NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	249.17
Volume:	265.631
LogP:	0.919
LogD:	1.315
LogS:	-0.119
# Rotatable Bonds:	1
TPSA:	36.2
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.911
Fsp3:	0.733
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:	-5.45
MDCK Permeability:	4.21602999267634e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.98
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	84.42366790771484%
Volume Distribution (VD):	1.621
Pgp-substrate:	23.18684196472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.248
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.685
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	14.609
Half-life (T1/2):	0.872

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.382
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.108
Carcinogencity:	0.95
Eye Corrosion:	0.909
Eye Irritation:	0.859
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC26589

Natural Product ID:	NPC26589
*Common Name:**	Nupharidine
IUPAC Name:	(1R,4S,7S,9aS)-4-(furan-3-yl)-1,7-dimethyl-5-oxido-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-5-ium
Synonyms:	Nupharidine
Standard InCHIKey:	HISDAJRMKAJROU-UNVGTVGXSA-N
Standard InCHI:	InChI=1S/C15H23NO2/c1-11-3-5-14-12(2)4-6-15(16(14,17)9-11)13-7-8-18-10-13/h7-8,10-12,14-15H,3-6,9H2,1-2H3/t11-,12+,14-,15-,16?/m0/s1
SMILES:	C[C@H]1CC[C@@H]2N(=O)(C1)[C@@H](CC[C@H]2C)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL203844
PubChem CID:	44409168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000222] Quinolizines

*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
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[14643343]
NPO33085	nuphar pumilum	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16413779]
NPO13972	Nuphar japonicum	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14850	Nuphar pumila	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13972	Nuphar japonicum	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13972	Nuphar japonicum	Species	Nymphaeaceae	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	8.0	%	PMID[523094]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	11.5	%	PMID[523094]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	0.6	%	PMID[523094]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	5.3	%	PMID[523094]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	4.1	%	PMID[523094]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-3.3	%	PMID[523094]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-9.0	%	PMID[523094]

☑ 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 NPC26589 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	252
0.1-0.2	1177
0.2-0.3	5297
0.3-0.4	12837
0.4-0.5	13209
0.5-0.6	9248
0.6-0.7	631
0.7-0.8	41
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473444
0.9333	High Similarity	NPC208170
0.9333	High Similarity	NPC216149
0.8881	High Similarity	NPC223873
0.7888	Intermediate Similarity	NPC70840
0.7888	Intermediate Similarity	NPC473245
0.7888	Intermediate Similarity	NPC176304
0.7744	Intermediate Similarity	NPC476236
0.7744	Intermediate Similarity	NPC472474
0.7744	Intermediate Similarity	NPC469964
0.756	Intermediate Similarity	NPC76433
0.756	Intermediate Similarity	NPC289167
0.756	Intermediate Similarity	NPC186957
0.7471	Intermediate Similarity	NPC297647
0.7317	Intermediate Similarity	NPC471651
0.725	Intermediate Similarity	NPC471649
0.7179	Intermediate Similarity	NPC471647
0.7179	Intermediate Similarity	NPC471646
0.7055	Intermediate Similarity	NPC133817
0.7055	Intermediate Similarity	NPC476443
0.702	Intermediate Similarity	NPC266425
0.695	Remote Similarity	NPC150895
0.6923	Remote Similarity	NPC243704
0.6853	Remote Similarity	NPC208906
0.6853	Remote Similarity	NPC144745
0.6831	Remote Similarity	NPC28054
0.6803	Remote Similarity	NPC16922
0.6797	Remote Similarity	NPC132308
0.6786	Remote Similarity	NPC105249
0.6783	Remote Similarity	NPC45536
0.6779	Remote Similarity	NPC74612
0.6759	Remote Similarity	NPC473969
0.6735	Remote Similarity	NPC26285
0.6735	Remote Similarity	NPC477967
0.6735	Remote Similarity	NPC317217
0.6725	Remote Similarity	NPC471648
0.6711	Remote Similarity	NPC179354
0.671	Remote Similarity	NPC196708
0.6667	Remote Similarity	NPC46536
0.6667	Remote Similarity	NPC23086
0.6667	Remote Similarity	NPC45389
0.6667	Remote Similarity	NPC138139
0.6644	Remote Similarity	NPC477965
0.6644	Remote Similarity	NPC65735
0.6644	Remote Similarity	NPC477038
0.6644	Remote Similarity	NPC188377
0.6624	Remote Similarity	NPC471316
0.6623	Remote Similarity	NPC83178
0.6622	Remote Similarity	NPC471549
0.6622	Remote Similarity	NPC473379
0.6621	Remote Similarity	NPC131801
0.66	Remote Similarity	NPC75557
0.66	Remote Similarity	NPC71274
0.6597	Remote Similarity	NPC205523
0.6579	Remote Similarity	NPC476917
0.6579	Remote Similarity	NPC477123
0.6579	Remote Similarity	NPC477966
0.6579	Remote Similarity	NPC477039
0.6579	Remote Similarity	NPC327527
0.6579	Remote Similarity	NPC112706
0.6579	Remote Similarity	NPC207294
0.6579	Remote Similarity	NPC477040
0.6571	Remote Similarity	NPC471521
0.6571	Remote Similarity	NPC473356
0.6561	Remote Similarity	NPC281104
0.6561	Remote Similarity	NPC106606
0.6558	Remote Similarity	NPC477645
0.6556	Remote Similarity	NPC474260
0.6556	Remote Similarity	NPC81912
0.6556	Remote Similarity	NPC329694
0.6556	Remote Similarity	NPC329922
0.6533	Remote Similarity	NPC243269
0.6533	Remote Similarity	NPC118853
0.6531	Remote Similarity	NPC137710
0.6525	Remote Similarity	NPC177331
0.6524	Remote Similarity	NPC214239
0.6517	Remote Similarity	NPC27887
0.6513	Remote Similarity	NPC305717
0.6513	Remote Similarity	NPC476016
0.6508	Remote Similarity	NPC41216
0.6507	Remote Similarity	NPC217180
0.6507	Remote Similarity	NPC312525
0.6506	Remote Similarity	NPC119669
0.6497	Remote Similarity	NPC222524
0.6494	Remote Similarity	NPC476925
0.649	Remote Similarity	NPC471074
0.649	Remote Similarity	NPC473885
0.649	Remote Similarity	NPC474829
0.649	Remote Similarity	NPC471559
0.6471	Remote Similarity	NPC474279
0.6471	Remote Similarity	NPC474438
0.6467	Remote Similarity	NPC476351
0.6452	Remote Similarity	NPC61788
0.6452	Remote Similarity	NPC298190
0.6452	Remote Similarity	NPC89133
0.6443	Remote Similarity	NPC115859
0.6443	Remote Similarity	NPC79557
0.6442	Remote Similarity	NPC469978
0.6429	Remote Similarity	NPC59502
0.6429	Remote Similarity	NPC471650
0.6417	Remote Similarity	NPC112937
0.6413	Remote Similarity	NPC473004
0.6405	Remote Similarity	NPC95567
0.6405	Remote Similarity	NPC474830
0.6405	Remote Similarity	NPC319140
0.64	Remote Similarity	NPC283284
0.64	Remote Similarity	NPC289911
0.6398	Remote Similarity	NPC174783
0.6398	Remote Similarity	NPC477258
0.6395	Remote Similarity	NPC153631
0.6395	Remote Similarity	NPC212918
0.6389	Remote Similarity	NPC1811
0.6389	Remote Similarity	NPC26157
0.6386	Remote Similarity	NPC469540
0.6386	Remote Similarity	NPC469539
0.6369	Remote Similarity	NPC327005
0.6369	Remote Similarity	NPC218838
0.6369	Remote Similarity	NPC471006
0.6369	Remote Similarity	NPC169766
0.6369	Remote Similarity	NPC470740
0.6358	Remote Similarity	NPC475818
0.6358	Remote Similarity	NPC471652
0.6343	Remote Similarity	NPC284842
0.6341	Remote Similarity	NPC189908
0.6339	Remote Similarity	NPC477259
0.6339	Remote Similarity	NPC169387
0.6333	Remote Similarity	NPC474136
0.6333	Remote Similarity	NPC1848
0.6323	Remote Similarity	NPC283079
0.6316	Remote Similarity	NPC285394
0.6316	Remote Similarity	NPC93653
0.6312	Remote Similarity	NPC310830
0.6312	Remote Similarity	NPC42400
0.631	Remote Similarity	NPC476579
0.6306	Remote Similarity	NPC473344
0.6306	Remote Similarity	NPC471817
0.6306	Remote Similarity	NPC473982
0.6306	Remote Similarity	NPC471544
0.6304	Remote Similarity	NPC473008
0.6301	Remote Similarity	NPC252004
0.6299	Remote Similarity	NPC137570
0.6291	Remote Similarity	NPC36255
0.6291	Remote Similarity	NPC263870
0.6289	Remote Similarity	NPC92941
0.6289	Remote Similarity	NPC476947
0.6289	Remote Similarity	NPC158525
0.6287	Remote Similarity	NPC470088
0.6278	Remote Similarity	NPC288305
0.6276	Remote Similarity	NPC22678
0.6273	Remote Similarity	NPC220094
0.6273	Remote Similarity	NPC476943
0.6267	Remote Similarity	NPC474817
0.6264	Remote Similarity	NPC473007
0.6264	Remote Similarity	NPC476569
0.625	Remote Similarity	NPC272899
0.625	Remote Similarity	NPC307682
0.625	Remote Similarity	NPC46896
0.625	Remote Similarity	NPC146872
0.6243	Remote Similarity	NPC135006
0.6243	Remote Similarity	NPC26353
0.6242	Remote Similarity	NPC130926
0.6242	Remote Similarity	NPC206007
0.6242	Remote Similarity	NPC87466
0.6242	Remote Similarity	NPC293424
0.6236	Remote Similarity	NPC67978
0.6236	Remote Similarity	NPC303581
0.6234	Remote Similarity	NPC470858
0.623	Remote Similarity	NPC311781
0.6229	Remote Similarity	NPC35345
0.6228	Remote Similarity	NPC7467
0.6225	Remote Similarity	NPC97566
0.6222	Remote Similarity	NPC35680
0.6221	Remote Similarity	NPC475326
0.6216	Remote Similarity	NPC79202
0.6216	Remote Similarity	NPC59035
0.6216	Remote Similarity	NPC316062
0.6216	Remote Similarity	NPC208890
0.6211	Remote Similarity	NPC470742
0.6211	Remote Similarity	NPC215109
0.6211	Remote Similarity	NPC170604
0.6211	Remote Similarity	NPC307401
0.6209	Remote Similarity	NPC130275
0.6209	Remote Similarity	NPC83115
0.6203	Remote Similarity	NPC470392
0.62	Remote Similarity	NPC4898
0.6198	Remote Similarity	NPC232533
0.6198	Remote Similarity	NPC97086
0.6198	Remote Similarity	NPC243483
0.6198	Remote Similarity	NPC140577
0.6198	Remote Similarity	NPC67346
0.6198	Remote Similarity	NPC43069
0.6197	Remote Similarity	NPC42471
0.6194	Remote Similarity	NPC246392
0.6194	Remote Similarity	NPC290955
0.6194	Remote Similarity	NPC473355
0.6194	Remote Similarity	NPC471501
0.6194	Remote Similarity	NPC141059
0.6194	Remote Similarity	NPC471573
0.6194	Remote Similarity	NPC471554
0.6188	Remote Similarity	NPC475828

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 NPC26589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	616
0.2-0.3	987
0.3-0.4	2273
0.4-0.5	3106
0.5-0.6	1733
0.6-0.7	239
0.7-0.8	6
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
0.7365	Intermediate Similarity	NPD3142	Approved
0.7365	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3140	Approved
0.6988	Remote Similarity	NPD6862	Phase 2
0.6962	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3446	Phase 1
0.6807	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1670	Discontinued
0.679	Remote Similarity	NPD3639	Approved
0.679	Remote Similarity	NPD3641	Approved
0.679	Remote Similarity	NPD3640	Phase 3
0.6788	Remote Similarity	NPD7577	Discontinued
0.6774	Remote Similarity	NPD743	Approved
0.6707	Remote Similarity	NPD5977	Approved
0.6707	Remote Similarity	NPD5978	Approved
0.6706	Remote Similarity	NPD5262	Discontinued
0.6687	Remote Similarity	NPD7317	Phase 3
0.6667	Remote Similarity	NPD2592	Discontinued
0.6627	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7318	Phase 3
0.6585	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5688	Approved
0.6561	Remote Similarity	NPD2569	Approved
0.6561	Remote Similarity	NPD2567	Approved
0.6561	Remote Similarity	NPD5689	Approved
0.6538	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1309	Phase 2
0.6529	Remote Similarity	NPD1307	Phase 2
0.6517	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6039	Approved
0.6488	Remote Similarity	NPD6844	Discontinued
0.6485	Remote Similarity	NPD3873	Phase 3
0.6485	Remote Similarity	NPD3869	Phase 3
0.6484	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4466	Phase 1
0.6456	Remote Similarity	NPD2200	Suspended
0.6453	Remote Similarity	NPD3862	Approved
0.6453	Remote Similarity	NPD3861	Approved
0.6447	Remote Similarity	NPD4098	Discontinued
0.6444	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4618	Approved
0.6433	Remote Similarity	NPD4622	Approved
0.6429	Remote Similarity	NPD5889	Approved
0.6429	Remote Similarity	NPD6386	Approved
0.6429	Remote Similarity	NPD5890	Approved
0.6429	Remote Similarity	NPD7291	Discontinued
0.6429	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6385	Approved
0.642	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2594	Approved
0.6419	Remote Similarity	NPD2595	Approved
0.64	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5313	Approved
0.6384	Remote Similarity	NPD5312	Approved
0.6379	Remote Similarity	NPD5186	Approved
0.6379	Remote Similarity	NPD5183	Approved
0.6374	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4662	Approved
0.6364	Remote Similarity	NPD4661	Approved
0.6359	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2904	Discontinued
0.6353	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3656	Approved
0.6331	Remote Similarity	NPD4424	Discontinued
0.6331	Remote Similarity	NPD4773	Phase 2
0.6331	Remote Similarity	NPD4772	Phase 2
0.6322	Remote Similarity	NPD2249	Approved
0.6322	Remote Similarity	NPD2247	Approved
0.6319	Remote Similarity	NPD6748	Discontinued
0.6316	Remote Similarity	NPD6321	Discontinued
0.6316	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5157	Phase 1
0.6316	Remote Similarity	NPD5159	Phase 2
0.6307	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4475	Approved
0.6306	Remote Similarity	NPD4474	Approved
0.6306	Remote Similarity	NPD7713	Phase 3
0.6299	Remote Similarity	NPD2987	Approved
0.6299	Remote Similarity	NPD2990	Approved
0.6296	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7427	Discontinued
0.6284	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6585	Discontinued
0.6264	Remote Similarity	NPD6618	Phase 2
0.6264	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4107	Approved
0.625	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1241	Discontinued
0.623	Remote Similarity	NPD4482	Phase 3
0.6229	Remote Similarity	NPD6107	Approved
0.6224	Remote Similarity	NPD5914	Approved
0.6222	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5967	Approved
0.6213	Remote Similarity	NPD2649	Approved
0.6213	Remote Similarity	NPD824	Approved
0.6213	Remote Similarity	NPD2651	Approved
0.6211	Remote Similarity	NPD7811	Phase 3
0.6211	Remote Similarity	NPD7810	Phase 3
0.6209	Remote Similarity	NPD1420	Approved
0.6209	Remote Similarity	NPD1421	Approved
0.6201	Remote Similarity	NPD4503	Phase 2
0.62	Remote Similarity	NPD6382	Discontinued
0.6199	Remote Similarity	NPD6280	Approved
0.6199	Remote Similarity	NPD6279	Approved
0.6198	Remote Similarity	NPD3533	Approved
0.6198	Remote Similarity	NPD2491	Approved
0.6198	Remote Similarity	NPD3448	Approved
0.6198	Remote Similarity	NPD3057	Approved
0.6198	Remote Similarity	NPD2972	Approved
0.6196	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5564	Approved
0.6186	Remote Similarity	NPD8161	Suspended
0.6184	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD5746	Approved
0.6173	Remote Similarity	NPD3156	Discontinued
0.6171	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4584	Approved
0.6159	Remote Similarity	NPD44	Approved
0.6159	Remote Similarity	NPD2654	Approved
0.6159	Remote Similarity	NPD6364	Approved
0.6158	Remote Similarity	NPD5242	Approved
0.6154	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD3153	Approved
0.6141	Remote Similarity	NPD3154	Approved
0.614	Remote Similarity	NPD6873	Phase 2
0.6136	Remote Similarity	NPD2680	Approved
0.6136	Remote Similarity	NPD2681	Approved
0.6133	Remote Similarity	NPD3823	Discontinued
0.6133	Remote Similarity	NPD2486	Discontinued
0.6126	Remote Similarity	NPD6874	Approved
0.6124	Remote Similarity	NPD2248	Approved
0.6124	Remote Similarity	NPD6894	Phase 1
0.6124	Remote Similarity	NPD2246	Approved
0.6118	Remote Similarity	NPD3294	Phase 2
0.6117	Remote Similarity	NPD6181	Discontinued
0.6111	Remote Similarity	NPD5676	Approved
0.6111	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD3124	Discontinued
0.6108	Remote Similarity	NPD7598	Phase 2
0.6105	Remote Similarity	NPD5355	Approved
0.6105	Remote Similarity	NPD5356	Approved
0.6103	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4166	Phase 2
0.6101	Remote Similarity	NPD5745	Approved
0.6099	Remote Similarity	NPD1298	Discontinued
0.6098	Remote Similarity	NPD3912	Discontinued
0.6098	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7131	Phase 3
0.6087	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7556	Discontinued
0.6076	Remote Similarity	NPD5163	Phase 2
0.6075	Remote Similarity	NPD7693	Approved
0.6074	Remote Similarity	NPD2240	Approved
0.6074	Remote Similarity	NPD4476	Approved
0.6074	Remote Similarity	NPD2239	Approved
0.6074	Remote Similarity	NPD1725	Approved
0.6074	Remote Similarity	NPD4477	Approved
0.6071	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2335	Discontinued
0.6067	Remote Similarity	NPD2388	Discontinued
0.6066	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD2199	Approved
0.6065	Remote Similarity	NPD2198	Approved
0.6062	Remote Similarity	NPD3373	Approved
0.6061	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2667	Approved
0.6053	Remote Similarity	NPD2668	Approved
0.6043	Remote Similarity	NPD4258	Approved
0.6043	Remote Similarity	NPD4259	Approved
0.6038	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD2186	Approved
0.6033	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7627	Approved
0.6031	Remote Similarity	NPD7626	Approved
0.6029	Remote Similarity	NPD3437	Discontinued
0.6026	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6357	Discontinued
0.6023	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3965	Phase 1
0.602	Remote Similarity	NPD5293	Phase 2
0.6012	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD3170	Approved

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