NPASS Compound

Structure

CID94488 OpenBabel06191715432D 23 23 0 0 0 0 0 0 0 0999 V2000 8.6603 0.0000 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 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 23 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 15 1 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.21
Volume:	353.239
LogP:	5.573
LogD:	4.007
LogS:	-4.186
# Rotatable Bonds:	11
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.231
Synthetic Accessibility Score:	2.589
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.79
MDCK Permeability:	2.1525273041334003e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	99.29582214355469%
Volume Distribution (VD):	5.031
Pgp-substrate:	1.5312360525131226%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.703
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.56
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.718
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	7.472
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.004
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.964
Carcinogencity:	0.121
Eye Corrosion:	0.01
Eye Irritation:	0.93
Respiratory Toxicity:	0.181

Download Data

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

Natural Product: NPC94488

Natural Product ID:	NPC94488
*Common Name:**	5-O-Ethylembelin
IUPAC Name:	5-ethoxy-2-hydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
Synonyms:	5-O-Ethylembelin
Standard InCHIKey:	BKAZNQWWINLHDW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H30O4/c1-3-5-6-7-8-9-10-11-12-13-15-18(21)16(20)14-17(19(15)22)23-4-2/h14,21H,3-13H2,1-2H3/p-1
SMILES:	CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)OCC)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463108
PubChem CID:	10358776
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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO31207	Oxalis erythrorhiza	Species	Oxalidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12963150]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO26772	Lysimachia punctata	Species	Primulaceae	Eukaryota	n.a.	root	n.a.	PMID[15890461]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
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]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	root	n.a.	n.a.	PMID[2778455]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29300477]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23736	Myrsine africana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26772	Lysimachia punctata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23736	Myrsine africana	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2.5	ug.mL-1	PMID[482570]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	2.7	ug.mL-1	PMID[482570]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[482570]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	1.3	ug.mL-1	PMID[482570]

☑ 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 NPC94488 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	167
0.1-0.2	1678
0.2-0.3	7888
0.3-0.4	17875
0.4-0.5	9271
0.5-0.6	4684
0.6-0.7	1029
0.7-0.8	75
0.8-0.85	7
0.85-0.9	12
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC243272
0.9538	High Similarity	NPC146376
0.9538	High Similarity	NPC263382
0.9538	High Similarity	NPC125578
0.9394	High Similarity	NPC262673
0.9254	High Similarity	NPC291062
0.9254	High Similarity	NPC94743
0.9062	High Similarity	NPC53109
0.9062	High Similarity	NPC143168
0.8955	High Similarity	NPC134385
0.8923	High Similarity	NPC7029
0.8923	High Similarity	NPC34622
0.8923	High Similarity	NPC474400
0.8857	High Similarity	NPC264178
0.8806	High Similarity	NPC474619
0.8788	High Similarity	NPC98897
0.8769	High Similarity	NPC477830
0.8769	High Similarity	NPC57463
0.8769	High Similarity	NPC151728
0.8657	High Similarity	NPC16119
0.8493	Intermediate Similarity	NPC473536
0.8438	Intermediate Similarity	NPC320421
0.8308	Intermediate Similarity	NPC473494
0.8	Intermediate Similarity	NPC251429
0.7879	Intermediate Similarity	NPC139056
0.7867	Intermediate Similarity	NPC477708
0.7681	Intermediate Similarity	NPC477707
0.7654	Intermediate Similarity	NPC132228
0.7654	Intermediate Similarity	NPC8518
0.7654	Intermediate Similarity	NPC6185
0.7654	Intermediate Similarity	NPC263997
0.7654	Intermediate Similarity	NPC241512
0.76	Intermediate Similarity	NPC147438
0.7564	Intermediate Similarity	NPC475681
0.7561	Intermediate Similarity	NPC472009
0.7538	Intermediate Similarity	NPC317796
0.75	Intermediate Similarity	NPC137396
0.75	Intermediate Similarity	NPC47450
0.747	Intermediate Similarity	NPC472007
0.7463	Intermediate Similarity	NPC200831
0.7463	Intermediate Similarity	NPC224103
0.7463	Intermediate Similarity	NPC299369
0.7439	Intermediate Similarity	NPC90287
0.7439	Intermediate Similarity	NPC470177
0.7432	Intermediate Similarity	NPC477455
0.7412	Intermediate Similarity	NPC474209
0.7412	Intermediate Similarity	NPC475823
0.7403	Intermediate Similarity	NPC26504
0.7385	Intermediate Similarity	NPC474805
0.7381	Intermediate Similarity	NPC472008
0.7381	Intermediate Similarity	NPC53454
0.7349	Intermediate Similarity	NPC203795
0.7308	Intermediate Similarity	NPC283087
0.7284	Intermediate Similarity	NPC103486
0.726	Intermediate Similarity	NPC298249
0.7229	Intermediate Similarity	NPC32037
0.7229	Intermediate Similarity	NPC474680
0.7229	Intermediate Similarity	NPC77971
0.7229	Intermediate Similarity	NPC133652
0.7215	Intermediate Similarity	NPC231739
0.7206	Intermediate Similarity	NPC192843
0.72	Intermediate Similarity	NPC173321
0.7162	Intermediate Similarity	NPC477452
0.716	Intermediate Similarity	NPC474085
0.716	Intermediate Similarity	NPC55869
0.716	Intermediate Similarity	NPC99308
0.7143	Intermediate Similarity	NPC143857
0.7143	Intermediate Similarity	NPC229252
0.7126	Intermediate Similarity	NPC146852
0.7105	Intermediate Similarity	NPC474539
0.7089	Intermediate Similarity	NPC471061
0.7079	Intermediate Similarity	NPC279313
0.7077	Intermediate Similarity	NPC22329
0.7067	Intermediate Similarity	NPC469914
0.7051	Intermediate Similarity	NPC175079
0.7045	Intermediate Similarity	NPC61275
0.7042	Intermediate Similarity	NPC40082
0.7037	Intermediate Similarity	NPC108955
0.7037	Intermediate Similarity	NPC91332
0.7037	Intermediate Similarity	NPC162741
0.7027	Intermediate Similarity	NPC473213
0.7011	Intermediate Similarity	NPC265856
0.7011	Intermediate Similarity	NPC471399
0.7011	Intermediate Similarity	NPC166554
0.7	Intermediate Similarity	NPC274927
0.7	Intermediate Similarity	NPC475994
0.7	Intermediate Similarity	NPC106851
0.7	Intermediate Similarity	NPC478122
0.6988	Remote Similarity	NPC477784
0.6988	Remote Similarity	NPC105803
0.6988	Remote Similarity	NPC477785
0.6988	Remote Similarity	NPC477786
0.6986	Remote Similarity	NPC176215
0.6986	Remote Similarity	NPC296436
0.6977	Remote Similarity	NPC475001
0.6977	Remote Similarity	NPC185059
0.6962	Remote Similarity	NPC110725
0.6962	Remote Similarity	NPC470525
0.6957	Remote Similarity	NPC281230
0.6951	Remote Similarity	NPC286229
0.6941	Remote Similarity	NPC261721
0.6932	Remote Similarity	NPC32944
0.6932	Remote Similarity	NPC193396
0.6923	Remote Similarity	NPC474321
0.6923	Remote Similarity	NPC20066
0.6923	Remote Similarity	NPC160540
0.6923	Remote Similarity	NPC220191
0.6914	Remote Similarity	NPC471740
0.6905	Remote Similarity	NPC474251
0.6905	Remote Similarity	NPC469884
0.6905	Remote Similarity	NPC469809
0.6901	Remote Similarity	NPC235242
0.6901	Remote Similarity	NPC122521
0.6901	Remote Similarity	NPC174447
0.6901	Remote Similarity	NPC251042
0.6897	Remote Similarity	NPC142159
0.6897	Remote Similarity	NPC95364
0.6897	Remote Similarity	NPC280833
0.6892	Remote Similarity	NPC83965
0.6892	Remote Similarity	NPC137163
0.6889	Remote Similarity	NPC91408
0.6875	Remote Similarity	NPC211279
0.686	Remote Similarity	NPC471738
0.6849	Remote Similarity	NPC328089
0.6849	Remote Similarity	NPC68343
0.6848	Remote Similarity	NPC300584
0.6842	Remote Similarity	NPC143396
0.6842	Remote Similarity	NPC250928
0.6842	Remote Similarity	NPC10758
0.6842	Remote Similarity	NPC474060
0.6829	Remote Similarity	NPC304795
0.6824	Remote Similarity	NPC307126
0.6824	Remote Similarity	NPC68303
0.6818	Remote Similarity	NPC469464
0.6818	Remote Similarity	NPC223093
0.6806	Remote Similarity	NPC15130
0.6806	Remote Similarity	NPC201939
0.6806	Remote Similarity	NPC473212
0.6806	Remote Similarity	NPC115752
0.6806	Remote Similarity	NPC138056
0.6806	Remote Similarity	NPC254449
0.679	Remote Similarity	NPC30321
0.679	Remote Similarity	NPC108816
0.679	Remote Similarity	NPC23778
0.679	Remote Similarity	NPC93763
0.6786	Remote Similarity	NPC185256
0.6786	Remote Similarity	NPC8091
0.6757	Remote Similarity	NPC474304
0.6757	Remote Similarity	NPC474329
0.6757	Remote Similarity	NPC61473
0.6753	Remote Similarity	NPC318766
0.675	Remote Similarity	NPC92080
0.6747	Remote Similarity	NPC474353
0.6747	Remote Similarity	NPC225515
0.6747	Remote Similarity	NPC275766
0.6747	Remote Similarity	NPC116797
0.6744	Remote Similarity	NPC202394
0.6742	Remote Similarity	NPC32552
0.6742	Remote Similarity	NPC219874
0.6742	Remote Similarity	NPC45579
0.6742	Remote Similarity	NPC26865
0.6742	Remote Similarity	NPC166110
0.6742	Remote Similarity	NPC248913
0.6737	Remote Similarity	NPC179208
0.6714	Remote Similarity	NPC268185
0.6712	Remote Similarity	NPC473211
0.6712	Remote Similarity	NPC473210
0.6711	Remote Similarity	NPC218477
0.6709	Remote Similarity	NPC227396
0.6707	Remote Similarity	NPC27817
0.6706	Remote Similarity	NPC474359
0.6703	Remote Similarity	NPC295347
0.6702	Remote Similarity	NPC469851
0.6667	Remote Similarity	NPC40170
0.6667	Remote Similarity	NPC109414
0.6667	Remote Similarity	NPC471225
0.6667	Remote Similarity	NPC272267
0.6667	Remote Similarity	NPC477487
0.6667	Remote Similarity	NPC84038
0.6667	Remote Similarity	NPC248193
0.6667	Remote Similarity	NPC316324
0.6667	Remote Similarity	NPC197089
0.6667	Remote Similarity	NPC243532
0.6667	Remote Similarity	NPC471739
0.6629	Remote Similarity	NPC113393
0.6629	Remote Similarity	NPC477684
0.6628	Remote Similarity	NPC79573
0.6628	Remote Similarity	NPC67081
0.6628	Remote Similarity	NPC307112
0.6628	Remote Similarity	NPC471223
0.6628	Remote Similarity	NPC187529
0.6628	Remote Similarity	NPC182383
0.6628	Remote Similarity	NPC2640
0.6628	Remote Similarity	NPC255174
0.6627	Remote Similarity	NPC2482
0.6627	Remote Similarity	NPC74086
0.6627	Remote Similarity	NPC472948
0.6627	Remote Similarity	NPC47653
0.6625	Remote Similarity	NPC114236
0.6625	Remote Similarity	NPC474885

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 NPC94488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	2438
0.2-0.3	4041
0.3-0.4	1896
0.4-0.5	386
0.5-0.6	224
0.6-0.7	15
0.7-0.8	2
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD3704	Approved
0.9062	High Similarity	NPD2664	Clinical (unspecified phase)
0.8657	High Similarity	NPD6108	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD4756	Discovery
0.7463	Intermediate Similarity	NPD8779	Phase 3
0.725	Intermediate Similarity	NPD4695	Discontinued
0.7123	Intermediate Similarity	NPD7331	Phase 2
0.6912	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD7341	Phase 2
0.6627	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3197	Phase 1
0.6588	Remote Similarity	NPD6110	Phase 1
0.6522	Remote Similarity	NPD5695	Phase 3
0.6404	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD6672	Approved
0.6395	Remote Similarity	NPD7154	Phase 3
0.6386	Remote Similarity	NPD3617	Approved
0.6383	Remote Similarity	NPD6083	Phase 2
0.6383	Remote Similarity	NPD6084	Phase 2
0.6377	Remote Similarity	NPD3172	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6333	Remote Similarity	NPD4753	Phase 2
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5696	Approved
0.6286	Remote Similarity	NPD4266	Approved
0.6286	Remote Similarity	NPD3194	Approved
0.6286	Remote Similarity	NPD3196	Approved
0.6286	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD1696	Phase 3
0.618	Remote Similarity	NPD5690	Phase 2
0.617	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD4197	Approved
0.6136	Remote Similarity	NPD3666	Approved
0.6136	Remote Similarity	NPD3665	Phase 1
0.6136	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5221	Approved
0.6105	Remote Similarity	NPD5222	Approved
0.6092	Remote Similarity	NPD3667	Approved
0.6087	Remote Similarity	NPD46	Approved
0.6087	Remote Similarity	NPD6698	Approved
0.6067	Remote Similarity	NPD5329	Approved
0.6067	Remote Similarity	NPD5363	Approved
0.6064	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD9090	Phase 3
0.6042	Remote Similarity	NPD5173	Approved
0.604	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD5280	Approved
0.598	Remote Similarity	NPD6011	Approved
0.598	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6899	Approved
0.5978	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6080	Approved
0.5978	Remote Similarity	NPD6904	Approved
0.5978	Remote Similarity	NPD6673	Approved
0.5977	Remote Similarity	NPD5369	Approved
0.5957	Remote Similarity	NPD6399	Phase 3
0.5955	Remote Similarity	NPD4786	Approved
0.5946	Remote Similarity	NPD6109	Phase 1
0.5941	Remote Similarity	NPD6402	Approved
0.5941	Remote Similarity	NPD6675	Approved
0.5941	Remote Similarity	NPD5739	Approved
0.5941	Remote Similarity	NPD7128	Approved
0.5938	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD6014	Approved
0.5922	Remote Similarity	NPD6012	Approved
0.5922	Remote Similarity	NPD6013	Approved
0.5918	Remote Similarity	NPD4696	Approved
0.5918	Remote Similarity	NPD5286	Approved
0.5918	Remote Similarity	NPD5285	Approved
0.5914	Remote Similarity	NPD5785	Approved
0.5914	Remote Similarity	NPD5692	Phase 3
0.5909	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4221	Approved
0.5909	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6435	Approved
0.5909	Remote Similarity	NPD4223	Phase 3
0.5889	Remote Similarity	NPD1694	Approved
0.5882	Remote Similarity	NPD5701	Approved
0.5876	Remote Similarity	NPD4755	Approved
0.5876	Remote Similarity	NPD7902	Approved
0.5865	Remote Similarity	NPD6883	Approved
0.5865	Remote Similarity	NPD7290	Approved
0.5865	Remote Similarity	NPD7102	Approved
0.5859	Remote Similarity	NPD5223	Approved
0.5857	Remote Similarity	NPD29	Approved
0.5857	Remote Similarity	NPD28	Approved
0.5851	Remote Similarity	NPD5694	Approved
0.5851	Remote Similarity	NPD6079	Approved
0.5851	Remote Similarity	NPD7515	Phase 2
0.5851	Remote Similarity	NPD6411	Approved
0.5851	Remote Similarity	NPD6050	Approved
0.5851	Remote Similarity	NPD5693	Phase 1
0.5843	Remote Similarity	NPD5362	Discontinued
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8039	Approved
0.5825	Remote Similarity	NPD7320	Approved
0.5824	Remote Similarity	NPD7146	Approved
0.5824	Remote Similarity	NPD6422	Discontinued
0.5824	Remote Similarity	NPD7521	Approved
0.5824	Remote Similarity	NPD6409	Approved
0.5824	Remote Similarity	NPD6684	Approved
0.5824	Remote Similarity	NPD5330	Approved
0.5824	Remote Similarity	NPD7334	Approved
0.581	Remote Similarity	NPD6847	Approved
0.581	Remote Similarity	NPD6649	Approved
0.581	Remote Similarity	NPD8130	Phase 1
0.581	Remote Similarity	NPD6650	Approved
0.581	Remote Similarity	NPD6617	Approved
0.581	Remote Similarity	NPD6869	Approved
0.5806	Remote Similarity	NPD5328	Approved
0.58	Remote Similarity	NPD5224	Approved
0.58	Remote Similarity	NPD5211	Phase 2
0.58	Remote Similarity	NPD5226	Approved
0.58	Remote Similarity	NPD4633	Approved
0.58	Remote Similarity	NPD5225	Approved
0.5797	Remote Similarity	NPD3173	Approved
0.5789	Remote Similarity	NPD5779	Approved
0.5789	Remote Similarity	NPD5778	Approved
0.5778	Remote Similarity	NPD3668	Phase 3
0.5769	Remote Similarity	NPD6373	Approved
0.5769	Remote Similarity	NPD6372	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5755	Remote Similarity	NPD8297	Approved
0.5755	Remote Similarity	NPD6882	Approved
0.5743	Remote Similarity	NPD5174	Approved
0.5743	Remote Similarity	NPD5175	Approved
0.573	Remote Similarity	NPD4270	Approved
0.573	Remote Similarity	NPD4269	Approved
0.5699	Remote Similarity	NPD6903	Approved
0.5699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4518	Approved
0.5686	Remote Similarity	NPD5141	Approved
0.5682	Remote Similarity	NPD5368	Approved
0.5682	Remote Similarity	NPD4252	Approved
0.5682	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.567	Remote Similarity	NPD5654	Approved
0.566	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5205	Approved
0.5652	Remote Similarity	NPD4689	Approved
0.5652	Remote Similarity	NPD4688	Approved
0.5652	Remote Similarity	NPD5786	Approved
0.5652	Remote Similarity	NPD4138	Approved
0.5652	Remote Similarity	NPD622	Approved
0.5652	Remote Similarity	NPD6098	Approved
0.5652	Remote Similarity	NPD4519	Discontinued
0.5652	Remote Similarity	NPD4693	Phase 3
0.5652	Remote Similarity	NPD4249	Approved
0.5652	Remote Similarity	NPD4690	Approved
0.5652	Remote Similarity	NPD4623	Approved
0.5632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4202	Approved
0.5625	Remote Similarity	NPD5133	Approved
0.5606	Remote Similarity	NPD9091	Suspended
0.5606	Remote Similarity	NPD9297	Discontinued

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