NPASS Compound

Structure

CID295436 OpenBabel06191716102D 39 43 0 0 0 0 0 0 0 0999 V2000 11.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7350 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4049 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1369 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8690 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5878 0.8090 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 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 20 2 0 0 0 0 11 17 1 0 0 0 0 12 38 1 0 0 0 0 13 21 1 0 0 0 0 13 25 2 0 0 0 0 14 18 1 0 0 0 0 14 35 1 0 0 0 0 15 22 2 0 0 0 0 15 36 1 0 0 0 0 16 26 1 0 0 0 0 16 39 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 32 2 0 0 0 0 25 38 1 0 0 0 0 26 33 2 0 0 0 0 26 37 1 0 0 0 0 27 34 2 0 0 0 0 27 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.1
Volume:	503.975
LogP:	4.751
LogD:	2.358
LogS:	-3.686
# Rotatable Bonds:	6
TPSA:	189.26
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	3.451
Fsp3:	0.111
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.345
MDCK Permeability:	1.4457376892096363e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.117
Human Intestinal Absorption (HIA):	0.857
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	82.83255004882812%
Volume Distribution (VD):	0.419
Pgp-substrate:	47.809898376464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.313
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.687
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	5.958
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.778
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.822
Skin Sensitization:	0.903
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.718
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC295436

Natural Product ID:	NPC295436
*Common Name:**	Alpha-Rubromycin
IUPAC Name:	methyl 7,8-dihydroxy-6-[2-(8-hydroxy-5,7-dimethoxy-4,9-dioxobenzo[f][1]benzofuran-2-yl)ethyl]-1-oxoisochromene-3-carboxylate
Synonyms:
Standard InCHIKey:	LQNGOIZVRFNQLO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H20O12/c1-35-14-9-15(36-2)22(30)19-18(14)21(29)13-8-12(38-25(13)24(19)32)5-4-10-6-11-7-16(26(33)37-3)39-27(34)17(11)23(31)20(10)28/h6-9,28,30-31H,4-5H2,1-3H3
SMILES:	COc1cc(c(c2c1C(=O)c1cc(CCc3cc4cc(C(=O)OC)oc(=O)c4c(c3O)O)oc1C2=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3347655
PubChem CID:	5378308
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO4378	Uvariastrum zenkeri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12747	Peronia verruculata	Species	Onchidiidae	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
EC50	2
IC50	1
MIC	7

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	>	200000.0	nM	PMID[486341]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	100000.0	nM	PMID[486342]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	>	100000.0	nM	PMID[486342]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.0	ug.mL-1	PMID[486342]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	1.5	ug.mL-1	PMID[486342]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.4	ug.mL-1	PMID[486342]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	>	24.0	ug.mL-1	PMID[486342]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	24.0	ug.mL-1	PMID[486342]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	24.0	ug.mL-1	PMID[486342]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	24.0	ug.mL-1	PMID[486342]

☑ 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 NPC295436 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	453
0.1-0.2	2028
0.2-0.3	4452
0.3-0.4	10174
0.4-0.5	7959
0.5-0.6	4138
0.6-0.7	5517
0.7-0.8	5114
0.8-0.85	1994
0.85-0.9	788
0.9-0.95	79
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC174486
0.9205	High Similarity	NPC475996
0.9205	High Similarity	NPC47883
0.92	High Similarity	NPC207467
0.9195	High Similarity	NPC245975
0.9191	High Similarity	NPC158226
0.9143	High Similarity	NPC8127
0.9143	High Similarity	NPC49667
0.9133	High Similarity	NPC109827
0.9133	High Similarity	NPC124470
0.9101	High Similarity	NPC71260
0.9096	High Similarity	NPC265795
0.9091	High Similarity	NPC77179
0.9091	High Similarity	NPC297807
0.9091	High Similarity	NPC98546
0.9091	High Similarity	NPC23553
0.9075	High Similarity	NPC163130
0.9075	High Similarity	NPC165979
0.9075	High Similarity	NPC49487
0.9075	High Similarity	NPC99613
0.9045	High Similarity	NPC471842
0.9045	High Similarity	NPC240508
0.9045	High Similarity	NPC228209
0.904	High Similarity	NPC473785
0.9029	High Similarity	NPC82217
0.9029	High Similarity	NPC65885
0.9029	High Similarity	NPC216842
0.9029	High Similarity	NPC476640
0.9023	High Similarity	NPC28042
0.9	High Similarity	NPC248315
0.8983	High Similarity	NPC221820
0.8977	High Similarity	NPC289244
0.8977	High Similarity	NPC287243
0.8971	High Similarity	NPC54098
0.8971	High Similarity	NPC230619
0.8966	High Similarity	NPC280493
0.8962	High Similarity	NPC314020
0.896	High Similarity	NPC29160
0.8956	High Similarity	NPC60848
0.8944	High Similarity	NPC226725
0.8939	High Similarity	NPC8927
0.8939	High Similarity	NPC182693
0.8939	High Similarity	NPC246153
0.8933	High Similarity	NPC476273
0.8927	High Similarity	NPC24258
0.8927	High Similarity	NPC471841
0.8927	High Similarity	NPC164384
0.892	High Similarity	NPC261471
0.892	High Similarity	NPC30550
0.892	High Similarity	NPC37606
0.892	High Similarity	NPC277510
0.8914	High Similarity	NPC218533
0.8914	High Similarity	NPC78830
0.8914	High Similarity	NPC476641
0.8908	High Similarity	NPC95715
0.8908	High Similarity	NPC234331
0.8895	High Similarity	NPC240808
0.8889	High Similarity	NPC154527
0.8876	High Similarity	NPC246877
0.887	High Similarity	NPC227906
0.8857	High Similarity	NPC247136
0.8857	High Similarity	NPC202470
0.8844	High Similarity	NPC270837
0.8844	High Similarity	NPC133065
0.8814	High Similarity	NPC310794
0.8814	High Similarity	NPC117450
0.8807	High Similarity	NPC72696
0.88	High Similarity	NPC76647
0.88	High Similarity	NPC50394
0.88	High Similarity	NPC86477
0.88	High Similarity	NPC470704
0.8793	High Similarity	NPC39306
0.8793	High Similarity	NPC45449
0.8793	High Similarity	NPC36320
0.8793	High Similarity	NPC29411
0.8786	High Similarity	NPC108767
0.8786	High Similarity	NPC294965
0.8779	High Similarity	NPC246478
0.8779	High Similarity	NPC84571
0.8778	High Similarity	NPC97523
0.8764	High Similarity	NPC139350
0.8757	High Similarity	NPC247964
0.8757	High Similarity	NPC473113
0.8743	High Similarity	NPC37870
0.8743	High Similarity	NPC30027
0.8736	High Similarity	NPC474350
0.8736	High Similarity	NPC263092
0.8736	High Similarity	NPC236132
0.8736	High Similarity	NPC1755
0.8736	High Similarity	NPC1706
0.8736	High Similarity	NPC470459
0.8736	High Similarity	NPC39305
0.8736	High Similarity	NPC59295
0.8736	High Similarity	NPC89131
0.8728	High Similarity	NPC66288
0.8728	High Similarity	NPC311740
0.8728	High Similarity	NPC258331
0.8722	High Similarity	NPC104682
0.8722	High Similarity	NPC113446
0.8715	High Similarity	NPC216307
0.8708	High Similarity	NPC233956
0.8708	High Similarity	NPC149846
0.8708	High Similarity	NPC473834
0.8701	High Similarity	NPC17219
0.8693	High Similarity	NPC126204
0.8693	High Similarity	NPC247973
0.8693	High Similarity	NPC107009
0.8686	High Similarity	NPC8070
0.8686	High Similarity	NPC470457
0.8686	High Similarity	NPC326520
0.8686	High Similarity	NPC37183
0.8686	High Similarity	NPC472450
0.8686	High Similarity	NPC26386
0.8686	High Similarity	NPC275780
0.8686	High Similarity	NPC239752
0.8681	High Similarity	NPC476170
0.8678	High Similarity	NPC238995
0.8678	High Similarity	NPC272722
0.8678	High Similarity	NPC81679
0.8678	High Similarity	NPC312056
0.8678	High Similarity	NPC84515
0.8674	High Similarity	NPC208069
0.8671	High Similarity	NPC14353
0.8671	High Similarity	NPC56085
0.8671	High Similarity	NPC243701
0.8671	High Similarity	NPC228785
0.8671	High Similarity	NPC130955
0.8663	High Similarity	NPC7973
0.8663	High Similarity	NPC199463
0.8663	High Similarity	NPC78302
0.8663	High Similarity	NPC472438
0.8663	High Similarity	NPC29841
0.8663	High Similarity	NPC235215
0.8663	High Similarity	NPC37543
0.8663	High Similarity	NPC263483
0.8659	High Similarity	NPC99591
0.8652	High Similarity	NPC174700
0.8652	High Similarity	NPC28589
0.8652	High Similarity	NPC248593
0.8636	High Similarity	NPC39091
0.8636	High Similarity	NPC277480
0.8636	High Similarity	NPC472452
0.8636	High Similarity	NPC170245
0.8636	High Similarity	NPC470462
0.8629	High Similarity	NPC300984
0.8629	High Similarity	NPC236521
0.8629	High Similarity	NPC189473
0.8629	High Similarity	NPC207690
0.8629	High Similarity	NPC477689
0.8629	High Similarity	NPC248638
0.8629	High Similarity	NPC23298
0.8629	High Similarity	NPC41301
0.8629	High Similarity	NPC152659
0.8626	High Similarity	NPC475656
0.8626	High Similarity	NPC475148
0.8621	High Similarity	NPC188486
0.8621	High Similarity	NPC40491
0.8621	High Similarity	NPC278052
0.8621	High Similarity	NPC61010
0.8619	High Similarity	NPC183843
0.8619	High Similarity	NPC212290
0.8613	High Similarity	NPC105242
0.8613	High Similarity	NPC25495
0.8613	High Similarity	NPC100123
0.8613	High Similarity	NPC261004
0.8613	High Similarity	NPC18772
0.8613	High Similarity	NPC130894
0.8613	High Similarity	NPC4481
0.8613	High Similarity	NPC152166
0.8613	High Similarity	NPC143828
0.8613	High Similarity	NPC300943
0.8613	High Similarity	NPC176300
0.8613	High Similarity	NPC253634
0.8613	High Similarity	NPC9609
0.8613	High Similarity	NPC22472
0.8613	High Similarity	NPC204854
0.8613	High Similarity	NPC195832
0.8613	High Similarity	NPC19687
0.8613	High Similarity	NPC196879
0.8613	High Similarity	NPC7846
0.8613	High Similarity	NPC288669
0.8613	High Similarity	NPC18607
0.8613	High Similarity	NPC45846
0.8613	High Similarity	NPC115798
0.8613	High Similarity	NPC191459
0.8613	High Similarity	NPC193842
0.8611	High Similarity	NPC107244
0.8611	High Similarity	NPC156955
0.8605	High Similarity	NPC5379
0.8605	High Similarity	NPC14561
0.8605	High Similarity	NPC200388
0.8605	High Similarity	NPC100916
0.8605	High Similarity	NPC55619
0.8605	High Similarity	NPC77807
0.8605	High Similarity	NPC268161
0.8605	High Similarity	NPC474520
0.8603	High Similarity	NPC181523
0.8596	High Similarity	NPC246716
0.8596	High Similarity	NPC20543
0.8596	High Similarity	NPC102277

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 NPC295436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	1041
0.2-0.3	2011
0.3-0.4	2708
0.4-0.5	1765
0.5-0.6	800
0.6-0.7	281
0.7-0.8	121
0.8-0.85	30
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8678	High Similarity	NPD6232	Discontinued
0.8636	High Similarity	NPD7473	Discontinued
0.8436	Intermediate Similarity	NPD5844	Phase 1
0.8391	Intermediate Similarity	NPD3882	Suspended
0.8382	Intermediate Similarity	NPD2801	Approved
0.8352	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8305	Intermediate Similarity	NPD1247	Approved
0.8286	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD6166	Phase 2
0.8268	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD3818	Discontinued
0.8146	Intermediate Similarity	NPD5494	Approved
0.8136	Intermediate Similarity	NPD7075	Discontinued
0.8111	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD919	Approved
0.8085	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD1465	Phase 2
0.8057	Intermediate Similarity	NPD7411	Suspended
0.8046	Intermediate Similarity	NPD3226	Approved
0.8043	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD5402	Approved
0.8011	Intermediate Similarity	NPD6801	Discontinued
0.8011	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7977	Intermediate Similarity	NPD1512	Approved
0.7966	Intermediate Similarity	NPD7819	Suspended
0.7966	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD6797	Phase 2
0.7919	Intermediate Similarity	NPD2534	Approved
0.7919	Intermediate Similarity	NPD2533	Approved
0.7919	Intermediate Similarity	NPD2532	Approved
0.7919	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD7251	Discontinued
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7869	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD1511	Approved
0.7861	Intermediate Similarity	NPD7808	Phase 3
0.7838	Intermediate Similarity	NPD7054	Approved
0.7831	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4380	Phase 2
0.7796	Intermediate Similarity	NPD7472	Approved
0.7796	Intermediate Similarity	NPD7074	Phase 3
0.779	Intermediate Similarity	NPD6234	Discontinued
0.7789	Intermediate Similarity	NPD8434	Phase 2
0.7759	Intermediate Similarity	NPD6799	Approved
0.7742	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7435	Discontinued
0.7637	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5403	Approved
0.7627	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD37	Approved
0.7609	Intermediate Similarity	NPD7199	Phase 2
0.7594	Intermediate Similarity	NPD7228	Approved
0.7586	Intermediate Similarity	NPD3750	Approved
0.7582	Intermediate Similarity	NPD4965	Approved
0.7582	Intermediate Similarity	NPD4966	Approved
0.7582	Intermediate Similarity	NPD4967	Phase 2
0.7582	Intermediate Similarity	NPD7768	Phase 2
0.7572	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD8313	Approved
0.7539	Intermediate Similarity	NPD8312	Approved
0.7538	Intermediate Similarity	NPD6780	Approved
0.7538	Intermediate Similarity	NPD6776	Approved
0.7538	Intermediate Similarity	NPD6781	Approved
0.7538	Intermediate Similarity	NPD6782	Approved
0.7538	Intermediate Similarity	NPD6779	Approved
0.7538	Intermediate Similarity	NPD6777	Approved
0.7538	Intermediate Similarity	NPD6778	Approved
0.7529	Intermediate Similarity	NPD1243	Approved
0.7529	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD1471	Phase 3
0.7513	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7874	Approved
0.7463	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7390	Discontinued
0.7457	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD2800	Approved
0.7416	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2344	Approved
0.7414	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7870	Phase 2
0.7389	Intermediate Similarity	NPD7871	Phase 2
0.7387	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD5710	Approved
0.738	Intermediate Similarity	NPD5711	Approved
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6190	Approved
0.734	Intermediate Similarity	NPD7697	Approved
0.734	Intermediate Similarity	NPD7696	Phase 3
0.734	Intermediate Similarity	NPD7698	Approved
0.7318	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3748	Approved
0.7299	Intermediate Similarity	NPD1510	Phase 2
0.7287	Intermediate Similarity	NPD3787	Discontinued
0.7286	Intermediate Similarity	NPD6534	Approved
0.7286	Intermediate Similarity	NPD6535	Approved
0.7283	Intermediate Similarity	NPD1607	Approved
0.7282	Intermediate Similarity	NPD7701	Phase 2
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7263	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7783	Phase 2
0.7257	Intermediate Similarity	NPD2796	Approved
0.7247	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD230	Phase 1
0.7216	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5953	Discontinued
0.72	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7229	Phase 3
0.7196	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4628	Phase 3
0.7178	Intermediate Similarity	NPD7699	Phase 2
0.7178	Intermediate Similarity	NPD7700	Phase 2
0.7177	Intermediate Similarity	NPD7801	Approved
0.7172	Intermediate Similarity	NPD4287	Approved
0.7168	Intermediate Similarity	NPD1240	Approved
0.7168	Intermediate Similarity	NPD943	Approved
0.7165	Intermediate Similarity	NPD7240	Approved
0.7159	Intermediate Similarity	NPD5404	Approved
0.7159	Intermediate Similarity	NPD5405	Approved
0.7159	Intermediate Similarity	NPD5408	Approved
0.7159	Intermediate Similarity	NPD5406	Approved
0.7159	Intermediate Similarity	NPD1551	Phase 2
0.7158	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8319	Approved
0.7136	Intermediate Similarity	NPD8320	Phase 1
0.7126	Intermediate Similarity	NPD447	Suspended
0.7104	Intermediate Similarity	NPD1653	Approved
0.7102	Intermediate Similarity	NPD2799	Discontinued
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD8285	Discontinued
0.7052	Intermediate Similarity	NPD2313	Discontinued
0.7039	Intermediate Similarity	NPD6823	Phase 2
0.7037	Intermediate Similarity	NPD7907	Approved
0.7033	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2403	Approved
0.7022	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7286	Phase 2
0.7	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7003	Approved
0.6973	Remote Similarity	NPD7458	Discontinued
0.6971	Remote Similarity	NPD4060	Phase 1
0.697	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6963	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD7177	Discontinued
0.6954	Remote Similarity	NPD3764	Approved
0.6954	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6808	Phase 2
0.6923	Remote Similarity	NPD7680	Approved
0.6914	Remote Similarity	NPD6233	Phase 2
0.6908	Remote Similarity	NPD2494	Approved
0.6908	Remote Similarity	NPD2493	Approved
0.6897	Remote Similarity	NPD6212	Phase 3
0.6897	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6213	Phase 3
0.6895	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6651	Approved
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7549	Discontinued
0.6866	Remote Similarity	NPD4111	Phase 1
0.6866	Remote Similarity	NPD4665	Approved
0.6857	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6798	Discontinued
0.6857	Remote Similarity	NPD3268	Approved
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD1933	Approved
0.6827	Remote Similarity	NPD3450	Approved
0.6827	Remote Similarity	NPD3452	Approved
0.6811	Remote Similarity	NPD6273	Approved
0.681	Remote Similarity	NPD4582	Approved
0.681	Remote Similarity	NPD4583	Approved
0.6804	Remote Similarity	NPD5242	Approved
0.6789	Remote Similarity	NPD4288	Approved
0.6789	Remote Similarity	NPD2296	Approved
0.6786	Remote Similarity	NPD8067	Phase 3
0.6786	Remote Similarity	NPD2163	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