NPASS Compound

Structure

NPC469606 OpenBabel07101719522D 21 24 0 0 1 0 0 0 0 0999 V2000 -2.5689 2.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8289 2.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5543 2.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0971 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7888 2.8528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6843 3.8473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 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 3 8 2 0 0 0 0 4 10 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 15 1 0 0 0 0 6 9 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 9 17 1 6 0 0 0 10 15 1 0 0 0 0 11 3 1 6 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 1 1 6 0 0 0 16 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.12
Volume:	284.472
LogP:	1.996
LogD:	1.572
LogS:	-3.436
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	5.191
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.362
MDCK Permeability:	5.890246757189743e-05
Pgp-inhibitor:	0.265
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.33

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.91
Plasma Protein Binding (PPB):	54.350502014160156%
Volume Distribution (VD):	0.577
Pgp-substrate:	64.29524993896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.716
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.669

ADMET: Excretion

Clearance (CL):	16.266
Half-life (T1/2):	0.424

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.928
Carcinogencity:	0.89
Eye Corrosion:	0.996
Eye Irritation:	0.938
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC469606

Natural Product ID:	NPC469606
*Common Name:**	NQUNKSRIHYKOIX-BWAHQPFKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NQUNKSRIHYKOIX-BWAHQPFKSA-N
Standard InCHI:	InChI=1S/C16H18O5/c1-15-5-9(17)6-16(2)13(15)11(21-14(16)19)3-8-7-20-12(18)4-10(8)15/h3-4,9,11,13,17H,5-7H2,1-2H3/t9-,11+,13?,15+,16-/m0/s1
SMILES:	CC12CC(CC3(C1C(C=C4C2=CC(=O)OC4)OC3=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094047
PubChem CID:	44613789
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO13187	Sclerotinia homoeocarpa	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19928902]
NPO13187	Sclerotinia homoeocarpa	Species	Sclerotiniaceae	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	9
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.0	ug.mL-1	PMID[546543]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	4.7	ug.mL-1	PMID[546543]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[546543]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[546543]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	=	0.41	ug.mL-1	PMID[546543]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.097	ug.mL-1	PMID[546543]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.084	ug.mL-1	PMID[546543]
NPT2	Others	Unspecified		Ratio IC50	=	11.9	n.a.	PMID[546543]
NPT2	Others	Unspecified		Ratio IC50	=	10.3	n.a.	PMID[546543]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	IC50	=	9090.0	nM	PMID[546543]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.2	ug.mL-1	PMID[546543]

☑ 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 NPC469606 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	189
0.1-0.2	930
0.2-0.3	3285
0.3-0.4	6481
0.4-0.5	13792
0.5-0.6	7676
0.6-0.7	6872
0.7-0.8	3150
0.8-0.85	293
0.85-0.9	24
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC273005
1.0	High Similarity	NPC31058
0.9691	High Similarity	NPC469607
0.91	High Similarity	NPC478208
0.899	High Similarity	NPC235369
0.8936	High Similarity	NPC469595
0.8936	High Similarity	NPC212679
0.8936	High Similarity	NPC220454
0.8922	High Similarity	NPC189075
0.8922	High Similarity	NPC275539
0.8878	High Similarity	NPC216478
0.8854	High Similarity	NPC250075
0.8835	High Similarity	NPC478210
0.8824	High Similarity	NPC110496
0.8788	High Similarity	NPC47024
0.8785	High Similarity	NPC53396
0.8785	High Similarity	NPC98249
0.8763	High Similarity	NPC183012
0.875	High Similarity	NPC478209
0.875	High Similarity	NPC478211
0.8737	High Similarity	NPC158488
0.8704	High Similarity	NPC284707
0.87	High Similarity	NPC244456
0.87	High Similarity	NPC469657
0.8687	High Similarity	NPC23364
0.8667	High Similarity	NPC188738
0.8667	High Similarity	NPC97939
0.8667	High Similarity	NPC247031
0.8667	High Similarity	NPC132790
0.8667	High Similarity	NPC100329
0.866	High Similarity	NPC477129
0.866	High Similarity	NPC477130
0.8646	High Similarity	NPC233345
0.8646	High Similarity	NPC186363
0.8614	High Similarity	NPC137430
0.8614	High Similarity	NPC165250
0.8614	High Similarity	NPC476081
0.86	High Similarity	NPC476299
0.86	High Similarity	NPC474012
0.8585	High Similarity	NPC12046
0.8585	High Similarity	NPC194951
0.8557	High Similarity	NPC475657
0.8544	High Similarity	NPC252296
0.8544	High Similarity	NPC34768
0.8542	High Similarity	NPC469372
0.8529	High Similarity	NPC8196
0.8529	High Similarity	NPC254202
0.8529	High Similarity	NPC99266
0.8529	High Similarity	NPC36688
0.8515	High Similarity	NPC472637
0.8505	High Similarity	NPC475966
0.8505	High Similarity	NPC478212
0.8505	High Similarity	NPC157441
0.8505	High Similarity	NPC25909
0.8491	Intermediate Similarity	NPC474846
0.8491	Intermediate Similarity	NPC469655
0.8491	Intermediate Similarity	NPC469656
0.8485	Intermediate Similarity	NPC112654
0.8469	Intermediate Similarity	NPC57117
0.8462	Intermediate Similarity	NPC184512
0.8462	Intermediate Similarity	NPC302788
0.844	Intermediate Similarity	NPC469684
0.8438	Intermediate Similarity	NPC168131
0.8416	Intermediate Similarity	NPC476767
0.84	Intermediate Similarity	NPC175351
0.84	Intermediate Similarity	NPC121402
0.84	Intermediate Similarity	NPC132753
0.84	Intermediate Similarity	NPC151681
0.84	Intermediate Similarity	NPC224356
0.84	Intermediate Similarity	NPC91695
0.84	Intermediate Similarity	NPC70145
0.84	Intermediate Similarity	NPC474343
0.8396	Intermediate Similarity	NPC210005
0.8384	Intermediate Similarity	NPC157686
0.8384	Intermediate Similarity	NPC259042
0.8381	Intermediate Similarity	NPC476802
0.8381	Intermediate Similarity	NPC89171
0.8365	Intermediate Similarity	NPC102352
0.8365	Intermediate Similarity	NPC477125
0.8351	Intermediate Similarity	NPC221111
0.8351	Intermediate Similarity	NPC280149
0.835	Intermediate Similarity	NPC471208
0.835	Intermediate Similarity	NPC159533
0.835	Intermediate Similarity	NPC120321
0.835	Intermediate Similarity	NPC134270
0.8349	Intermediate Similarity	NPC478216
0.8333	Intermediate Similarity	NPC469496
0.8333	Intermediate Similarity	NPC277771
0.8333	Intermediate Similarity	NPC471204
0.8333	Intermediate Similarity	NPC477128
0.8333	Intermediate Similarity	NPC469454
0.8333	Intermediate Similarity	NPC471412
0.8333	Intermediate Similarity	NPC97435
0.8333	Intermediate Similarity	NPC469463
0.8318	Intermediate Similarity	NPC474315
0.8318	Intermediate Similarity	NPC304180
0.8318	Intermediate Similarity	NPC179798
0.8316	Intermediate Similarity	NPC250981
0.8316	Intermediate Similarity	NPC6979
0.8302	Intermediate Similarity	NPC228477
0.8302	Intermediate Similarity	NPC137911
0.8302	Intermediate Similarity	NPC469370
0.83	Intermediate Similarity	NPC472363
0.83	Intermediate Similarity	NPC472362
0.83	Intermediate Similarity	NPC202833
0.83	Intermediate Similarity	NPC284518
0.83	Intermediate Similarity	NPC134072
0.83	Intermediate Similarity	NPC234993
0.83	Intermediate Similarity	NPC154526
0.8286	Intermediate Similarity	NPC187435
0.8286	Intermediate Similarity	NPC144854
0.8286	Intermediate Similarity	NPC179380
0.8286	Intermediate Similarity	NPC3316
0.8286	Intermediate Similarity	NPC143609
0.8286	Intermediate Similarity	NPC230541
0.8286	Intermediate Similarity	NPC133422
0.8286	Intermediate Similarity	NPC67321
0.8283	Intermediate Similarity	NPC225474
0.8283	Intermediate Similarity	NPC469596
0.8283	Intermediate Similarity	NPC148000
0.8273	Intermediate Similarity	NPC478204
0.8269	Intermediate Similarity	NPC146731
0.8269	Intermediate Similarity	NPC470321
0.8269	Intermediate Similarity	NPC264867
0.8269	Intermediate Similarity	NPC473207
0.8269	Intermediate Similarity	NPC81567
0.8269	Intermediate Similarity	NPC222161
0.8269	Intermediate Similarity	NPC296950
0.8269	Intermediate Similarity	NPC201880
0.8265	Intermediate Similarity	NPC72845
0.8265	Intermediate Similarity	NPC477574
0.8252	Intermediate Similarity	NPC114540
0.8252	Intermediate Similarity	NPC471363
0.8252	Intermediate Similarity	NPC295791
0.8252	Intermediate Similarity	NPC32577
0.8252	Intermediate Similarity	NPC162973
0.8252	Intermediate Similarity	NPC475320
0.8252	Intermediate Similarity	NPC58329
0.8252	Intermediate Similarity	NPC155332
0.8252	Intermediate Similarity	NPC238397
0.8247	Intermediate Similarity	NPC50488
0.8247	Intermediate Similarity	NPC474396
0.8247	Intermediate Similarity	NPC116620
0.8247	Intermediate Similarity	NPC5509
0.8241	Intermediate Similarity	NPC269530
0.8241	Intermediate Similarity	NPC236217
0.8235	Intermediate Similarity	NPC471413
0.8235	Intermediate Similarity	NPC251680
0.8229	Intermediate Similarity	NPC312561
0.8224	Intermediate Similarity	NPC472666
0.8224	Intermediate Similarity	NPC119550
0.8224	Intermediate Similarity	NPC286880
0.8224	Intermediate Similarity	NPC5103
0.8218	Intermediate Similarity	NPC208094
0.8218	Intermediate Similarity	NPC473963
0.8208	Intermediate Similarity	NPC277017
0.8208	Intermediate Similarity	NPC325054
0.8208	Intermediate Similarity	NPC151393
0.8208	Intermediate Similarity	NPC476479
0.8208	Intermediate Similarity	NPC154608
0.8208	Intermediate Similarity	NPC192813
0.8208	Intermediate Similarity	NPC322903
0.82	Intermediate Similarity	NPC295347
0.8198	Intermediate Similarity	NPC478205
0.8198	Intermediate Similarity	NPC108581
0.8198	Intermediate Similarity	NPC478206
0.819	Intermediate Similarity	NPC111952
0.819	Intermediate Similarity	NPC172867
0.819	Intermediate Similarity	NPC266570
0.819	Intermediate Similarity	NPC127609
0.8182	Intermediate Similarity	NPC139692
0.8182	Intermediate Similarity	NPC99653
0.8182	Intermediate Similarity	NPC166346
0.8173	Intermediate Similarity	NPC478057
0.8173	Intermediate Similarity	NPC475889
0.8173	Intermediate Similarity	NPC7644
0.8173	Intermediate Similarity	NPC95899
0.8173	Intermediate Similarity	NPC127933
0.8173	Intermediate Similarity	NPC7613
0.8165	Intermediate Similarity	NPC56448
0.8165	Intermediate Similarity	NPC474271
0.8163	Intermediate Similarity	NPC232202
0.8163	Intermediate Similarity	NPC281942
0.8163	Intermediate Similarity	NPC232426
0.8155	Intermediate Similarity	NPC81530
0.8155	Intermediate Similarity	NPC63249
0.8144	Intermediate Similarity	NPC477302
0.8144	Intermediate Similarity	NPC226863
0.8144	Intermediate Similarity	NPC24816
0.8137	Intermediate Similarity	NPC478056
0.8137	Intermediate Similarity	NPC108368
0.8137	Intermediate Similarity	NPC57079
0.8137	Intermediate Similarity	NPC222303
0.8131	Intermediate Similarity	NPC141350
0.8131	Intermediate Similarity	NPC112457
0.8131	Intermediate Similarity	NPC474243
0.8125	Intermediate Similarity	NPC471219
0.8125	Intermediate Similarity	NPC473226
0.8125	Intermediate Similarity	NPC475041
0.8125	Intermediate Similarity	NPC329692

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 NPC469606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1142
0.2-0.3	3306
0.3-0.4	2754
0.4-0.5	1164
0.5-0.6	311
0.6-0.7	236
0.7-0.8	81
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8317	Intermediate Similarity	NPD7638	Approved
0.8235	Intermediate Similarity	NPD7639	Approved
0.8235	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD6399	Phase 3
0.7798	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6686	Approved
0.7692	Intermediate Similarity	NPD7902	Approved
0.7685	Intermediate Similarity	NPD6008	Approved
0.7653	Intermediate Similarity	NPD1694	Approved
0.7632	Intermediate Similarity	NPD7115	Discovery
0.7589	Intermediate Similarity	NPD6053	Discontinued
0.7576	Intermediate Similarity	NPD3618	Phase 1
0.7573	Intermediate Similarity	NPD7748	Approved
0.757	Intermediate Similarity	NPD7632	Discontinued
0.7549	Intermediate Similarity	NPD7515	Phase 2
0.7526	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5779	Approved
0.7476	Intermediate Similarity	NPD5778	Approved
0.7455	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD7900	Approved
0.7379	Intermediate Similarity	NPD5281	Approved
0.7379	Intermediate Similarity	NPD5284	Approved
0.7379	Intermediate Similarity	NPD6411	Approved
0.7364	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD6675	Approved
0.7364	Intermediate Similarity	NPD7128	Approved
0.7364	Intermediate Similarity	NPD5739	Approved
0.7347	Intermediate Similarity	NPD3667	Approved
0.7321	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD6373	Approved
0.7297	Intermediate Similarity	NPD5697	Approved
0.7297	Intermediate Similarity	NPD5701	Approved
0.7282	Intermediate Similarity	NPD46	Approved
0.7282	Intermediate Similarity	NPD6698	Approved
0.7232	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD6011	Approved
0.7232	Intermediate Similarity	NPD7320	Approved
0.7232	Intermediate Similarity	NPD6899	Approved
0.7228	Intermediate Similarity	NPD5330	Approved
0.7228	Intermediate Similarity	NPD6684	Approved
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD7334	Approved
0.7228	Intermediate Similarity	NPD7521	Approved
0.7228	Intermediate Similarity	NPD7146	Approved
0.7228	Intermediate Similarity	NPD6409	Approved
0.7227	Intermediate Similarity	NPD8513	Phase 3
0.7217	Intermediate Similarity	NPD4632	Approved
0.72	Intermediate Similarity	NPD3665	Phase 1
0.72	Intermediate Similarity	NPD3133	Approved
0.72	Intermediate Similarity	NPD3666	Approved
0.72	Intermediate Similarity	NPD4786	Approved
0.7196	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD6083	Phase 2
0.7193	Intermediate Similarity	NPD6649	Approved
0.7193	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6101	Approved
0.7184	Intermediate Similarity	NPD5328	Approved
0.717	Intermediate Similarity	NPD5695	Phase 3
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6013	Approved
0.7168	Intermediate Similarity	NPD6014	Approved
0.7168	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD4202	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD5696	Approved
0.7115	Intermediate Similarity	NPD5207	Approved
0.7105	Intermediate Similarity	NPD6883	Approved
0.7105	Intermediate Similarity	NPD7290	Approved
0.7105	Intermediate Similarity	NPD7102	Approved
0.7103	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6672	Approved
0.7087	Intermediate Similarity	NPD6903	Approved
0.7087	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8517	Approved
0.7083	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.7048	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD8035	Phase 2
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7048	Intermediate Similarity	NPD6079	Approved
0.7048	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD6869	Approved
0.7043	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6847	Approved
0.7043	Intermediate Similarity	NPD8130	Phase 1
0.7043	Intermediate Similarity	NPD6617	Approved
0.7037	Intermediate Similarity	NPD4755	Approved
0.7034	Intermediate Similarity	NPD6009	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6319	Approved
0.6984	Remote Similarity	NPD7260	Phase 2
0.6983	Remote Similarity	NPD8297	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD6371	Approved
0.6952	Remote Similarity	NPD7838	Discovery
0.6952	Remote Similarity	NPD5785	Approved
0.6952	Remote Similarity	NPD5692	Phase 3
0.6944	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5221	Approved
0.6944	Remote Similarity	NPD5222	Approved
0.6942	Remote Similarity	NPD5983	Phase 2
0.6937	Remote Similarity	NPD5211	Phase 2
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5282	Discontinued
0.6911	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD4696	Approved
0.6909	Remote Similarity	NPD5285	Approved
0.6909	Remote Similarity	NPD6648	Approved
0.6909	Remote Similarity	NPD5286	Approved
0.6909	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5694	Approved
0.6887	Remote Similarity	NPD6050	Approved
0.6881	Remote Similarity	NPD5173	Approved
0.687	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3668	Phase 3
0.686	Remote Similarity	NPD6054	Approved
0.686	Remote Similarity	NPD6059	Approved
0.6857	Remote Similarity	NPD4753	Phase 2
0.6855	Remote Similarity	NPD6616	Approved
0.6847	Remote Similarity	NPD5223	Approved
0.6847	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7328	Approved
0.6833	Remote Similarity	NPD7327	Approved
0.6829	Remote Similarity	NPD8328	Phase 3
0.6829	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD3573	Approved
0.6814	Remote Similarity	NPD5141	Approved
0.6807	Remote Similarity	NPD6274	Approved
0.6804	Remote Similarity	NPD8039	Approved
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6015	Approved
0.6803	Remote Similarity	NPD8033	Approved
0.68	Remote Similarity	NPD4695	Discontinued
0.68	Remote Similarity	NPD8293	Discontinued
0.68	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD8074	Phase 3
0.6797	Remote Similarity	NPD6845	Suspended
0.6796	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5225	Approved
0.6786	Remote Similarity	NPD5224	Approved
0.6786	Remote Similarity	NPD5226	Approved
0.6786	Remote Similarity	NPD4633	Approved
0.678	Remote Similarity	NPD8133	Approved
0.6777	Remote Similarity	NPD7516	Approved
0.6759	Remote Similarity	NPD6001	Approved
0.675	Remote Similarity	NPD6317	Approved
0.6748	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD5988	Approved
0.6746	Remote Similarity	NPD7736	Approved
0.6731	Remote Similarity	NPD4694	Approved
0.6731	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5280	Approved
0.6731	Remote Similarity	NPD4623	Approved
0.6731	Remote Similarity	NPD4519	Discontinued
0.6729	Remote Similarity	NPD7983	Approved
0.6726	Remote Similarity	NPD4754	Approved
0.6726	Remote Similarity	NPD5174	Approved
0.6726	Remote Similarity	NPD5175	Approved
0.6721	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8294	Approved
0.672	Remote Similarity	NPD6336	Discontinued
0.6699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6080	Approved
0.6698	Remote Similarity	NPD6051	Approved
0.6698	Remote Similarity	NPD6673	Approved
0.6698	Remote Similarity	NPD6904	Approved
0.6698	Remote Similarity	NPD1695	Approved
0.6697	Remote Similarity	NPD5210	Approved
0.6697	Remote Similarity	NPD4629	Approved
0.6694	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD6313	Approved
0.6694	Remote Similarity	NPD6067	Discontinued
0.6694	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD7100	Approved
0.6635	Remote Similarity	NPD1696	Phase 3
0.6634	Remote Similarity	NPD8259	Clinical (unspecified phase)

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