NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	283.09
Volume:	244.236
LogP:	-2.164
LogD:	-1.521
LogS:	-1.179
# Rotatable Bonds:	2
TPSA:	160.24
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	4.222
Fsp3:	0.5
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:	-6.329
MDCK Permeability:	3.7683843402191997e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.839
Human Intestinal Absorption (HIA):	0.911
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.622
Plasma Protein Binding (PPB):	11.551918029785156%
Volume Distribution (VD):	0.607
Pgp-substrate:	80.00883483886719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.903
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	5.965
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.895
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.054
Carcinogencity:	0.811
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC164665

Natural Product ID:	NPC164665
*Common Name:**	Isoguanosine
IUPAC Name:	6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-2-one
Synonyms:	Isoguanosine
Standard InCHIKey:	MIKUYHXYGGJMLM-UUOKFMHZSA-N
Standard InCHI:	InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(O)nc2N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1688963
PubChem CID:	65085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0000479] 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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	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	2
ED50	2
Ki	4
Others	3

Activity Type	# Activity
Individual Protein	3
Organism	2
Others	3
Protein Family	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	94.0	nM	PMID[463314]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	94.0	nM	PMID[463316]
NPT2811	Individual Protein	Adenosine A1 receptor	Cavia porcellus	EC50	=	1148.15	nM	PMID[463317]
NPT2554	Protein Family	Adenosine A2 receptor	Rattus norvegicus	Ki	=	330.0	nM	PMID[463314]
NPT4749	Others	Adenosine receptors; A1 & A2	Rattus norvegicus	Ratio	=	3.5	n.a.	PMID[463314]
NPT32	Organism	Mus musculus	Mus musculus	ED50	>	100.0	mg.kg-1	PMID[463315]
NPT2554	Protein Family	Adenosine A2 receptor	Rattus norvegicus	Ki	=	331.0	nM	PMID[463316]
NPT4749	Others	Adenosine receptors; A1 & A2	Rattus norvegicus	Ratio	=	3.5	n.a.	PMID[463316]
NPT2812	Protein Family	Adenosine A2 receptor	Homo sapiens	EC50	=	79.43	nM	PMID[463317]
NPT4757	Others	Adenosine receptors; A1 & A2	Homo sapiens	Ratio	=	18.0	n.a.	PMID[463317]

☑ 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 NPC164665 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	841
0.1-0.2	29299
0.2-0.3	7892
0.3-0.4	3739
0.4-0.5	595
0.5-0.6	133
0.6-0.7	85
0.7-0.8	37
0.8-0.85	26
0.85-0.9	15
0.9-0.95	22
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC156461
0.9925	High Similarity	NPC21448
0.9925	High Similarity	NPC107374
0.9851	High Similarity	NPC189068
0.9778	High Similarity	NPC219313
0.9778	High Similarity	NPC269827
0.9778	High Similarity	NPC309832
0.9774	High Similarity	NPC229974
0.9624	High Similarity	NPC161659
0.9624	High Similarity	NPC209525
0.9496	High Similarity	NPC211025
0.9496	High Similarity	NPC185991
0.9496	High Similarity	NPC85689
0.9481	High Similarity	NPC314152
0.9478	High Similarity	NPC317821
0.9429	High Similarity	NPC321814
0.9429	High Similarity	NPC472816
0.9362	High Similarity	NPC302778
0.9362	High Similarity	NPC130586
0.9362	High Similarity	NPC212551
0.9362	High Similarity	NPC164952
0.9296	High Similarity	NPC174802
0.9281	High Similarity	NPC121222
0.9231	High Similarity	NPC224076
0.9167	High Similarity	NPC316618
0.9167	High Similarity	NPC226245
0.9167	High Similarity	NPC239737
0.9155	High Similarity	NPC207633
0.9118	High Similarity	NPC129756
0.9085	High Similarity	NPC161224
0.9034	High Similarity	NPC313754
0.9034	High Similarity	NPC54320
0.9034	High Similarity	NPC311197
0.9014	High Similarity	NPC150853
0.8966	High Similarity	NPC52238
0.8944	High Similarity	NPC136349
0.8859	High Similarity	NPC323091
0.8768	High Similarity	NPC33996
0.8759	High Similarity	NPC328479
0.8759	High Similarity	NPC320818
0.8618	High Similarity	NPC261595
0.8562	High Similarity	NPC321458
0.8562	High Similarity	NPC324033
0.8467	Intermediate Similarity	NPC195140
0.8408	Intermediate Similarity	NPC326529
0.84	Intermediate Similarity	NPC93365
0.8354	Intermediate Similarity	NPC319100
0.8354	Intermediate Similarity	NPC189261
0.8354	Intermediate Similarity	NPC324198
0.8312	Intermediate Similarity	NPC324484
0.8269	Intermediate Similarity	NPC326082
0.8269	Intermediate Similarity	NPC290959
0.8258	Intermediate Similarity	NPC325906
0.8227	Intermediate Similarity	NPC61198
0.8156	Intermediate Similarity	NPC262926
0.8085	Intermediate Similarity	NPC319221
0.8014	Intermediate Similarity	NPC324009
0.8013	Intermediate Similarity	NPC321052
0.7986	Intermediate Similarity	NPC30326
0.795	Intermediate Similarity	NPC313897
0.7905	Intermediate Similarity	NPC89147
0.7905	Intermediate Similarity	NPC274384
0.7838	Intermediate Similarity	NPC211820
0.7838	Intermediate Similarity	NPC251233
0.7823	Intermediate Similarity	NPC186619
0.7785	Intermediate Similarity	NPC177169
0.7733	Intermediate Similarity	NPC64705
0.7733	Intermediate Similarity	NPC232408
0.7725	Intermediate Similarity	NPC24589
0.7718	Intermediate Similarity	NPC318590
0.7692	Intermediate Similarity	NPC78941
0.7692	Intermediate Similarity	NPC282458
0.7667	Intermediate Similarity	NPC317746
0.7651	Intermediate Similarity	NPC74306
0.7651	Intermediate Similarity	NPC315642
0.7647	Intermediate Similarity	NPC326694
0.7485	Intermediate Similarity	NPC313514
0.7469	Intermediate Similarity	NPC33382
0.7423	Intermediate Similarity	NPC168702
0.7423	Intermediate Similarity	NPC125659
0.7333	Intermediate Similarity	NPC222174
0.7329	Intermediate Similarity	NPC321393
0.7284	Intermediate Similarity	NPC14590
0.7182	Intermediate Similarity	NPC276373
0.7163	Intermediate Similarity	NPC327579
0.7143	Intermediate Similarity	NPC5802
0.7104	Intermediate Similarity	NPC157821
0.709	Intermediate Similarity	NPC476564
0.7027	Intermediate Similarity	NPC246193
0.7027	Intermediate Similarity	NPC104011
0.6933	Remote Similarity	NPC57279
0.6918	Remote Similarity	NPC248007
0.6866	Remote Similarity	NPC174114
0.6866	Remote Similarity	NPC87981
0.6835	Remote Similarity	NPC312187
0.6835	Remote Similarity	NPC4837
0.6769	Remote Similarity	NPC250178
0.6712	Remote Similarity	NPC139776
0.6689	Remote Similarity	NPC287876
0.6623	Remote Similarity	NPC14330
0.6561	Remote Similarity	NPC103388
0.6535	Remote Similarity	NPC107160
0.6475	Remote Similarity	NPC18335
0.6439	Remote Similarity	NPC160666
0.6439	Remote Similarity	NPC21461
0.6407	Remote Similarity	NPC472834
0.6346	Remote Similarity	NPC158055
0.6291	Remote Similarity	NPC109322
0.6225	Remote Similarity	NPC5707
0.6216	Remote Similarity	NPC68938
0.6201	Remote Similarity	NPC164845
0.6122	Remote Similarity	NPC313547
0.6099	Remote Similarity	NPC476561
0.6098	Remote Similarity	NPC217656
0.6061	Remote Similarity	NPC89139
0.6049	Remote Similarity	NPC296437
0.6039	Remote Similarity	NPC180493
0.6012	Remote Similarity	NPC470266
0.6	Remote Similarity	NPC189314
0.5952	Remote Similarity	NPC244700
0.5939	Remote Similarity	NPC476528
0.5939	Remote Similarity	NPC476433
0.5904	Remote Similarity	NPC476520
0.5904	Remote Similarity	NPC474986
0.5904	Remote Similarity	NPC476013
0.5904	Remote Similarity	NPC476522
0.5896	Remote Similarity	NPC472833
0.5893	Remote Similarity	NPC476408
0.5882	Remote Similarity	NPC265111
0.5868	Remote Similarity	NPC476521
0.5862	Remote Similarity	NPC119133
0.5838	Remote Similarity	NPC473585
0.5795	Remote Similarity	NPC472832
0.5795	Remote Similarity	NPC18308
0.5793	Remote Similarity	NPC476562
0.5793	Remote Similarity	NPC476099
0.5759	Remote Similarity	NPC180462
0.5734	Remote Similarity	NPC293163
0.5724	Remote Similarity	NPC59314
0.5724	Remote Similarity	NPC10466
0.5663	Remote Similarity	NPC210947
0.5658	Remote Similarity	NPC63433
0.5629	Remote Similarity	NPC303899
0.5629	Remote Similarity	NPC256849
0.5629	Remote Similarity	NPC41958
0.56	Remote Similarity	NPC47936

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 NPC164665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2329
0.2-0.3	3134
0.3-0.4	2173
0.4-0.5	922
0.5-0.6	166
0.6-0.7	132
0.7-0.8	66
0.8-0.85	13
0.85-0.9	11
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9925	High Similarity	NPD250	Approved
0.9925	High Similarity	NPD249	Approved
0.9778	High Similarity	NPD195	Approved
0.9778	High Similarity	NPD186	Discovery
0.9496	High Similarity	NPD283	Approved
0.9481	High Similarity	NPD185	Approved
0.9362	High Similarity	NPD1750	Clinical (unspecified phase)
0.9362	High Similarity	NPD242	Approved
0.9362	High Similarity	NPD3107	Discontinued
0.9362	High Similarity	NPD1369	Phase 2
0.9362	High Similarity	NPD338	Approved
0.9343	High Similarity	NPD166	Approved
0.9333	High Similarity	NPD193	Suspended
0.9296	High Similarity	NPD339	Approved
0.9231	High Similarity	NPD169	Phase 2
0.9167	High Similarity	NPD1732	Phase 3
0.9167	High Similarity	NPD2646	Discontinued
0.9167	High Similarity	NPD2624	Phase 2
0.9034	High Similarity	NPD217	Approved
0.9034	High Similarity	NPD220	Clinical (unspecified phase)
0.9034	High Similarity	NPD218	Approved
0.9034	High Similarity	NPD216	Approved
0.9034	High Similarity	NPD219	Phase 3
0.8944	High Similarity	NPD548	Clinical (unspecified phase)
0.8828	High Similarity	NPD213	Clinical (unspecified phase)
0.8828	High Similarity	NPD214	Approved
0.8684	High Similarity	NPD2647	Phase 3
0.8618	High Similarity	NPD247	Clinical (unspecified phase)
0.8529	High Similarity	NPD248	Discontinued
0.8408	Intermediate Similarity	NPD5666	Phase 2
0.84	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD9632	Phase 3
0.8377	Intermediate Similarity	NPD7988	Suspended
0.8354	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1412	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1776	Approved
0.8258	Intermediate Similarity	NPD1777	Approved
0.8248	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD4716	Approved
0.8182	Intermediate Similarity	NPD3083	Approved
0.8148	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1692	Approved
0.8	Intermediate Similarity	NPD549	Approved
0.8	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5682	Phase 3
0.7952	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2632	Approved
0.7857	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2630	Approved
0.7801	Intermediate Similarity	NPD9633	Phase 3
0.7778	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9408	Phase 3
0.7667	Intermediate Similarity	NPD7158	Phase 1
0.7651	Intermediate Similarity	NPD582	Approved
0.7532	Intermediate Similarity	NPD3708	Phase 2
0.7485	Intermediate Similarity	NPD7138	Phase 2
0.7421	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3085	Phase 1
0.7372	Intermediate Similarity	NPD3086	Phase 3
0.7325	Intermediate Similarity	NPD231	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD9605	Phase 3
0.7299	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD9606	Approved
0.7213	Intermediate Similarity	NPD2876	Phase 3
0.7213	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3696	Approved
0.7171	Intermediate Similarity	NPD3695	Approved
0.7163	Intermediate Similarity	NPD9607	Approved
0.7135	Intermediate Similarity	NPD2824	Phase 2
0.7076	Intermediate Similarity	NPD1046	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD209	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD171	Discontinued
0.6984	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2902	Phase 2
0.6943	Remote Similarity	NPD1730	Discontinued
0.6933	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9084	Phase 2
0.6879	Remote Similarity	NPD9374	Approved
0.6878	Remote Similarity	NPD4495	Phase 1
0.6857	Remote Similarity	NPD9373	Approved
0.6836	Remote Similarity	NPD1063	Phase 2
0.6832	Remote Similarity	NPD353	Discontinued
0.6826	Remote Similarity	NPD527	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4240	Approved
0.6806	Remote Similarity	NPD307	Approved
0.6755	Remote Similarity	NPD282	Approved
0.6732	Remote Similarity	NPD1119	Phase 2
0.6689	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD775	Approved
0.6582	Remote Similarity	NPD1430	Approved
0.6582	Remote Similarity	NPD1431	Approved
0.6582	Remote Similarity	NPD5080	Phase 2
0.6582	Remote Similarity	NPD2253	Discontinued
0.6575	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1058	Discontinued
0.6531	Remote Similarity	NPD5079	Phase 2
0.6528	Remote Similarity	NPD9584	Phase 2
0.6484	Remote Similarity	NPD207	Discontinued
0.6481	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8836	Approved
0.6455	Remote Similarity	NPD4458	Phase 2
0.6455	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1127	Approved
0.6447	Remote Similarity	NPD1128	Approved
0.6424	Remote Similarity	NPD281	Approved
0.6419	Remote Similarity	NPD9409	Discontinued
0.6392	Remote Similarity	NPD799	Phase 1
0.6392	Remote Similarity	NPD1808	Phase 1
0.6346	Remote Similarity	NPD6840	Approved
0.6338	Remote Similarity	NPD9416	Phase 3
0.6338	Remote Similarity	NPD9417	Phase 3
0.6329	Remote Similarity	NPD6112	Approved
0.6319	Remote Similarity	NPD9375	Discontinued
0.6312	Remote Similarity	NPD1118	Discontinued
0.6291	Remote Similarity	NPD798	Discontinued
0.6266	Remote Similarity	NPD535	Approved
0.6266	Remote Similarity	NPD1120	Approved
0.6266	Remote Similarity	NPD1121	Approved
0.6241	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD8830	Phase 3
0.6203	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD515	Phase 1
0.6166	Remote Similarity	NPD5486	Discontinued
0.6154	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD757	Phase 3
0.6081	Remote Similarity	NPD9406	Approved
0.6073	Remote Similarity	NPD691	Discontinued
0.6071	Remote Similarity	NPD5458	Discontinued
0.6055	Remote Similarity	NPD8250	Phase 2
0.6041	Remote Similarity	NPD796	Phase 2
0.6039	Remote Similarity	NPD78	Approved
0.6039	Remote Similarity	NPD9544	Approved
0.6036	Remote Similarity	NPD7842	Phase 2
0.6	Remote Similarity	NPD8831	Approved
0.6	Remote Similarity	NPD8833	Approved
0.596	Remote Similarity	NPD9360	Approved
0.5951	Remote Similarity	NPD534	Phase 2
0.5951	Remote Similarity	NPD537	Phase 2
0.5894	Remote Similarity	NPD1368	Approved
0.5869	Remote Similarity	NPD5627	Approved
0.5862	Remote Similarity	NPD9291	Approved
0.586	Remote Similarity	NPD1085	Approved
0.586	Remote Similarity	NPD1775	Approved
0.5855	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD5768	Phase 2
0.5808	Remote Similarity	NPD9704	Approved
0.5806	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD1017	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD9366	Approved
0.5752	Remote Similarity	NPD578	Discontinued
0.5742	Remote Similarity	NPD6381	Phase 2
0.5738	Remote Similarity	NPD4089	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD9551	Approved
0.5732	Remote Similarity	NPD9550	Approved
0.5724	Remote Similarity	NPD8837	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD1355	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD1354	Approved
0.5723	Remote Similarity	NPD1356	Approved
0.5714	Remote Similarity	NPD580	Discontinued
0.5682	Remote Similarity	NPD3697	Discontinued
0.5672	Remote Similarity	NPD7323	Phase 2
0.567	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD6023	Discontinued
0.5659	Remote Similarity	NPD9582	Phase 3
0.565	Remote Similarity	NPD4714	Approved
0.565	Remote Similarity	NPD34	Approved
0.565	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.565	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD613	Phase 2
0.5633	Remote Similarity	NPD579	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD9358	Approved
0.5629	Remote Similarity	NPD9359	Approved
0.5619	Remote Similarity	NPD245	Suspended
0.5602	Remote Similarity	NPD2591	Phase 2
0.5602	Remote Similarity	NPD5757	Discontinued
0.56	Remote Similarity	NPD1731	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