NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.12
Volume:	243.952
LogP:	-1.974
LogD:	-0.597
LogS:	-1.659
# Rotatable Bonds:	2
TPSA:	131.04
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.373
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.539
MDCK Permeability:	4.51859159511514e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.972
20% Bioavailability (F20%):	0.949
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.36
Plasma Protein Binding (PPB):	13.537153244018555%
Volume Distribution (VD):	0.893
Pgp-substrate:	78.83516693115234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.497
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.273
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	3.322
Half-life (T1/2):	0.909

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.649
Carcinogencity:	0.115
Eye Corrosion:	0.004
Eye Irritation:	0.098
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC93365

Natural Product ID:	NPC93365
*Common Name:**	Aristeromycin
IUPAC Name:	(1R,2S,3R,5R)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
Synonyms:	Aristeromycin
Standard InCHIKey:	UGRNVLGKAGREKS-GCXDCGAKSA-N
Standard InCHI:	InChI=1S/C11H15N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h3-6,8-9,17-19H,1-2H2,(H2,12,13,14)/t5-,6-,8-,9+/m1/s1
SMILES:	C1[C@H](CO)[C@H]([C@H]([C@@H]1n1cnc2c(N)ncnc12)O)O
Synthetic Gene Cluster:	BGC0001514;
ChEMBL Identifier:	CHEMBL49935
PubChem CID:	65269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0003737] Nucleoside and nucleotide analogues [CHEMONTID:0003738] Cyclopentyl nucleosides [CHEMONTID:0003740] 1,3-substituted cyclopentyl nucleosides [CHEMONTID:0003718] 1,3-substituted cyclopentyl purine nucleosides

*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
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6752	Melandryum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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	4
ED50	1
IC50	8
Ki	7
Others	21

Activity Type	# Activity
Cell Line	11
CELL-LINE	1
Individual Protein	14
Organism	5
Others	9
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.5	ug.mL-1	PMID[507897]
NPT168	Cell Line	P388	Mus musculus	Inhibition	=	100.0	%	PMID[507899]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	65.0	%	PMID[507900]
NPT4057	Cell Line	L cells	Mus musculus	Control	=	81.0	%	PMID[507900]
NPT4057	Cell Line	L cells	Mus musculus	Control	=	134.0	%	PMID[507900]
NPT4058	Individual Protein	Adenosine deaminase	Mus musculus	Ki	=	9900.0	nM	PMID[507901]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	6260.0	nM	PMID[507902]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	2150.0	nM	PMID[507902]
NPT4059	Individual Protein	Adenosine A2b receptor	Homo sapiens	Ki	=	47300.0	nM	PMID[507902]
NPT1760	Individual Protein	Adenosine A3 receptor	Rattus norvegicus	Ki	=	20000.0	nM	PMID[507902]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Displacement	=	3.0	%	PMID[507903]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Displacement	=	0.0	%	PMID[507903]
NPT1760	Individual Protein	Adenosine A3 receptor	Rattus norvegicus	Ki	=	200000.0	nM	PMID[507903]
NPT4060	Individual Protein	Adenosylhomocysteinase	Plasmodium falciparum 3D7	IC50	=	57000.0	nM	PMID[507904]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	2000.0	nM	PMID[507907]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	2400.0	nM	PMID[507907]
NPT912	Individual Protein	Adenosylhomocysteinase	Homo sapiens	Inhibition	=	99.0	%	PMID[507900]
NPT912	Individual Protein	Adenosylhomocysteinase	Homo sapiens	Ki	=	110.0	nM	PMID[507900]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	67.0	uM	PMID[507901]
NPT2555	Others	Adenosine receptors; A1 & A3	Rattus norvegicus	Ratio	=	0.31	n.a.	PMID[507902]
NPT912	Individual Protein	Adenosylhomocysteinase	Homo sapiens	IC50	=	4850.0	nM	PMID[507904]
NPT2	Others	Unspecified		Ratio IC50	=	0.085	n.a.	PMID[507904]
NPT27	Others	Unspecified		Activity	=	22.4	%	PMID[507904]
NPT1019	Organism	Trichomonas vaginalis	Trichomonas vaginalis	IC50	=	10000.0	nM	PMID[507905]
NPT1019	Organism	Trichomonas vaginalis	Trichomonas vaginalis	GI	=	95.0	%	PMID[507905]
NPT1019	Organism	Trichomonas vaginalis	Trichomonas vaginalis	IC50	=	3.0	ug.mL-1	PMID[507905]
NPT912	Individual Protein	Adenosylhomocysteinase	Homo sapiens	IC50	=	303.0	nM	PMID[507906]
NPT912	Individual Protein	Adenosylhomocysteinase	Homo sapiens	IC50	=	1320.0	nM	PMID[507907]
NPT2	Others	Unspecified		EC50	>	50000.0	nM	PMID[507907]
NPT22224	CELL-LINE	Vero C1008	Chlorocebus sabaeus	CC50	>=	2400.0	nM	PMID[507907]
NPT25907	SINGLE PROTEIN	NS5	Zika virus	EC50	=	640.0	nM	PMID[507907]
NPT2	Others	Unspecified		EC50	=	800.0	nM	PMID[507907]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	3.8	n.a.	PMID[507907]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	7.9	n.a.	PMID[507907]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3000.0	nM	PMID[507908]
NPT2	Others	Unspecified		CC50	>	3000.0	nM	PMID[507908]

☑ 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 NPC93365 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	596
0.1-0.2	24732
0.2-0.3	11873
0.3-0.4	4242
0.4-0.5	925
0.5-0.6	191
0.6-0.7	60
0.7-0.8	58
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8456	Intermediate Similarity	NPC21448
0.8456	Intermediate Similarity	NPC156461
0.8456	Intermediate Similarity	NPC107374
0.8446	Intermediate Similarity	NPC229974
0.84	Intermediate Similarity	NPC189068
0.84	Intermediate Similarity	NPC164665
0.8344	Intermediate Similarity	NPC219313
0.8344	Intermediate Similarity	NPC269827
0.8344	Intermediate Similarity	NPC309832
0.8311	Intermediate Similarity	NPC161659
0.8311	Intermediate Similarity	NPC209525
0.8243	Intermediate Similarity	NPC129756
0.82	Intermediate Similarity	NPC314152
0.8188	Intermediate Similarity	NPC317821
0.8129	Intermediate Similarity	NPC185991
0.8129	Intermediate Similarity	NPC211025
0.8129	Intermediate Similarity	NPC85689
0.8077	Intermediate Similarity	NPC321814
0.8077	Intermediate Similarity	NPC472816
0.8054	Intermediate Similarity	NPC33996
0.8025	Intermediate Similarity	NPC164952
0.8025	Intermediate Similarity	NPC212551
0.8025	Intermediate Similarity	NPC130586
0.8025	Intermediate Similarity	NPC302778
0.7987	Intermediate Similarity	NPC239737
0.7975	Intermediate Similarity	NPC174802
0.7935	Intermediate Similarity	NPC121222
0.7925	Intermediate Similarity	NPC224076
0.7875	Intermediate Similarity	NPC226245
0.7875	Intermediate Similarity	NPC316618
0.7848	Intermediate Similarity	NPC207633
0.7798	Intermediate Similarity	NPC313897
0.7785	Intermediate Similarity	NPC161224
0.7771	Intermediate Similarity	NPC136349
0.7722	Intermediate Similarity	NPC150853
0.7654	Intermediate Similarity	NPC54320
0.7654	Intermediate Similarity	NPC311197
0.7654	Intermediate Similarity	NPC313754
0.7636	Intermediate Similarity	NPC323091
0.7625	Intermediate Similarity	NPC328479
0.7607	Intermediate Similarity	NPC195140
0.7593	Intermediate Similarity	NPC52238
0.756	Intermediate Similarity	NPC290959
0.7451	Intermediate Similarity	NPC320818
0.7442	Intermediate Similarity	NPC189261
0.7337	Intermediate Similarity	NPC261595
0.7294	Intermediate Similarity	NPC321458
0.7294	Intermediate Similarity	NPC324033
0.7283	Intermediate Similarity	NPC326529
0.7278	Intermediate Similarity	NPC324484
0.7241	Intermediate Similarity	NPC324198
0.7241	Intermediate Similarity	NPC319100
0.7235	Intermediate Similarity	NPC325906
0.7151	Intermediate Similarity	NPC326082
0.7006	Intermediate Similarity	NPC61198
0.7	Intermediate Similarity	NPC24589
0.6978	Remote Similarity	NPC282458
0.6978	Remote Similarity	NPC78941
0.6978	Remote Similarity	NPC313514
0.6943	Remote Similarity	NPC262926
0.6886	Remote Similarity	NPC321052
0.6813	Remote Similarity	NPC30326
0.6772	Remote Similarity	NPC319221
0.6768	Remote Similarity	NPC89147
0.6768	Remote Similarity	NPC274384
0.6709	Remote Similarity	NPC324009
0.6707	Remote Similarity	NPC211820
0.6707	Remote Similarity	NPC251233
0.6706	Remote Similarity	NPC472834
0.6687	Remote Similarity	NPC186619
0.6667	Remote Similarity	NPC177169
0.6648	Remote Similarity	NPC33382
0.6632	Remote Similarity	NPC276373
0.6627	Remote Similarity	NPC232408
0.6627	Remote Similarity	NPC64705
0.661	Remote Similarity	NPC125659
0.661	Remote Similarity	NPC168702
0.6606	Remote Similarity	NPC318590
0.6604	Remote Similarity	NPC57279
0.6598	Remote Similarity	NPC5802
0.6568	Remote Similarity	NPC326694
0.6566	Remote Similarity	NPC317746
0.6564	Remote Similarity	NPC157821
0.6545	Remote Similarity	NPC74306
0.6545	Remote Similarity	NPC315642
0.6536	Remote Similarity	NPC222174
0.6483	Remote Similarity	NPC476564
0.6478	Remote Similarity	NPC246193
0.6439	Remote Similarity	NPC250178
0.6393	Remote Similarity	NPC164845
0.6389	Remote Similarity	NPC174114
0.6389	Remote Similarity	NPC87981
0.6375	Remote Similarity	NPC104011
0.6369	Remote Similarity	NPC248007
0.6328	Remote Similarity	NPC321393
0.631	Remote Similarity	NPC217656
0.6292	Remote Similarity	NPC14590
0.6272	Remote Similarity	NPC89139
0.6267	Remote Similarity	NPC4837
0.6267	Remote Similarity	NPC312187
0.6265	Remote Similarity	NPC296437
0.6258	Remote Similarity	NPC327579
0.6228	Remote Similarity	NPC470266
0.6215	Remote Similarity	NPC160666
0.6178	Remote Similarity	NPC139776
0.6173	Remote Similarity	NPC287876
0.6163	Remote Similarity	NPC244700
0.6154	Remote Similarity	NPC476528
0.6154	Remote Similarity	NPC476433
0.615	Remote Similarity	NPC103388
0.6118	Remote Similarity	NPC476520
0.6118	Remote Similarity	NPC474986
0.6118	Remote Similarity	NPC476522
0.6118	Remote Similarity	NPC476013
0.6111	Remote Similarity	NPC14330
0.6105	Remote Similarity	NPC476408
0.6102	Remote Similarity	NPC472833
0.6082	Remote Similarity	NPC476521
0.6073	Remote Similarity	NPC265111
0.604	Remote Similarity	NPC18335
0.6032	Remote Similarity	NPC473585
0.6	Remote Similarity	NPC472832
0.6	Remote Similarity	NPC18308
0.6	Remote Similarity	NPC107160
0.5991	Remote Similarity	NPC21461
0.5982	Remote Similarity	NPC158055
0.5901	Remote Similarity	NPC109322
0.5823	Remote Similarity	NPC68938
0.5741	Remote Similarity	NPC5707
0.5732	Remote Similarity	NPC313547
0.5625	Remote Similarity	NPC189314

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 NPC93365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1687
0.2-0.3	3480
0.3-0.4	2309
0.4-0.5	1098
0.5-0.6	223
0.6-0.7	118
0.7-0.8	35
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD546	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD250	Approved
0.8456	Intermediate Similarity	NPD249	Approved
0.8377	Intermediate Similarity	NPD1750	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD186	Discovery
0.8344	Intermediate Similarity	NPD195	Approved
0.8322	Intermediate Similarity	NPD248	Discontinued
0.8291	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD185	Approved
0.8148	Intermediate Similarity	NPD2647	Phase 3
0.8141	Intermediate Similarity	NPD1369	Phase 2
0.8141	Intermediate Similarity	NPD3107	Discontinued
0.8129	Intermediate Similarity	NPD353	Discontinued
0.8129	Intermediate Similarity	NPD283	Approved
0.8101	Intermediate Similarity	NPD2624	Phase 2
0.8101	Intermediate Similarity	NPD1732	Phase 3
0.8101	Intermediate Similarity	NPD2646	Discontinued
0.8092	Intermediate Similarity	NPD166	Approved
0.8067	Intermediate Similarity	NPD193	Suspended
0.8025	Intermediate Similarity	NPD242	Approved
0.8025	Intermediate Similarity	NPD338	Approved
0.7975	Intermediate Similarity	NPD339	Approved
0.7925	Intermediate Similarity	NPD169	Phase 2
0.7798	Intermediate Similarity	NPD5666	Phase 2
0.7771	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD220	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD219	Phase 3
0.7654	Intermediate Similarity	NPD217	Approved
0.7654	Intermediate Similarity	NPD218	Approved
0.7654	Intermediate Similarity	NPD216	Approved
0.76	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5682	Phase 3
0.7595	Intermediate Similarity	NPD775	Approved
0.7578	Intermediate Similarity	NPD213	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD214	Approved
0.744	Intermediate Similarity	NPD7988	Suspended
0.7337	Intermediate Similarity	NPD247	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1776	Approved
0.7235	Intermediate Similarity	NPD1777	Approved
0.7216	Intermediate Similarity	NPD4716	Approved
0.72	Intermediate Similarity	NPD1412	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD9632	Phase 3
0.7118	Intermediate Similarity	NPD527	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1058	Discontinued
0.7095	Intermediate Similarity	NPD1692	Approved
0.7081	Intermediate Similarity	NPD7158	Phase 1
0.7059	Intermediate Similarity	NPD3083	Approved
0.7059	Intermediate Similarity	NPD9633	Phase 3
0.7006	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7138	Phase 2
0.6974	Remote Similarity	NPD9408	Phase 3
0.697	Remote Similarity	NPD3708	Phase 2
0.6923	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2631	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2630	Approved
0.6848	Remote Similarity	NPD2632	Approved
0.6835	Remote Similarity	NPD194	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD549	Approved
0.681	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2876	Phase 3
0.6753	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD307	Approved
0.6686	Remote Similarity	NPD536	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2824	Phase 2
0.6633	Remote Similarity	NPD2902	Phase 2
0.6633	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD582	Approved
0.6524	Remote Similarity	NPD3695	Approved
0.6524	Remote Similarity	NPD3696	Approved
0.6491	Remote Similarity	NPD231	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4054	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1119	Phase 2
0.64	Remote Similarity	NPD4074	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3085	Phase 1
0.6369	Remote Similarity	NPD9084	Phase 2
0.6368	Remote Similarity	NPD4495	Phase 1
0.6337	Remote Similarity	NPD3086	Phase 3
0.6331	Remote Similarity	NPD1730	Discontinued
0.6324	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4240	Approved
0.6299	Remote Similarity	NPD9606	Approved
0.6294	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD2253	Discontinued
0.6258	Remote Similarity	NPD9607	Approved
0.6258	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD282	Approved
0.6207	Remote Similarity	NPD9605	Phase 3
0.6184	Remote Similarity	NPD5080	Phase 2
0.6176	Remote Similarity	NPD171	Discontinued
0.6173	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD5079	Phase 2
0.6131	Remote Similarity	NPD4458	Phase 2
0.6131	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1063	Phase 2
0.6111	Remote Similarity	NPD5627	Approved
0.6108	Remote Similarity	NPD1808	Phase 1
0.6104	Remote Similarity	NPD9374	Approved
0.6095	Remote Similarity	NPD1430	Approved
0.6095	Remote Similarity	NPD1431	Approved
0.6078	Remote Similarity	NPD9373	Approved
0.6048	Remote Similarity	NPD537	Phase 2
0.6048	Remote Similarity	NPD534	Phase 2
0.6045	Remote Similarity	NPD5172	Phase 2
0.604	Remote Similarity	NPD8836	Approved
0.6036	Remote Similarity	NPD1118	Discontinued
0.6025	Remote Similarity	NPD281	Approved
0.5988	Remote Similarity	NPD515	Phase 1
0.5982	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6840	Approved
0.5966	Remote Similarity	NPD7842	Phase 2
0.5951	Remote Similarity	NPD1127	Approved
0.5951	Remote Similarity	NPD1128	Approved
0.5942	Remote Similarity	NPD4563	Phase 2
0.5917	Remote Similarity	NPD799	Phase 1
0.5909	Remote Similarity	NPD9375	Discontinued
0.5902	Remote Similarity	NPD796	Phase 2
0.5862	Remote Similarity	NPD5486	Discontinued
0.5859	Remote Similarity	NPD8250	Phase 2
0.5858	Remote Similarity	NPD6112	Approved
0.5854	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD1354	Approved
0.5854	Remote Similarity	NPD1356	Approved
0.5847	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD207	Discontinued
0.5813	Remote Similarity	NPD9409	Discontinued
0.5801	Remote Similarity	NPD5336	Phase 1
0.5801	Remote Similarity	NPD5337	Phase 1
0.5799	Remote Similarity	NPD1120	Approved
0.5799	Remote Similarity	NPD1121	Approved
0.5777	Remote Similarity	NPD5458	Discontinued
0.5767	Remote Similarity	NPD3081	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD8830	Phase 3
0.5728	Remote Similarity	NPD1915	Phase 1
0.5696	Remote Similarity	NPD757	Phase 3
0.5692	Remote Similarity	NPD2457	Phase 2
0.5692	Remote Similarity	NPD2456	Phase 2
0.5646	Remote Similarity	NPD4612	Discontinued
0.5635	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD3697	Discontinued
0.5625	Remote Similarity	NPD8833	Approved
0.5625	Remote Similarity	NPD8831	Approved
0.5616	Remote Similarity	NPD5703	Discontinued
0.561	Remote Similarity	NPD798	Discontinued
0.5602	Remote Similarity	NPD1085	Approved
0.5602	Remote Similarity	NPD1775	Approved
0.56	Remote Similarity	NPD2179	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