NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.13
Volume:	257.292
LogP:	2.221
LogD:	2.211
LogS:	-1.897
# Rotatable Bonds:	3
TPSA:	34.89
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.822
Synthetic Accessibility Score:	2.349
Fsp3:	0.333
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:	-4.765
MDCK Permeability:	2.0940002286806703e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.61
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	57.13299560546875%
Volume Distribution (VD):	1.482
Pgp-substrate:	19.1147518157959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.923
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.488
CYP2C9-inhibitor:	0.57
CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.205
CYP2D6-substrate:	0.65
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.432

ADMET: Excretion

Clearance (CL):	7.812
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.754
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.242
Carcinogencity:	0.752
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC472258

Natural Product ID:	NPC472258
*Common Name:**	YCDNFIFPTPRDLT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YCDNFIFPTPRDLT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16N2O/c18-15-11-16-13(14-7-4-10-17(14)15)9-8-12-5-2-1-3-6-12/h1-3,5-6,11H,4,7-10H2
SMILES:	C1CC2=C(N=CC(=O)N2C1)CCC3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355650
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000343] Pyrrolopyrazines

*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
NPO33000	myxobacteria	Order	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25397992]

☑ 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	8
MIC	12

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	5
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	41500.0	nM	PMID[536324]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	41500.0	nM	PMID[536324]
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	41500.0	nM	PMID[536324]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	41500.0	nM	PMID[536324]
NPT1460	Cell Line	L929	Mus musculus	IC50	>	41500.0	nM	PMID[536324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	41500.0	nM	PMID[536324]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	33.3	ug.mL-1	PMID[536324]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	>	66.6	ug.mL-1	PMID[536324]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	33.3	ug.mL-1	PMID[536324]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT2631	Organism	Chromobacterium violaceum	Chromobacterium violaceum	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	=	33.3	ug.mL-1	PMID[536324]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	66.6	ug.mL-1	PMID[536324]
NPT4584	Organism	Nocardia sp.	Nocardia sp.	MIC	=	66.6	ug.mL-1	PMID[536324]

☑ 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 NPC472258 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	582
0.1-0.2	9369
0.2-0.3	16655
0.3-0.4	10339
0.4-0.5	3222
0.5-0.6	1942
0.6-0.7	555
0.7-0.8	31
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7885	Intermediate Similarity	NPC275467
0.7812	Intermediate Similarity	NPC17497
0.7812	Intermediate Similarity	NPC305602
0.7679	Intermediate Similarity	NPC315276
0.7679	Intermediate Similarity	NPC285926
0.7679	Intermediate Similarity	NPC14672
0.7624	Intermediate Similarity	NPC256452
0.7525	Intermediate Similarity	NPC474974
0.7524	Intermediate Similarity	NPC329375
0.7477	Intermediate Similarity	NPC143516
0.7426	Intermediate Similarity	NPC473661
0.7407	Intermediate Similarity	NPC473498
0.7407	Intermediate Similarity	NPC130898
0.7407	Intermediate Similarity	NPC474804
0.7407	Intermediate Similarity	NPC474973
0.7407	Intermediate Similarity	NPC45033
0.7391	Intermediate Similarity	NPC220698
0.7368	Intermediate Similarity	NPC231986
0.7345	Intermediate Similarity	NPC33742
0.7273	Intermediate Similarity	NPC473676
0.7227	Intermediate Similarity	NPC175726
0.7227	Intermediate Similarity	NPC474082
0.7216	Intermediate Similarity	NPC474088
0.7156	Intermediate Similarity	NPC473418
0.7091	Intermediate Similarity	NPC471447
0.708	Intermediate Similarity	NPC475013
0.699	Remote Similarity	NPC226438
0.6975	Remote Similarity	NPC476990
0.6975	Remote Similarity	NPC200964
0.6957	Remote Similarity	NPC35850
0.6957	Remote Similarity	NPC276949
0.6957	Remote Similarity	NPC476048
0.6952	Remote Similarity	NPC161972
0.6952	Remote Similarity	NPC303045
0.6923	Remote Similarity	NPC470544
0.6917	Remote Similarity	NPC202521
0.6864	Remote Similarity	NPC470545
0.686	Remote Similarity	NPC252878
0.6857	Remote Similarity	NPC71140
0.6832	Remote Similarity	NPC203076
0.6822	Remote Similarity	NPC311242
0.6814	Remote Similarity	NPC164802
0.6807	Remote Similarity	NPC470546
0.6803	Remote Similarity	NPC46427
0.6803	Remote Similarity	NPC6975
0.6772	Remote Similarity	NPC207428
0.6765	Remote Similarity	NPC471638
0.6765	Remote Similarity	NPC53492
0.6752	Remote Similarity	NPC246904
0.6735	Remote Similarity	NPC475573
0.6735	Remote Similarity	NPC475289
0.6702	Remote Similarity	NPC244738
0.6699	Remote Similarity	NPC262393
0.6695	Remote Similarity	NPC473573
0.6694	Remote Similarity	NPC27833
0.6667	Remote Similarity	NPC473322
0.6667	Remote Similarity	NPC271642
0.6639	Remote Similarity	NPC71684
0.6639	Remote Similarity	NPC239357
0.6638	Remote Similarity	NPC275410
0.6614	Remote Similarity	NPC200589
0.6602	Remote Similarity	NPC473031
0.66	Remote Similarity	NPC14326
0.6579	Remote Similarity	NPC55529
0.6571	Remote Similarity	NPC316108
0.6571	Remote Similarity	NPC172128
0.6562	Remote Similarity	NPC98976
0.6562	Remote Similarity	NPC255447
0.6538	Remote Similarity	NPC12429
0.6535	Remote Similarity	NPC104070
0.6522	Remote Similarity	NPC77294
0.6515	Remote Similarity	NPC313694
0.6515	Remote Similarity	NPC242159
0.6512	Remote Similarity	NPC325479
0.6509	Remote Similarity	NPC245259
0.6495	Remote Similarity	NPC139658
0.6484	Remote Similarity	NPC300315
0.6476	Remote Similarity	NPC470877
0.6471	Remote Similarity	NPC169016
0.6455	Remote Similarity	NPC322598
0.6434	Remote Similarity	NPC130309
0.6422	Remote Similarity	NPC25565
0.6415	Remote Similarity	NPC159178
0.6415	Remote Similarity	NPC78041
0.6415	Remote Similarity	NPC209764
0.6415	Remote Similarity	NPC74936
0.6415	Remote Similarity	NPC471307
0.6415	Remote Similarity	NPC141139
0.6415	Remote Similarity	NPC121872
0.6408	Remote Similarity	NPC3210
0.6404	Remote Similarity	NPC167336
0.64	Remote Similarity	NPC283130
0.64	Remote Similarity	NPC328683
0.6389	Remote Similarity	NPC7067
0.6381	Remote Similarity	NPC325441
0.6364	Remote Similarity	NPC473501
0.6364	Remote Similarity	NPC475439
0.6356	Remote Similarity	NPC269340
0.6355	Remote Similarity	NPC470926
0.6336	Remote Similarity	NPC287401
0.633	Remote Similarity	NPC108339
0.6324	Remote Similarity	NPC238499
0.6316	Remote Similarity	NPC229235
0.6316	Remote Similarity	NPC469974
0.6299	Remote Similarity	NPC101719
0.6299	Remote Similarity	NPC474479
0.629	Remote Similarity	NPC316582
0.6289	Remote Similarity	NPC299134
0.6289	Remote Similarity	NPC112609
0.6289	Remote Similarity	NPC122327
0.6289	Remote Similarity	NPC113000
0.6288	Remote Similarity	NPC248283
0.6288	Remote Similarity	NPC141050
0.6279	Remote Similarity	NPC111428
0.6279	Remote Similarity	NPC469666
0.6277	Remote Similarity	NPC471680
0.6273	Remote Similarity	NPC471320
0.6273	Remote Similarity	NPC471319
0.6262	Remote Similarity	NPC476160
0.6262	Remote Similarity	NPC78154
0.6262	Remote Similarity	NPC258627
0.626	Remote Similarity	NPC228515
0.626	Remote Similarity	NPC264580
0.625	Remote Similarity	NPC476249
0.625	Remote Similarity	NPC186284
0.625	Remote Similarity	NPC125144
0.625	Remote Similarity	NPC187036
0.625	Remote Similarity	NPC22082
0.625	Remote Similarity	NPC12730
0.625	Remote Similarity	NPC121708
0.6239	Remote Similarity	NPC322040
0.6239	Remote Similarity	NPC471309
0.6228	Remote Similarity	NPC164859
0.6222	Remote Similarity	NPC65408
0.622	Remote Similarity	NPC22746
0.622	Remote Similarity	NPC222466
0.6214	Remote Similarity	NPC119677
0.6207	Remote Similarity	NPC274089
0.6207	Remote Similarity	NPC191215
0.6207	Remote Similarity	NPC327481
0.6202	Remote Similarity	NPC478079
0.6202	Remote Similarity	NPC319766
0.62	Remote Similarity	NPC12857
0.6195	Remote Similarity	NPC469457
0.6195	Remote Similarity	NPC474582
0.6194	Remote Similarity	NPC471265
0.6194	Remote Similarity	NPC471264
0.619	Remote Similarity	NPC258046
0.6182	Remote Similarity	NPC58674
0.6179	Remote Similarity	NPC192209
0.6176	Remote Similarity	NPC130251
0.6176	Remote Similarity	NPC476989
0.6172	Remote Similarity	NPC79698
0.616	Remote Similarity	NPC302169
0.6148	Remote Similarity	NPC89489
0.6148	Remote Similarity	NPC77992
0.6148	Remote Similarity	NPC98424
0.6148	Remote Similarity	NPC178662
0.6148	Remote Similarity	NPC470884
0.6148	Remote Similarity	NPC92784
0.6148	Remote Similarity	NPC122553
0.6148	Remote Similarity	NPC288232
0.6148	Remote Similarity	NPC476133
0.6143	Remote Similarity	NPC324445
0.614	Remote Similarity	NPC291610
0.6136	Remote Similarity	NPC194857
0.6136	Remote Similarity	NPC32858
0.6136	Remote Similarity	NPC473962
0.6136	Remote Similarity	NPC40364
0.6134	Remote Similarity	NPC319579
0.6131	Remote Similarity	NPC471164
0.6131	Remote Similarity	NPC301760
0.6131	Remote Similarity	NPC161069
0.6116	Remote Similarity	NPC296163
0.6107	Remote Similarity	NPC187231
0.6107	Remote Similarity	NPC226662
0.6103	Remote Similarity	NPC469560
0.61	Remote Similarity	NPC325662
0.61	Remote Similarity	NPC98269
0.61	Remote Similarity	NPC290638
0.6087	Remote Similarity	NPC202613
0.6087	Remote Similarity	NPC471317
0.608	Remote Similarity	NPC291962
0.608	Remote Similarity	NPC177684
0.6077	Remote Similarity	NPC476950
0.6074	Remote Similarity	NPC325599
0.6074	Remote Similarity	NPC471123
0.6074	Remote Similarity	NPC267508
0.6071	Remote Similarity	NPC33168
0.6061	Remote Similarity	NPC276699
0.6058	Remote Similarity	NPC269398
0.6058	Remote Similarity	NPC207554
0.6058	Remote Similarity	NPC263493
0.6053	Remote Similarity	NPC228400
0.6053	Remote Similarity	NPC214200
0.605	Remote Similarity	NPC158854
0.6048	Remote Similarity	NPC313449
0.6047	Remote Similarity	NPC171372
0.6045	Remote Similarity	NPC162417
0.6045	Remote Similarity	NPC316104

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 NPC472258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	751
0.2-0.3	906
0.3-0.4	2235
0.4-0.5	2864
0.5-0.6	1667
0.6-0.7	406
0.7-0.8	27
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
0.7692	Intermediate Similarity	NPD6588	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD4063	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD787	Suspended
0.7368	Intermediate Similarity	NPD1344	Phase 2
0.7364	Intermediate Similarity	NPD3581	Discontinued
0.732	Intermediate Similarity	NPD5178	Approved
0.7297	Intermediate Similarity	NPD2583	Phase 2
0.7238	Intermediate Similarity	NPD466	Approved
0.7196	Intermediate Similarity	NPD4803	Discontinued
0.717	Intermediate Similarity	NPD742	Approved
0.7128	Intermediate Similarity	NPD4144	Approved
0.7128	Intermediate Similarity	NPD4147	Approved
0.7103	Intermediate Similarity	NPD5630	Phase 1
0.7091	Intermediate Similarity	NPD7130	Phase 3
0.6979	Remote Similarity	NPD1051	Approved
0.6979	Remote Similarity	NPD1053	Approved
0.6979	Remote Similarity	NPD1052	Approved
0.6967	Remote Similarity	NPD2031	Discontinued
0.6957	Remote Similarity	NPD5179	Approved
0.6957	Remote Similarity	NPD5180	Approved
0.6957	Remote Similarity	NPD5181	Approved
0.6939	Remote Similarity	NPD4169	Approved
0.6939	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4170	Approved
0.6937	Remote Similarity	NPD1065	Approved
0.6937	Remote Similarity	NPD1064	Approved
0.6916	Remote Similarity	NPD1724	Approved
0.69	Remote Similarity	NPD5916	Discontinued
0.6887	Remote Similarity	NPD157	Clinical (unspecified phase)
0.687	Remote Similarity	NPD480	Approved
0.6864	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD1763	Approved
0.6847	Remote Similarity	NPD1766	Approved
0.6847	Remote Similarity	NPD1765	Approved
0.6847	Remote Similarity	NPD1767	Approved
0.6847	Remote Similarity	NPD1761	Approved
0.6847	Remote Similarity	NPD999	Phase 2
0.6837	Remote Similarity	NPD3035	Approved
0.6837	Remote Similarity	NPD472	Approved
0.6837	Remote Similarity	NPD4027	Approved
0.6837	Remote Similarity	NPD4026	Approved
0.6832	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3099	Discontinued
0.6827	Remote Similarity	NPD517	Discontinued
0.6814	Remote Similarity	NPD477	Phase 1
0.681	Remote Similarity	NPD3598	Phase 3
0.6807	Remote Similarity	NPD6345	Approved
0.6807	Remote Similarity	NPD6343	Approved
0.6803	Remote Similarity	NPD2584	Suspended
0.68	Remote Similarity	NPD2538	Approved
0.68	Remote Similarity	NPD2539	Approved
0.6774	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD603	Approved
0.6759	Remote Similarity	NPD4117	Approved
0.6735	Remote Similarity	NPD5372	Approved
0.6735	Remote Similarity	NPD5371	Approved
0.6731	Remote Similarity	NPD3344	Approved
0.6731	Remote Similarity	NPD3346	Approved
0.6729	Remote Similarity	NPD5964	Phase 2
0.6729	Remote Similarity	NPD5963	Phase 2
0.6727	Remote Similarity	NPD1419	Approved
0.6727	Remote Similarity	NPD813	Approved
0.6727	Remote Similarity	NPD2196	Discontinued
0.6727	Remote Similarity	NPD5716	Approved
0.6727	Remote Similarity	NPD1417	Approved
0.6727	Remote Similarity	NPD708	Approved
0.6723	Remote Similarity	NPD5990	Approved
0.6723	Remote Similarity	NPD5991	Approved
0.672	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD9728	Phase 1
0.6699	Remote Similarity	NPD3345	Approved
0.6696	Remote Similarity	NPD2192	Approved
0.6696	Remote Similarity	NPD2197	Approved
0.6694	Remote Similarity	NPD3064	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4655	Approved
0.6667	Remote Similarity	NPD4657	Approved
0.6667	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1099	Approved
0.6667	Remote Similarity	NPD1100	Approved
0.6667	Remote Similarity	NPD4636	Approved
0.6667	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5103	Approved
0.6667	Remote Similarity	NPD5859	Discontinued
0.664	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4094	Approved
0.6634	Remote Similarity	NPD785	Approved
0.6614	Remote Similarity	NPD6729	Phase 2
0.6612	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3551	Approved
0.6604	Remote Similarity	NPD1812	Approved
0.6604	Remote Similarity	NPD1814	Approved
0.6589	Remote Similarity	NPD941	Approved
0.6585	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6027	Approved
0.6577	Remote Similarity	NPD4119	Approved
0.6577	Remote Similarity	NPD6024	Approved
0.6574	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2205	Approved
0.6569	Remote Similarity	NPD2208	Approved
0.6555	Remote Similarity	NPD2622	Approved
0.6549	Remote Similarity	NPD959	Discontinued
0.6549	Remote Similarity	NPD5717	Approved
0.6549	Remote Similarity	NPD1677	Discontinued
0.6538	Remote Similarity	NPD5675	Discontinued
0.6535	Remote Similarity	NPD4635	Approved
0.6535	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD830	Approved
0.6535	Remote Similarity	NPD831	Approved
0.6532	Remote Similarity	NPD6408	Phase 1
0.6531	Remote Similarity	NPD295	Approved
0.6531	Remote Similarity	NPD296	Approved
0.6531	Remote Similarity	NPD293	Approved
0.6529	Remote Similarity	NPD998	Approved
0.6525	Remote Similarity	NPD5063	Approved
0.6525	Remote Similarity	NPD5064	Approved
0.6525	Remote Similarity	NPD23	Approved
0.6522	Remote Similarity	NPD2678	Approved
0.6522	Remote Similarity	NPD2679	Approved
0.6519	Remote Similarity	NPD5526	Phase 2
0.6519	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD3682	Approved
0.6518	Remote Similarity	NPD3357	Discontinued
0.6518	Remote Similarity	NPD3680	Approved
0.6509	Remote Similarity	NPD2998	Approved
0.6509	Remote Similarity	NPD3000	Approved
0.6509	Remote Similarity	NPD2997	Approved
0.6508	Remote Similarity	NPD2840	Approved
0.6505	Remote Similarity	NPD4409	Approved
0.6505	Remote Similarity	NPD4406	Approved
0.65	Remote Similarity	NPD7679	Phase 2
0.6496	Remote Similarity	NPD753	Approved
0.6484	Remote Similarity	NPD4125	Approved
0.6481	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2543	Discontinued
0.6471	Remote Similarity	NPD2508	Discontinued
0.6471	Remote Similarity	NPD5631	Phase 3
0.6465	Remote Similarity	NPD590	Approved
0.6465	Remote Similarity	NPD507	Approved
0.6465	Remote Similarity	NPD508	Approved
0.6465	Remote Similarity	NPD589	Approved
0.6457	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4761	Approved
0.6452	Remote Similarity	NPD4762	Approved
0.6449	Remote Similarity	NPD6690	Approved
0.6446	Remote Similarity	NPD2109	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2108	Phase 2
0.6442	Remote Similarity	NPD4145	Approved
0.6442	Remote Similarity	NPD4146	Approved
0.6441	Remote Similarity	NPD1764	Approved
0.6441	Remote Similarity	NPD4165	Phase 2
0.6441	Remote Similarity	NPD3066	Phase 2
0.6441	Remote Similarity	NPD1762	Approved
0.6435	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2648	Phase 3
0.6429	Remote Similarity	NPD2171	Approved
0.6429	Remote Similarity	NPD2961	Approved
0.6429	Remote Similarity	NPD2193	Phase 2
0.6429	Remote Similarity	NPD2962	Approved
0.6429	Remote Similarity	NPD6792	Phase 3
0.6422	Remote Similarity	NPD2895	Discontinued
0.6417	Remote Similarity	NPD1323	Discontinued
0.6412	Remote Similarity	NPD5272	Discontinued
0.6404	Remote Similarity	NPD1576	Approved
0.64	Remote Similarity	NPD3904	Approved
0.64	Remote Similarity	NPD3981	Approved
0.64	Remote Similarity	NPD3903	Approved
0.64	Remote Similarity	NPD3072	Approved
0.64	Remote Similarity	NPD3979	Approved
0.64	Remote Similarity	NPD3071	Approved
0.64	Remote Similarity	NPD478	Approved
0.64	Remote Similarity	NPD5335	Discontinued
0.64	Remote Similarity	NPD3073	Approved
0.6389	Remote Similarity	NPD720	Approved
0.6389	Remote Similarity	NPD197	Approved
0.6389	Remote Similarity	NPD199	Approved
0.6389	Remote Similarity	NPD6549	Approved
0.6389	Remote Similarity	NPD6548	Approved
0.6389	Remote Similarity	NPD719	Approved
0.6389	Remote Similarity	NPD1080	Approved
0.6387	Remote Similarity	NPD3147	Approved
0.6387	Remote Similarity	NPD3148	Approved
0.6387	Remote Similarity	NPD3149	Approved
0.6387	Remote Similarity	NPD3150	Approved
0.6387	Remote Similarity	NPD2659	Approved
0.6387	Remote Similarity	NPD2658	Approved
0.6385	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8643	Discontinued
0.6364	Remote Similarity	NPD3123	Discovery
0.6357	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2124	Approved
0.6355	Remote Similarity	NPD4543	Discontinued
0.6328	Remote Similarity	NPD3588	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