NPASS Compound

Structure

CID133422 OpenBabel06191715492D 26 29 0 0 1 0 0 0 0 0999 V2000 5.4975 0.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6749 1.8954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6789 1.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8570 0.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8056 2.5898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3718 -0.6218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2338 -0.0175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9853 -1.1064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9888 0.9519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6673 0.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 0.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1404 0.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1327 -0.5044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8219 -0.5177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9734 -0.9987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3826 1.0849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4300 0.8755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2343 0.0433 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4163 -0.8821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3654 -1.1064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6520 -1.0058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9658 -1.9616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1586 -1.5915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6071 2.0340 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 20 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 2 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 21 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	368.315
LogP:	4.27
LogD:	3.452
LogS:	-4.245
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	4.956
Fsp3:	0.571
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:	-4.804
MDCK Permeability:	2.3662525563850068e-05
Pgp-inhibitor:	0.817
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.908
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	99.54737091064453%
Volume Distribution (VD):	1.278
Pgp-substrate:	1.7484506368637085%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.811
CYP2C19-inhibitor:	0.447
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.743
CYP2D6-inhibitor:	0.123
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	2.796
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.243
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.763
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.876
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC133422

Natural Product ID:	NPC133422
*Common Name:**	Rosmaquinone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CEYZNONDZLXUNG-NYUBLWNDSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18H,6-8H2,1-5H3/t16-,17+,18-,21-/m0/s1
SMILES:	CC(C)C1=CC2=C(C(=O)C1=O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H]([C@H]2OC)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082065
PubChem CID:	46883407
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26020634]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8229021]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	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	10
MIC	11

Activity Type	# Activity
Cell Line	10
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	60000.0	nM	PMID[489468]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	60000.0	nM	PMID[489468]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	60000.0	nM	PMID[489468]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	43300.0	nM	PMID[489468]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	42500.0	nM	PMID[489468]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	36000.0	nM	PMID[489468]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	33800.0	nM	PMID[489468]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25400.0	nM	PMID[489468]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	22100.0	nM	PMID[489468]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	20.0	ug.mL-1	PMID[489468]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	20.0	ug.mL-1	PMID[489468]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	40.0	ug.mL-1	PMID[489468]
NPT1246	Organism	Salmonella	Salmonella	MIC	>	40.0	ug.mL-1	PMID[489468]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	40.0	ug.mL-1	PMID[489468]

☑ 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 NPC133422 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	237
0.1-0.2	1153
0.2-0.3	4170
0.3-0.4	8156
0.4-0.5	13812
0.5-0.6	8265
0.6-0.7	5672
0.7-0.8	1187
0.8-0.85	43
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9135	High Similarity	NPC286880
0.8692	High Similarity	NPC188738
0.8598	High Similarity	NPC253906
0.8571	High Similarity	NPC469607
0.8558	High Similarity	NPC254202
0.8532	High Similarity	NPC471204
0.8476	Intermediate Similarity	NPC470297
0.844	Intermediate Similarity	NPC265391
0.8426	Intermediate Similarity	NPC210005
0.8384	Intermediate Similarity	NPC152467
0.8333	Intermediate Similarity	NPC153239
0.8333	Intermediate Similarity	NPC469370
0.8317	Intermediate Similarity	NPC477130
0.8317	Intermediate Similarity	NPC477129
0.8286	Intermediate Similarity	NPC469606
0.8286	Intermediate Similarity	NPC31058
0.8286	Intermediate Similarity	NPC273005
0.8252	Intermediate Similarity	NPC226986
0.8241	Intermediate Similarity	NPC275539
0.8241	Intermediate Similarity	NPC189075
0.8224	Intermediate Similarity	NPC102352
0.8218	Intermediate Similarity	NPC475657
0.82	Intermediate Similarity	NPC212679
0.82	Intermediate Similarity	NPC220454
0.82	Intermediate Similarity	NPC469595
0.8182	Intermediate Similarity	NPC179798
0.8182	Intermediate Similarity	NPC304180
0.8173	Intermediate Similarity	NPC23364
0.8165	Intermediate Similarity	NPC112457
0.8148	Intermediate Similarity	NPC110496
0.8148	Intermediate Similarity	NPC180744
0.8148	Intermediate Similarity	NPC230541
0.8142	Intermediate Similarity	NPC53396
0.8142	Intermediate Similarity	NPC98249
0.8137	Intermediate Similarity	NPC470697
0.8131	Intermediate Similarity	NPC189616
0.8108	Intermediate Similarity	NPC476801
0.8108	Intermediate Similarity	NPC269530
0.81	Intermediate Similarity	NPC73995
0.8095	Intermediate Similarity	NPC476933
0.8091	Intermediate Similarity	NPC478211
0.8077	Intermediate Similarity	NPC84335
0.8077	Intermediate Similarity	NPC38530
0.8073	Intermediate Similarity	NPC277017
0.8073	Intermediate Similarity	NPC476802
0.8073	Intermediate Similarity	NPC154608
0.8073	Intermediate Similarity	NPC192813
0.8073	Intermediate Similarity	NPC89171
0.807	Intermediate Similarity	NPC284707
0.8058	Intermediate Similarity	NPC183012
0.8056	Intermediate Similarity	NPC478208
0.8053	Intermediate Similarity	NPC478216
0.8036	Intermediate Similarity	NPC469463
0.8036	Intermediate Similarity	NPC469454
0.8036	Intermediate Similarity	NPC56448
0.8036	Intermediate Similarity	NPC469496
0.802	Intermediate Similarity	NPC469372
0.8019	Intermediate Similarity	NPC472637
0.8018	Intermediate Similarity	NPC100329
0.8018	Intermediate Similarity	NPC247031
0.8018	Intermediate Similarity	NPC470246
0.8018	Intermediate Similarity	NPC132790
0.8018	Intermediate Similarity	NPC97939
0.8	Intermediate Similarity	NPC141350
0.8	Intermediate Similarity	NPC478210
0.8	Intermediate Similarity	NPC215831
0.8	Intermediate Similarity	NPC475520
0.7982	Intermediate Similarity	NPC3316
0.7982	Intermediate Similarity	NPC144854
0.7982	Intermediate Similarity	NPC284068
0.798	Intermediate Similarity	NPC220478
0.7965	Intermediate Similarity	NPC474181
0.7961	Intermediate Similarity	NPC250075
0.7961	Intermediate Similarity	NPC38830
0.7946	Intermediate Similarity	NPC12046
0.7946	Intermediate Similarity	NPC472002
0.7946	Intermediate Similarity	NPC194951
0.7944	Intermediate Similarity	NPC235369
0.7941	Intermediate Similarity	NPC473944
0.7928	Intermediate Similarity	NPC5103
0.7925	Intermediate Similarity	NPC471413
0.7925	Intermediate Similarity	NPC470761
0.7925	Intermediate Similarity	NPC104861
0.7925	Intermediate Similarity	NPC473219
0.7921	Intermediate Similarity	NPC173042
0.7913	Intermediate Similarity	NPC473720
0.7909	Intermediate Similarity	NPC19412
0.7905	Intermediate Similarity	NPC474343
0.7905	Intermediate Similarity	NPC23680
0.79	Intermediate Similarity	NPC175293
0.7895	Intermediate Similarity	NPC477509
0.7895	Intermediate Similarity	NPC176840
0.7895	Intermediate Similarity	NPC270478
0.7895	Intermediate Similarity	NPC190286
0.789	Intermediate Similarity	NPC181357
0.789	Intermediate Similarity	NPC477125
0.7879	Intermediate Similarity	NPC110405
0.7876	Intermediate Similarity	NPC25909
0.7876	Intermediate Similarity	NPC157441
0.7876	Intermediate Similarity	NPC470120
0.7876	Intermediate Similarity	NPC475966
0.787	Intermediate Similarity	NPC275583
0.787	Intermediate Similarity	NPC132395
0.787	Intermediate Similarity	NPC471364
0.787	Intermediate Similarity	NPC475321
0.787	Intermediate Similarity	NPC471365
0.7857	Intermediate Similarity	NPC469656
0.7857	Intermediate Similarity	NPC474846
0.7857	Intermediate Similarity	NPC469655
0.785	Intermediate Similarity	NPC471412
0.7845	Intermediate Similarity	NPC305260
0.7845	Intermediate Similarity	NPC475775
0.7845	Intermediate Similarity	NPC476529
0.7845	Intermediate Similarity	NPC270850
0.783	Intermediate Similarity	NPC471932
0.783	Intermediate Similarity	NPC176845
0.783	Intermediate Similarity	NPC216478
0.7826	Intermediate Similarity	NPC472927
0.7826	Intermediate Similarity	NPC473968
0.7826	Intermediate Similarity	NPC469684
0.7826	Intermediate Similarity	NPC23046
0.7822	Intermediate Similarity	NPC477128
0.7822	Intermediate Similarity	NPC226863
0.7818	Intermediate Similarity	NPC473037
0.7815	Intermediate Similarity	NPC24651
0.781	Intermediate Similarity	NPC112654
0.7798	Intermediate Similarity	NPC477127
0.7798	Intermediate Similarity	NPC146731
0.7788	Intermediate Similarity	NPC222834
0.7788	Intermediate Similarity	NPC84893
0.7788	Intermediate Similarity	NPC56525
0.7788	Intermediate Similarity	NPC474841
0.7788	Intermediate Similarity	NPC471446
0.7788	Intermediate Similarity	NPC473434
0.7778	Intermediate Similarity	NPC162973
0.7778	Intermediate Similarity	NPC107338
0.7778	Intermediate Similarity	NPC295791
0.7778	Intermediate Similarity	NPC80781
0.7778	Intermediate Similarity	NPC474585
0.7778	Intermediate Similarity	NPC137430
0.7778	Intermediate Similarity	NPC293753
0.7778	Intermediate Similarity	NPC109607
0.7778	Intermediate Similarity	NPC234892
0.7778	Intermediate Similarity	NPC149869
0.7768	Intermediate Similarity	NPC478209
0.7767	Intermediate Similarity	NPC233437
0.7767	Intermediate Similarity	NPC207641
0.7767	Intermediate Similarity	NPC49420
0.7759	Intermediate Similarity	NPC153440
0.7759	Intermediate Similarity	NPC106644
0.7759	Intermediate Similarity	NPC470420
0.7757	Intermediate Similarity	NPC47024
0.7748	Intermediate Similarity	NPC295244
0.7745	Intermediate Similarity	NPC284561
0.7736	Intermediate Similarity	NPC292133
0.7736	Intermediate Similarity	NPC110937
0.7731	Intermediate Similarity	NPC120724
0.7727	Intermediate Similarity	NPC127609
0.7719	Intermediate Similarity	NPC478212
0.7719	Intermediate Similarity	NPC474271
0.7714	Intermediate Similarity	NPC274417
0.7712	Intermediate Similarity	NPC310511
0.7712	Intermediate Similarity	NPC204731
0.7706	Intermediate Similarity	NPC282233
0.7706	Intermediate Similarity	NPC159442
0.7706	Intermediate Similarity	NPC99266
0.7706	Intermediate Similarity	NPC95585
0.7706	Intermediate Similarity	NPC8196
0.77	Intermediate Similarity	NPC189311
0.77	Intermediate Similarity	NPC177932
0.7699	Intermediate Similarity	NPC115303
0.7699	Intermediate Similarity	NPC472928
0.7692	Intermediate Similarity	NPC5292
0.7692	Intermediate Similarity	NPC79117
0.7692	Intermediate Similarity	NPC472933
0.7692	Intermediate Similarity	NPC475041
0.7685	Intermediate Similarity	NPC168319
0.7685	Intermediate Similarity	NPC81530
0.7685	Intermediate Similarity	NPC194028
0.7679	Intermediate Similarity	NPC286174
0.7679	Intermediate Similarity	NPC77947
0.7677	Intermediate Similarity	NPC22611
0.7672	Intermediate Similarity	NPC478204
0.7672	Intermediate Similarity	NPC472934
0.767	Intermediate Similarity	NPC471818
0.767	Intermediate Similarity	NPC158488
0.767	Intermediate Similarity	NPC475776
0.7667	Intermediate Similarity	NPC8369
0.7664	Intermediate Similarity	NPC478056
0.7664	Intermediate Similarity	NPC252295
0.7658	Intermediate Similarity	NPC143609
0.7658	Intermediate Similarity	NPC302788
0.7652	Intermediate Similarity	NPC117712
0.7652	Intermediate Similarity	NPC90472
0.7647	Intermediate Similarity	NPC312833
0.7647	Intermediate Similarity	NPC170538
0.7642	Intermediate Similarity	NPC29952
0.7642	Intermediate Similarity	NPC202833
0.7636	Intermediate Similarity	NPC96268
0.7636	Intermediate Similarity	NPC296950

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 NPC133422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1360
0.2-0.3	3689
0.3-0.4	2509
0.4-0.5	924
0.5-0.6	268
0.6-0.7	185
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7727	Intermediate Similarity	NPD6008	Approved
0.77	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7260	Phase 2
0.7339	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7244	Intermediate Similarity	NPD6845	Suspended
0.7228	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7115	Discovery
0.7212	Intermediate Similarity	NPD3573	Approved
0.7119	Intermediate Similarity	NPD4632	Approved
0.7091	Intermediate Similarity	NPD7902	Approved
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5207	Approved
0.6983	Remote Similarity	NPD6686	Approved
0.6972	Remote Similarity	NPD7748	Approved
0.6952	Remote Similarity	NPD7334	Approved
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6942	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6911	Remote Similarity	NPD6319	Approved
0.6909	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5697	Approved
0.6891	Remote Similarity	NPD8297	Approved
0.6881	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD5779	Approved
0.6855	Remote Similarity	NPD8516	Approved
0.6855	Remote Similarity	NPD8515	Approved
0.6855	Remote Similarity	NPD8517	Approved
0.6855	Remote Similarity	NPD5983	Phase 2
0.6855	Remote Similarity	NPD8513	Phase 3
0.6852	Remote Similarity	NPD5692	Phase 3
0.6847	Remote Similarity	NPD4697	Phase 3
0.6838	Remote Similarity	NPD6011	Approved
0.6838	Remote Similarity	NPD6899	Approved
0.6838	Remote Similarity	NPD6881	Approved
0.6825	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD5737	Approved
0.6822	Remote Similarity	NPD6672	Approved
0.681	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6402	Approved
0.681	Remote Similarity	NPD6675	Approved
0.681	Remote Similarity	NPD5739	Approved
0.6792	Remote Similarity	NPD3618	Phase 1
0.6789	Remote Similarity	NPD6079	Approved
0.6789	Remote Similarity	NPD5694	Approved
0.6789	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD7515	Phase 2
0.6789	Remote Similarity	NPD5693	Phase 1
0.6789	Remote Similarity	NPD6050	Approved
0.678	Remote Similarity	NPD6014	Approved
0.678	Remote Similarity	NPD6013	Approved
0.678	Remote Similarity	NPD6012	Approved
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD7507	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6759	Remote Similarity	NPD5328	Approved
0.6752	Remote Similarity	NPD5701	Approved
0.6746	Remote Similarity	NPD7604	Phase 2
0.6726	Remote Similarity	NPD5696	Approved
0.6723	Remote Similarity	NPD7290	Approved
0.6723	Remote Similarity	NPD6883	Approved
0.6723	Remote Similarity	NPD7102	Approved
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD6016	Approved
0.6719	Remote Similarity	NPD7078	Approved
0.6696	Remote Similarity	NPD5221	Approved
0.6696	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5222	Approved
0.6696	Remote Similarity	NPD7632	Discontinued
0.6695	Remote Similarity	NPD7320	Approved
0.6695	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6641	Remote Similarity	NPD6336	Discontinued
0.664	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5173	Approved
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6615	Remote Similarity	NPD7319	Approved
0.6614	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD6882	Approved
0.6612	Remote Similarity	NPD6053	Discontinued
0.6607	Remote Similarity	NPD5695	Phase 3
0.6607	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6101	Approved
0.6589	Remote Similarity	NPD8293	Discontinued
0.6589	Remote Similarity	NPD8074	Phase 3
0.6579	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5209	Approved
0.6552	Remote Similarity	NPD5211	Phase 2
0.6549	Remote Similarity	NPD7732	Phase 3
0.6545	Remote Similarity	NPD46	Approved
0.6545	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD8039	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4696	Approved
0.6522	Remote Similarity	NPD5286	Approved
0.6522	Remote Similarity	NPD5285	Approved
0.6491	Remote Similarity	NPD4755	Approved
0.6481	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD5223	Approved
0.646	Remote Similarity	NPD5654	Approved
0.6457	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7503	Approved
0.6455	Remote Similarity	NPD6673	Approved
0.6455	Remote Similarity	NPD6904	Approved
0.6455	Remote Similarity	NPD6080	Approved
0.6455	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD6274	Approved
0.6449	Remote Similarity	NPD3668	Phase 3
0.6446	Remote Similarity	NPD6371	Approved
0.6446	Remote Similarity	NPD4634	Approved
0.6441	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD3667	Approved
0.641	Remote Similarity	NPD5224	Approved
0.641	Remote Similarity	NPD5226	Approved
0.641	Remote Similarity	NPD4633	Approved
0.641	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD6317	Approved
0.6396	Remote Similarity	NPD5785	Approved
0.6379	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6356	Remote Similarity	NPD5174	Approved
0.6356	Remote Similarity	NPD5175	Approved
0.6349	Remote Similarity	NPD6314	Approved
0.6349	Remote Similarity	NPD6313	Approved
0.6349	Remote Similarity	NPD6335	Approved
0.6348	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD6084	Phase 2
0.6348	Remote Similarity	NPD5959	Approved
0.6339	Remote Similarity	NPD8035	Phase 2
0.6339	Remote Similarity	NPD8034	Phase 2
0.6339	Remote Similarity	NPD7983	Approved
0.6333	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD1695	Approved
0.6306	Remote Similarity	NPD6051	Approved
0.6299	Remote Similarity	NPD7100	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6296	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD3666	Approved
0.6296	Remote Similarity	NPD3665	Phase 1
0.6296	Remote Similarity	NPD4786	Approved
0.6288	Remote Similarity	NPD6033	Approved
0.6283	Remote Similarity	NPD4202	Approved
0.6275	Remote Similarity	NPD4058	Approved
0.6275	Remote Similarity	NPD4687	Approved
0.6275	Remote Similarity	NPD5733	Approved
0.627	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7614	Phase 1
0.625	Remote Similarity	NPD7838	Discovery
0.6239	Remote Similarity	NPD1696	Phase 3
0.6238	Remote Similarity	NPD5276	Approved
0.6231	Remote Similarity	NPD6067	Discontinued
0.6226	Remote Similarity	NPD4695	Discontinued
0.622	Remote Similarity	NPD7328	Approved
0.622	Remote Similarity	NPD7327	Approved
0.6218	Remote Similarity	NPD4754	Approved
0.6209	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8033	Approved
0.6198	Remote Similarity	NPD6614	Approved
0.6195	Remote Similarity	NPD7637	Suspended
0.6182	Remote Similarity	NPD4694	Approved
0.6182	Remote Similarity	NPD6098	Approved
0.6182	Remote Similarity	NPD5280	Approved
0.6172	Remote Similarity	NPD7516	Approved
0.6148	Remote Similarity	NPD5128	Approved
0.6148	Remote Similarity	NPD5168	Approved
0.6148	Remote Similarity	NPD4730	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