NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.09
Volume:	193.381
LogP:	1.162
LogD:	0.871
LogS:	-1.273
# Rotatable Bonds:	0
TPSA:	32.34
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	3.097
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.64
MDCK Permeability:	2.2847945729154162e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.239

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	29.12401580810547%
Volume Distribution (VD):	4.736
Pgp-substrate:	62.413700103759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.255
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.218
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.152
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	11.272
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.217
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.268
Carcinogencity:	0.756
Eye Corrosion:	0.026
Eye Irritation:	0.067
Respiratory Toxicity:	0.336

Download Data

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

Natural Product: NPC283130

Natural Product ID:	NPC283130
*Common Name:**	Vasicine
IUPAC Name:	(3S)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Synonyms:	Vasicine
Standard InCHIKey:	YIICVSCAKJMMDJ-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1
SMILES:	O[C@H]1CCN2C1=Nc1ccccc1C2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2163791
PubChem CID:	667496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28128938]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736972]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14686	Justicia adhatoda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2611	Dalbergia variabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14686	Justicia adhatoda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1085	Peganum harmala	Species	Nitrariaceae	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	3
Others	4

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	30.11	%	PMID[521644]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	3130.0	nM	PMID[521644]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	15410.0	nM	PMID[521646]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	85.7	%	PMID[521644]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	2530.0	nM	PMID[521644]
NPT22036	CELL-LINE	HL	Homo sapiens	Activity	=	102.2	%	PMID[521645]
NPT5310	Organism	Chlamydophila pneumoniae	Chlamydophila pneumoniae	Inhibition	=	-1.4	%	PMID[521645]

☑ 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 NPC283130 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	217
0.1-0.2	2985
0.2-0.3	18091
0.3-0.4	13572
0.4-0.5	5303
0.5-0.6	2329
0.6-0.7	193
0.7-0.8	3
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328683
0.873	High Similarity	NPC226662
0.8696	High Similarity	NPC164802
0.8456	Intermediate Similarity	NPC324445
0.763	Intermediate Similarity	NPC207428
0.748	Intermediate Similarity	NPC288232
0.7206	Intermediate Similarity	NPC476950
0.7155	Intermediate Similarity	NPC78154
0.7039	Intermediate Similarity	NPC94167
0.7039	Intermediate Similarity	NPC172937
0.6972	Remote Similarity	NPC300299
0.6948	Remote Similarity	NPC154478
0.6923	Remote Similarity	NPC296163
0.6901	Remote Similarity	NPC184437
0.6897	Remote Similarity	NPC207554
0.6875	Remote Similarity	NPC122553
0.6818	Remote Similarity	NPC84317
0.68	Remote Similarity	NPC178681
0.6797	Remote Similarity	NPC471132
0.6794	Remote Similarity	NPC314141
0.6794	Remote Similarity	NPC187036
0.6786	Remote Similarity	NPC197680
0.6786	Remote Similarity	NPC259098
0.6781	Remote Similarity	NPC243162
0.6761	Remote Similarity	NPC476685
0.6761	Remote Similarity	NPC476687
0.6761	Remote Similarity	NPC476689
0.6742	Remote Similarity	NPC205652
0.6733	Remote Similarity	NPC472100
0.673	Remote Similarity	NPC300631
0.6716	Remote Similarity	NPC192209
0.6714	Remote Similarity	NPC478079
0.6711	Remote Similarity	NPC472103
0.6709	Remote Similarity	NPC138293
0.6709	Remote Similarity	NPC113056
0.6667	Remote Similarity	NPC474082
0.6667	Remote Similarity	NPC175726
0.6645	Remote Similarity	NPC321617
0.6593	Remote Similarity	NPC313449
0.6571	Remote Similarity	NPC325013
0.6556	Remote Similarity	NPC470824
0.6552	Remote Similarity	NPC15839
0.6544	Remote Similarity	NPC264580
0.6524	Remote Similarity	NPC475594
0.651	Remote Similarity	NPC186284
0.651	Remote Similarity	NPC470301
0.651	Remote Similarity	NPC2823
0.651	Remote Similarity	NPC471574
0.651	Remote Similarity	NPC22082
0.6504	Remote Similarity	NPC108339
0.6493	Remote Similarity	NPC470550
0.6486	Remote Similarity	NPC83214
0.6485	Remote Similarity	NPC475607
0.6457	Remote Similarity	NPC291610
0.6456	Remote Similarity	NPC104345
0.6449	Remote Similarity	NPC317564
0.6449	Remote Similarity	NPC326232
0.6446	Remote Similarity	NPC474081
0.6444	Remote Similarity	NPC101139
0.6438	Remote Similarity	NPC476231
0.6438	Remote Similarity	NPC88970
0.6433	Remote Similarity	NPC470507
0.6414	Remote Similarity	NPC325479
0.6407	Remote Similarity	NPC474041
0.6407	Remote Similarity	NPC475761
0.6406	Remote Similarity	NPC474430
0.64	Remote Similarity	NPC472258
0.6397	Remote Similarity	NPC147957
0.6393	Remote Similarity	NPC226438
0.6392	Remote Similarity	NPC477157
0.6392	Remote Similarity	NPC477156
0.6382	Remote Similarity	NPC136002
0.6379	Remote Similarity	NPC307456
0.6376	Remote Similarity	NPC125746
0.6375	Remote Similarity	NPC68650
0.6369	Remote Similarity	NPC295021
0.6369	Remote Similarity	NPC475685
0.6358	Remote Similarity	NPC471130
0.634	Remote Similarity	NPC116519
0.6336	Remote Similarity	NPC37584
0.6327	Remote Similarity	NPC313352
0.632	Remote Similarity	NPC471320
0.632	Remote Similarity	NPC471319
0.6306	Remote Similarity	NPC469975
0.6303	Remote Similarity	NPC470498
0.6299	Remote Similarity	NPC264589
0.629	Remote Similarity	NPC476483
0.6289	Remote Similarity	NPC141353
0.6282	Remote Similarity	NPC37548
0.6277	Remote Similarity	NPC285926
0.6277	Remote Similarity	NPC315276
0.6277	Remote Similarity	NPC14672
0.6264	Remote Similarity	NPC471196
0.6264	Remote Similarity	NPC471195
0.6259	Remote Similarity	NPC291962
0.6259	Remote Similarity	NPC177684
0.625	Remote Similarity	NPC477155
0.625	Remote Similarity	NPC238499
0.625	Remote Similarity	NPC326575
0.6243	Remote Similarity	NPC473815
0.6241	Remote Similarity	NPC252878
0.624	Remote Similarity	NPC303045
0.624	Remote Similarity	NPC161972
0.6235	Remote Similarity	NPC472117
0.6231	Remote Similarity	NPC113326
0.6231	Remote Similarity	NPC88267
0.6231	Remote Similarity	NPC224610
0.6231	Remote Similarity	NPC194390
0.6228	Remote Similarity	NPC329688
0.6228	Remote Similarity	NPC189812
0.6226	Remote Similarity	NPC471458
0.622	Remote Similarity	NPC49217
0.622	Remote Similarity	NPC54988
0.6214	Remote Similarity	NPC258531
0.6214	Remote Similarity	NPC161956
0.6214	Remote Similarity	NPC112373
0.6213	Remote Similarity	NPC133261
0.6205	Remote Similarity	NPC158129
0.6197	Remote Similarity	NPC46427
0.619	Remote Similarity	NPC22079
0.6184	Remote Similarity	NPC104483
0.6181	Remote Similarity	NPC250476
0.6178	Remote Similarity	NPC187951
0.6173	Remote Similarity	NPC477158
0.617	Remote Similarity	NPC257490
0.6169	Remote Similarity	NPC311330
0.6168	Remote Similarity	NPC34508
0.6165	Remote Similarity	NPC302790
0.6164	Remote Similarity	NPC9856
0.616	Remote Similarity	NPC7067
0.616	Remote Similarity	NPC469330
0.6154	Remote Similarity	NPC68354
0.6154	Remote Similarity	NPC254798
0.6154	Remote Similarity	NPC212799
0.6149	Remote Similarity	NPC256893
0.6142	Remote Similarity	NPC311242
0.6131	Remote Similarity	NPC275305
0.6131	Remote Similarity	NPC37423
0.6129	Remote Similarity	NPC242556
0.6125	Remote Similarity	NPC38736
0.6119	Remote Similarity	NPC470127
0.6107	Remote Similarity	NPC469974
0.6104	Remote Similarity	NPC277157
0.6099	Remote Similarity	NPC316582
0.6099	Remote Similarity	NPC476990
0.6098	Remote Similarity	NPC470877
0.6095	Remote Similarity	NPC472122
0.6095	Remote Similarity	NPC24594
0.609	Remote Similarity	NPC314372
0.6087	Remote Similarity	NPC469785
0.6087	Remote Similarity	NPC285469
0.6081	Remote Similarity	NPC53044
0.6074	Remote Similarity	NPC473320
0.6074	Remote Similarity	NPC472102
0.6074	Remote Similarity	NPC279918
0.6074	Remote Similarity	NPC309531
0.6069	Remote Similarity	NPC470003
0.6066	Remote Similarity	NPC262295
0.6065	Remote Similarity	NPC190296
0.6062	Remote Similarity	NPC281094
0.6061	Remote Similarity	NPC143516
0.6056	Remote Similarity	NPC475915
0.6056	Remote Similarity	NPC202521
0.6054	Remote Similarity	NPC187231
0.6054	Remote Similarity	NPC314431
0.6051	Remote Similarity	NPC143872
0.6049	Remote Similarity	NPC153694
0.6049	Remote Similarity	NPC211525
0.6049	Remote Similarity	NPC469762
0.6048	Remote Similarity	NPC209764
0.6048	Remote Similarity	NPC121872
0.6048	Remote Similarity	NPC471307
0.6048	Remote Similarity	NPC78041
0.6048	Remote Similarity	NPC74936
0.6048	Remote Similarity	NPC159178
0.6048	Remote Similarity	NPC141139
0.6045	Remote Similarity	NPC473676
0.6043	Remote Similarity	NPC313673
0.6038	Remote Similarity	NPC154602
0.6038	Remote Similarity	NPC475763
0.6037	Remote Similarity	NPC472120
0.6037	Remote Similarity	NPC472121
0.6037	Remote Similarity	NPC472101
0.6037	Remote Similarity	NPC282231
0.6032	Remote Similarity	NPC322040
0.6026	Remote Similarity	NPC198988
0.6026	Remote Similarity	NPC159589
0.6023	Remote Similarity	NPC270009
0.6023	Remote Similarity	NPC176199
0.6023	Remote Similarity	NPC215795
0.6015	Remote Similarity	NPC474804
0.6015	Remote Similarity	NPC474973
0.6015	Remote Similarity	NPC130898
0.6014	Remote Similarity	NPC265605
0.6014	Remote Similarity	NPC182570
0.6014	Remote Similarity	NPC33742
0.6014	Remote Similarity	NPC48564
0.6013	Remote Similarity	NPC130251
0.6012	Remote Similarity	NPC148468
0.6012	Remote Similarity	NPC355

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 NPC283130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	522
0.2-0.3	1040
0.3-0.4	1508
0.4-0.5	3612
0.5-0.6	2081
0.6-0.7	213
0.7-0.8	36
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD478	Approved
0.8696	High Similarity	NPD477	Phase 1
0.7561	Intermediate Similarity	NPD1107	Approved
0.7561	Intermediate Similarity	NPD1108	Approved
0.748	Intermediate Similarity	NPD2679	Approved
0.748	Intermediate Similarity	NPD2678	Approved
0.7426	Intermediate Similarity	NPD1001	Discontinued
0.7424	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1419	Approved
0.7417	Intermediate Similarity	NPD1417	Approved
0.7381	Intermediate Similarity	NPD1762	Approved
0.7381	Intermediate Similarity	NPD1764	Approved
0.7355	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2622	Approved
0.7323	Intermediate Similarity	NPD3148	Approved
0.7323	Intermediate Similarity	NPD3150	Approved
0.7323	Intermediate Similarity	NPD2659	Approved
0.7323	Intermediate Similarity	NPD2658	Approved
0.7323	Intermediate Similarity	NPD3149	Approved
0.7323	Intermediate Similarity	NPD3147	Approved
0.7176	Intermediate Similarity	NPD5657	Phase 3
0.7164	Intermediate Similarity	NPD519	Approved
0.7163	Intermediate Similarity	NPD406	Approved
0.7163	Intermediate Similarity	NPD407	Approved
0.7154	Intermediate Similarity	NPD1344	Phase 2
0.712	Intermediate Similarity	NPD2243	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6575	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2093	Discontinued
0.7068	Intermediate Similarity	NPD2340	Discontinued
0.7059	Intermediate Similarity	NPD986	Discontinued
0.7039	Intermediate Similarity	NPD6396	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2527	Approved
0.7039	Intermediate Similarity	NPD6395	Phase 2
0.7023	Intermediate Similarity	NPD2464	Approved
0.7023	Intermediate Similarity	NPD6660	Discontinued
0.7023	Intermediate Similarity	NPD6069	Approved
0.7023	Intermediate Similarity	NPD2467	Approved
0.7023	Intermediate Similarity	NPD2463	Approved
0.7023	Intermediate Similarity	NPD6070	Approved
0.7008	Intermediate Similarity	NPD1539	Approved
0.7	Intermediate Similarity	NPD5631	Phase 3
0.7	Intermediate Similarity	NPD1813	Discontinued
0.6992	Remote Similarity	NPD2210	Approved
0.6992	Remote Similarity	NPD2212	Approved
0.6984	Remote Similarity	NPD1111	Phase 3
0.6984	Remote Similarity	NPD1112	Phase 3
0.696	Remote Similarity	NPD563	Approved
0.696	Remote Similarity	NPD564	Approved
0.6917	Remote Similarity	NPD18	Approved
0.6917	Remote Similarity	NPD1216	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1728	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6301	Phase 2
0.6846	Remote Similarity	NPD1524	Phase 1
0.6831	Remote Similarity	NPD1594	Phase 3
0.6831	Remote Similarity	NPD1595	Approved
0.6812	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4857	Phase 1
0.6794	Remote Similarity	NPD23	Approved
0.6786	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD665	Phase 2
0.6763	Remote Similarity	NPD6900	Discontinued
0.6761	Remote Similarity	NPD1920	Approved
0.6761	Remote Similarity	NPD1919	Approved
0.6759	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD1479	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2546	Approved
0.673	Remote Similarity	NPD2545	Approved
0.6716	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD153	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1324	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7342	Discontinued
0.6691	Remote Similarity	NPD2143	Discontinued
0.6667	Remote Similarity	NPD5060	Phase 1
0.6667	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6017	Discontinued
0.6667	Remote Similarity	NPD7200	Approved
0.6645	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4552	Approved
0.6645	Remote Similarity	NPD4553	Approved
0.6643	Remote Similarity	NPD2113	Approved
0.662	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD1663	Discontinued
0.6601	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4047	Discontinued
0.6597	Remote Similarity	NPD1316	Discontinued
0.6597	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1516	Approved
0.6593	Remote Similarity	NPD7481	Approved
0.6593	Remote Similarity	NPD7480	Approved
0.6582	Remote Similarity	NPD5989	Phase 1
0.6581	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1080	Approved
0.6554	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7582	Discontinued
0.6547	Remote Similarity	NPD7461	Approved
0.6541	Remote Similarity	NPD1656	Phase 2
0.6541	Remote Similarity	NPD452	Phase 1
0.6541	Remote Similarity	NPD453	Phase 1
0.6536	Remote Similarity	NPD5423	Phase 2
0.6536	Remote Similarity	NPD979	Approved
0.6525	Remote Similarity	NPD2840	Approved
0.6512	Remote Similarity	NPD3545	Approved
0.6512	Remote Similarity	NPD990	Approved
0.6512	Remote Similarity	NPD993	Approved
0.6512	Remote Similarity	NPD3546	Approved
0.6512	Remote Similarity	NPD1065	Approved
0.6512	Remote Similarity	NPD1064	Approved
0.651	Remote Similarity	NPD3520	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6557	Phase 2
0.6497	Remote Similarity	NPD2326	Approved
0.6496	Remote Similarity	NPD764	Phase 3
0.6494	Remote Similarity	NPD2356	Phase 1
0.6475	Remote Similarity	NPD2131	Approved
0.6463	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4115	Approved
0.6462	Remote Similarity	NPD4114	Approved
0.6458	Remote Similarity	NPD1500	Approved
0.6449	Remote Similarity	NPD1525	Approved
0.6449	Remote Similarity	NPD6892	Discontinued
0.6446	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD224	Phase 2
0.6438	Remote Similarity	NPD3034	Discontinued
0.6438	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD414	Discontinued
0.6429	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4942	Approved
0.6424	Remote Similarity	NPD2928	Phase 2
0.6423	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD456	Approved
0.6412	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1949	Approved
0.6408	Remote Similarity	NPD1950	Approved
0.6405	Remote Similarity	NPD3629	Approved
0.6405	Remote Similarity	NPD3630	Approved
0.6403	Remote Similarity	NPD678	Discontinued
0.6402	Remote Similarity	NPD3883	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.638	Remote Similarity	NPD4640	Approved
0.638	Remote Similarity	NPD4639	Approved
0.638	Remote Similarity	NPD4638	Approved
0.6377	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2591	Phase 2
0.637	Remote Similarity	NPD2112	Phase 2
0.6364	Remote Similarity	NPD4116	Approved
0.6364	Remote Similarity	NPD3588	Discontinued
0.6364	Remote Similarity	NPD5570	Discontinued
0.6364	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.635	Remote Similarity	NPD457	Approved
0.6346	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3841	Phase 3
0.6345	Remote Similarity	NPD4867	Approved
0.6345	Remote Similarity	NPD4866	Approved
0.6338	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5253	Approved
0.6336	Remote Similarity	NPD6300	Approved
0.6336	Remote Similarity	NPD6299	Approved
0.6319	Remote Similarity	NPD9701	Discontinued
0.6316	Remote Similarity	NPD2129	Approved
0.6312	Remote Similarity	NPD1498	Approved
0.6306	Remote Similarity	NPD3612	Phase 2
0.6301	Remote Similarity	NPD988	Discontinued
0.6301	Remote Similarity	NPD1186	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5179	Approved
0.6296	Remote Similarity	NPD5181	Approved
0.6296	Remote Similarity	NPD5180	Approved
0.6294	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1953	Discontinued
0.629	Remote Similarity	NPD1394	Approved
0.6289	Remote Similarity	NPD2468	Approved
0.6289	Remote Similarity	NPD2469	Approved
0.6289	Remote Similarity	NPD951	Approved
0.6287	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2791	Discontinued
0.6279	Remote Similarity	NPD1396	Approved
0.6275	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2038	Approved
0.6269	Remote Similarity	NPD3001	Approved
0.6269	Remote Similarity	NPD2039	Approved
0.6269	Remote Similarity	NPD2999	Approved
0.6259	Remote Similarity	NPD2817	Discontinued
0.6258	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6378	Approved
0.6258	Remote Similarity	NPD1886	Approved
0.6241	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD3548	Approved
0.6234	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1068	Approved
0.6233	Remote Similarity	NPD3654	Approved
0.6226	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6285	Phase 2

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