NPASS Compound

Structure

NPC223223 OpenBabel07101718302D 30 33 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 3.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 2.3781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0772 2.0691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0772 1.0691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 0.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4862 4.0723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 2.6569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8862 0.4813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5383 1.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 8 1 0 0 0 0 2 6 1 0 0 0 0 2 20 1 0 0 0 0 3 7 2 0 0 0 0 3 21 1 0 0 0 0 4 25 1 0 0 0 0 5 22 2 0 0 0 0 5 24 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 7 22 1 0 0 0 0 8 12 2 0 0 0 0 8 26 1 0 0 0 0 9 4 1 6 0 0 0 9 13 1 0 0 0 0 9 30 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 1 0 0 0 14 16 1 0 0 0 0 14 29 1 1 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 24 1 6 0 0 0 16 30 1 0 0 0 0 17 20 2 3 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	404.357
LogP:	0.237
LogD:	0.122
LogS:	-2.34
# Rotatable Bonds:	4
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	4.002
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.319
MDCK Permeability:	2.7395353754400276e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.301
Human Intestinal Absorption (HIA):	0.639
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	93.04460906982422%
Volume Distribution (VD):	0.495
Pgp-substrate:	6.235072612762451%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.139
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.04

ADMET: Excretion

Clearance (CL):	5.719
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.47
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.654
Carcinogencity:	0.146
Eye Corrosion:	0.003
Eye Irritation:	0.177
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC223223

Natural Product ID:	NPC223223
*Common Name:**	2-N-(2,3-Dibromo-4,5-Dihydroxybenzylamino)Deoxyguanosine
IUPAC Name:	(2R,3R,4S,5R)-2-[2-[(2,3-dibromo-4,5-dihydroxyphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Synonyms:
Standard InCHIKey:	CXRBCOSPCCTAOA-APGPQJPKSA-N
Standard InCHI:	InChI=1S/C17H17Br2N5O6/c18-10-6(1-8(26)12(27)11(10)19)2-20-17-21-3-7-15(23-17)24(5-22-7)16-14(29)13(28)9(4-25)30-16/h1,3,5,9,13-14,16,25-29H,2,4H2,(H,20,21,23)/t9-,13-,14-,16-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(=NCc1cc(O)c(c(c1Br)Br)O)[nH]c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509018
PubChem CID:	11203613
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
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217289]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921411]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499317]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	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
IC50	5
Others	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[517470]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[517470]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[517470]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[517470]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[517470]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	>	100.0	ug.mL-1	PMID[517470]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC50	>	100.0	ug.mL-1	PMID[517470]
NPT20	Organism	Candida albicans	Candida albicans	MIC50	>	100.0	ug.mL-1	PMID[517470]

☑ 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 NPC223223 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	8385
0.2-0.3	11697
0.3-0.4	15229
0.4-0.5	4605
0.5-0.6	1738
0.6-0.7	196
0.7-0.8	4
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7665	Intermediate Similarity	NPC250178
0.7054	Intermediate Similarity	NPC160666
0.6706	Remote Similarity	NPC477795
0.6706	Remote Similarity	NPC477796
0.6706	Remote Similarity	NPC477806
0.6706	Remote Similarity	NPC477805
0.6667	Remote Similarity	NPC115595
0.6575	Remote Similarity	NPC288747
0.657	Remote Similarity	NPC308906
0.656	Remote Similarity	NPC191557
0.6513	Remote Similarity	NPC113369
0.6504	Remote Similarity	NPC35761
0.6493	Remote Similarity	NPC469975
0.6492	Remote Similarity	NPC237978
0.6489	Remote Similarity	NPC129885
0.6417	Remote Similarity	NPC242923
0.6386	Remote Similarity	NPC107160
0.6367	Remote Similarity	NPC136924
0.6356	Remote Similarity	NPC46970
0.634	Remote Similarity	NPC150447
0.6308	Remote Similarity	NPC472068
0.629	Remote Similarity	NPC470501
0.6288	Remote Similarity	NPC249113
0.6286	Remote Similarity	NPC12100
0.625	Remote Similarity	NPC470502
0.625	Remote Similarity	NPC17305
0.62	Remote Similarity	NPC470503
0.6198	Remote Similarity	NPC472066
0.6198	Remote Similarity	NPC472067
0.6198	Remote Similarity	NPC472031
0.6189	Remote Similarity	NPC314882
0.6135	Remote Similarity	NPC167908
0.6122	Remote Similarity	NPC471603
0.6118	Remote Similarity	NPC21461
0.6109	Remote Similarity	NPC158055
0.6097	Remote Similarity	NPC478006
0.6096	Remote Similarity	NPC179896
0.6094	Remote Similarity	NPC328924
0.6081	Remote Similarity	NPC315467
0.6066	Remote Similarity	NPC80596
0.6063	Remote Similarity	NPC323244
0.6058	Remote Similarity	NPC478009
0.6038	Remote Similarity	NPC82472
0.6031	Remote Similarity	NPC295452
0.6031	Remote Similarity	NPC171393
0.6026	Remote Similarity	NPC475120
0.6023	Remote Similarity	NPC272549
0.6017	Remote Similarity	NPC473941
0.6009	Remote Similarity	NPC96275
0.6008	Remote Similarity	NPC476124
0.6008	Remote Similarity	NPC130570
0.6	Remote Similarity	NPC467439
0.5992	Remote Similarity	NPC280638
0.5991	Remote Similarity	NPC475688
0.5985	Remote Similarity	NPC314056
0.5983	Remote Similarity	NPC246591
0.5975	Remote Similarity	NPC54537
0.597	Remote Similarity	NPC39092
0.5951	Remote Similarity	NPC246518
0.595	Remote Similarity	NPC478011
0.5942	Remote Similarity	NPC478010
0.5929	Remote Similarity	NPC314176
0.5927	Remote Similarity	NPC128084
0.5925	Remote Similarity	NPC470504
0.5923	Remote Similarity	NPC33064
0.5921	Remote Similarity	NPC478013
0.5893	Remote Similarity	NPC77101
0.5878	Remote Similarity	NPC476121
0.5874	Remote Similarity	NPC477633
0.5858	Remote Similarity	NPC80514
0.5847	Remote Similarity	NPC5145
0.584	Remote Similarity	NPC266931
0.5837	Remote Similarity	NPC60006
0.5836	Remote Similarity	NPC478012
0.5816	Remote Similarity	NPC477634
0.5798	Remote Similarity	NPC245348
0.5785	Remote Similarity	NPC321592
0.5785	Remote Similarity	NPC54803
0.5782	Remote Similarity	NPC41982
0.5777	Remote Similarity	NPC477610
0.5774	Remote Similarity	NPC471614
0.5772	Remote Similarity	NPC470500
0.5769	Remote Similarity	NPC223409
0.5769	Remote Similarity	NPC95240
0.5769	Remote Similarity	NPC322135
0.5768	Remote Similarity	NPC222018
0.5766	Remote Similarity	NPC478005
0.5765	Remote Similarity	NPC478007
0.5756	Remote Similarity	NPC56271
0.5753	Remote Similarity	NPC244536
0.5745	Remote Similarity	NPC74619
0.5737	Remote Similarity	NPC316981
0.5736	Remote Similarity	NPC125597
0.5731	Remote Similarity	NPC100547
0.5731	Remote Similarity	NPC142901
0.5726	Remote Similarity	NPC326634
0.5725	Remote Similarity	NPC89987
0.572	Remote Similarity	NPC478008
0.5714	Remote Similarity	NPC472289
0.5709	Remote Similarity	NPC238945
0.5709	Remote Similarity	NPC470505
0.5703	Remote Similarity	NPC18348
0.5701	Remote Similarity	NPC226514
0.5699	Remote Similarity	NPC181081
0.5698	Remote Similarity	NPC28945
0.5694	Remote Similarity	NPC117980
0.5692	Remote Similarity	NPC124920
0.5692	Remote Similarity	NPC118559
0.5692	Remote Similarity	NPC304307
0.5692	Remote Similarity	NPC261251
0.5692	Remote Similarity	NPC34580
0.5689	Remote Similarity	NPC37205
0.5689	Remote Similarity	NPC160931
0.5687	Remote Similarity	NPC14288
0.5686	Remote Similarity	NPC477609
0.5682	Remote Similarity	NPC208898
0.5682	Remote Similarity	NPC245055
0.5681	Remote Similarity	NPC473317
0.5677	Remote Similarity	NPC30540
0.567	Remote Similarity	NPC156003
0.5659	Remote Similarity	NPC243633
0.5659	Remote Similarity	NPC175150
0.5654	Remote Similarity	NPC214142
0.5652	Remote Similarity	NPC222174
0.5652	Remote Similarity	NPC63109
0.5647	Remote Similarity	NPC477114
0.5644	Remote Similarity	NPC220852
0.5644	Remote Similarity	NPC138018
0.5643	Remote Similarity	NPC99666
0.564	Remote Similarity	NPC71238
0.5635	Remote Similarity	NPC54981
0.5634	Remote Similarity	NPC81175
0.563	Remote Similarity	NPC284141
0.563	Remote Similarity	NPC49172
0.5625	Remote Similarity	NPC469594
0.5622	Remote Similarity	NPC225857
0.5618	Remote Similarity	NPC469589
0.5615	Remote Similarity	NPC469731
0.5608	Remote Similarity	NPC74969
0.5607	Remote Similarity	NPC471591
0.5605	Remote Similarity	NPC103388
0.5604	Remote Similarity	NPC51854
0.5603	Remote Similarity	NPC292958

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 NPC223223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	870
0.2-0.3	1219
0.3-0.4	2656
0.4-0.5	2369
0.5-0.6	1462
0.6-0.7	237
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7156	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4080	Discontinued
0.6872	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7486	Phase 1
0.6777	Remote Similarity	NPD5703	Discontinued
0.6763	Remote Similarity	NPD6036	Suspended
0.6748	Remote Similarity	NPD2984	Phase 2
0.6724	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3042	Approved
0.6708	Remote Similarity	NPD3043	Approved
0.6695	Remote Similarity	NPD2876	Phase 3
0.6695	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6381	Phase 2
0.6638	Remote Similarity	NPD2824	Phase 2
0.6623	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3612	Phase 2
0.6488	Remote Similarity	NPD2530	Phase 2
0.6488	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2902	Phase 2
0.6455	Remote Similarity	NPD3254	Phase 1
0.6455	Remote Similarity	NPD3255	Phase 1
0.6446	Remote Similarity	NPD5287	Discontinued
0.6434	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD534	Phase 2
0.6367	Remote Similarity	NPD537	Phase 2
0.6342	Remote Similarity	NPD5051	Phase 1
0.6333	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6643	Discontinued
0.63	Remote Similarity	NPD5107	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8442	Discontinued
0.6281	Remote Similarity	NPD4131	Phase 3
0.6271	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.625	Remote Similarity	NPD796	Phase 2
0.6224	Remote Similarity	NPD4612	Discontinued
0.6221	Remote Similarity	NPD5007	Approved
0.6206	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6023	Discontinued
0.619	Remote Similarity	NPD5567	Approved
0.6157	Remote Similarity	NPD4847	Phase 1
0.6154	Remote Similarity	NPD5080	Phase 2
0.6148	Remote Similarity	NPD949	Phase 1
0.6145	Remote Similarity	NPD6856	Discontinued
0.6141	Remote Similarity	NPD2060	Approved
0.6139	Remote Similarity	NPD2929	Clinical (unspecified phase)
0.6137	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4916	Discontinued
0.6126	Remote Similarity	NPD8292	Phase 2
0.6126	Remote Similarity	NPD2349	Phase 3
0.6113	Remote Similarity	NPD5079	Phase 2
0.6111	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD994	Phase 2
0.6111	Remote Similarity	NPD996	Phase 2
0.6109	Remote Similarity	NPD6840	Approved
0.6103	Remote Similarity	NPD5052	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1915	Phase 1
0.6096	Remote Similarity	NPD1954	Phase 1
0.6096	Remote Similarity	NPD2535	Discontinued
0.6092	Remote Similarity	NPD1231	Phase 3
0.6083	Remote Similarity	NPD5486	Discontinued
0.6062	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD3343	Phase 3
0.6038	Remote Similarity	NPD6351	Discovery
0.6016	Remote Similarity	NPD6708	Discontinued
0.6015	Remote Similarity	NPD6244	Phase 3
0.6015	Remote Similarity	NPD6243	Phase 3
0.6008	Remote Similarity	NPD5458	Discontinued
0.6008	Remote Similarity	NPD7620	Phase 2
0.5992	Remote Similarity	NPD2794	Discontinued
0.5985	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4048	Approved
0.5975	Remote Similarity	NPD3633	Approved
0.5975	Remote Similarity	NPD3634	Approved
0.597	Remote Similarity	NPD6473	Phase 1
0.5961	Remote Similarity	NPD1273	Discontinued
0.5958	Remote Similarity	NPD3814	Phase 1
0.5957	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD5905	Phase 1
0.5945	Remote Similarity	NPD6197	Approved
0.594	Remote Similarity	NPD8250	Phase 2
0.5938	Remote Similarity	NPD705	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD2769	Approved
0.5924	Remote Similarity	NPD978	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3938	Phase 1
0.5922	Remote Similarity	NPD4890	Phase 2
0.5911	Remote Similarity	NPD6743	Phase 2
0.5911	Remote Similarity	NPD6742	Phase 2
0.5907	Remote Similarity	NPD6153	Approved
0.5894	Remote Similarity	NPD7117	Phase 2
0.5891	Remote Similarity	NPD4925	Approved
0.5889	Remote Similarity	NPD5539	Phase 2
0.5872	Remote Similarity	NPD536	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6216	Approved
0.5869	Remote Similarity	NPD4995	Approved
0.5869	Remote Similarity	NPD4996	Approved
0.5867	Remote Similarity	NPD2786	Discontinued
0.5865	Remote Similarity	NPD1286	Suspended
0.5862	Remote Similarity	NPD3838	Phase 3
0.5862	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD7112	Discontinued
0.5856	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD2762	Phase 2
0.5849	Remote Similarity	NPD5833	Phase 1
0.5847	Remote Similarity	NPD4495	Phase 1
0.5847	Remote Similarity	NPD5645	Phase 3
0.5844	Remote Similarity	NPD4458	Phase 2
0.5844	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD5116	Phase 1
0.5833	Remote Similarity	NPD5949	Phase 3
0.5827	Remote Similarity	NPD2348	Phase 3
0.582	Remote Similarity	NPD4070	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD4358	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD6848	Phase 1
0.5808	Remote Similarity	NPD8106	Phase 2
0.5806	Remote Similarity	NPD1297	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7726	Phase 1
0.5801	Remote Similarity	NPD5018	Phase 3
0.5794	Remote Similarity	NPD5612	Discontinued
0.5789	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1197	Approved
0.5787	Remote Similarity	NPD6501	Approved
0.5787	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD6500	Approved
0.5785	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6482	Phase 1
0.5774	Remote Similarity	NPD6536	Approved
0.5774	Remote Similarity	NPD6537	Approved
0.5772	Remote Similarity	NPD1287	Phase 2
0.5771	Remote Similarity	NPD2813	Phase 3
0.5771	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.5768	Remote Similarity	NPD5802	Phase 2
0.5768	Remote Similarity	NPD6572	Phase 2
0.5768	Remote Similarity	NPD6573	Phase 3
0.5763	Remote Similarity	NPD7757	Approved
0.5763	Remote Similarity	NPD7758	Approved
0.576	Remote Similarity	NPD6763	Discontinued
0.5756	Remote Similarity	NPD5008	Approved
0.5754	Remote Similarity	NPD6528	Phase 1
0.5753	Remote Similarity	NPD4984	Phase 2
0.5753	Remote Similarity	NPD4086	Phase 1
0.5751	Remote Similarity	NPD2600	Approved
0.5751	Remote Similarity	NPD2601	Approved
0.5751	Remote Similarity	NPD2599	Approved
0.5745	Remote Similarity	NPD7684	Approved
0.5745	Remote Similarity	NPD7682	Approved
0.5742	Remote Similarity	NPD4187	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD3886	Phase 1
0.5737	Remote Similarity	NPD6202	Discontinued
0.5736	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4714	Approved
0.5732	Remote Similarity	NPD34	Approved
0.5731	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD2526	Phase 2
0.5726	Remote Similarity	NPD2523	Phase 2
0.5721	Remote Similarity	NPD4010	Discontinued
0.572	Remote Similarity	NPD7588	Discontinued
0.572	Remote Similarity	NPD722	Clinical (unspecified phase)
0.572	Remote Similarity	NPD8321	Discontinued
0.572	Remote Similarity	NPD4654	Phase 1
0.5714	Remote Similarity	NPD7051	Phase 3
0.5714	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4157	Discontinued
0.5714	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.5709	Remote Similarity	NPD7067	Approved
0.5709	Remote Similarity	NPD8271	Discontinued
0.5709	Remote Similarity	NPD7068	Approved
0.5708	Remote Similarity	NPD2127	Suspended
0.5708	Remote Similarity	NPD1234	Discontinued
0.5704	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD7897	Phase 3
0.5703	Remote Similarity	NPD4306	Phase 1
0.5703	Remote Similarity	NPD5529	Phase 1
0.5703	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD5878	Approved
0.5699	Remote Similarity	NPD5875	Approved
0.5697	Remote Similarity	NPD3570	Phase 2
0.5697	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.5695	Remote Similarity	NPD3405	Phase 3
0.5693	Remote Similarity	NPD3872	Phase 3
0.569	Remote Similarity	NPD1043	Phase 3
0.5688	Remote Similarity	NPD3959	Phase 2
0.5688	Remote Similarity	NPD3962	Phase 2
0.5684	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3358	Approved
0.5683	Remote Similarity	NPD5644	Phase 1
0.568	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD691	Discontinued
0.5677	Remote Similarity	NPD6906	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD6605	Phase 3
0.5673	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD1838	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