	NPC168753
0.8663	High Similarity	NPC118274
0.8613	High Similarity	NPC10871
0.8588	High Similarity	NPC475393
0.8545	High Similarity	NPC151895
0.8545	High Similarity	NPC220858
0.8545	High Similarity	NPC88249
0.8545	High Similarity	NPC192768
0.8545	High Similarity	NPC97221
0.8529	High Similarity	NPC60186
0.8485	Intermediate Similarity	NPC103379
0.8485	Intermediate Similarity	NPC477565
0.8475	Intermediate Similarity	NPC474507
0.8471	Intermediate Similarity	NPC119649
0.8471	Intermediate Similarity	NPC230956
0.8471	Intermediate Similarity	NPC205255
0.8471	Intermediate Similarity	NPC271388
0.8471	Intermediate Similarity	NPC235143
0.8454	Intermediate Similarity	NPC82056
0.8448	Intermediate Similarity	NPC109925
0.8446	Intermediate Similarity	NPC38964
0.8439	Intermediate Similarity	NPC474931
0.8439	Intermediate Similarity	NPC306555
0.8439	Intermediate Similarity	NPC145832
0.8439	Intermediate Similarity	NPC158376
0.8439	Intermediate Similarity	NPC117188
0.8439	Intermediate Similarity	NPC205421
0.8439	Intermediate Similarity	NPC12053
0.8439	Intermediate Similarity	NPC81218
0.843	Intermediate Similarity	NPC96603
0.843	Intermediate Similarity	NPC276944
0.843	Intermediate Similarity	NPC284183
0.843	Intermediate Similarity	NPC306843
0.843	Intermediate Similarity	NPC232514
0.843	Intermediate Similarity	NPC253043
0.843	Intermediate Similarity	NPC238530
0.843	Intermediate Similarity	NPC78222
0.843	Intermediate Similarity	NPC212794
0.843	Intermediate Similarity	NPC4138
0.843	Intermediate Similarity	NPC196447
0.843	Intermediate Similarity	NPC136508
0.843	Intermediate Similarity	NPC121275
0.843	Intermediate Similarity	NPC477563
0.843	Intermediate Similarity	NPC13504
0.8427	Intermediate Similarity	NPC257269
0.8427	Intermediate Similarity	NPC230276
0.8424	Intermediate Similarity	NPC24233
0.8424	Intermediate Similarity	NPC147390
0.8424	Intermediate Similarity	NPC246587
0.8424	Intermediate Similarity	NPC135538
0.8424	Intermediate Similarity	NPC428
0.8424	Intermediate Similarity	NPC476571
0.8421	Intermediate Similarity	NPC80759
0.8421	Intermediate Similarity	NPC79402
0.8412	Intermediate Similarity	NPC221864
0.8372	Intermediate Similarity	NPC324144
0.8371	Intermediate Similarity	NPC40496
0.8371	Intermediate Similarity	NPC32154
0.8371	Intermediate Similarity	NPC119068
0.8364	Intermediate Similarity	NPC210437
0.8364	Intermediate Similarity	NPC476151
0.8364	Intermediate Similarity	NPC476144
0.8364	Intermediate Similarity	NPC179825
0.8364	Intermediate Similarity	NPC321505
0.8364	Intermediate Similarity	NPC191376
0.8364	Intermediate Similarity	NPC51957
0.8364	Intermediate Similarity	NPC106295
0.8364	Intermediate Similarity	NPC16107
0.8362	Intermediate Similarity	NPC148709
0.8362	Intermediate Similarity	NPC476577
0.8362	Intermediate Similarity	NPC173416
0.8313	Intermediate Similarity	NPC7467
0.8266	Intermediate Similarity	NPC1229
0.8258	Intermediate Similarity	NPC241704
0.8256	Intermediate Similarity	NPC166014
0.8256	Intermediate Similarity	NPC27410
0.8242	Intermediate Similarity	NPC185838

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 NPC254441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	792
0.2-0.3	1192
0.3-0.4	2208
0.4-0.5	2416
0.5-0.6	1548
0.6-0.7	643
0.7-0.8	133
0.8-0.85	3
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9939	High Similarity	NPD8053	Approved
0.9939	High Similarity	NPD8054	Approved
0.9515	High Similarity	NPD8252	Approved
0.9515	High Similarity	NPD8251	Approved
0.9515	High Similarity	NPD8099	Discontinued
0.9458	High Similarity	NPD8156	Discontinued
0.8533	High Similarity	NPD8095	Phase 1
0.8371	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4584	Approved
0.8304	Intermediate Similarity	NPD6788	Approved
0.8142	Intermediate Similarity	NPD7906	Approved
0.807	Intermediate Similarity	NPD4772	Phase 2
0.807	Intermediate Similarity	NPD4773	Phase 2
0.8023	Intermediate Similarity	NPD7298	Approved
0.8	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6071	Discontinued
0.7943	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7833	Phase 2
0.7943	Intermediate Similarity	NPD7831	Phase 2
0.7923	Intermediate Similarity	NPD7310	Approved
0.7923	Intermediate Similarity	NPD7313	Approved
0.7923	Intermediate Similarity	NPD7311	Approved
0.7923	Intermediate Similarity	NPD7312	Approved
0.788	Intermediate Similarity	NPD7309	Approved
0.7877	Intermediate Similarity	NPD27	Approved
0.7877	Intermediate Similarity	NPD2489	Approved
0.7865	Intermediate Similarity	NPD3051	Approved
0.7849	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4577	Approved
0.7826	Intermediate Similarity	NPD4578	Approved
0.7824	Intermediate Similarity	NPD7447	Phase 1
0.7824	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2969	Approved
0.7821	Intermediate Similarity	NPD2970	Approved
0.7796	Intermediate Similarity	NPD4663	Approved
0.7753	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2563	Approved
0.7727	Intermediate Similarity	NPD2560	Approved
0.7676	Intermediate Similarity	NPD7549	Discontinued
0.7667	Intermediate Similarity	NPD4010	Discontinued
0.7661	Intermediate Similarity	NPD7212	Phase 2
0.7661	Intermediate Similarity	NPD7213	Phase 3
0.7616	Intermediate Similarity	NPD1424	Approved
0.7605	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2898	Approved
0.7558	Intermediate Similarity	NPD2420	Approved
0.7558	Intermediate Similarity	NPD2421	Approved
0.7544	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4055	Discovery
0.7529	Intermediate Similarity	NPD6031	Approved
0.7529	Intermediate Similarity	NPD6030	Approved
0.75	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD4675	Approved
0.7459	Intermediate Similarity	NPD5677	Discontinued
0.7443	Intermediate Similarity	NPD4017	Approved
0.7442	Intermediate Similarity	NPD5241	Discontinued
0.7429	Intermediate Similarity	NPD3641	Approved
0.7429	Intermediate Similarity	NPD3640	Phase 3
0.7429	Intermediate Similarity	NPD3639	Approved
0.7418	Intermediate Similarity	NPD7802	Discontinued
0.7418	Intermediate Similarity	NPD6107	Approved
0.7411	Intermediate Similarity	NPD2494	Approved
0.7411	Intermediate Similarity	NPD3452	Approved
0.7411	Intermediate Similarity	NPD3450	Approved
0.7411	Intermediate Similarity	NPD2493	Approved
0.7399	Intermediate Similarity	NPD3845	Phase 1
0.7396	Intermediate Similarity	NPD2488	Approved
0.7396	Intermediate Similarity	NPD2490	Approved
0.7391	Intermediate Similarity	NPD4481	Phase 3
0.7389	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4005	Discontinued
0.733	Intermediate Similarity	NPD2122	Discontinued
0.7321	Intermediate Similarity	NPD6997	Phase 2
0.7316	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4474	Approved
0.7305	Intermediate Similarity	NPD4475	Approved
0.73	Intermediate Similarity	NPD4582	Approved
0.73	Intermediate Similarity	NPD4583	Approved
0.7297	Intermediate Similarity	NPD8152	Approved
0.7297	Intermediate Similarity	NPD8153	Approved
0.7283	Intermediate Similarity	NPD6748	Discontinued
0.7282	Intermediate Similarity	NPD7047	Phase 3
0.7278	Intermediate Similarity	NPD5772	Approved
0.7278	Intermediate Similarity	NPD5773	Approved
0.7263	Intermediate Similarity	NPD6072	Discontinued
0.7257	Intermediate Similarity	NPD3124	Discontinued
0.7257	Intermediate Similarity	NPD7598	Phase 2
0.7253	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4002	Approved
0.725	Intermediate Similarity	NPD4004	Approved
0.7246	Intermediate Similarity	NPD5718	Phase 2
0.7235	Intermediate Similarity	NPD2200	Suspended
0.7229	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5177	Phase 3
0.7216	Intermediate Similarity	NPD4123	Phase 3
0.7208	Intermediate Similarity	NPD2974	Approved
0.7208	Intermediate Similarity	NPD2975	Approved
0.7208	Intermediate Similarity	NPD2973	Approved
0.72	Intermediate Similarity	NPD5005	Approved
0.72	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5006	Approved
0.7196	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7466	Approved
0.7182	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5312	Approved
0.7181	Intermediate Similarity	NPD5313	Approved
0.7175	Intermediate Similarity	NPD6090	Discontinued
0.7169	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7827	Phase 1
0.7135	Intermediate Similarity	NPD6853	Approved
0.7135	Intermediate Similarity	NPD6851	Approved
0.7127	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6297	Approved
0.71	Intermediate Similarity	NPD4580	Approved
0.709	Intermediate Similarity	NPD42	Phase 2
0.709	Intermediate Similarity	NPD6042	Phase 2
0.7083	Intermediate Similarity	NPD2968	Approved
0.7083	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2971	Approved
0.7074	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3692	Discontinued
0.7044	Intermediate Similarity	NPD4040	Phase 1
0.7041	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6896	Approved
0.7035	Intermediate Similarity	NPD6111	Discontinued
0.7035	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6895	Approved
0.7029	Intermediate Similarity	NPD4236	Phase 3
0.7029	Intermediate Similarity	NPD3060	Approved
0.7029	Intermediate Similarity	NPD4237	Approved
0.7029	Intermediate Similarity	NPD4162	Approved
0.7022	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6667	Approved
0.7006	Intermediate Similarity	NPD6666	Approved
0.7006	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4166	Phase 2
0.7	Intermediate Similarity	NPD2674	Phase 3
0.7	Intermediate Similarity	NPD4420	Approved
0.7	Intermediate Similarity	NPD4873	Discontinued
0.6995	Remote Similarity	NPD2978	Approved
0.6995	Remote Similarity	NPD4585	Approved
0.6995	Remote Similarity	NPD2977	Approved
0.6984	Remote Similarity	NPD5938	Phase 3
0.6982	Remote Similarity	NPD3027	Phase 3
0.6982	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5089	Approved
0.6978	Remote Similarity	NPD5090	Approved
0.6973	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7037	Approved
0.6968	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7479	Phase 2
0.6959	Remote Similarity	NPD2238	Phase 2
0.6949	Remote Similarity	NPD2677	Approved
0.6949	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5160	Discontinued
0.6939	Remote Similarity	NPD7291	Discontinued
0.6936	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4666	Phase 3
0.6897	Remote Similarity	NPD1753	Discontinued
0.6893	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7907	Approved
0.6864	Remote Similarity	NPD6723	Discontinued
0.6859	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6841	Approved
0.6853	Remote Similarity	NPD6842	Approved
0.6853	Remote Similarity	NPD6843	Phase 3
0.6851	Remote Similarity	NPD5976	Discontinued
0.6845	Remote Similarity	NPD5709	Phase 3
0.6842	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3144	Approved
0.6842	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD3145	Approved
0.6842	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7280	Phase 3
0.6821	Remote Similarity	NPD7281	Phase 3
0.6818	Remote Similarity	NPD3656	Approved

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