NPASS Compound

Structure

NPC176304 OpenBabel07101718302D 35 41 0 0 1 0 0 0 0 0999 V2000 4.8684 1.8852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 0.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6428 -0.7509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8794 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7415 -2.6350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8936 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8849 1.5717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0724 -3.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2026 -2.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2634 -1.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0659 -0.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4617 0.9717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2415 -1.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4672 0.8672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 1.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6482 -0.8554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 0.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0605 -0.0464 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.1588 -2.9714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -2.0443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 22 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 11 1 0 0 0 0 7 25 1 0 0 0 0 8 12 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 13 33 1 0 0 0 0 14 34 1 0 0 0 0 15 23 2 0 0 0 0 15 33 1 0 0 0 0 16 24 2 0 0 0 0 16 34 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 18 31 1 0 0 0 0 19 30 1 0 0 0 0 19 32 1 0 0 0 0 20 29 1 0 0 0 0 20 35 1 0 0 0 0 21 1 1 6 0 0 0 21 25 1 0 0 0 0 22 2 1 1 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 6 0 0 0 27 31 1 1 0 0 0 28 32 1 6 0 0 0 29 11 1 1 0 0 0 30 12 1 6 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.3
Volume:	515.078
LogP:	5.479
LogD:	4.868
LogS:	-5.047
# Rotatable Bonds:	2
TPSA:	32.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	6.09
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.95
MDCK Permeability:	6.998516255407594e-06
Pgp-inhibitor:	0.863
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.128
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	97.44184112548828%
Volume Distribution (VD):	0.804
Pgp-substrate:	2.445173740386963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.996
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	13.474
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.215
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.034
Carcinogencity:	0.854
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC176304

Natural Product ID:	NPC176304
*Common Name:**	Neothiobinupharidine
IUPAC Name:	n.a.
Synonyms:	Neothiobinupharidine
Standard InCHIKey:	WBMOHCBEBDKSBI-GUUMEGLWSA-N
Standard InCHI:	InChI=1S/C30H42N2O2S/c1-21-3-5-27(23-9-13-33-15-23)31-18-29(11-7-25(21)31)17-30(35-20-29)12-8-26-22(2)4-6-28(32(26)19-30)24-10-14-34-16-24/h9-10,13-16,21-22,25-28H,3-8,11-12,17-20H2,1-2H3/t21-,22-,25+,26+,27+,28+,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@H](N2[C@H]1CC[C@@]1(C2)CS[C@@]2(C1)CC[C@@H]1N(C2)[C@@H](CC[C@H]1C)c1cocc1)c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138622
PubChem CID:	12313251
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]

☑ 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	22

Activity Type	# Activity
Cell Line	22

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	11.9	%	PMID[481648]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	18.9	%	PMID[481648]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	33.2	%	PMID[481648]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	28.3	%	PMID[481648]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	-1.2	%	PMID[481649]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	40.1	%	PMID[481649]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	5.2	%	PMID[481649]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	50.7	%	PMID[481649]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	5.4	%	PMID[481649]
NPT466	Cell Line	U-937	Homo sapiens	Inhibition	=	65.6	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	4.4	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	-8.9	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	24.7	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	8.9	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	4.0	%	PMID[481649]
NPT169	Cell Line	B16-F10	Mus musculus	Inhibition	=	30.2	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-1.0	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-4.1	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	7.5	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-3.4	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	-0.8	%	PMID[481649]
NPT453	Cell Line	HT-1080	Homo sapiens	Inhibition	=	38.0	%	PMID[481649]

☑ 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 NPC176304 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	365
0.1-0.2	1594
0.2-0.3	5393
0.3-0.4	14756
0.4-0.5	16961
0.5-0.6	3453
0.6-0.7	159
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70840
1.0	High Similarity	NPC473245
0.9811	High Similarity	NPC469964
0.9811	High Similarity	NPC472474
0.9811	High Similarity	NPC476236
0.9571	High Similarity	NPC76433
0.9571	High Similarity	NPC289167
0.9571	High Similarity	NPC186957
0.9455	High Similarity	NPC297647
0.8269	Intermediate Similarity	NPC216149
0.8269	Intermediate Similarity	NPC208170
0.7927	Intermediate Similarity	NPC223873
0.7888	Intermediate Similarity	NPC26589
0.7888	Intermediate Similarity	NPC473444
0.7111	Intermediate Similarity	NPC471651
0.6949	Remote Similarity	NPC471649
0.6686	Remote Similarity	NPC471646
0.6686	Remote Similarity	NPC471647
0.6646	Remote Similarity	NPC28054
0.6564	Remote Similarity	NPC317217
0.6527	Remote Similarity	NPC476917
0.6527	Remote Similarity	NPC327527
0.6522	Remote Similarity	NPC243704
0.6506	Remote Similarity	NPC74612
0.6503	Remote Similarity	NPC133817
0.6503	Remote Similarity	NPC476443
0.6497	Remote Similarity	NPC189908
0.6485	Remote Similarity	NPC477965
0.6485	Remote Similarity	NPC477038
0.6463	Remote Similarity	NPC477967
0.645	Remote Similarity	NPC476925
0.6438	Remote Similarity	NPC150895
0.6433	Remote Similarity	NPC471006
0.6429	Remote Similarity	NPC477966
0.6429	Remote Similarity	NPC477039
0.6429	Remote Similarity	NPC477123
0.6429	Remote Similarity	NPC477040
0.6424	Remote Similarity	NPC16922
0.6402	Remote Similarity	NPC471648
0.6396	Remote Similarity	NPC471650
0.6358	Remote Similarity	NPC208906
0.6358	Remote Similarity	NPC144745
0.6347	Remote Similarity	NPC179354
0.6337	Remote Similarity	NPC266425
0.6316	Remote Similarity	NPC298190
0.631	Remote Similarity	NPC23086
0.631	Remote Similarity	NPC46536
0.631	Remote Similarity	NPC138139
0.628	Remote Similarity	NPC473969
0.6272	Remote Similarity	NPC83178
0.6262	Remote Similarity	NPC473005
0.6244	Remote Similarity	NPC268170
0.6235	Remote Similarity	NPC112706
0.6235	Remote Similarity	NPC207294
0.6221	Remote Similarity	NPC89133
0.6212	Remote Similarity	NPC149571
0.62	Remote Similarity	NPC45389
0.619	Remote Similarity	NPC65735
0.619	Remote Similarity	NPC83115
0.619	Remote Similarity	NPC243269
0.619	Remote Similarity	NPC188377
0.6188	Remote Similarity	NPC105249
0.6176	Remote Similarity	NPC95567
0.6176	Remote Similarity	NPC319140
0.6171	Remote Similarity	NPC92941
0.6168	Remote Similarity	NPC36255
0.6159	Remote Similarity	NPC131801
0.6159	Remote Similarity	NPC212918
0.6154	Remote Similarity	NPC71274
0.6154	Remote Similarity	NPC303010
0.6154	Remote Similarity	NPC41216
0.6154	Remote Similarity	NPC75557
0.6142	Remote Similarity	NPC27887
0.6136	Remote Similarity	NPC307682
0.6136	Remote Similarity	NPC146872
0.6127	Remote Similarity	NPC61788
0.6127	Remote Similarity	NPC477258
0.6127	Remote Similarity	NPC174783
0.6122	Remote Similarity	NPC222524
0.612	Remote Similarity	NPC214239
0.6118	Remote Similarity	NPC81912
0.6118	Remote Similarity	NPC329922
0.6118	Remote Similarity	NPC329694
0.6118	Remote Similarity	NPC474260
0.6102	Remote Similarity	NPC42400
0.6102	Remote Similarity	NPC470742
0.6102	Remote Similarity	NPC310830
0.6098	Remote Similarity	NPC45536
0.6092	Remote Similarity	NPC471817
0.6092	Remote Similarity	NPC473982
0.6089	Remote Similarity	NPC56197
0.6084	Remote Similarity	NPC4898
0.6082	Remote Similarity	NPC476016
0.6082	Remote Similarity	NPC137570
0.608	Remote Similarity	NPC128683
0.608	Remote Similarity	NPC476947
0.608	Remote Similarity	NPC473007
0.6077	Remote Similarity	NPC470741
0.6071	Remote Similarity	NPC471549
0.6071	Remote Similarity	NPC473379
0.607	Remote Similarity	NPC477259
0.607	Remote Similarity	NPC169387
0.6067	Remote Similarity	NPC476943
0.6067	Remote Similarity	NPC236532
0.6067	Remote Similarity	NPC220094
0.6066	Remote Similarity	NPC470999
0.6061	Remote Similarity	NPC312525
0.6061	Remote Similarity	NPC217180
0.6059	Remote Similarity	NPC473004
0.6059	Remote Similarity	NPC473885
0.6059	Remote Similarity	NPC230979
0.6059	Remote Similarity	NPC471074
0.6057	Remote Similarity	NPC218838
0.6057	Remote Similarity	NPC470740
0.6056	Remote Similarity	NPC20500
0.6047	Remote Similarity	NPC474438
0.6047	Remote Similarity	NPC474279
0.6047	Remote Similarity	NPC473006
0.6044	Remote Similarity	NPC142113
0.6037	Remote Similarity	NPC205523
0.6036	Remote Similarity	NPC476436
0.6036	Remote Similarity	NPC476351
0.6036	Remote Similarity	NPC272899
0.6034	Remote Similarity	NPC90953
0.602	Remote Similarity	NPC329731
0.602	Remote Similarity	NPC4910
0.6019	Remote Similarity	NPC163867
0.6012	Remote Similarity	NPC59502
0.6011	Remote Similarity	NPC471316
0.6011	Remote Similarity	NPC170604
0.6011	Remote Similarity	NPC307401
0.6011	Remote Similarity	NPC215109
0.601	Remote Similarity	NPC327005
0.601	Remote Similarity	NPC477526
0.6	Remote Similarity	NPC473356
0.6	Remote Similarity	NPC255861
0.6	Remote Similarity	NPC118853
0.6	Remote Similarity	NPC93574
0.6	Remote Similarity	NPC471007
0.6	Remote Similarity	NPC471521
0.6	Remote Similarity	NPC130275
0.6	Remote Similarity	NPC102760
0.5991	Remote Similarity	NPC38964
0.599	Remote Similarity	NPC471652
0.599	Remote Similarity	NPC112937
0.599	Remote Similarity	NPC100863
0.5989	Remote Similarity	NPC223415
0.5989	Remote Similarity	NPC158525
0.5988	Remote Similarity	NPC474830
0.5988	Remote Similarity	NPC137710
0.5981	Remote Similarity	NPC311781
0.598	Remote Similarity	NPC472358
0.5979	Remote Similarity	NPC284842
0.5978	Remote Similarity	NPC346
0.5978	Remote Similarity	NPC276676
0.5977	Remote Similarity	NPC21460
0.5976	Remote Similarity	NPC283284
0.5976	Remote Similarity	NPC289911
0.5976	Remote Similarity	NPC26285
0.5968	Remote Similarity	NPC471001
0.5967	Remote Similarity	NPC205765
0.5965	Remote Similarity	NPC471559
0.5965	Remote Similarity	NPC474829
0.5963	Remote Similarity	NPC177331
0.5961	Remote Similarity	NPC473008
0.5956	Remote Similarity	NPC199044
0.5956	Remote Similarity	NPC238843
0.5955	Remote Similarity	NPC281104
0.5955	Remote Similarity	NPC46896
0.5952	Remote Similarity	NPC243483
0.5952	Remote Similarity	NPC43069
0.5952	Remote Similarity	NPC97086
0.5952	Remote Similarity	NPC232533
0.5952	Remote Similarity	NPC140577
0.5952	Remote Similarity	NPC67346
0.5946	Remote Similarity	NPC470941
0.5946	Remote Similarity	NPC476937
0.5946	Remote Similarity	NPC476938
0.5946	Remote Similarity	NPC10088
0.5946	Remote Similarity	NPC250228
0.5944	Remote Similarity	NPC202260
0.5943	Remote Similarity	NPC477645
0.5943	Remote Similarity	NPC17681
0.5941	Remote Similarity	NPC475818
0.5941	Remote Similarity	NPC21425
0.5936	Remote Similarity	NPC476936
0.5936	Remote Similarity	NPC476122
0.5936	Remote Similarity	NPC196846
0.5936	Remote Similarity	NPC196864
0.5936	Remote Similarity	NPC477404
0.5934	Remote Similarity	NPC473152
0.5933	Remote Similarity	NPC120671
0.5933	Remote Similarity	NPC226652
0.5933	Remote Similarity	NPC72788
0.5933	Remote Similarity	NPC138830
0.5933	Remote Similarity	NPC314100
0.5928	Remote Similarity	NPC87466
0.5926	Remote Similarity	NPC471863
0.5924	Remote Similarity	NPC185456
0.5924	Remote Similarity	NPC56731

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 NPC176304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	657
0.2-0.3	995
0.3-0.4	2818
0.4-0.5	3397
0.5-0.6	1004
0.6-0.7	46
0.7-0.8	0
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
0.7207	Intermediate Similarity	NPD5262	Discontinued
0.7158	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3862	Approved
0.6685	Remote Similarity	NPD3861	Approved
0.6541	Remote Similarity	NPD6862	Phase 2
0.6529	Remote Similarity	NPD3140	Approved
0.6529	Remote Similarity	NPD3142	Approved
0.6467	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7577	Discontinued
0.6432	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5564	Approved
0.6396	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6598	Approved
0.6321	Remote Similarity	NPD6597	Approved
0.631	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5980	Discovery
0.625	Remote Similarity	NPD8161	Suspended
0.6231	Remote Similarity	NPD7291	Discontinued
0.6212	Remote Similarity	NPD6990	Approved
0.6212	Remote Similarity	NPD6989	Approved
0.6209	Remote Similarity	NPD6890	Discontinued
0.6203	Remote Similarity	NPD5978	Approved
0.6203	Remote Similarity	NPD5977	Approved
0.6188	Remote Similarity	NPD3124	Discontinued
0.6186	Remote Similarity	NPD4503	Phase 2
0.6185	Remote Similarity	NPD7713	Phase 3
0.6183	Remote Similarity	NPD7317	Phase 3
0.6183	Remote Similarity	NPD6844	Discontinued
0.6175	Remote Similarity	NPD3639	Approved
0.6175	Remote Similarity	NPD3640	Phase 3
0.6175	Remote Similarity	NPD3641	Approved
0.6169	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD3446	Phase 1
0.6165	Remote Similarity	NPD5228	Phase 3
0.6163	Remote Similarity	NPD6039	Approved
0.6162	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD6321	Discontinued
0.6134	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7318	Phase 3
0.6106	Remote Similarity	NPD7626	Approved
0.6106	Remote Similarity	NPD7627	Approved
0.6096	Remote Similarity	NPD5356	Approved
0.6096	Remote Similarity	NPD5355	Approved
0.6095	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1670	Discontinued
0.608	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6618	Phase 2
0.608	Remote Similarity	NPD4483	Discontinued
0.6049	Remote Similarity	NPD6834	Approved
0.6045	Remote Similarity	NPD743	Approved
0.6045	Remote Similarity	NPD5689	Approved
0.6045	Remote Similarity	NPD5688	Approved
0.6044	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD5890	Approved
0.6043	Remote Similarity	NPD5889	Approved
0.6039	Remote Similarity	NPD7811	Phase 3
0.6039	Remote Similarity	NPD7810	Phase 3
0.6033	Remote Similarity	NPD6390	Discontinued
0.6029	Remote Similarity	NPD4466	Phase 1
0.6022	Remote Similarity	NPD6748	Discontinued
0.602	Remote Similarity	NPD5313	Approved
0.602	Remote Similarity	NPD5312	Approved
0.601	Remote Similarity	NPD5186	Approved
0.601	Remote Similarity	NPD5183	Approved
0.601	Remote Similarity	NPD4107	Approved
0.6	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3802	Phase 3
0.6	Remote Similarity	NPD3873	Phase 3
0.6	Remote Similarity	NPD3869	Phase 3
0.6	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD5025	Approved
0.599	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4482	Phase 3
0.5978	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6250	Discontinued
0.5971	Remote Similarity	NPD3659	Discontinued
0.5969	Remote Similarity	NPD1309	Phase 2
0.5969	Remote Similarity	NPD1307	Phase 2
0.5969	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6385	Approved
0.5957	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6873	Phase 2
0.5957	Remote Similarity	NPD4424	Discontinued
0.5957	Remote Similarity	NPD6386	Approved
0.5955	Remote Similarity	NPD2569	Approved
0.5955	Remote Similarity	NPD2567	Approved
0.5953	Remote Similarity	NPD5676	Approved
0.5952	Remote Similarity	NPD3448	Approved
0.5952	Remote Similarity	NPD3057	Approved
0.5952	Remote Similarity	NPD2972	Approved
0.5952	Remote Similarity	NPD2491	Approved
0.5952	Remote Similarity	NPD3533	Approved
0.5949	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6894	Phase 1
0.5944	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD2512	Phase 3
0.5932	Remote Similarity	NPD4618	Approved
0.5932	Remote Similarity	NPD4622	Approved
0.593	Remote Similarity	NPD4098	Discontinued
0.5924	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD7598	Phase 2
0.5917	Remote Similarity	NPD7047	Phase 3
0.5914	Remote Similarity	NPD7427	Discontinued
0.5911	Remote Similarity	NPD7693	Approved
0.5909	Remote Similarity	NPD5485	Approved
0.5909	Remote Similarity	NPD5484	Approved
0.5905	Remote Similarity	NPD7162	Approved
0.5904	Remote Similarity	NPD2592	Discontinued
0.5904	Remote Similarity	NPD6585	Discontinued
0.589	Remote Similarity	NPD4989	Phase 2
0.589	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6874	Approved
0.588	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD44	Approved
0.5879	Remote Similarity	NPD6364	Approved
0.5876	Remote Similarity	NPD6107	Approved
0.5873	Remote Similarity	NPD4773	Phase 2
0.5873	Remote Similarity	NPD4772	Phase 2
0.5872	Remote Similarity	NPD4679	Discontinued
0.5872	Remote Similarity	NPD5293	Phase 2
0.5871	Remote Similarity	NPD7281	Phase 3
0.5871	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7280	Phase 3
0.5867	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD2200	Suspended
0.5865	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7298	Approved
0.5842	Remote Similarity	NPD7248	Discontinued
0.5842	Remote Similarity	NPD6280	Approved
0.5842	Remote Similarity	NPD6279	Approved
0.5837	Remote Similarity	NPD4420	Approved
0.5833	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.583	Remote Similarity	NPD6997	Phase 2
0.5825	Remote Similarity	NPD2904	Discontinued
0.5825	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD4474	Approved
0.5819	Remote Similarity	NPD4475	Approved
0.5815	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5159	Phase 2
0.5814	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5157	Phase 1
0.5808	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4661	Approved
0.5806	Remote Similarity	NPD4584	Approved
0.5806	Remote Similarity	NPD4662	Approved
0.5802	Remote Similarity	NPD5005	Approved
0.5802	Remote Similarity	NPD5006	Approved
0.5802	Remote Similarity	NPD7316	Discontinued
0.5799	Remote Similarity	NPD2595	Approved
0.5799	Remote Similarity	NPD6382	Discontinued
0.5799	Remote Similarity	NPD2594	Approved
0.5795	Remote Similarity	NPD2247	Approved
0.5795	Remote Similarity	NPD2249	Approved
0.5792	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6677	Suspended
0.5787	Remote Similarity	NPD1194	Discontinued
0.5785	Remote Similarity	NPD7556	Discontinued
0.5784	Remote Similarity	NPD7440	Discontinued
0.5784	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6891	Phase 2
0.5782	Remote Similarity	NPD5457	Discontinued
0.5781	Remote Similarity	NPD5967	Approved
0.5771	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3656	Approved
0.5767	Remote Similarity	NPD6357	Discontinued
0.5765	Remote Similarity	NPD7608	Discontinued
0.5765	Remote Similarity	NPD4166	Phase 2
0.576	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.576	Remote Similarity	NPD5914	Approved
0.5756	Remote Similarity	NPD5852	Approved
0.5756	Remote Similarity	NPD5851	Approved
0.5746	Remote Similarity	NPD6380	Phase 1
0.5745	Remote Similarity	NPD7131	Phase 3
0.5743	Remote Similarity	NPD8069	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data