NPASS Compound

Structure

CID29650 OpenBabel06191715352D 26 28 0 0 0 0 0 0 0 0999 V2000 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 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 5.1962 -0.0000 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 4.3301 -0.5000 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 0.0000 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 -0.5000 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 -0.8660 1.5000 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 -1.7321 1.0000 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 1.7321 -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 0.8660 1.5000 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 1.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 1 23 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 2 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.15
Volume:	368.102
LogP:	3.872
LogD:	3.884
LogS:	-4.544
# Rotatable Bonds:	4
TPSA:	53.35
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	2.507
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.578
MDCK Permeability:	3.17240810545627e-05
Pgp-inhibitor:	0.803
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	98.62211608886719%
Volume Distribution (VD):	0.311
Pgp-substrate:	1.5141050815582275%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.434
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.349
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.758
CYP3A4-substrate:	0.678

ADMET: Excretion

Clearance (CL):	9.387
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.1
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.484

Download Data

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

Natural Product: NPC29650

Natural Product ID:	NPC29650
*Common Name:**	Nocazine B
IUPAC Name:	(3Z,6Z)-3-benzylidene-5-methoxy-6-[(4-methoxyphenyl)methylidene]-1-methylpyrazin-2-one
Synonyms:	Nocazine B
Standard InCHIKey:	NCBOROGHSUXZPE-SXQSXHJWSA-N
Standard InCHI:	InChI=1S/C21H20N2O3/c1-23-19(14-16-9-11-17(25-2)12-10-16)20(26-3)22-18(21(23)24)13-15-7-5-4-6-8-15/h4-14H,1-3H3/b18-13-,19-14-
SMILES:	COc1n/c(=Cc2ccccc2)/c(=O)n(/c/1=Cc1ccc(cc1)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835446
PubChem CID:	56600877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001346] Diazines [CHEMONTID:0000067] Pyrazines [CHEMONTID:0002563] Methoxypyrazines

*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
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	isolated from marine sediments	The estuary of Yellow River, Dongying, Shandong Province, China	n.a.	PMID[21958359]
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	n.a.	spore	n.a.	PMID[21958359]
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	100000.0	nM	PMID[533906]
NPT81	Cell Line	A549	Homo sapiens	IC5	>=	100.0	uM	PMID[533906]

☑ 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 NPC29650 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	365
0.1-0.2	3538
0.2-0.3	13435
0.3-0.4	3411
0.4-0.5	17669
0.5-0.6	4075
0.6-0.7	201
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC138365
0.8582	High Similarity	NPC9373
0.8	Intermediate Similarity	NPC258992
0.7939	Intermediate Similarity	NPC323948
0.7883	Intermediate Similarity	NPC218323
0.7761	Intermediate Similarity	NPC41801
0.7652	Intermediate Similarity	NPC303370
0.7552	Intermediate Similarity	NPC266425
0.7426	Intermediate Similarity	NPC256369
0.7358	Intermediate Similarity	NPC254700
0.7347	Intermediate Similarity	NPC214036
0.7347	Intermediate Similarity	NPC113236
0.7319	Intermediate Similarity	NPC83279
0.7261	Intermediate Similarity	NPC319320
0.7261	Intermediate Similarity	NPC287757
0.7241	Intermediate Similarity	NPC471953
0.7218	Intermediate Similarity	NPC166837
0.7174	Intermediate Similarity	NPC43275
0.7163	Intermediate Similarity	NPC211218
0.7163	Intermediate Similarity	NPC255253
0.7162	Intermediate Similarity	NPC469808
0.7143	Intermediate Similarity	NPC324081
0.7133	Intermediate Similarity	NPC212850
0.7133	Intermediate Similarity	NPC83289
0.7133	Intermediate Similarity	NPC189724
0.7123	Intermediate Similarity	NPC274732
0.7122	Intermediate Similarity	NPC263835
0.7121	Intermediate Similarity	NPC146530
0.7114	Intermediate Similarity	NPC470707
0.7095	Intermediate Similarity	NPC136330
0.7095	Intermediate Similarity	NPC196609
0.7095	Intermediate Similarity	NPC205178
0.7095	Intermediate Similarity	NPC251454
0.7095	Intermediate Similarity	NPC230698
0.7095	Intermediate Similarity	NPC73883
0.7095	Intermediate Similarity	NPC277042
0.7095	Intermediate Similarity	NPC255817
0.7087	Intermediate Similarity	NPC175298
0.7078	Intermediate Similarity	NPC296085
0.7067	Intermediate Similarity	NPC231572
0.7059	Intermediate Similarity	NPC247298
0.7047	Intermediate Similarity	NPC307682
0.7047	Intermediate Similarity	NPC99078
0.7034	Intermediate Similarity	NPC283079
0.7027	Intermediate Similarity	NPC328419
0.7027	Intermediate Similarity	NPC193673
0.7027	Intermediate Similarity	NPC103947
0.7027	Intermediate Similarity	NPC167096
0.7027	Intermediate Similarity	NPC159150
0.7027	Intermediate Similarity	NPC94280
0.7027	Intermediate Similarity	NPC45783
0.7007	Intermediate Similarity	NPC118419
0.7	Intermediate Similarity	NPC252107
0.7	Intermediate Similarity	NPC220923
0.6993	Remote Similarity	NPC95733
0.6993	Remote Similarity	NPC62101
0.6986	Remote Similarity	NPC200555
0.6986	Remote Similarity	NPC196026
0.698	Remote Similarity	NPC96406
0.6977	Remote Similarity	NPC13755
0.697	Remote Similarity	NPC326447
0.6968	Remote Similarity	NPC71629
0.6968	Remote Similarity	NPC245974
0.6962	Remote Similarity	NPC474852
0.6954	Remote Similarity	NPC476989
0.6948	Remote Similarity	NPC244338
0.6947	Remote Similarity	NPC109637
0.6944	Remote Similarity	NPC29477
0.6944	Remote Similarity	NPC476249
0.6933	Remote Similarity	NPC137172
0.6933	Remote Similarity	NPC77992
0.6933	Remote Similarity	NPC145446
0.6917	Remote Similarity	NPC157473
0.6917	Remote Similarity	NPC151530
0.6903	Remote Similarity	NPC189908
0.6894	Remote Similarity	NPC301163
0.6892	Remote Similarity	NPC217574
0.689	Remote Similarity	NPC314861
0.6887	Remote Similarity	NPC95366
0.6887	Remote Similarity	NPC248505
0.6886	Remote Similarity	NPC164608
0.6884	Remote Similarity	NPC37302
0.6883	Remote Similarity	NPC473804
0.6871	Remote Similarity	NPC472923
0.687	Remote Similarity	NPC179686
0.6867	Remote Similarity	NPC11147
0.6866	Remote Similarity	NPC309982
0.6852	Remote Similarity	NPC231862
0.6849	Remote Similarity	NPC186898
0.6846	Remote Similarity	NPC169766
0.6842	Remote Similarity	NPC176971
0.6839	Remote Similarity	NPC119569
0.6839	Remote Similarity	NPC80928
0.6835	Remote Similarity	NPC19290
0.6824	Remote Similarity	NPC257390
0.6821	Remote Similarity	NPC313694
0.6821	Remote Similarity	NPC242159
0.6818	Remote Similarity	NPC2518
0.6818	Remote Similarity	NPC266741
0.681	Remote Similarity	NPC289776
0.681	Remote Similarity	NPC133470
0.681	Remote Similarity	NPC191863
0.6788	Remote Similarity	NPC473502
0.6786	Remote Similarity	NPC469954
0.6786	Remote Similarity	NPC280001
0.6786	Remote Similarity	NPC185738
0.6781	Remote Similarity	NPC301713
0.6776	Remote Similarity	NPC193528
0.6774	Remote Similarity	NPC81026
0.6772	Remote Similarity	NPC470019
0.6767	Remote Similarity	NPC128730
0.6765	Remote Similarity	NPC473809
0.6765	Remote Similarity	NPC181905
0.6763	Remote Similarity	NPC315542
0.6761	Remote Similarity	NPC321133
0.6755	Remote Similarity	NPC209195
0.6755	Remote Similarity	NPC237227
0.6755	Remote Similarity	NPC13826
0.6738	Remote Similarity	NPC277460
0.6738	Remote Similarity	NPC220698
0.6736	Remote Similarity	NPC471315
0.6736	Remote Similarity	NPC471314
0.6735	Remote Similarity	NPC172403
0.6735	Remote Similarity	NPC251571
0.6733	Remote Similarity	NPC297584
0.6731	Remote Similarity	NPC16188
0.673	Remote Similarity	NPC182119
0.6726	Remote Similarity	NPC248670
0.6725	Remote Similarity	NPC32064
0.6719	Remote Similarity	NPC471581
0.6716	Remote Similarity	NPC113457
0.6714	Remote Similarity	NPC82963
0.6713	Remote Similarity	NPC473051
0.6713	Remote Similarity	NPC473050
0.6712	Remote Similarity	NPC250476
0.6709	Remote Similarity	NPC473491
0.6708	Remote Similarity	NPC476580
0.6708	Remote Similarity	NPC58661
0.6707	Remote Similarity	NPC196091
0.6707	Remote Similarity	NPC57105
0.6689	Remote Similarity	NPC274441
0.6689	Remote Similarity	NPC303993
0.6689	Remote Similarity	NPC155838
0.6687	Remote Similarity	NPC39431
0.6686	Remote Similarity	NPC158277
0.6686	Remote Similarity	NPC279871
0.6667	Remote Similarity	NPC318862
0.6667	Remote Similarity	NPC470392
0.6667	Remote Similarity	NPC311737
0.6667	Remote Similarity	NPC208022
0.6667	Remote Similarity	NPC471316
0.6667	Remote Similarity	NPC99886
0.6667	Remote Similarity	NPC84325
0.6667	Remote Similarity	NPC233702
0.6667	Remote Similarity	NPC300166
0.6667	Remote Similarity	NPC38458
0.6667	Remote Similarity	NPC259134
0.6667	Remote Similarity	NPC177844
0.6667	Remote Similarity	NPC8002
0.6648	Remote Similarity	NPC198401
0.6647	Remote Similarity	NPC186617
0.6645	Remote Similarity	NPC180647
0.6644	Remote Similarity	NPC195749
0.6644	Remote Similarity	NPC35961
0.6644	Remote Similarity	NPC52029
0.6643	Remote Similarity	NPC296526
0.6643	Remote Similarity	NPC252817
0.6627	Remote Similarity	NPC473748
0.6627	Remote Similarity	NPC299582
0.6626	Remote Similarity	NPC169742
0.6623	Remote Similarity	NPC132308
0.6619	Remote Similarity	NPC90903
0.6618	Remote Similarity	NPC201959
0.6614	Remote Similarity	NPC71853
0.661	Remote Similarity	NPC174629
0.6607	Remote Similarity	NPC471568
0.6607	Remote Similarity	NPC473693
0.6599	Remote Similarity	NPC124776
0.6597	Remote Similarity	NPC269843
0.6597	Remote Similarity	NPC109083
0.6597	Remote Similarity	NPC224814
0.6597	Remote Similarity	NPC60962
0.6597	Remote Similarity	NPC471877
0.6597	Remote Similarity	NPC131868
0.6597	Remote Similarity	NPC14007
0.6597	Remote Similarity	NPC189844
0.6596	Remote Similarity	NPC268317
0.6585	Remote Similarity	NPC57512
0.6579	Remote Similarity	NPC282477
0.6579	Remote Similarity	NPC284855
0.6571	Remote Similarity	NPC313886
0.6571	Remote Similarity	NPC138083
0.657	Remote Similarity	NPC269750
0.657	Remote Similarity	NPC194671
0.6569	Remote Similarity	NPC474272
0.6569	Remote Similarity	NPC82016
0.6567	Remote Similarity	NPC12987
0.6567	Remote Similarity	NPC474603
0.6565	Remote Similarity	NPC313918
0.6562	Remote Similarity	NPC321956

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 NPC29650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	751
0.2-0.3	956
0.3-0.4	1334
0.4-0.5	3815
0.5-0.6	1919
0.6-0.7	139
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD5481	Discontinued
0.8358	Intermediate Similarity	NPD4993	Discontinued
0.7733	Intermediate Similarity	NPD7131	Phase 3
0.7463	Intermediate Similarity	NPD3596	Phase 2
0.7415	Intermediate Similarity	NPD1725	Approved
0.7372	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2335	Discontinued
0.7353	Intermediate Similarity	NPD6581	Approved
0.7353	Intermediate Similarity	NPD6580	Approved
0.7351	Intermediate Similarity	NPD3281	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5746	Approved
0.719	Intermediate Similarity	NPD5297	Approved
0.7174	Intermediate Similarity	NPD2594	Approved
0.7174	Intermediate Similarity	NPD2595	Approved
0.7163	Intermediate Similarity	NPD6539	Approved
0.7163	Intermediate Similarity	NPD6582	Phase 2
0.7163	Intermediate Similarity	NPD6540	Phase 3
0.7163	Intermediate Similarity	NPD6542	Approved
0.7163	Intermediate Similarity	NPD6583	Phase 3
0.7163	Intermediate Similarity	NPD6543	Approved
0.7132	Intermediate Similarity	NPD2557	Approved
0.7123	Intermediate Similarity	NPD5745	Approved
0.7114	Intermediate Similarity	NPD3260	Discontinued
0.7097	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2492	Phase 1
0.7076	Intermediate Similarity	NPD4515	Suspended
0.7063	Intermediate Similarity	NPD5967	Approved
0.7059	Intermediate Similarity	NPD2219	Phase 1
0.7055	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3311	Phase 1
0.7044	Intermediate Similarity	NPD3312	Phase 1
0.7014	Intermediate Similarity	NPD6584	Phase 3
0.7014	Intermediate Similarity	NPD7018	Phase 2
0.6993	Remote Similarity	NPD6541	Approved
0.6993	Remote Similarity	NPD6538	Approved
0.698	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3134	Approved
0.697	Remote Similarity	NPD2388	Discontinued
0.6939	Remote Similarity	NPD5718	Phase 2
0.6939	Remote Similarity	NPD7294	Phase 1
0.6937	Remote Similarity	NPD7317	Phase 3
0.6923	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2987	Approved
0.6897	Remote Similarity	NPD2990	Approved
0.6894	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2245	Discovery
0.6886	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2922	Phase 1
0.6875	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3368	Phase 2
0.6871	Remote Similarity	NPD8031	Discontinued
0.6855	Remote Similarity	NPD2312	Discontinued
0.6852	Remote Similarity	NPD7318	Phase 3
0.6848	Remote Similarity	NPD7485	Phase 3
0.6848	Remote Similarity	NPD7484	Phase 3
0.6842	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5688	Approved
0.6821	Remote Similarity	NPD5689	Approved
0.6821	Remote Similarity	NPD743	Approved
0.6818	Remote Similarity	NPD5289	Phase 2
0.6809	Remote Similarity	NPD6382	Discontinued
0.6807	Remote Similarity	NPD5183	Approved
0.6807	Remote Similarity	NPD5186	Approved
0.6806	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4622	Approved
0.68	Remote Similarity	NPD4618	Approved
0.6797	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1358	Approved
0.679	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5536	Phase 2
0.6779	Remote Similarity	NPD7265	Discontinued
0.6776	Remote Similarity	NPD6380	Phase 1
0.6774	Remote Similarity	NPD2086	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2085	Suspended
0.6761	Remote Similarity	NPD2667	Approved
0.6761	Remote Similarity	NPD2668	Approved
0.6757	Remote Similarity	NPD5163	Phase 2
0.6757	Remote Similarity	NPD6179	Discontinued
0.6752	Remote Similarity	NPD4357	Discontinued
0.6748	Remote Similarity	NPD2415	Discontinued
0.6743	Remote Similarity	NPD4157	Discontinued
0.6733	Remote Similarity	NPD3142	Approved
0.6733	Remote Similarity	NPD3140	Approved
0.6727	Remote Similarity	NPD6862	Phase 2
0.6713	Remote Similarity	NPD3447	Discontinued
0.6713	Remote Similarity	NPD3421	Phase 3
0.671	Remote Similarity	NPD6364	Approved
0.671	Remote Similarity	NPD2460	Phase 3
0.671	Remote Similarity	NPD44	Approved
0.671	Remote Similarity	NPD2459	Approved
0.671	Remote Similarity	NPD2458	Approved
0.6709	Remote Similarity	NPD4123	Phase 3
0.6708	Remote Similarity	NPD2592	Discontinued
0.6691	Remote Similarity	NPD5451	Approved
0.669	Remote Similarity	NPD1669	Approved
0.669	Remote Similarity	NPD1421	Approved
0.669	Remote Similarity	NPD4129	Approved
0.669	Remote Similarity	NPD1420	Approved
0.6688	Remote Similarity	NPD5756	Phase 2
0.6685	Remote Similarity	NPD7810	Phase 3
0.6685	Remote Similarity	NPD7811	Phase 3
0.6667	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4205	Phase 3
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7291	Discontinued
0.6647	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6063	Approved
0.6645	Remote Similarity	NPD3052	Approved
0.6645	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3054	Approved
0.663	Remote Similarity	NPD3802	Phase 3
0.6629	Remote Similarity	NPD4372	Phase 1
0.6627	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2486	Discontinued
0.6608	Remote Similarity	NPD3793	Phase 3
0.6608	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5847	Phase 1
0.6607	Remote Similarity	NPD7608	Discontinued
0.66	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3568	Approved
0.6599	Remote Similarity	NPD3567	Approved
0.6599	Remote Similarity	NPD4098	Discontinued
0.6597	Remote Similarity	NPD3847	Discontinued
0.6597	Remote Similarity	NPD3294	Phase 2
0.659	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5267	Discontinued
0.6582	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5295	Discontinued
0.6577	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2985	Phase 3
0.6576	Remote Similarity	NPD6510	Phase 1
0.6576	Remote Similarity	NPD6511	Phase 1
0.6575	Remote Similarity	NPD3685	Discontinued
0.6573	Remote Similarity	NPD3444	Approved
0.6573	Remote Similarity	NPD3443	Approved
0.6573	Remote Similarity	NPD3445	Approved
0.657	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7303	Discontinued
0.6561	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3530	Approved
0.6556	Remote Similarity	NPD3531	Approved
0.6556	Remote Similarity	NPD1423	Approved
0.6556	Remote Similarity	NPD3532	Approved
0.6556	Remote Similarity	NPD7477	Discontinued
0.6554	Remote Similarity	NPD7905	Discontinued
0.655	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2889	Approved
0.6548	Remote Similarity	NPD6379	Discontinued
0.6548	Remote Similarity	NPD2888	Approved
0.6548	Remote Similarity	NPD2890	Approved
0.6548	Remote Similarity	NPD2516	Approved
0.6548	Remote Similarity	NPD2017	Approved
0.6547	Remote Similarity	NPD821	Approved
0.6545	Remote Similarity	NPD1012	Discontinued
0.6544	Remote Similarity	NPD5373	Approved
0.6544	Remote Similarity	NPD5374	Approved
0.6543	Remote Similarity	NPD3769	Discontinued
0.6541	Remote Similarity	NPD4188	Approved
0.6541	Remote Similarity	NPD4189	Approved
0.6536	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6297	Approved
0.6532	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5858	Discontinued
0.6524	Remote Similarity	NPD7263	Phase 2
0.6524	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1670	Discontinued
0.6522	Remote Similarity	NPD3627	Approved
0.6522	Remote Similarity	NPD2671	Approved
0.6522	Remote Similarity	NPD2673	Approved
0.6519	Remote Similarity	NPD3692	Discontinued
0.6517	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1393	Approved
0.6512	Remote Similarity	NPD3965	Phase 1
0.651	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8149	Discontinued
0.651	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2517	Approved
0.6507	Remote Similarity	NPD3972	Approved
0.6503	Remote Similarity	NPD4675	Approved
0.6503	Remote Similarity	NPD4678	Approved
0.65	Remote Similarity	NPD1241	Discontinued
0.65	Remote Similarity	NPD3985	Discontinued
0.65	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3146	Approved
0.6497	Remote Similarity	NPD4434	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