NPASS Compound

Structure

NPC7029 OpenBabel07101719522D 25 25 0 0 0 0 0 0 0 0999 V2000 12.1244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.7321 1.0000 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 0.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.14
Volume:	374.273
LogP:	2.253
LogD:	2.753
LogS:	-4.164
# Rotatable Bonds:	3
TPSA:	66.46
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	3.416
Fsp3:	0.381
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:	-4.902
MDCK Permeability:	4.919767889077775e-05
Pgp-inhibitor:	0.857
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	90.50196075439453%
Volume Distribution (VD):	1.814
Pgp-substrate:	5.46574592590332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.601
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.935
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.936
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	9.237
Half-life (T1/2):	0.214

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.57
AMES Toxicity:	0.271
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.04
Carcinogencity:	0.738
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC7029

Natural Product ID:	NPC7029
*Common Name:**	2,5-Dihydroxyl-3-Undecyl-1,4-Benzoquinone
IUPAC Name:	2,5-dihydroxy-3-pentadecylcyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	GXDURRGUXLDZKN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-20(24)18(22)16-19(23)21(17)25/h16,22,25H,2-15H2,1H3
SMILES:	CCCCCCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462998
PubChem CID:	4187769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	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
MIC	2
Others	3

Activity Type	# Activity
Cell Line	5
Individual Protein	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1420.0	nM	PMID[505641]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1860.0	nM	PMID[505641]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	1510.0	nM	PMID[505641]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	1830.0	nM	PMID[505641]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1440.0	nM	PMID[505641]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	4300.0	nM	PMID[505643]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	230.0	nM	PMID[505643]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	10000.0	nM	PMID[505643]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	61.7	%	PMID[505643]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Activity	=	87.7	%	PMID[505643]
NPT3167	Individual Protein	Macrophage-expressed gene 1 protein	Homo sapiens	IC50	=	2100.0	nM	PMID[505643]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	105.0	ug.mL-1	PMID[505642]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	107.0	ug.mL-1	PMID[505642]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Activity	=	103.4	%	PMID[505643]

☑ 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 NPC7029 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	146
0.1-0.2	1974
0.2-0.3	10379
0.3-0.4	17527
0.4-0.5	7972
0.5-0.6	3875
0.6-0.7	719
0.7-0.8	77
0.8-0.85	8
0.85-0.9	6
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC143168
0.9831	High Similarity	NPC53109
0.95	High Similarity	NPC477830
0.9365	High Similarity	NPC263382
0.9365	High Similarity	NPC146376
0.9365	High Similarity	NPC125578
0.9206	High Similarity	NPC243272
0.9153	High Similarity	NPC320421
0.9077	High Similarity	NPC291062
0.9077	High Similarity	NPC94743
0.8923	High Similarity	NPC262673
0.8923	High Similarity	NPC94488
0.8676	High Similarity	NPC264178
0.8615	High Similarity	NPC474619
0.8594	High Similarity	NPC98897
0.8571	High Similarity	NPC477707
0.8462	Intermediate Similarity	NPC16119
0.8438	Intermediate Similarity	NPC34622
0.8438	Intermediate Similarity	NPC474400
0.8281	Intermediate Similarity	NPC151728
0.8281	Intermediate Similarity	NPC57463
0.8209	Intermediate Similarity	NPC134385
0.8169	Intermediate Similarity	NPC477708
0.8136	Intermediate Similarity	NPC137396
0.7826	Intermediate Similarity	NPC469914
0.7812	Intermediate Similarity	NPC106851
0.7812	Intermediate Similarity	NPC274927
0.7812	Intermediate Similarity	NPC473494
0.7808	Intermediate Similarity	NPC473536
0.7778	Intermediate Similarity	NPC192843
0.7632	Intermediate Similarity	NPC55869
0.7576	Intermediate Similarity	NPC40082
0.7534	Intermediate Similarity	NPC175079
0.75	Intermediate Similarity	NPC61473
0.75	Intermediate Similarity	NPC281230
0.75	Intermediate Similarity	NPC108955
0.7467	Intermediate Similarity	NPC231739
0.7436	Intermediate Similarity	NPC105803
0.7432	Intermediate Similarity	NPC110725
0.7429	Intermediate Similarity	NPC477452
0.7424	Intermediate Similarity	NPC235242
0.7424	Intermediate Similarity	NPC122521
0.7424	Intermediate Similarity	NPC251042
0.7424	Intermediate Similarity	NPC174447
0.7385	Intermediate Similarity	NPC139056
0.7377	Intermediate Similarity	NPC477458
0.7344	Intermediate Similarity	NPC477201
0.7333	Intermediate Similarity	NPC471061
0.7324	Intermediate Similarity	NPC474060
0.7313	Intermediate Similarity	NPC115752
0.7313	Intermediate Similarity	NPC15130
0.7313	Intermediate Similarity	NPC138056
0.7313	Intermediate Similarity	NPC473212
0.7313	Intermediate Similarity	NPC254449
0.7308	Intermediate Similarity	NPC103486
0.7286	Intermediate Similarity	NPC251429
0.725	Intermediate Similarity	NPC132228
0.725	Intermediate Similarity	NPC6185
0.725	Intermediate Similarity	NPC474680
0.725	Intermediate Similarity	NPC8518
0.725	Intermediate Similarity	NPC241512
0.725	Intermediate Similarity	NPC32037
0.725	Intermediate Similarity	NPC263997
0.7237	Intermediate Similarity	NPC30321
0.7231	Intermediate Similarity	NPC224103
0.7231	Intermediate Similarity	NPC200831
0.7231	Intermediate Similarity	NPC299369
0.7222	Intermediate Similarity	NPC173321
0.7215	Intermediate Similarity	NPC477784
0.7215	Intermediate Similarity	NPC477785
0.7215	Intermediate Similarity	NPC477786
0.7206	Intermediate Similarity	NPC473211
0.7206	Intermediate Similarity	NPC473210
0.72	Intermediate Similarity	NPC92080
0.7179	Intermediate Similarity	NPC225515
0.7179	Intermediate Similarity	NPC275766
0.7162	Intermediate Similarity	NPC147438
0.7143	Intermediate Similarity	NPC137163
0.7143	Intermediate Similarity	NPC27817
0.7143	Intermediate Similarity	NPC197089
0.7042	Intermediate Similarity	NPC473213
0.7037	Intermediate Similarity	NPC77971
0.7037	Intermediate Similarity	NPC470177
0.7031	Intermediate Similarity	NPC88966
0.7031	Intermediate Similarity	NPC85813
0.7031	Intermediate Similarity	NPC281972
0.7031	Intermediate Similarity	NPC154245
0.7031	Intermediate Similarity	NPC290563
0.7031	Intermediate Similarity	NPC87564
0.7031	Intermediate Similarity	NPC32467
0.7031	Intermediate Similarity	NPC317796
0.7031	Intermediate Similarity	NPC25417
0.7031	Intermediate Similarity	NPC6095
0.7031	Intermediate Similarity	NPC424
0.7031	Intermediate Similarity	NPC87394
0.7031	Intermediate Similarity	NPC261831
0.7013	Intermediate Similarity	NPC74410
0.7013	Intermediate Similarity	NPC475994
0.7013	Intermediate Similarity	NPC189485
0.7013	Intermediate Similarity	NPC478122
0.7	Intermediate Similarity	NPC53733
0.6986	Remote Similarity	NPC477455
0.6974	Remote Similarity	NPC26504
0.6974	Remote Similarity	NPC180886
0.6974	Remote Similarity	NPC1254
0.6974	Remote Similarity	NPC470525
0.697	Remote Similarity	NPC268185
0.697	Remote Similarity	NPC283502
0.6962	Remote Similarity	NPC189237
0.6962	Remote Similarity	NPC472684
0.6962	Remote Similarity	NPC44963
0.6962	Remote Similarity	NPC278459
0.6951	Remote Similarity	NPC203795
0.6951	Remote Similarity	NPC472009
0.6944	Remote Similarity	NPC476614
0.6933	Remote Similarity	NPC227396
0.6933	Remote Similarity	NPC122244
0.6923	Remote Similarity	NPC192329
0.6923	Remote Similarity	NPC475681
0.6912	Remote Similarity	NPC143857
0.6912	Remote Similarity	NPC229252
0.6912	Remote Similarity	NPC243532
0.6905	Remote Similarity	NPC68148
0.6905	Remote Similarity	NPC65615
0.6905	Remote Similarity	NPC112454
0.6892	Remote Similarity	NPC474539
0.6892	Remote Similarity	NPC144627
0.6892	Remote Similarity	NPC84790
0.6883	Remote Similarity	NPC266124
0.6883	Remote Similarity	NPC211279
0.6883	Remote Similarity	NPC283087
0.6875	Remote Similarity	NPC321062
0.6875	Remote Similarity	NPC474805
0.6875	Remote Similarity	NPC139029
0.6875	Remote Similarity	NPC294548
0.6875	Remote Similarity	NPC70387
0.6875	Remote Similarity	NPC1813
0.6875	Remote Similarity	NPC36061
0.6875	Remote Similarity	NPC47450
0.6867	Remote Similarity	NPC472007
0.6866	Remote Similarity	NPC34416
0.6857	Remote Similarity	NPC150162
0.6849	Remote Similarity	NPC10758
0.6849	Remote Similarity	NPC143396
0.6849	Remote Similarity	NPC250928
0.6849	Remote Similarity	NPC67608
0.6842	Remote Similarity	NPC251435
0.6835	Remote Similarity	NPC2482
0.6835	Remote Similarity	NPC18955
0.6835	Remote Similarity	NPC74086
0.6833	Remote Similarity	NPC191337
0.6829	Remote Similarity	NPC469993
0.6824	Remote Similarity	NPC475823
0.6824	Remote Similarity	NPC474209
0.6824	Remote Similarity	NPC471399
0.6818	Remote Similarity	NPC18951
0.6818	Remote Similarity	NPC325977
0.6812	Remote Similarity	NPC201939
0.6806	Remote Similarity	NPC278895
0.68	Remote Similarity	NPC247586
0.6795	Remote Similarity	NPC207772
0.6795	Remote Similarity	NPC248624
0.6795	Remote Similarity	NPC275494
0.6795	Remote Similarity	NPC471409
0.6795	Remote Similarity	NPC476808
0.679	Remote Similarity	NPC258985
0.6786	Remote Similarity	NPC472008
0.6786	Remote Similarity	NPC53454
0.6786	Remote Similarity	NPC58271
0.6782	Remote Similarity	NPC23170
0.6774	Remote Similarity	NPC145311
0.6761	Remote Similarity	NPC474329
0.6761	Remote Similarity	NPC296436
0.6761	Remote Similarity	NPC176215
0.6761	Remote Similarity	NPC474304
0.6757	Remote Similarity	NPC203819
0.6757	Remote Similarity	NPC318766
0.6753	Remote Similarity	NPC76966
0.6753	Remote Similarity	NPC186554
0.675	Remote Similarity	NPC474085
0.675	Remote Similarity	NPC475863
0.675	Remote Similarity	NPC99308
0.675	Remote Similarity	NPC116797
0.675	Remote Similarity	NPC470034
0.6744	Remote Similarity	NPC174167
0.6744	Remote Similarity	NPC45579
0.6744	Remote Similarity	NPC470036
0.6744	Remote Similarity	NPC146852
0.6719	Remote Similarity	NPC92114
0.6719	Remote Similarity	NPC281245
0.6711	Remote Similarity	NPC474321
0.6711	Remote Similarity	NPC160540
0.6706	Remote Similarity	NPC474918
0.6705	Remote Similarity	NPC147232
0.6667	Remote Similarity	NPC477686
0.6667	Remote Similarity	NPC25771
0.6667	Remote Similarity	NPC15325
0.6667	Remote Similarity	NPC165711
0.6667	Remote Similarity	NPC100719
0.6667	Remote Similarity	NPC474391

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 NPC7029 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	2706
0.2-0.3	4152
0.3-0.4	1597
0.4-0.5	341
0.5-0.6	186
0.6-0.7	24
0.7-0.8	4
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9831	High Similarity	NPD2664	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD3704	Approved
0.8056	Intermediate Similarity	NPD4756	Discovery
0.791	Intermediate Similarity	NPD7331	Phase 2
0.7733	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD7341	Phase 2
0.7231	Intermediate Similarity	NPD8779	Phase 3
0.7031	Intermediate Similarity	NPD4266	Approved
0.7031	Intermediate Similarity	NPD3195	Phase 2
0.7031	Intermediate Similarity	NPD3194	Approved
0.7031	Intermediate Similarity	NPD3196	Approved
0.6923	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3172	Approved
0.6857	Remote Similarity	NPD3197	Phase 1
0.6835	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3617	Approved
0.6627	Remote Similarity	NPD5329	Approved
0.6562	Remote Similarity	NPD29	Approved
0.6562	Remote Similarity	NPD28	Approved
0.6548	Remote Similarity	NPD5690	Phase 2
0.6506	Remote Similarity	NPD4197	Approved
0.6463	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4694	Approved
0.6353	Remote Similarity	NPD5280	Approved
0.6353	Remote Similarity	NPD5279	Phase 3
0.6322	Remote Similarity	NPD4753	Phase 2
0.6265	Remote Similarity	NPD4221	Approved
0.6265	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD3173	Approved
0.6235	Remote Similarity	NPD5363	Approved
0.6235	Remote Similarity	NPD1696	Phase 3
0.6222	Remote Similarity	NPD5282	Discontinued
0.619	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6118	Remote Similarity	NPD4786	Approved
0.6118	Remote Similarity	NPD3666	Approved
0.6118	Remote Similarity	NPD3133	Approved
0.6118	Remote Similarity	NPD3665	Phase 1
0.6094	Remote Similarity	NPD622	Approved
0.6087	Remote Similarity	NPD5222	Approved
0.6087	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5221	Approved
0.6071	Remote Similarity	NPD3667	Approved
0.6023	Remote Similarity	NPD5737	Approved
0.6023	Remote Similarity	NPD4518	Approved
0.6023	Remote Similarity	NPD6672	Approved
0.6022	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD7154	Phase 3
0.5978	Remote Similarity	NPD5695	Phase 3
0.5977	Remote Similarity	NPD4623	Approved
0.5977	Remote Similarity	NPD4688	Approved
0.5977	Remote Similarity	NPD4519	Discontinued
0.5977	Remote Similarity	NPD3618	Phase 1
0.5977	Remote Similarity	NPD4693	Phase 3
0.5977	Remote Similarity	NPD4138	Approved
0.5977	Remote Similarity	NPD4690	Approved
0.5977	Remote Similarity	NPD5205	Approved
0.5977	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD6080	Approved
0.5955	Remote Similarity	NPD6904	Approved
0.5955	Remote Similarity	NPD6673	Approved
0.5955	Remote Similarity	NPD5328	Approved
0.5952	Remote Similarity	NPD5369	Approved
0.5934	Remote Similarity	NPD5133	Approved
0.5914	Remote Similarity	NPD7614	Phase 1
0.5914	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD4691	Approved
0.5895	Remote Similarity	NPD4696	Approved
0.5895	Remote Similarity	NPD5285	Approved
0.5895	Remote Similarity	NPD5286	Approved
0.5889	Remote Similarity	NPD5785	Approved
0.5889	Remote Similarity	NPD46	Approved
0.5889	Remote Similarity	NPD6698	Approved
0.5882	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD4270	Approved
0.587	Remote Similarity	NPD7748	Approved
0.5851	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD4252	Approved
0.5833	Remote Similarity	NPD5783	Phase 3
0.5833	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5824	Remote Similarity	NPD6050	Approved
0.5824	Remote Similarity	NPD5281	Approved
0.5824	Remote Similarity	NPD5284	Approved
0.5814	Remote Similarity	NPD5362	Discontinued
0.5789	Remote Similarity	NPD5696	Approved
0.5783	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD4222	Approved
0.5781	Remote Similarity	NPD39	Approved
0.5781	Remote Similarity	NPD3174	Discontinued
0.5778	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6101	Approved
0.5773	Remote Similarity	NPD5224	Approved
0.5773	Remote Similarity	NPD5225	Approved
0.5773	Remote Similarity	NPD4633	Approved
0.5773	Remote Similarity	NPD5211	Phase 2
0.5773	Remote Similarity	NPD5091	Approved
0.5773	Remote Similarity	NPD5226	Approved
0.5769	Remote Similarity	NPD4137	Phase 3
0.5761	Remote Similarity	NPD6399	Phase 3
0.5753	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD3668	Phase 3
0.5729	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD5692	Phase 3
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4096	Approved
0.5714	Remote Similarity	NPD4195	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5699	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD6435	Approved
0.5696	Remote Similarity	NPD4747	Approved
0.5684	Remote Similarity	NPD7902	Approved
0.5679	Remote Similarity	NPD4058	Approved
0.5679	Remote Similarity	NPD5733	Approved
0.5657	Remote Similarity	NPD5141	Approved
0.5652	Remote Similarity	NPD6411	Approved
0.5652	Remote Similarity	NPD5694	Approved
0.5652	Remote Similarity	NPD5693	Phase 1
0.5645	Remote Similarity	NPD2270	Approved
0.5644	Remote Similarity	NPD6899	Approved
0.5644	Remote Similarity	NPD6881	Approved
0.5632	Remote Similarity	NPD4788	Approved
0.5625	Remote Similarity	NPD5276	Approved
0.5618	Remote Similarity	NPD5786	Approved
0.5618	Remote Similarity	NPD5330	Approved
0.5618	Remote Similarity	NPD6684	Approved
0.5618	Remote Similarity	NPD6098	Approved
0.5618	Remote Similarity	NPD6422	Discontinued
0.5618	Remote Similarity	NPD7521	Approved
0.5618	Remote Similarity	NPD7334	Approved
0.5618	Remote Similarity	NPD7146	Approved
0.5618	Remote Similarity	NPD6409	Approved
0.561	Remote Similarity	NPD8039	Approved
0.56	Remote Similarity	NPD7128	Approved
0.56	Remote Similarity	NPD5739	Approved
0.56	Remote Similarity	NPD6402	Approved
0.56	Remote Similarity	NPD6675	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