NPASS Compound

Structure

NPC472632 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 -2.2212 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9965 2.5872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 -1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 1.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5482 0.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 1.1248 0.4659 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 0.0000 -2.0000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2553 1.6213 0.0000 C 0 0 0 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 10 15 2 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 16 20 1 0 0 0 0 16 25 2 0 0 0 0 17 21 2 0 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 15 1 1 0 0 0 19 32 1 0 0 0 0 20 33 1 0 0 0 0 21 31 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 25 30 1 0 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.2
Volume:	464.466
LogP:	5.092
LogD:	3.487
LogS:	-3.683
# Rotatable Bonds:	5
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	4.123
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	1.3920071978645865e-05
Pgp-inhibitor:	0.52
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	92.21261596679688%
Volume Distribution (VD):	0.97
Pgp-substrate:	9.12818431854248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.585
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.518
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	16.954
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.442
Skin Sensitization:	0.537
Carcinogencity:	0.536
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC472632

Natural Product ID:	NPC472632
*Common Name:**	KGEXXFMIHPTSAT-YQFJPLGNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KGEXXFMIHPTSAT-YQFJPLGNSA-N
Standard InCHI:	InChI=1S/C26H30O7/c1-14(2)6-5-9-26(3)23(29)11-16-20(33-26)13-22-24(25(16)30)18(28)12-19(32-22)15-7-8-17(27)21(10-15)31-4/h6-8,10,13,19,23,27,29-30H,5,9,11-12H2,1-4H3/t19-,23?,26?/m0/s1
SMILES:	CC(=CCCC1(C(CC2=C(C3=C(C=C2O1)OC(CC3=O)C4=CC(=C(C=C4)O)OC)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581352
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	<	10000.0	nM	PMID[453860]

☑ 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 NPC472632 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	404
0.1-0.2	1607
0.2-0.3	3952
0.3-0.4	9751
0.4-0.5	8513
0.5-0.6	3392
0.6-0.7	4798
0.7-0.8	5434
0.8-0.85	2880
0.85-0.9	1525
0.9-0.95	363
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC474033
0.9935	High Similarity	NPC474034
0.9934	High Similarity	NPC174953
0.9869	High Similarity	NPC474038
0.9869	High Similarity	NPC471210
0.9868	High Similarity	NPC473990
0.9804	High Similarity	NPC118256
0.9804	High Similarity	NPC192686
0.9804	High Similarity	NPC119209
0.9804	High Similarity	NPC475784
0.9803	High Similarity	NPC27337
0.9803	High Similarity	NPC471209
0.9803	High Similarity	NPC472598
0.9803	High Similarity	NPC474055
0.9744	High Similarity	NPC471213
0.9742	High Similarity	NPC472625
0.974	High Similarity	NPC471211
0.974	High Similarity	NPC472634
0.974	High Similarity	NPC471212
0.974	High Similarity	NPC26326
0.974	High Similarity	NPC134783
0.9737	High Similarity	NPC35038
0.9737	High Similarity	NPC195796
0.9737	High Similarity	NPC278778
0.9737	High Similarity	NPC291878
0.9679	High Similarity	NPC293319
0.9679	High Similarity	NPC62261
0.9677	High Similarity	NPC472635
0.9677	High Similarity	NPC476247
0.9675	High Similarity	NPC282009
0.9675	High Similarity	NPC287328
0.9675	High Similarity	NPC472624
0.9675	High Similarity	NPC472630
0.9675	High Similarity	NPC472631
0.9673	High Similarity	NPC284820
0.9673	High Similarity	NPC473272
0.9673	High Similarity	NPC291508
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9671	High Similarity	NPC321779
0.9615	High Similarity	NPC186686
0.9615	High Similarity	NPC124038
0.9613	High Similarity	NPC471499
0.9613	High Similarity	NPC142252
0.961	High Similarity	NPC22192
0.961	High Similarity	NPC117418
0.961	High Similarity	NPC53545
0.9608	High Similarity	NPC209614
0.9608	High Similarity	NPC470328
0.9608	High Similarity	NPC472626
0.9605	High Similarity	NPC192083
0.9605	High Similarity	NPC74924
0.9605	High Similarity	NPC18727
0.9605	High Similarity	NPC213896
0.9557	High Similarity	NPC474024
0.9557	High Similarity	NPC6588
0.9557	High Similarity	NPC477154
0.9557	High Similarity	NPC117854
0.9551	High Similarity	NPC474150
0.9551	High Similarity	NPC474162
0.9548	High Similarity	NPC470326
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC52889
0.9545	High Similarity	NPC223787
0.9542	High Similarity	NPC226025
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC106976
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC475790
0.9494	High Similarity	NPC43319
0.9487	High Similarity	NPC158188
0.9487	High Similarity	NPC289771
0.9487	High Similarity	NPC173137
0.9484	High Similarity	NPC74178
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC204879
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC184755
0.9481	High Similarity	NPC471985
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC470600
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9477	High Similarity	NPC298692
0.9474	High Similarity	NPC474021
0.9474	High Similarity	NPC474023
0.9434	High Similarity	NPC218226
0.9434	High Similarity	NPC477502
0.943	High Similarity	NPC224280
0.943	High Similarity	NPC36916
0.943	High Similarity	NPC58223
0.943	High Similarity	NPC108433
0.943	High Similarity	NPC36
0.943	High Similarity	NPC72787
0.943	High Similarity	NPC7154
0.943	High Similarity	NPC7688
0.943	High Similarity	NPC125039
0.943	High Similarity	NPC300053
0.9427	High Similarity	NPC220912
0.9427	High Similarity	NPC201800
0.9427	High Similarity	NPC83922
0.9427	High Similarity	NPC472448
0.9427	High Similarity	NPC472964
0.9423	High Similarity	NPC472902
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC470183
0.9423	High Similarity	NPC204290
0.9423	High Similarity	NPC471976
0.9423	High Similarity	NPC328102
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC67876
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC474681
0.9419	High Similarity	NPC218313
0.9419	High Similarity	NPC78071
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC234255
0.9416	High Similarity	NPC477958
0.9416	High Similarity	NPC256925
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC168247
0.9416	High Similarity	NPC152951
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC472912
0.9408	High Similarity	NPC338131
0.9379	High Similarity	NPC256760
0.9375	High Similarity	NPC288813
0.9375	High Similarity	NPC475212
0.9371	High Similarity	NPC236934
0.9371	High Similarity	NPC120593
0.9371	High Similarity	NPC5778
0.9371	High Similarity	NPC119589
0.9367	High Similarity	NPC248638
0.9367	High Similarity	NPC236521
0.9367	High Similarity	NPC152659
0.9363	High Similarity	NPC288131
0.9363	High Similarity	NPC349525
0.9363	High Similarity	NPC305987
0.9363	High Similarity	NPC228383
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC29876
0.9363	High Similarity	NPC167678
0.9363	High Similarity	NPC198829
0.9363	High Similarity	NPC66618
0.9363	High Similarity	NPC113163
0.9363	High Similarity	NPC84324
0.9363	High Similarity	NPC165970
0.9363	High Similarity	NPC3629
0.9359	High Similarity	NPC172202
0.9359	High Similarity	NPC284127
0.9359	High Similarity	NPC476410
0.9359	High Similarity	NPC187792
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC133970
0.9355	High Similarity	NPC6633
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC5322
0.9355	High Similarity	NPC24640
0.9355	High Similarity	NPC208152
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC282307
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC250922
0.9355	High Similarity	NPC170026
0.9355	High Similarity	NPC471500
0.9355	High Similarity	NPC78492
0.9355	High Similarity	NPC472455
0.9351	High Similarity	NPC33051
0.9351	High Similarity	NPC227337
0.9351	High Similarity	NPC223701
0.9351	High Similarity	NPC70433
0.9351	High Similarity	NPC49402
0.9351	High Similarity	NPC7989
0.9351	High Similarity	NPC273462
0.9351	High Similarity	NPC472583
0.9351	High Similarity	NPC170492
0.9346	High Similarity	NPC472422
0.9346	High Similarity	NPC472420
0.9346	High Similarity	NPC471676
0.9346	High Similarity	NPC244577
0.9346	High Similarity	NPC263384
0.9346	High Similarity	NPC471677
0.9321	High Similarity	NPC208668
0.9317	High Similarity	NPC103307
0.9317	High Similarity	NPC78734
0.9317	High Similarity	NPC150767
0.9317	High Similarity	NPC279209

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 NPC472632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	913
0.2-0.3	1781
0.3-0.4	2617
0.4-0.5	1813
0.5-0.6	993
0.6-0.7	482
0.7-0.8	142
0.8-0.85	28
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9539	High Similarity	NPD1934	Approved
0.943	High Similarity	NPD6166	Phase 2
0.943	High Similarity	NPD6167	Clinical (unspecified phase)
0.943	High Similarity	NPD6168	Clinical (unspecified phase)
0.9198	High Similarity	NPD7074	Phase 3
0.9136	High Similarity	NPD7054	Approved
0.9103	High Similarity	NPD2801	Approved
0.908	High Similarity	NPD7472	Approved
0.9032	High Similarity	NPD4380	Phase 2
0.8938	High Similarity	NPD5494	Approved
0.8909	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8855	High Similarity	NPD7251	Discontinued
0.8841	High Similarity	NPD3818	Discontinued
0.8802	High Similarity	NPD7808	Phase 3
0.8774	High Similarity	NPD1512	Approved
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD7075	Discontinued
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.869	High Similarity	NPD4338	Clinical (unspecified phase)
0.8688	High Similarity	NPD3817	Phase 2
0.8675	High Similarity	NPD7804	Clinical (unspecified phase)
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8563	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD6959	Discontinued
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD6801	Discontinued
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8312	Intermediate Similarity	NPD2796	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD5402	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7976	Intermediate Similarity	NPD919	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5401	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD2800	Approved
0.7811	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7661	Intermediate Similarity	NPD6234	Discontinued
0.7651	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7609	Intermediate Similarity	NPD4360	Phase 2
0.7609	Intermediate Similarity	NPD4363	Phase 3
0.7607	Intermediate Similarity	NPD6190	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.759	Intermediate Similarity	NPD920	Approved
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7574	Intermediate Similarity	NPD37	Approved
0.7547	Intermediate Similarity	NPD6651	Approved
0.7544	Intermediate Similarity	NPD4967	Phase 2
0.7544	Intermediate Similarity	NPD4965	Approved
0.7544	Intermediate Similarity	NPD4966	Approved
0.7539	Intermediate Similarity	NPD7584	Approved
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7486	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7455	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7453	Intermediate Similarity	NPD3748	Approved
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9494	Approved
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7423	Intermediate Similarity	NPD2424	Discontinued
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2344	Approved
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7240	Approved
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD3823	Discontinued
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7197	Intermediate Similarity	NPD1203	Approved
0.7196	Intermediate Similarity	NPD4361	Phase 2
0.7196	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2309	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD7585	Approved
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD7801	Approved
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7098	Intermediate Similarity	NPD2494	Approved
0.7098	Intermediate Similarity	NPD2493	Approved
0.7092	Intermediate Similarity	NPD7583	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7077	Intermediate Similarity	NPD8320	Phase 1
0.7077	Intermediate Similarity	NPD8319	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD4661	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