NPASS Compound

Structure

NPC476365 OpenBabel07101719152D 49 53 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 43 1 0 0 0 0 3 44 1 0 0 0 0 4 45 1 0 0 0 0 5 46 1 0 0 0 0 6 9 1 0 0 0 0 6 19 2 0 0 0 0 7 10 2 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 28 1 0 0 0 0 13 21 2 0 0 0 0 13 30 1 0 0 0 0 14 21 1 0 0 0 0 14 31 2 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 29 2 0 0 0 0 17 26 1 0 0 0 0 17 27 1 0 0 0 0 18 47 1 0 0 0 0 19 36 1 0 0 0 0 20 34 1 0 0 0 0 22 37 1 0 0 0 0 23 38 1 0 0 0 0 24 28 2 0 0 0 0 24 39 1 0 0 0 0 25 33 2 0 0 0 0 25 40 1 0 0 0 0 26 33 1 0 0 0 0 26 41 2 0 0 0 0 27 21 1 6 0 0 0 27 48 1 0 0 0 0 28 43 1 0 0 0 0 29 33 1 0 0 0 0 29 48 1 0 0 0 0 30 35 2 0 0 0 0 30 44 1 0 0 0 0 31 35 1 0 0 0 0 31 45 1 0 0 0 0 32 18 1 6 0 0 0 32 34 1 0 0 0 0 32 49 1 0 0 0 0 34 46 1 6 0 0 0 35 49 1 0 0 0 0 36 42 2 0 0 0 0 36 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.22
Volume:	665.792
LogP:	4.72
LogD:	3.435
LogS:	-4.136
# Rotatable Bonds:	14
TPSA:	179.67
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.128
Synthetic Accessibility Score:	4.12
Fsp3:	0.278
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.931
MDCK Permeability:	4.255798921803944e-05
Pgp-inhibitor:	0.614
Pgp-substrate:	0.159
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	91.40343475341797%
Volume Distribution (VD):	0.474
Pgp-substrate:	11.524324417114258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.416
CYP2D6-substrate:	0.524
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	11.662
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.931
Carcinogencity:	0.178
Eye Corrosion:	0.003
Eye Irritation:	0.866
Respiratory Toxicity:	0.188

Download Data

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

Natural Product: NPC476365

Natural Product ID:	NPC476365
*Common Name:**	Quiquelignan B
IUPAC Name:	[(2R,3S)-2-[4-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-2,6-dimethoxyphenoxy]-3-ethoxy-3-(4-hydroxy-3-methoxyphenyl)propyl] 4-hydroxybenzoate
Synonyms:	Quiquelignan B
Standard InCHIKey:	YYWLXVXQUMWOMA-YBLXTWFBSA-N
Standard InCHI:	InChI=1S/C36H36O13/c1-5-46-34(20-8-11-24(39)28(12-20)43-2)32(18-47-36(42)19-6-9-22(37)10-7-19)49-35-30(44-3)13-21(14-31(35)45-4)27-17-26(41)33-25(40)15-23(38)16-29(33)48-27/h6-16,27,32,34,37-40H,5,17-18H2,1-4H3/t27-,32+,34-/m0/s1
SMILES:	CCO[C@@H](c1ccc(c(c1)OC)O)[C@H](Oc1c(OC)cc(cc1OC)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)COC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL589759
PubChem CID:	46232230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

*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
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20056545]
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20825224]

☑ 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	4
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	36000.0	nM	PMID[496482]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	85.0	%	PMID[496482]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19900.0	nM	PMID[496482]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43300.0	nM	PMID[496482]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[496482]

☑ 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 NPC476365 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	387
0.1-0.2	1621
0.2-0.3	3981
0.3-0.4	8984
0.4-0.5	9184
0.5-0.6	3597
0.6-0.7	4735
0.7-0.8	5480
0.8-0.85	2845
0.85-0.9	1633
0.9-0.95	243
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC477840
0.9571	High Similarity	NPC476370
0.9518	High Similarity	NPC471030
0.9512	High Similarity	NPC476374
0.95	High Similarity	NPC219927
0.95	High Similarity	NPC476372
0.95	High Similarity	NPC477841
0.95	High Similarity	NPC476371
0.9448	High Similarity	NPC475212
0.9437	High Similarity	NPC158188
0.9375	High Similarity	NPC53889
0.9375	High Similarity	NPC476373
0.9345	High Similarity	NPC117668
0.9317	High Similarity	NPC66618
0.9317	High Similarity	NPC113163
0.9317	High Similarity	NPC288131
0.9317	High Similarity	NPC305987
0.9317	High Similarity	NPC165970
0.9317	High Similarity	NPC84324
0.9313	High Similarity	NPC87317
0.9294	High Similarity	NPC104910
0.9294	High Similarity	NPC474093
0.9277	High Similarity	NPC172033
0.9277	High Similarity	NPC472993
0.9277	High Similarity	NPC175230
0.9277	High Similarity	NPC88560
0.9273	High Similarity	NPC180768
0.9268	High Similarity	NPC14662
0.9268	High Similarity	NPC243877
0.9268	High Similarity	NPC473818
0.9264	High Similarity	NPC7154
0.9264	High Similarity	NPC72787
0.9264	High Similarity	NPC7688
0.9264	High Similarity	NPC36
0.9264	High Similarity	NPC471788
0.9264	High Similarity	NPC125039
0.9264	High Similarity	NPC36916
0.9264	High Similarity	NPC58223
0.9259	High Similarity	NPC476247
0.9255	High Similarity	NPC101731
0.925	High Similarity	NPC114179
0.925	High Similarity	NPC156818
0.925	High Similarity	NPC38779
0.925	High Similarity	NPC160512
0.925	High Similarity	NPC68324
0.925	High Similarity	NPC289322
0.924	High Similarity	NPC475179
0.9217	High Similarity	NPC81332
0.9217	High Similarity	NPC262580
0.9217	High Similarity	NPC212038
0.9217	High Similarity	NPC289396
0.9217	High Similarity	NPC67134
0.9217	High Similarity	NPC271848
0.9217	High Similarity	NPC47140
0.9198	High Similarity	NPC142252
0.9198	High Similarity	NPC112418
0.9193	High Similarity	NPC476410
0.9193	High Similarity	NPC172202
0.9193	High Similarity	NPC284127
0.9187	High Similarity	NPC88803
0.9187	High Similarity	NPC104983
0.9187	High Similarity	NPC250436
0.9187	High Similarity	NPC291948
0.9187	High Similarity	NPC300845
0.9182	High Similarity	NPC469888
0.9182	High Similarity	NPC18727
0.9176	High Similarity	NPC199172
0.9176	High Similarity	NPC35924
0.9162	High Similarity	NPC98583
0.9157	High Similarity	NPC149011
0.9157	High Similarity	NPC204937
0.9146	High Similarity	NPC142614
0.9141	High Similarity	NPC471745
0.9136	High Similarity	NPC24164
0.9136	High Similarity	NPC471744
0.9136	High Similarity	NPC188967
0.913	High Similarity	NPC183
0.913	High Similarity	NPC222689
0.913	High Similarity	NPC63454
0.913	High Similarity	NPC108456
0.913	High Similarity	NPC183851
0.913	High Similarity	NPC112954
0.913	High Similarity	NPC291508
0.913	High Similarity	NPC35598
0.9128	High Similarity	NPC97817
0.9128	High Similarity	NPC65489
0.9128	High Similarity	NPC72554
0.9128	High Similarity	NPC30011
0.9123	High Similarity	NPC21359
0.9123	High Similarity	NPC25946
0.9123	High Similarity	NPC470720
0.9123	High Similarity	NPC470717
0.9123	High Similarity	NPC231254
0.9123	High Similarity	NPC470713
0.9123	High Similarity	NPC460984
0.9119	High Similarity	NPC219582
0.9119	High Similarity	NPC236637
0.9119	High Similarity	NPC302950
0.9119	High Similarity	NPC474656
0.9118	High Similarity	NPC469371
0.9112	High Similarity	NPC476619
0.9112	High Similarity	NPC139571
0.9112	High Similarity	NPC476622
0.9112	High Similarity	NPC477895
0.9112	High Similarity	NPC476621
0.9112	High Similarity	NPC476623
0.9112	High Similarity	NPC217520
0.9112	High Similarity	NPC476620
0.9112	High Similarity	NPC472387
0.9112	High Similarity	NPC476618
0.9102	High Similarity	NPC100251
0.9096	High Similarity	NPC476279
0.9091	High Similarity	NPC13481
0.9091	High Similarity	NPC171985
0.9091	High Similarity	NPC207575
0.9091	High Similarity	NPC320741
0.9091	High Similarity	NPC224851
0.9085	High Similarity	NPC272064
0.908	High Similarity	NPC471212
0.908	High Similarity	NPC26326
0.908	High Similarity	NPC471210
0.908	High Similarity	NPC471211
0.908	High Similarity	NPC472634
0.908	High Similarity	NPC264302
0.9074	High Similarity	NPC190487
0.9074	High Similarity	NPC154304
0.907	High Similarity	NPC295625
0.907	High Similarity	NPC473554
0.907	High Similarity	NPC470719
0.907	High Similarity	NPC112380
0.9068	High Similarity	NPC35038
0.9068	High Similarity	NPC278778
0.9068	High Similarity	NPC470328
0.9068	High Similarity	NPC291878
0.9068	High Similarity	NPC472626
0.9068	High Similarity	NPC318432
0.9068	High Similarity	NPC195796
0.9068	High Similarity	NPC209614
0.9064	High Similarity	NPC241781
0.9064	High Similarity	NPC470718
0.9064	High Similarity	NPC97119
0.9064	High Similarity	NPC135831
0.9064	High Similarity	NPC162394
0.9064	High Similarity	NPC156785
0.9064	High Similarity	NPC297503
0.9059	High Similarity	NPC185275
0.9059	High Similarity	NPC324742
0.9053	High Similarity	NPC472991
0.9053	High Similarity	NPC472992
0.9042	High Similarity	NPC51326
0.9042	High Similarity	NPC44328
0.9042	High Similarity	NPC177731
0.9042	High Similarity	NPC231194
0.9042	High Similarity	NPC105095
0.9042	High Similarity	NPC79056
0.9036	High Similarity	NPC260266
0.9036	High Similarity	NPC295082
0.9036	High Similarity	NPC116745
0.9036	High Similarity	NPC229729
0.9024	High Similarity	NPC472964
0.9024	High Similarity	NPC474033
0.9024	High Similarity	NPC474034
0.9024	High Similarity	NPC201800
0.9018	High Similarity	NPC472631
0.9018	High Similarity	NPC472630
0.9018	High Similarity	NPC119209
0.9018	High Similarity	NPC118256
0.9018	High Similarity	NPC192686
0.9017	High Similarity	NPC469649
0.9017	High Similarity	NPC260521
0.9012	High Similarity	NPC48208
0.9012	High Similarity	NPC210084
0.9012	High Similarity	NPC162869
0.9012	High Similarity	NPC223860
0.9012	High Similarity	NPC474055
0.9012	High Similarity	NPC471479
0.9012	High Similarity	NPC67876
0.9012	High Similarity	NPC185526
0.9012	High Similarity	NPC52530
0.9012	High Similarity	NPC249560
0.9012	High Similarity	NPC470416
0.9012	High Similarity	NPC299520
0.9012	High Similarity	NPC475267
0.9012	High Similarity	NPC474836
0.9012	High Similarity	NPC471515
0.9012	High Similarity	NPC129684
0.9012	High Similarity	NPC275977
0.9012	High Similarity	NPC156057
0.9012	High Similarity	NPC99597
0.9012	High Similarity	NPC472598
0.9012	High Similarity	NPC27337
0.9012	High Similarity	NPC474208
0.9006	High Similarity	NPC45849
0.9006	High Similarity	NPC200761
0.9006	High Similarity	NPC470327
0.9006	High Similarity	NPC226025
0.9006	High Similarity	NPC477503
0.9	High Similarity	NPC265380
0.9	High Similarity	NPC267549
0.9	High Similarity	NPC472912

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 NPC476365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	934
0.2-0.3	1815
0.3-0.4	2573
0.4-0.5	1823
0.5-0.6	986
0.6-0.7	464
0.7-0.8	147
0.8-0.85	28
0.85-0.9	24
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9264	High Similarity	NPD6168	Clinical (unspecified phase)
0.9264	High Similarity	NPD6167	Clinical (unspecified phase)
0.9264	High Similarity	NPD6166	Phase 2
0.9187	High Similarity	NPD4868	Clinical (unspecified phase)
0.9119	High Similarity	NPD1934	Approved
0.9102	High Similarity	NPD7993	Clinical (unspecified phase)
0.9042	High Similarity	NPD7074	Phase 3
0.8982	High Similarity	NPD7054	Approved
0.8944	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD7472	Approved
0.878	High Similarity	NPD7075	Discontinued
0.8773	High Similarity	NPD3817	Phase 2
0.8772	High Similarity	NPD7808	Phase 3
0.8713	High Similarity	NPD7251	Discontinued
0.8712	High Similarity	NPD2801	Approved
0.8698	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD7852	Clinical (unspecified phase)
0.8663	High Similarity	NPD4338	Clinical (unspecified phase)
0.8655	High Similarity	NPD6797	Phase 2
0.8606	High Similarity	NPD3882	Suspended
0.8598	High Similarity	NPD7819	Suspended
0.8598	High Similarity	NPD7096	Clinical (unspecified phase)
0.8589	High Similarity	NPD7411	Suspended
0.8554	High Similarity	NPD4381	Clinical (unspecified phase)
0.8545	High Similarity	NPD8443	Clinical (unspecified phase)
0.8538	High Similarity	NPD5844	Phase 1
0.8529	High Similarity	NPD7473	Discontinued
0.8528	High Similarity	NPD4380	Phase 2
0.8512	High Similarity	NPD6959	Discontinued
0.85	High Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD7768	Phase 2
0.8475	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6232	Discontinued
0.843	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD1465	Phase 2
0.8343	Intermediate Similarity	NPD5494	Approved
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8302	Intermediate Similarity	NPD1549	Phase 2
0.8272	Intermediate Similarity	NPD6799	Approved
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD5402	Approved
0.8192	Intermediate Similarity	NPD8312	Approved
0.8192	Intermediate Similarity	NPD8313	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD5403	Approved
0.8121	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD3749	Approved
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6599	Discontinued
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7199	Phase 2
0.7866	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD1240	Approved
0.7861	Intermediate Similarity	NPD919	Approved
0.7853	Intermediate Similarity	NPD7228	Approved
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7824	Intermediate Similarity	NPD8151	Discontinued
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7807	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7764	Intermediate Similarity	NPD1607	Approved
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7758	Intermediate Similarity	NPD4628	Phase 3
0.7751	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD943	Approved
0.775	Intermediate Similarity	NPD1613	Approved
0.7744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6190	Approved
0.7702	Intermediate Similarity	NPD447	Suspended
0.7663	Intermediate Similarity	NPD8150	Discontinued
0.7654	Intermediate Similarity	NPD3751	Discontinued
0.7627	Intermediate Similarity	NPD3787	Discontinued
0.7619	Intermediate Similarity	NPD7390	Discontinued
0.761	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD1933	Approved
0.7574	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD37	Approved
0.7571	Intermediate Similarity	NPD1247	Approved
0.7571	Intermediate Similarity	NPD8127	Discontinued
0.7565	Intermediate Similarity	NPD7435	Discontinued
0.7562	Intermediate Similarity	NPD3027	Phase 3
0.7561	Intermediate Similarity	NPD3748	Approved
0.7547	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4965	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7527	Intermediate Similarity	NPD5953	Discontinued
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD920	Approved
0.7475	Intermediate Similarity	NPD7783	Phase 2
0.7475	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD7266	Discontinued
0.744	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8166	Discontinued
0.7436	Intermediate Similarity	NPD7871	Phase 2
0.7436	Intermediate Similarity	NPD7870	Phase 2
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7399	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4908	Phase 1
0.7391	Intermediate Similarity	NPD7240	Approved
0.7386	Intermediate Similarity	NPD5353	Approved
0.7385	Intermediate Similarity	NPD7698	Approved
0.7385	Intermediate Similarity	NPD7696	Phase 3
0.7385	Intermediate Similarity	NPD7697	Approved
0.7381	Intermediate Similarity	NPD1243	Approved
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7549	Discontinued
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7348	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7701	Phase 2
0.7312	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD5405	Approved
0.7305	Intermediate Similarity	NPD5404	Approved
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD5406	Approved
0.7305	Intermediate Similarity	NPD5408	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7301	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7293	Intermediate Similarity	NPD5242	Approved
0.7278	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7584	Approved
0.7262	Intermediate Similarity	NPD2344	Approved
0.7259	Intermediate Similarity	NPD8320	Phase 1
0.7259	Intermediate Similarity	NPD8319	Approved
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD7229	Phase 3
0.7229	Intermediate Similarity	NPD6651	Approved
0.7222	Intermediate Similarity	NPD9494	Approved
0.7216	Intermediate Similarity	NPD6386	Approved
0.7216	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7216	Intermediate Similarity	NPD6385	Approved
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7214	Intermediate Similarity	NPD7801	Approved
0.7211	Intermediate Similarity	NPD4287	Approved
0.7208	Intermediate Similarity	NPD7680	Approved
0.7204	Intermediate Similarity	NPD7038	Approved
0.7204	Intermediate Similarity	NPD7039	Approved
0.7188	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7174	Intermediate Similarity	NPD7177	Discontinued
0.717	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD7003	Approved
0.7126	Intermediate Similarity	NPD6273	Approved
0.7125	Intermediate Similarity	NPD9269	Phase 2
0.7125	Intermediate Similarity	NPD9717	Approved
0.7093	Intermediate Similarity	NPD2309	Approved
0.7092	Intermediate Similarity	NPD8285	Discontinued
0.7092	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3268	Approved
0.7079	Intermediate Similarity	NPD6844	Discontinued
0.7076	Intermediate Similarity	NPD1652	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