NPASS Compound

Structure

NPC87609 OpenBabel07101719252D 29 31 0 0 0 0 0 0 0 0999 V2000 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -3.4641 1.0000 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 4.3301 1.5000 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 3.4641 1.0000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 -2.5981 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 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 0.8660 -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 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 -1.7321 1.0000 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 -0.8660 2.5000 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 0.8660 -1.5000 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 1.7321 3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.16
Volume:	415.577
LogP:	5.725
LogD:	3.425
LogS:	-4.288
# Rotatable Bonds:	5
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	2.782
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.789
MDCK Permeability:	1.621983028599061e-05
Pgp-inhibitor:	0.663
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.731

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	96.25013732910156%
Volume Distribution (VD):	0.448
Pgp-substrate:	3.4820027351379395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.617
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	6.875
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.345
Carcinogencity:	0.17
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.453

Download Data

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

Natural Product: NPC87609

Natural Product ID:	NPC87609
*Common Name:**	Isomesuol
IUPAC Name:	5,7-dihydroxy-6-(3-methylbut-2-enyl)-8-(2-methylpropanoyl)-4-phenylchromen-2-one
Synonyms:	Isomesuol
Standard InCHIKey:	HFESPLMGUIFVMR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H24O5/c1-13(2)10-11-16-22(27)19-17(15-8-6-5-7-9-15)12-18(25)29-24(19)20(23(16)28)21(26)14(3)4/h5-10,12,14,27-28H,11H2,1-4H3
SMILES:	CC(=CCc1c(O)c2c(cc(=O)oc2c(c1O)C(=O)C(C)C)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383592
PubChem CID:	5277587
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]

☑ 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
GI50	3
IC50	1
Others	5

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	31900.0	nM	PMID[488703]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	36.7	%	PMID[488703]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	34.3	%	PMID[488703]
NPT460	Cell Line	MT2	Homo sapiens	Cell death	=	11.5	%	PMID[488703]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.7	ug.mL-1	PMID[488704]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[488704]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[488704]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	67.0	%	PMID[488703]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	67.1	%	PMID[488703]

☑ 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 NPC87609 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	380
0.1-0.2	1619
0.2-0.3	3863
0.3-0.4	9644
0.4-0.5	9034
0.5-0.6	3863
0.6-0.7	6000
0.7-0.8	4585
0.8-0.85	2155
0.85-0.9	1257
0.9-0.95	250
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196459
1.0	High Similarity	NPC470296
1.0	High Similarity	NPC94794
1.0	High Similarity	NPC112791
1.0	High Similarity	NPC188632
0.9928	High Similarity	NPC1886
0.9928	High Similarity	NPC178627
0.9928	High Similarity	NPC196137
0.9928	High Similarity	NPC469935
0.9927	High Similarity	NPC36181
0.9856	High Similarity	NPC181388
0.9856	High Similarity	NPC470322
0.9856	High Similarity	NPC154217
0.9786	High Similarity	NPC249942
0.9786	High Similarity	NPC297886
0.9716	High Similarity	NPC208303
0.9716	High Similarity	NPC161864
0.9716	High Similarity	NPC469933
0.9714	High Similarity	NPC57470
0.9648	High Similarity	NPC19238
0.9648	High Similarity	NPC469932
0.9645	High Similarity	NPC140120
0.9645	High Similarity	NPC180477
0.9643	High Similarity	NPC469953
0.958	High Similarity	NPC474735
0.9568	High Similarity	NPC282300
0.9568	High Similarity	NPC470555
0.9565	High Similarity	NPC216978
0.9565	High Similarity	NPC96565
0.9565	High Similarity	NPC55018
0.9565	High Similarity	NPC301217
0.9565	High Similarity	NPC220062
0.9565	High Similarity	NPC303633
0.9565	High Similarity	NPC473209
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC53181
0.9562	High Similarity	NPC474624
0.9562	High Similarity	NPC138047
0.9562	High Similarity	NPC131782
0.9514	High Similarity	NPC290671
0.951	High Similarity	NPC104236
0.951	High Similarity	NPC164205
0.9496	High Similarity	NPC221173
0.9496	High Similarity	NPC159275
0.9496	High Similarity	NPC172986
0.9496	High Similarity	NPC270883
0.9496	High Similarity	NPC261227
0.9496	High Similarity	NPC241100
0.9493	High Similarity	NPC219584
0.9493	High Similarity	NPC470083
0.9493	High Similarity	NPC199458
0.9493	High Similarity	NPC183639
0.9493	High Similarity	NPC201395
0.9444	High Similarity	NPC151973
0.9429	High Similarity	NPC205006
0.9429	High Similarity	NPC147688
0.9429	High Similarity	NPC64908
0.9429	High Similarity	NPC156590
0.9429	High Similarity	NPC110969
0.9429	High Similarity	NPC118840
0.9424	High Similarity	NPC78913
0.9424	High Similarity	NPC241975
0.9424	High Similarity	NPC472343
0.9424	High Similarity	NPC19476
0.9424	High Similarity	NPC18260
0.9379	High Similarity	NPC312549
0.9379	High Similarity	NPC209142
0.9366	High Similarity	NPC326500
0.9362	High Similarity	NPC78803
0.9362	High Similarity	NPC62840
0.9362	High Similarity	NPC226636
0.9362	High Similarity	NPC217083
0.9362	High Similarity	NPC293852
0.9362	High Similarity	NPC214236
0.9362	High Similarity	NPC299080
0.9362	High Similarity	NPC11561
0.9362	High Similarity	NPC266725
0.9362	High Similarity	NPC59739
0.9362	High Similarity	NPC200694
0.9357	High Similarity	NPC150522
0.9357	High Similarity	NPC69769
0.9357	High Similarity	NPC305355
0.9357	High Similarity	NPC235239
0.9357	High Similarity	NPC475680
0.9353	High Similarity	NPC470669
0.9353	High Similarity	NPC470668
0.9348	High Similarity	NPC13408
0.932	High Similarity	NPC469934
0.9301	High Similarity	NPC476088
0.9301	High Similarity	NPC153758
0.9301	High Similarity	NPC474161
0.9296	High Similarity	NPC190637
0.9296	High Similarity	NPC278249
0.9296	High Similarity	NPC11700
0.9296	High Similarity	NPC219915
0.9296	High Similarity	NPC212932
0.9296	High Similarity	NPC9117
0.9296	High Similarity	NPC293053
0.9296	High Similarity	NPC107177
0.9296	High Similarity	NPC81697
0.9296	High Similarity	NPC24821
0.9296	High Similarity	NPC38219
0.9296	High Similarity	NPC125894
0.9296	High Similarity	NPC223812
0.9296	High Similarity	NPC77794
0.9296	High Similarity	NPC85162
0.9291	High Similarity	NPC14871
0.9291	High Similarity	NPC103362
0.9291	High Similarity	NPC248372
0.9291	High Similarity	NPC110038
0.9286	High Similarity	NPC240305
0.9286	High Similarity	NPC470986
0.9281	High Similarity	NPC332594
0.9257	High Similarity	NPC469936
0.9257	High Similarity	NPC475797
0.9257	High Similarity	NPC129053
0.9257	High Similarity	NPC78554
0.9257	High Similarity	NPC109967
0.9257	High Similarity	NPC474738
0.9257	High Similarity	NPC474609
0.9257	High Similarity	NPC321372
0.9231	High Similarity	NPC473013
0.9231	High Similarity	NPC311741
0.9231	High Similarity	NPC235217
0.9231	High Similarity	NPC216538
0.9231	High Similarity	NPC257236
0.9231	High Similarity	NPC131568
0.9231	High Similarity	NPC473014
0.9231	High Similarity	NPC473015
0.9231	High Similarity	NPC234629
0.9231	High Similarity	NPC271288
0.9231	High Similarity	NPC131579
0.9231	High Similarity	NPC273538
0.9231	High Similarity	NPC278175
0.9231	High Similarity	NPC319752
0.9225	High Similarity	NPC324134
0.9225	High Similarity	NPC194432
0.9225	High Similarity	NPC296917
0.9225	High Similarity	NPC125855
0.9225	High Similarity	NPC76372
0.9225	High Similarity	NPC66515
0.9225	High Similarity	NPC161506
0.9225	High Similarity	NPC228504
0.9225	High Similarity	NPC148757
0.9225	High Similarity	NPC166482
0.9225	High Similarity	NPC10937
0.9225	High Similarity	NPC220998
0.9225	High Similarity	NPC177354
0.9225	High Similarity	NPC182852
0.9225	High Similarity	NPC64915
0.9225	High Similarity	NPC167624
0.9225	High Similarity	NPC107572
0.9225	High Similarity	NPC470556
0.9225	High Similarity	NPC227579
0.9225	High Similarity	NPC166934
0.9225	High Similarity	NPC144499
0.9225	High Similarity	NPC223500
0.9225	High Similarity	NPC1089
0.9225	High Similarity	NPC473042
0.9225	High Similarity	NPC78
0.9225	High Similarity	NPC37496
0.9225	High Similarity	NPC32739
0.9225	High Similarity	NPC40833
0.9225	High Similarity	NPC324436
0.9225	High Similarity	NPC328164
0.9225	High Similarity	NPC265040
0.9225	High Similarity	NPC76338
0.9225	High Similarity	NPC306829
0.922	High Similarity	NPC76445
0.922	High Similarity	NPC284550
0.922	High Similarity	NPC129853
0.9214	High Similarity	NPC272844
0.9214	High Similarity	NPC254168
0.9214	High Similarity	NPC248995
0.9209	High Similarity	NPC29353
0.9209	High Similarity	NPC124784
0.9209	High Similarity	NPC194281
0.9209	High Similarity	NPC47815
0.9209	High Similarity	NPC231772
0.9209	High Similarity	NPC174999
0.9209	High Similarity	NPC473887
0.9209	High Similarity	NPC127447
0.9209	High Similarity	NPC234133
0.9203	High Similarity	NPC103842
0.9189	High Similarity	NPC108937
0.9189	High Similarity	NPC279218
0.9167	High Similarity	NPC111786
0.9167	High Similarity	NPC220418
0.9167	High Similarity	NPC301276
0.9167	High Similarity	NPC214774
0.9167	High Similarity	NPC178343
0.9167	High Similarity	NPC475052
0.9167	High Similarity	NPC20488
0.9167	High Similarity	NPC312973
0.9167	High Similarity	NPC83357
0.9167	High Similarity	NPC195621
0.9167	High Similarity	NPC267375
0.9167	High Similarity	NPC306488
0.9167	High Similarity	NPC285630
0.9167	High Similarity	NPC54577

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 NPC87609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	964
0.2-0.3	1547
0.3-0.4	2564
0.4-0.5	2006
0.5-0.6	1169
0.6-0.7	364
0.7-0.8	122
0.8-0.85	39
0.85-0.9	19
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD7410	Clinical (unspecified phase)
0.9231	High Similarity	NPD4378	Clinical (unspecified phase)
0.8986	High Similarity	NPD7411	Suspended
0.8873	High Similarity	NPD1550	Clinical (unspecified phase)
0.8873	High Similarity	NPD1552	Clinical (unspecified phase)
0.8816	High Similarity	NPD7075	Discontinued
0.8811	High Similarity	NPD1549	Phase 2
0.88	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8742	High Similarity	NPD7819	Suspended
0.8732	High Similarity	NPD1510	Phase 2
0.8714	High Similarity	NPD1240	Approved
0.869	High Similarity	NPD3750	Approved
0.8684	High Similarity	NPD8443	Clinical (unspecified phase)
0.8671	High Similarity	NPD2796	Approved
0.8639	High Similarity	NPD6799	Approved
0.8621	High Similarity	NPD1243	Approved
0.8621	High Similarity	NPD7421	Clinical (unspecified phase)
0.8618	High Similarity	NPD2393	Clinical (unspecified phase)
0.8592	High Similarity	NPD1607	Approved
0.8552	High Similarity	NPD970	Clinical (unspecified phase)
0.8543	High Similarity	NPD4380	Phase 2
0.8514	High Similarity	NPD1511	Approved
0.8506	High Similarity	NPD7768	Phase 2
0.8481	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD2799	Discontinued
0.8452	Intermediate Similarity	NPD3749	Approved
0.844	Intermediate Similarity	NPD2313	Discontinued
0.844	Intermediate Similarity	NPD3268	Approved
0.844	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6599	Discontinued
0.84	Intermediate Similarity	NPD1512	Approved
0.8377	Intermediate Similarity	NPD2801	Approved
0.8367	Intermediate Similarity	NPD2800	Approved
0.8345	Intermediate Similarity	NPD3748	Approved
0.8345	Intermediate Similarity	NPD2797	Approved
0.8345	Intermediate Similarity	NPD1203	Approved
0.8344	Intermediate Similarity	NPD920	Approved
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6651	Approved
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1934	Approved
0.8288	Intermediate Similarity	NPD1551	Phase 2
0.8288	Intermediate Similarity	NPD2935	Discontinued
0.8224	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2533	Approved
0.8212	Intermediate Similarity	NPD2534	Approved
0.8212	Intermediate Similarity	NPD2532	Approved
0.821	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7473	Discontinued
0.8188	Intermediate Similarity	NPD422	Phase 1
0.8138	Intermediate Similarity	NPD5124	Phase 1
0.8138	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD9717	Approved
0.8125	Intermediate Similarity	NPD6232	Discontinued
0.8117	Intermediate Similarity	NPD3226	Approved
0.811	Intermediate Similarity	NPD5953	Discontinued
0.8098	Intermediate Similarity	NPD7286	Phase 2
0.8092	Intermediate Similarity	NPD5401	Approved
0.8085	Intermediate Similarity	NPD3266	Approved
0.8085	Intermediate Similarity	NPD3267	Approved
0.8067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.8042	Intermediate Similarity	NPD6832	Phase 2
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8014	Intermediate Similarity	NPD3225	Approved
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2346	Discontinued
0.7973	Intermediate Similarity	NPD7033	Discontinued
0.7973	Intermediate Similarity	NPD4308	Phase 3
0.7947	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD919	Approved
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6166	Phase 2
0.7914	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2798	Approved
0.7888	Intermediate Similarity	NPD5494	Approved
0.7879	Intermediate Similarity	NPD7054	Approved
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7867	Intermediate Similarity	NPD2344	Approved
0.7862	Intermediate Similarity	NPD5402	Approved
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.7831	Intermediate Similarity	NPD7472	Approved
0.7831	Intermediate Similarity	NPD7074	Phase 3
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1296	Phase 2
0.78	Intermediate Similarity	NPD6100	Approved
0.78	Intermediate Similarity	NPD6099	Approved
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7746	Intermediate Similarity	NPD1608	Approved
0.7738	Intermediate Similarity	NPD7251	Discontinued
0.7733	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4307	Phase 2
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7688	Intermediate Similarity	NPD1465	Phase 2
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2309	Approved
0.7643	Intermediate Similarity	NPD1548	Phase 1
0.764	Intermediate Similarity	NPD4288	Approved
0.761	Intermediate Similarity	NPD6585	Discontinued
0.7584	Intermediate Similarity	NPD943	Approved
0.7576	Intermediate Similarity	NPD5710	Approved
0.7576	Intermediate Similarity	NPD5711	Approved
0.7568	Intermediate Similarity	NPD411	Approved
0.7566	Intermediate Similarity	NPD5404	Approved
0.7566	Intermediate Similarity	NPD5408	Approved
0.7566	Intermediate Similarity	NPD5406	Approved
0.7566	Intermediate Similarity	NPD5405	Approved
0.7564	Intermediate Similarity	NPD7390	Discontinued
0.7562	Intermediate Similarity	NPD5889	Approved
0.7562	Intermediate Similarity	NPD5890	Approved
0.7557	Intermediate Similarity	NPD4360	Phase 2
0.7557	Intermediate Similarity	NPD4363	Phase 3
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7552	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7458	Discontinued
0.7535	Intermediate Similarity	NPD17	Approved
0.7533	Intermediate Similarity	NPD1933	Approved
0.7533	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD447	Suspended
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4287	Approved
0.7518	Intermediate Similarity	NPD9545	Approved
0.7516	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.7484	Intermediate Similarity	NPD7003	Approved
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7229	Phase 3
0.7468	Intermediate Similarity	NPD5049	Phase 3
0.7466	Intermediate Similarity	NPD1164	Approved
0.745	Intermediate Similarity	NPD3764	Approved
0.745	Intermediate Similarity	NPD6798	Discontinued
0.7438	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2654	Approved
0.7415	Intermediate Similarity	NPD1019	Discontinued
0.741	Intermediate Similarity	NPD1247	Approved
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7379	Intermediate Similarity	NPD1481	Phase 2
0.7342	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5535	Approved
0.7325	Intermediate Similarity	NPD2354	Approved
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.731	Intermediate Similarity	NPD1729	Discontinued
0.731	Intermediate Similarity	NPD1535	Discovery
0.7308	Intermediate Similarity	NPD1652	Phase 2
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD6002	Phase 3
0.729	Intermediate Similarity	NPD6004	Phase 3
0.729	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1894	Discontinued
0.726	Intermediate Similarity	NPD3972	Approved
0.725	Intermediate Similarity	NPD6273	Approved
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD4477	Approved
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2353	Approved
0.7178	Intermediate Similarity	NPD6502	Phase 2
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.7162	Intermediate Similarity	NPD1283	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6971	Discontinued
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7114	Intermediate Similarity	NPD1470	Approved
0.7112	Intermediate Similarity	NPD7584	Approved
0.7108	Intermediate Similarity	NPD2296	Approved
0.7107	Intermediate Similarity	NPD3887	Approved
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7091	Intermediate Similarity	NPD37	Approved
0.7086	Intermediate Similarity	NPD2614	Approved
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.707	Intermediate Similarity	NPD1471	Phase 3
0.7066	Intermediate Similarity	NPD4965	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