NPASS Compound

Structure

CID250178 OpenBabel06191716052D 27 30 0 0 1 0 0 0 0 0999 V2000 -6.4582 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7261 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4582 2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7261 2.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7916 -2.0350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 0.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 2.5477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9941 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7261 -0.9523 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.5477 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7861 -1.9305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6418 0.4307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5921 3.5477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1160 -1.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 -2.5772 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 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 18 1 0 0 0 0 6 23 1 0 0 0 0 7 19 2 0 0 0 0 7 20 1 0 0 0 0 8 21 2 0 0 0 0 8 22 1 0 0 0 0 10 24 1 0 0 0 0 11 6 1 6 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 1 0 0 0 14 17 1 0 0 0 0 14 26 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 22 1 6 0 0 0 17 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.14
Volume:	348.842
LogP:	-0.266
LogD:	0.122
LogS:	-2.476
# Rotatable Bonds:	4
TPSA:	149.01
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	4.087
Fsp3:	0.353
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:	-5.855
MDCK Permeability:	3.7582403820124455e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.57
Plasma Protein Binding (PPB):	46.413063049316406%
Volume Distribution (VD):	2.97
Pgp-substrate:	58.788692474365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.258
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	11.493
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.222
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.283
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.382

Download Data

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

Natural Product: NPC250178

Natural Product ID:	NPC250178
*Common Name:**	N6-(4-Hydroxybenzyl)Adenine Riboside
IUPAC Name:	(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(4-hydroxyphenyl)methylamino]purin-9-yl]oxolane-3,4-diol
Synonyms:	N6-(4-Hydroxybenzyl)Adenine Riboside
Standard InCHIKey:	UGVIXKXYLBAZND-LSCFUAHRSA-N
Standard InCHI:	InChI=1S/C17H19N5O5/c23-6-11-13(25)14(26)17(27-11)22-8-21-12-15(19-7-20-16(12)22)18-5-9-1-3-10(24)4-2-9/h1-4,7-8,11,13-14,17,23-26H,5-6H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1
SMILES:	c1cc(ccc1CNc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL224024
PubChem CID:	10474479
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
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22309	Gastrodia elata	Species	Orchidaceae	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	1
IC50	2
Ki	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	IC50	=	4660.0	nM	PMID[483387]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	=	2620.0	nM	PMID[483387]
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	=	37.0	nM	PMID[483387]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	6770.0	nM	PMID[483388]

☑ 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 NPC250178 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	552
0.1-0.2	4231
0.2-0.3	12956
0.3-0.4	15121
0.4-0.5	6352
0.5-0.6	2944
0.6-0.7	508
0.7-0.8	30
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9135	High Similarity	NPC160666
0.8119	Intermediate Similarity	NPC107160
0.7949	Intermediate Similarity	NPC150447
0.7848	Intermediate Similarity	NPC21461
0.7665	Intermediate Similarity	NPC223223
0.7604	Intermediate Similarity	NPC471603
0.7588	Intermediate Similarity	NPC158055
0.7422	Intermediate Similarity	NPC130570
0.7412	Intermediate Similarity	NPC115595
0.7318	Intermediate Similarity	NPC242923
0.7225	Intermediate Similarity	NPC313514
0.7197	Intermediate Similarity	NPC472068
0.7194	Intermediate Similarity	NPC239737
0.719	Intermediate Similarity	NPC472289
0.7143	Intermediate Similarity	NPC477806
0.7143	Intermediate Similarity	NPC477795
0.7143	Intermediate Similarity	NPC477805
0.7143	Intermediate Similarity	NPC477796
0.7137	Intermediate Similarity	NPC472067
0.7137	Intermediate Similarity	NPC472066
0.7137	Intermediate Similarity	NPC472031
0.7101	Intermediate Similarity	NPC171393
0.7101	Intermediate Similarity	NPC295452
0.7094	Intermediate Similarity	NPC222174
0.7078	Intermediate Similarity	NPC103388
0.7029	Intermediate Similarity	NPC39092
0.7018	Intermediate Similarity	NPC308906
0.6986	Remote Similarity	NPC144114
0.698	Remote Similarity	NPC314882
0.6974	Remote Similarity	NPC150853
0.6968	Remote Similarity	NPC470500
0.6944	Remote Similarity	NPC280638
0.694	Remote Similarity	NPC35761
0.6923	Remote Similarity	NPC237978
0.6919	Remote Similarity	NPC469975
0.6916	Remote Similarity	NPC50511
0.6907	Remote Similarity	NPC328924
0.6889	Remote Similarity	NPC5145
0.688	Remote Similarity	NPC323244
0.6869	Remote Similarity	NPC230805
0.685	Remote Similarity	NPC311197
0.685	Remote Similarity	NPC54320
0.685	Remote Similarity	NPC313754
0.6845	Remote Similarity	NPC164664
0.6838	Remote Similarity	NPC315467
0.6832	Remote Similarity	NPC477633
0.6829	Remote Similarity	NPC168702
0.6829	Remote Similarity	NPC125659
0.6827	Remote Similarity	NPC63109
0.6825	Remote Similarity	NPC477891
0.6811	Remote Similarity	NPC478009
0.6804	Remote Similarity	NPC156461
0.6804	Remote Similarity	NPC107374
0.6804	Remote Similarity	NPC21448
0.68	Remote Similarity	NPC52238
0.6797	Remote Similarity	NPC136924
0.6781	Remote Similarity	NPC46970
0.6769	Remote Similarity	NPC189068
0.6769	Remote Similarity	NPC164665
0.6735	Remote Similarity	NPC219313
0.6735	Remote Similarity	NPC309832
0.6735	Remote Similarity	NPC269827
0.6733	Remote Similarity	NPC74619
0.6733	Remote Similarity	NPC478006
0.6731	Remote Similarity	NPC476688
0.6731	Remote Similarity	NPC476686
0.6731	Remote Similarity	NPC105758
0.6724	Remote Similarity	NPC48317
0.6715	Remote Similarity	NPC278874
0.6701	Remote Similarity	NPC229974
0.6699	Remote Similarity	NPC208060
0.6697	Remote Similarity	NPC324149
0.6696	Remote Similarity	NPC469589
0.6694	Remote Similarity	NPC56271
0.6694	Remote Similarity	NPC30540
0.6681	Remote Similarity	NPC469594
0.668	Remote Similarity	NPC478011
0.668	Remote Similarity	NPC478010
0.6654	Remote Similarity	NPC314176
0.6654	Remote Similarity	NPC477634
0.6653	Remote Similarity	NPC125597
0.6652	Remote Similarity	NPC471080
0.6652	Remote Similarity	NPC208751
0.6652	Remote Similarity	NPC469592
0.6639	Remote Similarity	NPC81175
0.6624	Remote Similarity	NPC103687
0.6624	Remote Similarity	NPC132631
0.6618	Remote Similarity	NPC33382
0.6618	Remote Similarity	NPC138018
0.6618	Remote Similarity	NPC261595
0.6617	Remote Similarity	NPC302778
0.6617	Remote Similarity	NPC212551
0.6607	Remote Similarity	NPC54537
0.6602	Remote Similarity	NPC314056
0.6602	Remote Similarity	NPC224632
0.66	Remote Similarity	NPC211025
0.66	Remote Similarity	NPC85689
0.66	Remote Similarity	NPC185991
0.6598	Remote Similarity	NPC161659
0.6598	Remote Similarity	NPC209525
0.6597	Remote Similarity	NPC110151
0.6596	Remote Similarity	NPC473317
0.6593	Remote Similarity	NPC475070
0.659	Remote Similarity	NPC254762
0.6588	Remote Similarity	NPC313897
0.6588	Remote Similarity	NPC317054
0.6587	Remote Similarity	NPC321458
0.6587	Remote Similarity	NPC324033
0.6586	Remote Similarity	NPC51854
0.6584	Remote Similarity	NPC174802
0.6584	Remote Similarity	NPC28945
0.6574	Remote Similarity	NPC62510
0.6567	Remote Similarity	NPC207633
0.6567	Remote Similarity	NPC321814
0.6567	Remote Similarity	NPC12100
0.6567	Remote Similarity	NPC472816
0.6555	Remote Similarity	NPC2497
0.6552	Remote Similarity	NPC478012
0.6552	Remote Similarity	NPC224076
0.6546	Remote Similarity	NPC9729
0.6535	Remote Similarity	NPC130586
0.6535	Remote Similarity	NPC164952
0.6531	Remote Similarity	NPC471614
0.6531	Remote Similarity	NPC314152
0.6529	Remote Similarity	NPC220852
0.6527	Remote Similarity	NPC476492
0.6527	Remote Similarity	NPC244536
0.6525	Remote Similarity	NPC478013
0.6525	Remote Similarity	NPC17305
0.652	Remote Similarity	NPC226245
0.6513	Remote Similarity	NPC313884
0.6513	Remote Similarity	NPC317821
0.6513	Remote Similarity	NPC98371
0.6512	Remote Similarity	NPC314394
0.6509	Remote Similarity	NPC282247
0.6504	Remote Similarity	NPC99891
0.6498	Remote Similarity	NPC470501
0.6496	Remote Similarity	NPC238945
0.6492	Remote Similarity	NPC472434
0.6489	Remote Similarity	NPC77101
0.6485	Remote Similarity	NPC319232
0.6485	Remote Similarity	NPC24370
0.6476	Remote Similarity	NPC53144
0.6473	Remote Similarity	NPC192315
0.6471	Remote Similarity	NPC99666
0.6468	Remote Similarity	NPC467439
0.6463	Remote Similarity	NPC477861
0.6462	Remote Similarity	NPC129756
0.6461	Remote Similarity	NPC323752
0.6458	Remote Similarity	NPC187145
0.6458	Remote Similarity	NPC6215
0.6456	Remote Similarity	NPC470502
0.6453	Remote Similarity	NPC8022
0.6453	Remote Similarity	NPC470799
0.6453	Remote Similarity	NPC62995
0.645	Remote Similarity	NPC121222
0.6449	Remote Similarity	NPC285343
0.6444	Remote Similarity	NPC476167
0.6444	Remote Similarity	NPC18487
0.6441	Remote Similarity	NPC213530
0.6441	Remote Similarity	NPC193267
0.644	Remote Similarity	NPC471891
0.6439	Remote Similarity	NPC93365
0.6439	Remote Similarity	NPC316618
0.6436	Remote Similarity	NPC161224
0.6432	Remote Similarity	NPC470678
0.6426	Remote Similarity	NPC304926
0.6426	Remote Similarity	NPC476041
0.642	Remote Similarity	NPC89987
0.6406	Remote Similarity	NPC48938
0.6405	Remote Similarity	NPC326363
0.6404	Remote Similarity	NPC200836
0.6402	Remote Similarity	NPC470503
0.64	Remote Similarity	NPC472284
0.6398	Remote Similarity	NPC319456
0.6395	Remote Similarity	NPC26679
0.6394	Remote Similarity	NPC324203
0.6394	Remote Similarity	NPC322976
0.6394	Remote Similarity	NPC63338
0.6387	Remote Similarity	NPC310118
0.6384	Remote Similarity	NPC242209
0.6383	Remote Similarity	NPC288349
0.6383	Remote Similarity	NPC477110
0.6379	Remote Similarity	NPC476451
0.6379	Remote Similarity	NPC113369
0.6372	Remote Similarity	NPC474767
0.6368	Remote Similarity	NPC266931
0.6367	Remote Similarity	NPC325976
0.6364	Remote Similarity	NPC46580
0.6364	Remote Similarity	NPC314954
0.6364	Remote Similarity	NPC323091
0.636	Remote Similarity	NPC211813
0.6355	Remote Similarity	NPC326529
0.6348	Remote Similarity	NPC472287
0.6348	Remote Similarity	NPC472111
0.6348	Remote Similarity	NPC472286
0.6344	Remote Similarity	NPC249040
0.6337	Remote Similarity	NPC69843
0.6332	Remote Similarity	NPC157821
0.6332	Remote Similarity	NPC223427

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 NPC250178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	713
0.2-0.3	830
0.3-0.4	1810
0.4-0.5	2826
0.5-0.6	2021
0.6-0.7	651
0.7-0.8	69
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8844	High Similarity	NPD2965	Clinical (unspecified phase)
0.88	High Similarity	NPD2876	Phase 3
0.88	High Similarity	NPD2877	Clinical (unspecified phase)
0.8713	High Similarity	NPD2824	Phase 2
0.8454	Intermediate Similarity	NPD2903	Clinical (unspecified phase)
0.8454	Intermediate Similarity	NPD2902	Phase 2
0.8325	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD5703	Discontinued
0.8037	Intermediate Similarity	NPD5080	Phase 2
0.7991	Intermediate Similarity	NPD5079	Phase 2
0.7899	Intermediate Similarity	NPD6023	Discontinued
0.788	Intermediate Similarity	NPD537	Phase 2
0.788	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD534	Phase 2
0.7857	Intermediate Similarity	NPD4080	Discontinued
0.7844	Intermediate Similarity	NPD3590	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD796	Phase 2
0.7748	Intermediate Similarity	NPD1273	Discontinued
0.7678	Intermediate Similarity	NPD5486	Discontinued
0.7674	Intermediate Similarity	NPD4495	Phase 1
0.7664	Intermediate Similarity	NPD4612	Discontinued
0.7623	Intermediate Similarity	NPD3042	Approved
0.7623	Intermediate Similarity	NPD3043	Approved
0.7588	Intermediate Similarity	NPD6840	Approved
0.757	Intermediate Similarity	NPD5458	Discontinued
0.7559	Intermediate Similarity	NPD34	Approved
0.7559	Intermediate Similarity	NPD4713	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4715	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4714	Approved
0.7534	Intermediate Similarity	NPD6036	Suspended
0.7511	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD8250	Phase 2
0.7465	Intermediate Similarity	NPD4459	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4458	Phase 2
0.7458	Intermediate Similarity	NPD6351	Discovery
0.7442	Intermediate Similarity	NPD1915	Phase 1
0.7411	Intermediate Similarity	NPD6381	Phase 2
0.7373	Intermediate Similarity	NPD2451	Phase 2
0.7373	Intermediate Similarity	NPD2450	Phase 2
0.7373	Intermediate Similarity	NPD2452	Phase 2
0.7373	Intermediate Similarity	NPD7486	Phase 1
0.7373	Intermediate Similarity	NPD2453	Phase 2
0.7342	Intermediate Similarity	NPD6643	Discontinued
0.7339	Intermediate Similarity	NPD3849	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD3602	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1571	Phase 2
0.729	Intermediate Similarity	NPD5665	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5627	Approved
0.7273	Intermediate Similarity	NPD1572	Phase 2
0.7256	Intermediate Similarity	NPD4599	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4654	Phase 1
0.7249	Intermediate Similarity	NPD5567	Approved
0.7249	Intermediate Similarity	NPD6326	Phase 2
0.7248	Intermediate Similarity	NPD7323	Phase 2
0.7241	Intermediate Similarity	NPD4306	Phase 1
0.7232	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8442	Discontinued
0.7225	Intermediate Similarity	NPD7138	Phase 2
0.7224	Intermediate Similarity	NPD7706	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6573	Phase 3
0.7215	Intermediate Similarity	NPD6572	Phase 2
0.721	Intermediate Similarity	NPD6760	Discontinued
0.7181	Intermediate Similarity	NPD4187	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6327	Phase 1
0.7149	Intermediate Similarity	NPD1954	Phase 1
0.7137	Intermediate Similarity	NPD7273	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2591	Phase 2
0.7089	Intermediate Similarity	NPD1234	Discontinued
0.7087	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7068	Approved
0.7071	Intermediate Similarity	NPD5802	Phase 2
0.7071	Intermediate Similarity	NPD7067	Approved
0.7066	Intermediate Similarity	NPD6243	Phase 3
0.7066	Intermediate Similarity	NPD6244	Phase 3
0.7061	Intermediate Similarity	NPD6856	Discontinued
0.7056	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7051	Phase 3
0.7054	Intermediate Similarity	NPD2794	Discontinued
0.7054	Intermediate Similarity	NPD6202	Discontinued
0.7051	Intermediate Similarity	NPD3814	Phase 1
0.7046	Intermediate Similarity	NPD6605	Phase 3
0.7037	Intermediate Similarity	NPD5878	Approved
0.7037	Intermediate Similarity	NPD5875	Approved
0.7031	Intermediate Similarity	NPD7726	Phase 1
0.703	Intermediate Similarity	NPD5269	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5644	Phase 1
0.702	Intermediate Similarity	NPD2646	Discontinued
0.7019	Intermediate Similarity	NPD4716	Approved
0.7013	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4401	Phase 2
0.7013	Intermediate Similarity	NPD4403	Phase 3
0.7	Intermediate Similarity	NPD7620	Phase 2
0.7	Intermediate Similarity	NPD3343	Phase 3
0.6996	Remote Similarity	NPD1624	Phase 2
0.6995	Remote Similarity	NPD2647	Phase 3
0.6992	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3838	Phase 3
0.6991	Remote Similarity	NPD6528	Phase 1
0.6986	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1197	Approved
0.6964	Remote Similarity	NPD8321	Discontinued
0.696	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5949	Phase 3
0.6958	Remote Similarity	NPD6473	Phase 1
0.6949	Remote Similarity	NPD6186	Approved
0.6948	Remote Similarity	NPD7504	Discontinued
0.6946	Remote Similarity	NPD5905	Phase 1
0.6946	Remote Similarity	NPD6992	Phase 2
0.6934	Remote Similarity	NPD7757	Approved
0.6934	Remote Similarity	NPD7758	Approved
0.6933	Remote Similarity	NPD6763	Discontinued
0.6933	Remote Similarity	NPD4563	Phase 2
0.693	Remote Similarity	NPD2127	Suspended
0.6927	Remote Similarity	NPD5885	Approved
0.6926	Remote Similarity	NPD6482	Phase 1
0.6919	Remote Similarity	NPD3612	Phase 2
0.6916	Remote Similarity	NPD429	Approved
0.6909	Remote Similarity	NPD6307	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5116	Phase 1
0.6904	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4925	Approved
0.6887	Remote Similarity	NPD2762	Phase 2
0.6886	Remote Similarity	NPD7112	Discontinued
0.6884	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6589	Phase 1
0.688	Remote Similarity	NPD8292	Phase 2
0.6875	Remote Similarity	NPD5529	Phase 1
0.6875	Remote Similarity	NPD2929	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3107	Discontinued
0.6869	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4996	Approved
0.6864	Remote Similarity	NPD4995	Approved
0.6864	Remote Similarity	NPD2062	Phase 2
0.6863	Remote Similarity	NPD5509	Phase 1
0.6861	Remote Similarity	NPD2060	Approved
0.6858	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4916	Discontinued
0.685	Remote Similarity	NPD220	Clinical (unspecified phase)
0.685	Remote Similarity	NPD218	Approved
0.685	Remote Similarity	NPD216	Approved
0.685	Remote Similarity	NPD3255	Phase 1
0.685	Remote Similarity	NPD219	Phase 3
0.685	Remote Similarity	NPD217	Approved
0.685	Remote Similarity	NPD3254	Phase 1
0.6844	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5539	Phase 2
0.6837	Remote Similarity	NPD1043	Phase 3
0.6835	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6750	Phase 2
0.6831	Remote Similarity	NPD3962	Phase 2
0.6831	Remote Similarity	NPD3959	Phase 2
0.6824	Remote Similarity	NPD5045	Phase 2
0.6824	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.682	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5833	Phase 1
0.6816	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6192	Phase 3
0.6814	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3013	Phase 3
0.6812	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6957	Approved
0.6812	Remote Similarity	NPD6958	Approved
0.6812	Remote Similarity	NPD6711	Approved
0.681	Remote Similarity	NPD4414	Discontinued
0.6809	Remote Similarity	NPD6175	Phase 3
0.6809	Remote Similarity	NPD2349	Phase 3
0.6806	Remote Similarity	NPD1286	Suspended
0.6805	Remote Similarity	NPD7117	Phase 2
0.6804	Remote Similarity	NPD250	Approved
0.6804	Remote Similarity	NPD249	Approved
0.6802	Remote Similarity	NPD3811	Discontinued
0.6802	Remote Similarity	NPD6743	Phase 2
0.6802	Remote Similarity	NPD6742	Phase 2
0.6798	Remote Similarity	NPD6216	Approved
0.6798	Remote Similarity	NPD5868	Approved
0.6793	Remote Similarity	NPD8004	Discontinued
0.6791	Remote Similarity	NPD207	Discontinued
0.679	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1750	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1369	Phase 2
0.6784	Remote Similarity	NPD4131	Phase 3
0.6778	Remote Similarity	NPD2757	Phase 2
0.6777	Remote Similarity	NPD3872	Phase 3
0.6776	Remote Similarity	NPD5876	Phase 3
0.6776	Remote Similarity	NPD5877	Phase 3
0.6776	Remote Similarity	NPD706	Phase 1
0.6776	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2624	Phase 2
0.6762	Remote Similarity	NPD5044	Phase 2
0.6759	Remote Similarity	NPD2410	Phase 2
0.6759	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6754	Phase 3

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