NPASS Compound

Structure

NPC290030 OpenBabel07101718242D 30 31 0 0 0 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 1.7321 -1.0000 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 0.0000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 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 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 2.5981 3.5000 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 4.3301 3.5000 0.0000 C 0 0 0 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 2 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 18 20 2 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 27 2 0 0 0 0 23 25 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.21
Volume:	444.066
LogP:	5.718
LogD:	3.988
LogS:	-3.158
# Rotatable Bonds:	9
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	2.851
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.935
MDCK Permeability:	1.929671452671755e-05
Pgp-inhibitor:	0.498
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.18343353271484%
Volume Distribution (VD):	0.474
Pgp-substrate:	0.7471070289611816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.187
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.957
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.435
CYP3A4-substrate:	0.158

ADMET: Excretion

Clearance (CL):	11.314
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.325
Skin Sensitization:	0.954
Carcinogencity:	0.083
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC290030

Natural Product ID:	NPC290030
*Common Name:**	2-Geranyl-2',3,4,4'-Tetrahydroxydihyrochalcone
IUPAC Name:	1-(2,4-dihydroxyphenyl)-3-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]propan-1-one
Synonyms:
Standard InCHIKey:	FVNFXIPJDHVJGE-REZTVBANSA-N
Standard InCHI:	InChI=1S/C25H30O5/c1-16(2)5-4-6-17(3)7-11-20-18(9-14-23(28)25(20)30)8-13-22(27)21-12-10-19(26)15-24(21)29/h5,7,9-10,12,14-15,26,28-30H,4,6,8,11,13H2,1-3H3/b17-7+
SMILES:	C/C(=CCc1c(CCC(=O)c2ccc(cc2O)O)ccc(c1O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523392
PubChem CID:	6449829
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	bud covers	n.a.	n.a.	PMID[11975520]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[12662107]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8171	Artocarpus altilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8171	Artocarpus altilis	Species	Moraceae	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	5

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3595	Individual Protein	Cathepsin K	Homo sapiens	IC50	=	170.0	nM	PMID[460886]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	80600.0	nM	PMID[460887]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	42900.0	nM	PMID[460887]
NPT610	Others	Molecular identity unknown		IC50	=	23600.0	nM	PMID[460887]
NPT27	Others	Unspecified		IC50	>	75000.0	nM	PMID[460887]

☑ 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 NPC290030 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	367
0.1-0.2	1561
0.2-0.3	3877
0.3-0.4	11155
0.4-0.5	7593
0.5-0.6	4303
0.6-0.7	6209
0.7-0.8	6211
0.8-0.85	1184
0.85-0.9	206
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC472903
0.9701	High Similarity	NPC472904
0.9621	High Similarity	NPC194764
0.9621	High Similarity	NPC264112
0.9621	High Similarity	NPC65005
0.9466	High Similarity	NPC135801
0.9462	High Similarity	NPC26697
0.9462	High Similarity	NPC244441
0.9462	High Similarity	NPC233056
0.9389	High Similarity	NPC469526
0.9389	High Similarity	NPC34070
0.9385	High Similarity	NPC92624
0.9338	High Similarity	NPC203063
0.9328	High Similarity	NPC223836
0.9323	High Similarity	NPC282780
0.9323	High Similarity	NPC166480
0.9313	High Similarity	NPC259942
0.9137	High Similarity	NPC238629
0.9091	High Similarity	NPC85131
0.9084	High Similarity	NPC107672
0.9077	High Similarity	NPC477454
0.9065	High Similarity	NPC291078
0.9051	High Similarity	NPC175552
0.9028	High Similarity	NPC35
0.9008	High Similarity	NPC473691
0.9008	High Similarity	NPC8745
0.9	High Similarity	NPC13238
0.9	High Similarity	NPC471417
0.8986	High Similarity	NPC138099
0.8986	High Similarity	NPC242994
0.8971	High Similarity	NPC72918
0.8947	High Similarity	NPC109123
0.8947	High Similarity	NPC474998
0.8939	High Similarity	NPC100067
0.8939	High Similarity	NPC266689
0.8939	High Similarity	NPC169250
0.8939	High Similarity	NPC98254
0.8939	High Similarity	NPC103356
0.8939	High Similarity	NPC190043
0.8939	High Similarity	NPC30501
0.8939	High Similarity	NPC162612
0.8939	High Similarity	NPC72158
0.8939	High Similarity	NPC105157
0.8939	High Similarity	NPC23126
0.8931	High Similarity	NPC10926
0.8929	High Similarity	NPC301178
0.8929	High Similarity	NPC284556
0.8921	High Similarity	NPC181560
0.8921	High Similarity	NPC169452
0.8913	High Similarity	NPC416
0.8913	High Similarity	NPC61398
0.8913	High Similarity	NPC123714
0.8905	High Similarity	NPC191976
0.8905	High Similarity	NPC118919
0.8904	High Similarity	NPC472905
0.8897	High Similarity	NPC44437
0.8889	High Similarity	NPC175738
0.8881	High Similarity	NPC247477
0.8881	High Similarity	NPC17840
0.8872	High Similarity	NPC473017
0.8872	High Similarity	NPC21305
0.8872	High Similarity	NPC221777
0.8865	High Similarity	NPC287722
0.8865	High Similarity	NPC254659
0.8864	High Similarity	NPC267846
0.8864	High Similarity	NPC62952
0.8846	High Similarity	NPC32032
0.8846	High Similarity	NPC133909
0.8841	High Similarity	NPC170742
0.8841	High Similarity	NPC53414
0.8841	High Similarity	NPC471905
0.8841	High Similarity	NPC53206
0.8824	High Similarity	NPC294226
0.8824	High Similarity	NPC267205
0.8803	High Similarity	NPC142165
0.8797	High Similarity	NPC116513
0.8794	High Similarity	NPC193555
0.8794	High Similarity	NPC49108
0.8784	High Similarity	NPC472907
0.8776	High Similarity	NPC93552
0.8769	High Similarity	NPC19174
0.8769	High Similarity	NPC115159
0.8769	High Similarity	NPC45438
0.8769	High Similarity	NPC196976
0.8769	High Similarity	NPC224273
0.8769	High Similarity	NPC242895
0.8769	High Similarity	NPC143427
0.8769	High Similarity	NPC267552
0.8769	High Similarity	NPC156139
0.8769	High Similarity	NPC73532
0.8768	High Similarity	NPC254847
0.8759	High Similarity	NPC38545
0.8759	High Similarity	NPC171916
0.8741	High Similarity	NPC117609
0.8732	High Similarity	NPC119663
0.8725	High Similarity	NPC472963
0.8716	High Similarity	NPC67396
0.8716	High Similarity	NPC38898
0.8707	High Similarity	NPC474993
0.8707	High Similarity	NPC312338
0.8707	High Similarity	NPC149889
0.8705	High Similarity	NPC147418
0.8699	High Similarity	NPC48949
0.8699	High Similarity	NPC280295
0.8699	High Similarity	NPC472279
0.8696	High Similarity	NPC258502
0.8696	High Similarity	NPC129752
0.8692	High Similarity	NPC297186
0.8692	High Similarity	NPC248363
0.8692	High Similarity	NPC149246
0.869	High Similarity	NPC238279
0.869	High Similarity	NPC166036
0.869	High Similarity	NPC80710
0.869	High Similarity	NPC203747
0.869	High Similarity	NPC203077
0.869	High Similarity	NPC254702
0.869	High Similarity	NPC194653
0.869	High Similarity	NPC471907
0.869	High Similarity	NPC139364
0.8686	High Similarity	NPC139074
0.8686	High Similarity	NPC213485
0.8686	High Similarity	NPC40524
0.8681	High Similarity	NPC138978
0.8676	High Similarity	NPC475042
0.8671	High Similarity	NPC244691
0.8671	High Similarity	NPC38065
0.8671	High Similarity	NPC257025
0.8671	High Similarity	NPC207732
0.8671	High Similarity	NPC105213
0.8671	High Similarity	NPC242893
0.8662	High Similarity	NPC137649
0.8662	High Similarity	NPC135524
0.8658	High Similarity	NPC24640
0.8657	High Similarity	NPC156539
0.8649	High Similarity	NPC89474
0.8649	High Similarity	NPC107109
0.8647	High Similarity	NPC201728
0.8647	High Similarity	NPC262671
0.8639	High Similarity	NPC154345
0.8639	High Similarity	NPC256406
0.863	High Similarity	NPC264289
0.863	High Similarity	NPC92722
0.863	High Similarity	NPC102003
0.863	High Similarity	NPC200060
0.863	High Similarity	NPC69430
0.863	High Similarity	NPC333691
0.863	High Similarity	NPC195763
0.863	High Similarity	NPC264550
0.863	High Similarity	NPC139293
0.863	High Similarity	NPC142876
0.863	High Similarity	NPC40290
0.8621	High Similarity	NPC476463
0.8615	High Similarity	NPC159525
0.8611	High Similarity	NPC157133
0.8609	High Similarity	NPC474960
0.8609	High Similarity	NPC472902
0.8603	High Similarity	NPC147757
0.8601	High Similarity	NPC313047
0.8601	High Similarity	NPC474203
0.8601	High Similarity	NPC295712
0.8601	High Similarity	NPC451542
0.86	High Similarity	NPC136674
0.86	High Similarity	NPC273843
0.86	High Similarity	NPC37543
0.86	High Similarity	NPC199463
0.86	High Similarity	NPC178976
0.8593	High Similarity	NPC41263
0.8593	High Similarity	NPC179898
0.8593	High Similarity	NPC95537
0.8592	High Similarity	NPC305845
0.8592	High Similarity	NPC204045
0.8592	High Similarity	NPC110419
0.8592	High Similarity	NPC246638
0.8591	High Similarity	NPC56786
0.8591	High Similarity	NPC80534
0.8582	High Similarity	NPC472368
0.8582	High Similarity	NPC162939
0.8582	High Similarity	NPC471819
0.8582	High Similarity	NPC143438
0.8581	High Similarity	NPC323626
0.8581	High Similarity	NPC324233
0.8581	High Similarity	NPC237994
0.8571	High Similarity	NPC213603
0.8571	High Similarity	NPC88804
0.8571	High Similarity	NPC151473
0.8571	High Similarity	NPC472367
0.8571	High Similarity	NPC10467
0.8571	High Similarity	NPC53001
0.8571	High Similarity	NPC473391
0.8571	High Similarity	NPC476333
0.8571	High Similarity	NPC3825
0.8571	High Similarity	NPC472364
0.8562	High Similarity	NPC474903
0.8562	High Similarity	NPC131451
0.8562	High Similarity	NPC15329
0.8562	High Similarity	NPC287395
0.8562	High Similarity	NPC183655
0.8561	High Similarity	NPC309765
0.8561	High Similarity	NPC290803
0.8561	High Similarity	NPC70859

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 NPC290030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	962
0.2-0.3	1498
0.3-0.4	2872
0.4-0.5	1942
0.5-0.6	1054
0.6-0.7	363
0.7-0.8	108
0.8-0.85	12
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9466	High Similarity	NPD943	Approved
0.9044	High Similarity	NPD651	Clinical (unspecified phase)
0.8768	High Similarity	NPD1509	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD7390	Discontinued
0.8414	Intermediate Similarity	NPD1511	Approved
0.84	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8299	Intermediate Similarity	NPD1512	Approved
0.8289	Intermediate Similarity	NPD3882	Suspended
0.8278	Intermediate Similarity	NPD2801	Approved
0.8235	Intermediate Similarity	NPD1470	Approved
0.8214	Intermediate Similarity	NPD1240	Approved
0.8209	Intermediate Similarity	NPD1201	Approved
0.8148	Intermediate Similarity	NPD9269	Phase 2
0.8112	Intermediate Similarity	NPD1510	Phase 2
0.8099	Intermediate Similarity	NPD1607	Approved
0.8056	Intermediate Similarity	NPD5406	Approved
0.8056	Intermediate Similarity	NPD5405	Approved
0.8056	Intermediate Similarity	NPD5404	Approved
0.8056	Intermediate Similarity	NPD5408	Approved
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7473	Discontinued
0.7945	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6166	Phase 2
0.7922	Intermediate Similarity	NPD7819	Suspended
0.7902	Intermediate Similarity	NPD230	Phase 1
0.7895	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9268	Approved
0.7843	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7823	Intermediate Similarity	NPD1549	Phase 2
0.7756	Intermediate Similarity	NPD3817	Phase 2
0.7755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7074	Phase 3
0.7718	Intermediate Similarity	NPD3750	Approved
0.7714	Intermediate Similarity	NPD1164	Approved
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7687	Intermediate Similarity	NPD2935	Discontinued
0.7687	Intermediate Similarity	NPD2796	Approved
0.7682	Intermediate Similarity	NPD6799	Approved
0.7669	Intermediate Similarity	NPD7054	Approved
0.7658	Intermediate Similarity	NPD7075	Discontinued
0.7634	Intermediate Similarity	NPD3022	Approved
0.7634	Intermediate Similarity	NPD3021	Approved
0.7622	Intermediate Similarity	NPD7472	Approved
0.7616	Intermediate Similarity	NPD3300	Phase 2
0.7613	Intermediate Similarity	NPD6599	Discontinued
0.758	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6797	Phase 2
0.7562	Intermediate Similarity	NPD5494	Approved
0.7547	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3749	Approved
0.7532	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7251	Discontinued
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7464	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7452	Intermediate Similarity	NPD7411	Suspended
0.7423	Intermediate Similarity	NPD3926	Phase 2
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6801	Discontinued
0.74	Intermediate Similarity	NPD2344	Approved
0.7383	Intermediate Similarity	NPD3748	Approved
0.7381	Intermediate Similarity	NPD7808	Phase 3
0.7381	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3764	Approved
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD2800	Approved
0.7293	Intermediate Similarity	NPD9266	Approved
0.7293	Intermediate Similarity	NPD74	Approved
0.7292	Intermediate Similarity	NPD2798	Approved
0.7286	Intermediate Similarity	NPD3019	Approved
0.7286	Intermediate Similarity	NPD2932	Approved
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7262	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3027	Phase 3
0.7255	Intermediate Similarity	NPD8166	Discontinued
0.7255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6651	Approved
0.7246	Intermediate Similarity	NPD9493	Approved
0.7241	Intermediate Similarity	NPD9494	Approved
0.7239	Intermediate Similarity	NPD4750	Phase 3
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD6100	Approved
0.7218	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9264	Approved
0.7218	Intermediate Similarity	NPD9263	Approved
0.7218	Intermediate Similarity	NPD9267	Approved
0.7215	Intermediate Similarity	NPD3226	Approved
0.7208	Intermediate Similarity	NPD2309	Approved
0.7192	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD447	Suspended
0.7178	Intermediate Similarity	NPD919	Approved
0.7171	Intermediate Similarity	NPD2346	Discontinued
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6020	Phase 2
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7103	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD5402	Approved
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.7091	Intermediate Similarity	NPD1247	Approved
0.7089	Intermediate Similarity	NPD5403	Approved
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1243	Approved
0.7073	Intermediate Similarity	NPD6234	Discontinued
0.7039	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9545	Approved
0.7014	Intermediate Similarity	NPD3972	Approved
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6978	Remote Similarity	NPD9281	Approved
0.6975	Remote Similarity	NPD37	Approved
0.6962	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD5953	Discontinued
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3020	Approved
0.6946	Remote Similarity	NPD5711	Approved
0.6946	Remote Similarity	NPD5710	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1876	Approved
0.6917	Remote Similarity	NPD9261	Approved
0.6897	Remote Similarity	NPD9717	Approved
0.6894	Remote Similarity	NPD3455	Phase 2
0.6882	Remote Similarity	NPD3751	Discontinued
0.6879	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD920	Approved
0.6875	Remote Similarity	NPD3023	Approved
0.6867	Remote Similarity	NPD2313	Discontinued
0.6867	Remote Similarity	NPD3268	Approved
0.6859	Remote Similarity	NPD2654	Approved
0.6857	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3025	Approved
0.6853	Remote Similarity	NPD3024	Approved
0.6848	Remote Similarity	NPD4967	Phase 2
0.6848	Remote Similarity	NPD4965	Approved
0.6848	Remote Similarity	NPD4966	Approved
0.6846	Remote Similarity	NPD2859	Approved
0.6846	Remote Similarity	NPD2860	Approved
0.6846	Remote Similarity	NPD6832	Phase 2
0.6842	Remote Similarity	NPD7286	Phase 2
0.6842	Remote Similarity	NPD1933	Approved
0.6839	Remote Similarity	NPD1471	Phase 3
0.6839	Remote Similarity	NPD7266	Discontinued
0.6835	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5536	Phase 2
0.6824	Remote Similarity	NPD258	Approved
0.6824	Remote Similarity	NPD257	Approved
0.6815	Remote Similarity	NPD7003	Approved
0.6805	Remote Similarity	NPD5242	Approved
0.68	Remote Similarity	NPD4625	Phase 3
0.679	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD4288	Approved
0.6784	Remote Similarity	NPD7228	Approved
0.6781	Remote Similarity	NPD1608	Approved
0.6778	Remote Similarity	NPD6535	Approved
0.6778	Remote Similarity	NPD6534	Approved
0.6769	Remote Similarity	NPD2934	Approved
0.6769	Remote Similarity	NPD2933	Approved
0.6757	Remote Similarity	NPD2797	Approved
0.6755	Remote Similarity	NPD411	Approved
0.675	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3787	Discontinued
0.6738	Remote Similarity	NPD5951	Approved
0.6736	Remote Similarity	NPD1651	Approved
0.6735	Remote Similarity	NPD1755	Approved
0.6733	Remote Similarity	NPD4908	Phase 1
0.6732	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5031	Approved
0.6724	Remote Similarity	NPD5027	Approved
0.6724	Remote Similarity	NPD5029	Approved
0.6714	Remote Similarity	NPD7635	Approved
0.6712	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4308	Phase 3
0.6689	Remote Similarity	NPD1283	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