NPASS Compound

Structure

NPC160898 OpenBabel07101719512D 27 32 0 0 0 0 0 0 0 0999 V2000 3.4263 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 -3.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5602 -2.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5602 -4.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 -3.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2404 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -3.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4483 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 -2.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1425 -3.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -2.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2459 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 -3.3052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 -3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 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 0.7431 -4.1143 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -3.8698 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6778 -1.3624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0936 -3.3187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 7 2 0 0 0 0 4 9 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 27 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.07
Volume:	342.288
LogP:	3.434
LogD:	2.56
LogS:	-6.63
# Rotatable Bonds:	0
TPSA:	118.21
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.216
Synthetic Accessibility Score:	2.796
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.832
MDCK Permeability:	4.93275410917704e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.666
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	92.82005310058594%
Volume Distribution (VD):	0.728
Pgp-substrate:	9.314573287963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.296
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.556
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	3.022
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.336
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.922
Carcinogencity:	0.108
Eye Corrosion:	0.003
Eye Irritation:	0.811
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC160898

Natural Product ID:	NPC160898
*Common Name:**	BJIPXXAEQIWODL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BJIPXXAEQIWODL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H11N3O4/c24-11-5-8-10(6-12(11)25)22-18-14(8)16-15(19(26)23-20(16)27)13-7-3-1-2-4-9(7)21-17(13)18/h1-6,21-22,24-25H,(H,23,26,27)
SMILES:	Oc1cc2c(cc1O)[nH]c1c2c2C(=O)N=C(c2c2c1[nH]c1c2cccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL193468
PubChem CID:	11268312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	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	5
Others	18

Activity Type	# Activity
Cell Line	3
Individual Protein	14
Protein Family	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]
NPT301	Individual Protein	Vascular endothelial growth factor receptor 1	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	0.84	ug.mL-1	PMID[514252]
NPT1178	Cell Line	KB 3-1	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[514252]
NPT1344	Individual Protein	Serine/threonine-protein kinase EEF2K	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.1	ug.mL-1	PMID[514252]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	80.0	%	PMID[514252]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]
NPT1896	Individual Protein	Zinc finger protein GLI1	Homo sapiens	IC50	=	1800.0	nM	PMID[514253]
NPT5108	Individual Protein	Zinc finger protein GLI2	Homo sapiens	IC50	=	2700.0	nM	PMID[514253]
NPT321	Protein Family	cAMP-dependent protein kinase (PKA)	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	Inhibition	=	80.0	%	PMID[514252]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	Inhibition	<	50.0	%	PMID[514252]

☑ 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 NPC160898 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	701
0.1-0.2	4026
0.2-0.3	13308
0.3-0.4	8036
0.4-0.5	12251
0.5-0.6	2835
0.6-0.7	1349
0.7-0.8	179
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC132329
0.8791	High Similarity	NPC31700
0.8571	High Similarity	NPC294620
0.8502	High Similarity	NPC45048
0.8462	Intermediate Similarity	NPC279589
0.8253	Intermediate Similarity	NPC472844
0.8189	Intermediate Similarity	NPC89549
0.8151	Intermediate Similarity	NPC107836
0.8053	Intermediate Similarity	NPC264285
0.7946	Intermediate Similarity	NPC9894
0.7913	Intermediate Similarity	NPC16352
0.7884	Intermediate Similarity	NPC178858
0.7834	Intermediate Similarity	NPC195314
0.7778	Intermediate Similarity	NPC325297
0.7763	Intermediate Similarity	NPC153042
0.7741	Intermediate Similarity	NPC6786
0.7733	Intermediate Similarity	NPC86834
0.7733	Intermediate Similarity	NPC210828
0.7733	Intermediate Similarity	NPC39679
0.7725	Intermediate Similarity	NPC211416
0.7709	Intermediate Similarity	NPC23294
0.7696	Intermediate Similarity	NPC293151
0.7672	Intermediate Similarity	NPC86078
0.7665	Intermediate Similarity	NPC303951
0.7632	Intermediate Similarity	NPC294375
0.7625	Intermediate Similarity	NPC473187
0.7611	Intermediate Similarity	NPC270918
0.7597	Intermediate Similarity	NPC276657
0.7574	Intermediate Similarity	NPC51388
0.7573	Intermediate Similarity	NPC207686
0.7555	Intermediate Similarity	NPC87413
0.7542	Intermediate Similarity	NPC473182
0.7523	Intermediate Similarity	NPC474188
0.7521	Intermediate Similarity	NPC252251
0.7511	Intermediate Similarity	NPC227908
0.75	Intermediate Similarity	NPC3207
0.749	Intermediate Similarity	NPC209174
0.748	Intermediate Similarity	NPC78609
0.748	Intermediate Similarity	NPC1203
0.7478	Intermediate Similarity	NPC134848
0.7468	Intermediate Similarity	NPC179287
0.7458	Intermediate Similarity	NPC477531
0.7458	Intermediate Similarity	NPC474701
0.7456	Intermediate Similarity	NPC283117
0.7456	Intermediate Similarity	NPC193777
0.7447	Intermediate Similarity	NPC150239
0.7443	Intermediate Similarity	NPC246700
0.7443	Intermediate Similarity	NPC128751
0.7436	Intermediate Similarity	NPC46561
0.7436	Intermediate Similarity	NPC247803
0.7425	Intermediate Similarity	NPC322064
0.7409	Intermediate Similarity	NPC106833
0.7409	Intermediate Similarity	NPC469497
0.74	Intermediate Similarity	NPC473188
0.7388	Intermediate Similarity	NPC472207
0.738	Intermediate Similarity	NPC249583
0.738	Intermediate Similarity	NPC4687
0.7375	Intermediate Similarity	NPC274640
0.7373	Intermediate Similarity	NPC174760
0.7371	Intermediate Similarity	NPC48353
0.7357	Intermediate Similarity	NPC135887
0.7357	Intermediate Similarity	NPC199277
0.7349	Intermediate Similarity	NPC218388
0.7342	Intermediate Similarity	NPC280799
0.7336	Intermediate Similarity	NPC300156
0.7336	Intermediate Similarity	NPC45190
0.7325	Intermediate Similarity	NPC223427
0.732	Intermediate Similarity	NPC91868
0.732	Intermediate Similarity	NPC63971
0.7315	Intermediate Similarity	NPC88363
0.7308	Intermediate Similarity	NPC118228
0.7306	Intermediate Similarity	NPC94943
0.7303	Intermediate Similarity	NPC194740
0.7294	Intermediate Similarity	NPC212535
0.7287	Intermediate Similarity	NPC475844
0.7277	Intermediate Similarity	NPC276517
0.726	Intermediate Similarity	NPC190007
0.7257	Intermediate Similarity	NPC131887
0.7257	Intermediate Similarity	NPC306376
0.7257	Intermediate Similarity	NPC208084
0.7246	Intermediate Similarity	NPC169402
0.7238	Intermediate Similarity	NPC220851
0.7238	Intermediate Similarity	NPC144452
0.7236	Intermediate Similarity	NPC15801
0.7236	Intermediate Similarity	NPC473183
0.7229	Intermediate Similarity	NPC244741
0.7227	Intermediate Similarity	NPC225279
0.7224	Intermediate Similarity	NPC277351
0.7222	Intermediate Similarity	NPC308137
0.7222	Intermediate Similarity	NPC310211
0.722	Intermediate Similarity	NPC202503
0.7212	Intermediate Similarity	NPC472842
0.7205	Intermediate Similarity	NPC476073
0.7185	Intermediate Similarity	NPC473179
0.7181	Intermediate Similarity	NPC132385
0.7178	Intermediate Similarity	NPC476818
0.7174	Intermediate Similarity	NPC476098
0.7173	Intermediate Similarity	NPC27041
0.7166	Intermediate Similarity	NPC235685
0.7161	Intermediate Similarity	NPC116238
0.7154	Intermediate Similarity	NPC39370
0.7154	Intermediate Similarity	NPC473184
0.7149	Intermediate Similarity	NPC12344
0.7143	Intermediate Similarity	NPC184408
0.7143	Intermediate Similarity	NPC303658
0.7137	Intermediate Similarity	NPC101350
0.7137	Intermediate Similarity	NPC41679
0.7131	Intermediate Similarity	NPC469928
0.7131	Intermediate Similarity	NPC330009
0.7126	Intermediate Similarity	NPC227824
0.7125	Intermediate Similarity	NPC198503
0.7125	Intermediate Similarity	NPC60621
0.7125	Intermediate Similarity	NPC477532
0.7124	Intermediate Similarity	NPC326634
0.7118	Intermediate Similarity	NPC213308
0.7109	Intermediate Similarity	NPC303374
0.7102	Intermediate Similarity	NPC474688
0.7094	Intermediate Similarity	NPC201697
0.7085	Intermediate Similarity	NPC94428
0.7085	Intermediate Similarity	NPC263937
0.7085	Intermediate Similarity	NPC325976
0.7073	Intermediate Similarity	NPC473186
0.7069	Intermediate Similarity	NPC475070
0.7068	Intermediate Similarity	NPC470784
0.7068	Intermediate Similarity	NPC82472
0.7064	Intermediate Similarity	NPC124086
0.7064	Intermediate Similarity	NPC5145
0.7061	Intermediate Similarity	NPC141454
0.7061	Intermediate Similarity	NPC326363
0.7061	Intermediate Similarity	NPC243834
0.7061	Intermediate Similarity	NPC70956
0.7059	Intermediate Similarity	NPC473800
0.7056	Intermediate Similarity	NPC477549
0.7054	Intermediate Similarity	NPC63109
0.7051	Intermediate Similarity	NPC474409
0.7049	Intermediate Similarity	NPC473185
0.7048	Intermediate Similarity	NPC131017
0.7046	Intermediate Similarity	NPC89508
0.7037	Intermediate Similarity	NPC98371
0.7037	Intermediate Similarity	NPC313884
0.7029	Intermediate Similarity	NPC305984
0.7029	Intermediate Similarity	NPC312645
0.7028	Intermediate Similarity	NPC184680
0.7026	Intermediate Similarity	NPC165599
0.7014	Intermediate Similarity	NPC207620
0.7009	Intermediate Similarity	NPC183777
0.7004	Intermediate Similarity	NPC244543
0.7	Intermediate Similarity	NPC470785
0.7	Intermediate Similarity	NPC11408
0.7	Intermediate Similarity	NPC72980
0.6996	Remote Similarity	NPC208522
0.6996	Remote Similarity	NPC229893
0.6992	Remote Similarity	NPC67401
0.6992	Remote Similarity	NPC199667
0.6992	Remote Similarity	NPC181081
0.6989	Remote Similarity	NPC169716
0.6988	Remote Similarity	NPC475746
0.6988	Remote Similarity	NPC472843
0.6987	Remote Similarity	NPC77555
0.6983	Remote Similarity	NPC475085
0.6983	Remote Similarity	NPC475112
0.6983	Remote Similarity	NPC291535
0.698	Remote Similarity	NPC270515
0.6975	Remote Similarity	NPC39500
0.6972	Remote Similarity	NPC41501
0.6969	Remote Similarity	NPC469734
0.6966	Remote Similarity	NPC175602
0.6962	Remote Similarity	NPC74619
0.6962	Remote Similarity	NPC187501
0.696	Remote Similarity	NPC99666
0.6958	Remote Similarity	NPC304926
0.6958	Remote Similarity	NPC476041
0.6953	Remote Similarity	NPC162484
0.6953	Remote Similarity	NPC53144
0.6953	Remote Similarity	NPC165964
0.695	Remote Similarity	NPC478083
0.6949	Remote Similarity	NPC473181
0.6946	Remote Similarity	NPC298449
0.6946	Remote Similarity	NPC190401
0.6946	Remote Similarity	NPC239763
0.6944	Remote Similarity	NPC217554
0.6942	Remote Similarity	NPC323969
0.6939	Remote Similarity	NPC470018
0.6939	Remote Similarity	NPC214980
0.6936	Remote Similarity	NPC321428
0.6936	Remote Similarity	NPC88008
0.6935	Remote Similarity	NPC472846
0.6933	Remote Similarity	NPC473180
0.6933	Remote Similarity	NPC110182
0.6933	Remote Similarity	NPC219087
0.6929	Remote Similarity	NPC284141
0.6926	Remote Similarity	NPC122436
0.692	Remote Similarity	NPC295228
0.6917	Remote Similarity	NPC183407
0.6911	Remote Similarity	NPC470126
0.691	Remote Similarity	NPC211813
0.6907	Remote Similarity	NPC90185
0.6907	Remote Similarity	NPC171787
0.6904	Remote Similarity	NPC266931
0.6904	Remote Similarity	NPC250448

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 NPC160898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	706
0.2-0.3	1039
0.3-0.4	2060
0.4-0.5	2825
0.5-0.6	1709
0.6-0.7	425
0.7-0.8	18
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8834	High Similarity	NPD3746	Discontinued
0.8163	Intermediate Similarity	NPD6456	Discontinued
0.8063	Intermediate Similarity	NPD7181	Phase 3
0.7689	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD5488	Discontinued
0.7348	Intermediate Similarity	NPD2916	Discontinued
0.7339	Intermediate Similarity	NPD7921	Approved
0.7311	Intermediate Similarity	NPD6995	Phase 1
0.7198	Intermediate Similarity	NPD6376	Discontinued
0.7149	Intermediate Similarity	NPD8396	Approved
0.7149	Intermediate Similarity	NPD8395	Approved
0.7121	Intermediate Similarity	NPD8091	Phase 3
0.7095	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3776	Discontinued
0.7069	Intermediate Similarity	NPD5426	Phase 3
0.7069	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6531	Approved
0.7066	Intermediate Similarity	NPD6530	Approved
0.7051	Intermediate Similarity	NPD5658	Approved
0.7049	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6978	Phase 2
0.7042	Intermediate Similarity	NPD6455	Phase 3
0.7037	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7036	Intermediate Similarity	NPD5807	Phase 2
0.7012	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD4885	Approved
0.7	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7688	Phase 1
0.6955	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6945	Remote Similarity	NPD8349	Phase 1
0.694	Remote Similarity	NPD4511	Phase 1
0.6938	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5901	Discontinued
0.692	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4845	Discontinued
0.6897	Remote Similarity	NPD484	Approved
0.6894	Remote Similarity	NPD7803	Approved
0.6894	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8364	Approved
0.688	Remote Similarity	NPD8363	Approved
0.687	Remote Similarity	NPD7603	Discontinued
0.6867	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4561	Discontinued
0.6833	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7956	Approved
0.6832	Remote Similarity	NPD7955	Approved
0.6828	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5482	Discontinued
0.6822	Remote Similarity	NPD3986	Discontinued
0.6809	Remote Similarity	NPD8358	Approved
0.679	Remote Similarity	NPD8465	Approved
0.679	Remote Similarity	NPD8467	Approved
0.679	Remote Similarity	NPD8466	Approved
0.679	Remote Similarity	NPD8429	Approved
0.679	Remote Similarity	NPD8427	Approved
0.679	Remote Similarity	NPD8428	Approved
0.6784	Remote Similarity	NPD7770	Phase 3
0.6783	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6999	Discontinued
0.6781	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8016	Phase 3
0.6769	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7948	Phase 1
0.6762	Remote Similarity	NPD3258	Approved
0.6762	Remote Similarity	NPD8524	Approved
0.6757	Remote Similarity	NPD7769	Phase 3
0.6752	Remote Similarity	NPD8459	Approved
0.6752	Remote Similarity	NPD8460	Approved
0.6751	Remote Similarity	NPD5530	Phase 1
0.6749	Remote Similarity	NPD5164	Discontinued
0.6747	Remote Similarity	NPD7767	Approved
0.6742	Remote Similarity	NPD7708	Approved
0.6735	Remote Similarity	NPD6242	Discontinued
0.6732	Remote Similarity	NPD3962	Phase 2
0.6732	Remote Similarity	NPD3959	Phase 2
0.673	Remote Similarity	NPD7772	Phase 3
0.6722	Remote Similarity	NPD2794	Discontinued
0.6722	Remote Similarity	NPD8093	Discontinued
0.6721	Remote Similarity	NPD7395	Discontinued
0.672	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6716	Phase 1
0.6706	Remote Similarity	NPD4373	Phase 2
0.6706	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7665	Phase 2
0.6695	Remote Similarity	NPD7666	Phase 3
0.6692	Remote Similarity	NPD3809	Discontinued
0.6691	Remote Similarity	NPD8425	Approved
0.6691	Remote Similarity	NPD8426	Approved
0.669	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2844	Phase 3
0.6681	Remote Similarity	NPD7001	Phase 3
0.668	Remote Similarity	NPD6142	Phase 3
0.6667	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5903	Approved
0.6667	Remote Similarity	NPD5445	Approved
0.6667	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5902	Approved
0.6667	Remote Similarity	NPD3257	Approved
0.6654	Remote Similarity	NPD6517	Phase 3
0.6653	Remote Similarity	NPD8096	Phase 3
0.6653	Remote Similarity	NPD8097	Phase 3
0.664	Remote Similarity	NPD5506	Approved
0.664	Remote Similarity	NPD5507	Approved
0.664	Remote Similarity	NPD4328	Approved
0.6629	Remote Similarity	NPD5399	Discovery
0.6627	Remote Similarity	NPD6962	Phase 2
0.6617	Remote Similarity	NPD6228	Discontinued
0.6612	Remote Similarity	NPD5939	Approved
0.6612	Remote Similarity	NPD5936	Approved
0.6599	Remote Similarity	NPD5930	Phase 3
0.6598	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4952	Phase 3
0.6587	Remote Similarity	NPD8512	Phase 3
0.6585	Remote Similarity	NPD5632	Approved
0.6584	Remote Similarity	NPD4852	Phase 2
0.6581	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6494	Phase 2
0.6574	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5612	Discontinued
0.6557	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3243	Approved
0.6557	Remote Similarity	NPD8094	Discontinued
0.6553	Remote Similarity	NPD8463	Approved
0.655	Remote Similarity	NPD6790	Phase 1
0.655	Remote Similarity	NPD7417	Discontinued
0.6549	Remote Similarity	NPD2951	Discontinued
0.6549	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5416	Discontinued
0.6531	Remote Similarity	NPD4897	Phase 2
0.6527	Remote Similarity	NPD4558	Phase 2
0.6525	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5479	Discontinued
0.652	Remote Similarity	NPD7689	Approved
0.6519	Remote Similarity	NPD5450	Discontinued
0.6515	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5429	Discontinued
0.6512	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6733	Discontinued
0.6502	Remote Similarity	NPD1326	Approved
0.6502	Remote Similarity	NPD1325	Approved
0.6502	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8098	Approved
0.6498	Remote Similarity	NPD5805	Approved
0.6494	Remote Similarity	NPD4948	Discontinued
0.6492	Remote Similarity	NPD4312	Approved
0.6481	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7924	Phase 2
0.6471	Remote Similarity	NPD7925	Phase 2
0.6464	Remote Similarity	NPD8046	Discontinued
0.6456	Remote Similarity	NPD7946	Pre-registration
0.6453	Remote Similarity	NPD6742	Phase 2
0.6453	Remote Similarity	NPD6743	Phase 2
0.6452	Remote Similarity	NPD7878	Phase 2
0.6445	Remote Similarity	NPD7415	Suspended
0.6444	Remote Similarity	NPD6145	Phase 1
0.6443	Remote Similarity	NPD6165	Phase 2
0.6443	Remote Similarity	NPD6164	Phase 2
0.6437	Remote Similarity	NPD8160	Phase 2
0.6434	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8489	Phase 1
0.6432	Remote Similarity	NPD4795	Phase 2
0.6432	Remote Similarity	NPD6987	Phase 1
0.6429	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD3763	Approved
0.6426	Remote Similarity	NPD7996	Phase 2
0.6422	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6975	Discontinued
0.6414	Remote Similarity	NPD5003	Discontinued
0.6408	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2762	Phase 2
0.6405	Remote Similarity	NPD3003	Approved
0.6405	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6245	Phase 2
0.6402	Remote Similarity	NPD7397	Approved
0.6402	Remote Similarity	NPD7398	Approved
0.6402	Remote Similarity	NPD8102	Discontinued
0.6398	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5821	Approved
0.6395	Remote Similarity	NPD1534	Approved
0.6391	Remote Similarity	NPD3318	Approved
0.6391	Remote Similarity	NPD3320	Approved
0.6391	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3319	Phase 1
0.639	Remote Similarity	NPD2920	Discontinued
0.6386	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5937	Approved
0.6382	Remote Similarity	NPD7301	Phase 3
0.6381	Remote Similarity	NPD7558	Phase 2
0.6379	Remote Similarity	NPD7222	Phase 2
0.6379	Remote Similarity	NPD6290	Phase 2
0.6379	Remote Similarity	NPD7452	Approved
0.6379	Remote Similarity	NPD7453	Approved
0.6376	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8149	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