NPASS Compound

Structure

NPC228936 OpenBabel07101718182D 23 25 0 0 0 0 0 0 0 0999 V2000 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2557 -1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 2.5981 1.5000 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 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 -1.2515 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 -1.2515 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 1.7321 -2.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2084 -1.8750 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 14 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 12 16 2 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 15 17 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 21 2 0 0 0 0 19 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.14
Volume:	334.086
LogP:	4.936
LogD:	3.92
LogS:	-6.443
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.605
Synthetic Accessibility Score:	3.405
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.772
MDCK Permeability:	2.51078399742255e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	94.05750274658203%
Volume Distribution (VD):	1.283
Pgp-substrate:	3.492486000061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.901
CYP2C9-substrate:	0.264
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.629
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	3.92
Half-life (T1/2):	0.041

ADMET: Toxicity

hERG Blockers:	0.511
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.456
AMES Toxicity:	0.795
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.864
Carcinogencity:	0.928
Eye Corrosion:	0.004
Eye Irritation:	0.554
Respiratory Toxicity:	0.727

Download Data

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

Natural Product: NPC228936

Natural Product ID:	NPC228936
*Common Name:**	DSVUOBIQVPVZST-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DSVUOBIQVPVZST-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O3/c1-11(2)6-5-7-14-10-23-20-13(4)18(21)19(22)16-12(3)8-9-15(14)17(16)20/h6,8-10H,5,7H2,1-4H3
SMILES:	CC(=CCCC1=COC2=C(C)C(=O)C(=O)c3c2c1ccc3C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252517
PubChem CID:	57525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO33460	Eremophila neglecta	Species	Scrophulariaceae	Eukaryota	n.a.	Australian desert	n.a.	PMID[17844993]
NPO33460	Eremophila neglecta	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26636180]

☑ 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
MIC	21
Others	7

Activity Type	# Activity
NON-MOLECULAR	4
Organism	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25300.0	nM	PMID[491481]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	6500.0	nM	PMID[491481]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	101600.0	nM	PMID[491481]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	202.9	uM	PMID[491481]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	50.6	uM	PMID[491481]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	12.7	uM	PMID[491481]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MBC	=	202.9	uM	PMID[491481]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT1549	Organism	Vibrio cholerae	Vibrio cholerae	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT5579	Organism	Aeromonas punctata	Aeromonas caviae	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>=	1024.0	ug.mL-1	PMID[491482]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI	=	75.0	%	PMID[491482]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[491482]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[491482]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[491482]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	256.0	ug.mL-1	PMID[491482]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	16.0	ug.mL-1	PMID[491482]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	32.0	ug.mL-1	PMID[491482]

☑ 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 NPC228936 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	276
0.1-0.2	1418
0.2-0.3	3101
0.3-0.4	9393
0.4-0.5	11152
0.5-0.6	9530
0.6-0.7	7027
0.7-0.8	739
0.8-0.85	43
0.85-0.9	8
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9811	High Similarity	NPC13784
0.9364	High Similarity	NPC135730
0.9182	High Similarity	NPC196075
0.9123	High Similarity	NPC988
0.9123	High Similarity	NPC238861
0.9123	High Similarity	NPC77000
0.9123	High Similarity	NPC289432
0.9043	High Similarity	NPC144547
0.9	High Similarity	NPC212415
0.8929	High Similarity	NPC474095
0.8839	High Similarity	NPC477411
0.8814	High Similarity	NPC51079
0.8793	High Similarity	NPC232958
0.8684	High Similarity	NPC226093
0.8571	High Similarity	NPC210089
0.8435	Intermediate Similarity	NPC474408
0.8407	Intermediate Similarity	NPC474157
0.8407	Intermediate Similarity	NPC291799
0.8348	Intermediate Similarity	NPC326664
0.8319	Intermediate Similarity	NPC273837
0.8304	Intermediate Similarity	NPC470391
0.8288	Intermediate Similarity	NPC209632
0.8279	Intermediate Similarity	NPC295664
0.8276	Intermediate Similarity	NPC470764
0.8276	Intermediate Similarity	NPC210092
0.8273	Intermediate Similarity	NPC60679
0.8246	Intermediate Similarity	NPC474057
0.8246	Intermediate Similarity	NPC137315
0.8198	Intermediate Similarity	NPC114594
0.8174	Intermediate Similarity	NPC79496
0.8125	Intermediate Similarity	NPC310662
0.8103	Intermediate Similarity	NPC272524
0.8099	Intermediate Similarity	NPC472981
0.8087	Intermediate Similarity	NPC167504
0.8083	Intermediate Similarity	NPC204784
0.808	Intermediate Similarity	NPC428300
0.807	Intermediate Similarity	NPC17417
0.807	Intermediate Similarity	NPC192577
0.807	Intermediate Similarity	NPC269023
0.807	Intermediate Similarity	NPC99846
0.807	Intermediate Similarity	NPC83628
0.807	Intermediate Similarity	NPC10251
0.807	Intermediate Similarity	NPC265407
0.8053	Intermediate Similarity	NPC30594
0.8053	Intermediate Similarity	NPC37622
0.8051	Intermediate Similarity	NPC471616
0.8047	Intermediate Similarity	NPC183103
0.8034	Intermediate Similarity	NPC67377
0.8034	Intermediate Similarity	NPC307651
0.8034	Intermediate Similarity	NPC308744
0.8034	Intermediate Similarity	NPC196673
0.8017	Intermediate Similarity	NPC270699
0.8017	Intermediate Similarity	NPC82899
0.8	Intermediate Similarity	NPC318173
0.8	Intermediate Similarity	NPC196246
0.8	Intermediate Similarity	NPC251854
0.8	Intermediate Similarity	NPC93084
0.8	Intermediate Similarity	NPC214067
0.7982	Intermediate Similarity	NPC56493
0.7982	Intermediate Similarity	NPC203732
0.7969	Intermediate Similarity	NPC239134
0.7966	Intermediate Similarity	NPC474685
0.7965	Intermediate Similarity	NPC172483
0.7963	Intermediate Similarity	NPC5472
0.7953	Intermediate Similarity	NPC57552
0.7949	Intermediate Similarity	NPC128368
0.7946	Intermediate Similarity	NPC301943
0.7946	Intermediate Similarity	NPC474365
0.7931	Intermediate Similarity	NPC305912
0.7931	Intermediate Similarity	NPC1082
0.7928	Intermediate Similarity	NPC112552
0.7917	Intermediate Similarity	NPC222968
0.7917	Intermediate Similarity	NPC228318
0.7917	Intermediate Similarity	NPC80605
0.7917	Intermediate Similarity	NPC323440
0.7895	Intermediate Similarity	NPC119271
0.7881	Intermediate Similarity	NPC241851
0.7876	Intermediate Similarity	NPC31786
0.7869	Intermediate Similarity	NPC476225
0.7863	Intermediate Similarity	NPC292834
0.7863	Intermediate Similarity	NPC309056
0.7857	Intermediate Similarity	NPC177925
0.7857	Intermediate Similarity	NPC474737
0.7857	Intermediate Similarity	NPC51292
0.7846	Intermediate Similarity	NPC59459
0.7846	Intermediate Similarity	NPC470406
0.7845	Intermediate Similarity	NPC174099
0.7833	Intermediate Similarity	NPC190298
0.7829	Intermediate Similarity	NPC164295
0.7815	Intermediate Similarity	NPC221275
0.7815	Intermediate Similarity	NPC306740
0.7812	Intermediate Similarity	NPC471832
0.7798	Intermediate Similarity	NPC260233
0.7797	Intermediate Similarity	NPC143768
0.7795	Intermediate Similarity	NPC51448
0.7795	Intermediate Similarity	NPC115797
0.7788	Intermediate Similarity	NPC274443
0.7788	Intermediate Similarity	NPC89886
0.7788	Intermediate Similarity	NPC247976
0.7786	Intermediate Similarity	NPC212207
0.7778	Intermediate Similarity	NPC155232
0.7778	Intermediate Similarity	NPC153885
0.7778	Intermediate Similarity	NPC265513
0.7769	Intermediate Similarity	NPC469954
0.7769	Intermediate Similarity	NPC45794
0.7768	Intermediate Similarity	NPC70624
0.7761	Intermediate Similarity	NPC470407
0.776	Intermediate Similarity	NPC318067
0.776	Intermediate Similarity	NPC85511
0.776	Intermediate Similarity	NPC328107
0.776	Intermediate Similarity	NPC228739
0.776	Intermediate Similarity	NPC182646
0.7759	Intermediate Similarity	NPC469636
0.775	Intermediate Similarity	NPC149691
0.7748	Intermediate Similarity	NPC78701
0.7748	Intermediate Similarity	NPC35448
0.7744	Intermediate Similarity	NPC301341
0.7744	Intermediate Similarity	NPC186647
0.7731	Intermediate Similarity	NPC153053
0.7727	Intermediate Similarity	NPC22644
0.7712	Intermediate Similarity	NPC321852
0.7712	Intermediate Similarity	NPC280789
0.7712	Intermediate Similarity	NPC471188
0.7706	Intermediate Similarity	NPC238219
0.7699	Intermediate Similarity	NPC222390
0.7699	Intermediate Similarity	NPC244427
0.7699	Intermediate Similarity	NPC188895
0.7698	Intermediate Similarity	NPC75432
0.7692	Intermediate Similarity	NPC279596
0.7692	Intermediate Similarity	NPC477412
0.7685	Intermediate Similarity	NPC133461
0.768	Intermediate Similarity	NPC65627
0.768	Intermediate Similarity	NPC223351
0.7679	Intermediate Similarity	NPC146351
0.7679	Intermediate Similarity	NPC325497
0.7679	Intermediate Similarity	NPC476042
0.7679	Intermediate Similarity	NPC203925
0.7672	Intermediate Similarity	NPC470007
0.7669	Intermediate Similarity	NPC471670
0.7667	Intermediate Similarity	NPC93181
0.7661	Intermediate Similarity	NPC50872
0.7658	Intermediate Similarity	NPC276775
0.7658	Intermediate Similarity	NPC249912
0.7658	Intermediate Similarity	NPC92754
0.7658	Intermediate Similarity	NPC239185
0.7652	Intermediate Similarity	NPC1249
0.7652	Intermediate Similarity	NPC23894
0.7647	Intermediate Similarity	NPC161611
0.7647	Intermediate Similarity	NPC470253
0.7638	Intermediate Similarity	NPC476599
0.7638	Intermediate Similarity	NPC236405
0.7636	Intermediate Similarity	NPC130398
0.7634	Intermediate Similarity	NPC476644
0.7627	Intermediate Similarity	NPC243355
0.7627	Intermediate Similarity	NPC260818
0.7623	Intermediate Similarity	NPC61651
0.7612	Intermediate Similarity	NPC284184
0.7612	Intermediate Similarity	NPC119542
0.7611	Intermediate Similarity	NPC42211
0.7609	Intermediate Similarity	NPC471451
0.7607	Intermediate Similarity	NPC85493
0.7607	Intermediate Similarity	NPC474364
0.76	Intermediate Similarity	NPC269923
0.76	Intermediate Similarity	NPC167323
0.7594	Intermediate Similarity	NPC89504
0.7594	Intermediate Similarity	NPC95485
0.7594	Intermediate Similarity	NPC88065
0.7594	Intermediate Similarity	NPC217914
0.7593	Intermediate Similarity	NPC173413
0.7589	Intermediate Similarity	NPC75724
0.7589	Intermediate Similarity	NPC49994
0.7589	Intermediate Similarity	NPC225060
0.7589	Intermediate Similarity	NPC134882
0.7586	Intermediate Similarity	NPC100767
0.7586	Intermediate Similarity	NPC83409
0.7586	Intermediate Similarity	NPC185763
0.7583	Intermediate Similarity	NPC471721
0.7581	Intermediate Similarity	NPC473243
0.7578	Intermediate Similarity	NPC474264
0.7563	Intermediate Similarity	NPC186128
0.7563	Intermediate Similarity	NPC66208
0.7563	Intermediate Similarity	NPC23332
0.7559	Intermediate Similarity	NPC199273
0.7559	Intermediate Similarity	NPC246166
0.7557	Intermediate Similarity	NPC472394
0.7544	Intermediate Similarity	NPC45613
0.7541	Intermediate Similarity	NPC158157
0.7541	Intermediate Similarity	NPC469843
0.7538	Intermediate Similarity	NPC82712
0.7537	Intermediate Similarity	NPC232996
0.7537	Intermediate Similarity	NPC475549
0.7536	Intermediate Similarity	NPC117674
0.7523	Intermediate Similarity	NPC284475
0.7522	Intermediate Similarity	NPC118343
0.7521	Intermediate Similarity	NPC211439
0.7521	Intermediate Similarity	NPC274839
0.7521	Intermediate Similarity	NPC112903
0.7521	Intermediate Similarity	NPC215419
0.7521	Intermediate Similarity	NPC186933
0.7519	Intermediate Similarity	NPC45537

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 NPC228936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	999
0.2-0.3	1051
0.3-0.4	2717
0.4-0.5	2426
0.5-0.6	1286
0.6-0.7	372
0.7-0.8	35
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9123	High Similarity	NPD3412	Clinical (unspecified phase)
0.9	High Similarity	NPD1609	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD2182	Approved
0.7876	Intermediate Similarity	NPD164	Approved
0.7823	Intermediate Similarity	NPD3972	Approved
0.7674	Intermediate Similarity	NPD7008	Discontinued
0.7674	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5951	Approved
0.7658	Intermediate Similarity	NPD3495	Discontinued
0.7642	Intermediate Similarity	NPD1651	Approved
0.7627	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7609	Phase 3
0.7522	Intermediate Similarity	NPD1238	Approved
0.752	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7631	Approved
0.744	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1241	Discontinued
0.7422	Intermediate Similarity	NPD1876	Approved
0.7414	Intermediate Similarity	NPD5909	Discontinued
0.7402	Intermediate Similarity	NPD4878	Approved
0.7323	Intermediate Similarity	NPD6287	Discontinued
0.7323	Intermediate Similarity	NPD1281	Approved
0.7315	Intermediate Similarity	NPD650	Approved
0.7308	Intermediate Similarity	NPD2798	Approved
0.7299	Intermediate Similarity	NPD2346	Discontinued
0.7265	Intermediate Similarity	NPD1237	Approved
0.7257	Intermediate Similarity	NPD1989	Approved
0.725	Intermediate Similarity	NPD2067	Discontinued
0.7222	Intermediate Similarity	NPD5691	Approved
0.7217	Intermediate Similarity	NPD2066	Phase 3
0.7188	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1929	Approved
0.7179	Intermediate Similarity	NPD1930	Approved
0.7179	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3317	Approved
0.7164	Intermediate Similarity	NPD7713	Phase 3
0.7154	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7111	Intermediate Similarity	NPD2979	Phase 3
0.7097	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2313	Discontinued
0.7031	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD1087	Approved
0.6978	Remote Similarity	NPD2796	Approved
0.6977	Remote Similarity	NPD4879	Approved
0.697	Remote Similarity	NPD3266	Approved
0.697	Remote Similarity	NPD3267	Approved
0.6953	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1932	Approved
0.6935	Remote Similarity	NPD6858	Approved
0.6935	Remote Similarity	NPD7094	Approved
0.693	Remote Similarity	NPD1202	Approved
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD7236	Approved
0.6923	Remote Similarity	NPD1201	Approved
0.6917	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD9259	Approved
0.6909	Remote Similarity	NPD9257	Approved
0.6906	Remote Similarity	NPD3748	Approved
0.6906	Remote Similarity	NPD2799	Discontinued
0.6899	Remote Similarity	NPD2932	Approved
0.6889	Remote Similarity	NPD6039	Approved
0.688	Remote Similarity	NPD6010	Discontinued
0.6875	Remote Similarity	NPD9545	Approved
0.6871	Remote Similarity	NPD3226	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.687	Remote Similarity	NPD1693	Approved
0.6861	Remote Similarity	NPD4307	Phase 2
0.6861	Remote Similarity	NPD3142	Approved
0.6861	Remote Similarity	NPD3140	Approved
0.6857	Remote Similarity	NPD2531	Phase 2
0.6857	Remote Similarity	NPD2438	Suspended
0.6853	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.685	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1470	Approved
0.6842	Remote Similarity	NPD2797	Approved
0.6838	Remote Similarity	NPD3268	Approved
0.6838	Remote Similarity	NPD3764	Approved
0.6822	Remote Similarity	NPD3025	Approved
0.6822	Remote Similarity	NPD3024	Approved
0.6815	Remote Similarity	NPD6832	Phase 2
0.6814	Remote Similarity	NPD1086	Approved
0.6814	Remote Similarity	NPD1089	Approved
0.6814	Remote Similarity	NPD1090	Approved
0.6809	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7239	Suspended
0.6794	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8032	Phase 2
0.6783	Remote Similarity	NPD4628	Phase 3
0.6781	Remote Similarity	NPD6273	Approved
0.6772	Remote Similarity	NPD4198	Discontinued
0.6769	Remote Similarity	NPD3019	Approved
0.6763	Remote Similarity	NPD1607	Approved
0.6757	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2329	Discontinued
0.6744	Remote Similarity	NPD7009	Phase 2
0.6726	Remote Similarity	NPD800	Approved
0.6724	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD9493	Approved
0.6718	Remote Similarity	NPD3026	Approved
0.6718	Remote Similarity	NPD3023	Approved
0.6712	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2533	Approved
0.6712	Remote Similarity	NPD2534	Approved
0.6712	Remote Similarity	NPD2532	Approved
0.6696	Remote Similarity	NPD1282	Approved
0.6696	Remote Similarity	NPD1088	Approved
0.6694	Remote Similarity	NPD3047	Approved
0.6694	Remote Similarity	NPD3046	Approved
0.6694	Remote Similarity	NPD3048	Approved
0.6693	Remote Similarity	NPD2629	Approved
0.6692	Remote Similarity	NPD5157	Phase 1
0.6692	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5159	Phase 2
0.6689	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2788	Approved
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD7610	Discontinued
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6645	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2199	Approved
0.6642	Remote Similarity	NPD2198	Approved
0.6642	Remote Similarity	NPD5667	Approved
0.6641	Remote Similarity	NPD5125	Phase 3
0.6641	Remote Similarity	NPD17	Approved
0.6641	Remote Similarity	NPD5126	Approved
0.6638	Remote Similarity	NPD1563	Approved
0.662	Remote Similarity	NPD2935	Discontinued
0.662	Remote Similarity	NPD4477	Approved
0.662	Remote Similarity	NPD4476	Approved
0.6619	Remote Similarity	NPD3373	Approved
0.6619	Remote Similarity	NPD1240	Approved
0.6617	Remote Similarity	NPD6637	Approved
0.6609	Remote Similarity	NPD1239	Approved
0.6606	Remote Similarity	NPD942	Approved
0.6599	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3134	Approved
0.6573	Remote Similarity	NPD2344	Approved
0.6571	Remote Similarity	NPD4622	Approved
0.6571	Remote Similarity	NPD4618	Approved
0.6569	Remote Similarity	NPD7055	Discontinued
0.6567	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5889	Approved
0.6556	Remote Similarity	NPD5890	Approved
0.6555	Remote Similarity	NPD9495	Approved
0.6552	Remote Similarity	NPD8166	Discontinued
0.6552	Remote Similarity	NPD1508	Approved
0.6544	Remote Similarity	NPD4980	Approved
0.6531	Remote Similarity	NPD3950	Discontinued
0.6522	Remote Similarity	NPD6966	Discovery
0.6507	Remote Similarity	NPD3887	Approved
0.6503	Remote Similarity	NPD5408	Approved
0.6503	Remote Similarity	NPD5406	Approved
0.6503	Remote Similarity	NPD5404	Approved
0.6503	Remote Similarity	NPD5405	Approved
0.6497	Remote Similarity	NPD6232	Discontinued
0.6496	Remote Similarity	NPD9494	Approved
0.6493	Remote Similarity	NPD1608	Approved
0.649	Remote Similarity	NPD6599	Discontinued
0.649	Remote Similarity	NPD4380	Phase 2
0.6489	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1894	Discontinued
0.6486	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5688	Approved
0.6479	Remote Similarity	NPD5689	Approved
0.6478	Remote Similarity	NPD7473	Discontinued
0.6475	Remote Similarity	NPD6647	Phase 2
0.6471	Remote Similarity	NPD1566	Phase 3
0.6471	Remote Similarity	NPD1565	Approved
0.6471	Remote Similarity	NPD1564	Approved
0.6458	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7411	Suspended
0.6446	Remote Similarity	NPD2549	Approved
0.6446	Remote Similarity	NPD2555	Approved
0.6446	Remote Similarity	NPD2558	Approved
0.6446	Remote Similarity	NPD2552	Approved
0.6446	Remote Similarity	NPD2550	Approved
0.6446	Remote Similarity	NPD2553	Approved
0.6444	Remote Similarity	NPD5327	Phase 3
0.6441	Remote Similarity	NPD9260	Approved
0.6439	Remote Similarity	NPD5585	Approved
0.6438	Remote Similarity	NPD1878	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