NPASS Compound

Structure

CID138365 OpenBabel06191715492D 28 30 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 -6.9282 -1.0000 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 -4.3301 0.5000 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 0.0000 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 -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 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 -5.1962 -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 -6.0622 -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 24 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	175.06
Volume:	179.798
LogP:	2.452
LogD:	2.642
LogS:	-2.897
# Rotatable Bonds:	2
TPSA:	42.09
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	1.688
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.521
MDCK Permeability:	1.5764544514240697e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.128
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.337

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	77.29608917236328%
Volume Distribution (VD):	1.069
Pgp-substrate:	22.43720054626465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.334
CYP2C9-inhibitor:	0.394
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.449
CYP2D6-substrate:	0.755
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	9.205
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.419
Drug-inuced Liver Injury (DILI):	0.686
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.494
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.573
Carcinogencity:	0.096
Eye Corrosion:	0.035
Eye Irritation:	0.978
Respiratory Toxicity:	0.239

Download Data

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

Natural Product: NPC138365

Natural Product ID:	NPC138365
*Common Name:**	Nocazine A
IUPAC Name:	(3Z,6Z)-5-methoxy-3,6-bis[(4-methoxyphenyl)methylidene]-1-methylpyrazin-2-one
Synonyms:	Nocazine A
Standard InCHIKey:	PIZYGUXDBZYKHO-AXPXABNXSA-N
Standard InCHI:	InChI=1S/C22H22N2O4/c1-24-20(14-16-7-11-18(27-3)12-8-16)21(28-4)23-19(22(24)25)13-15-5-9-17(26-2)10-6-15/h5-14H,1-4H3/b19-13-,20-14-
SMILES:	Cn1/c(=Cc2ccc(cc2)OC)/c(n/c(=Cc2ccc(cc2)OC)/c1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1833989
PubChem CID:	56600876
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[486171]
NPT81	Cell Line	A549	Homo sapiens	IC5	>=	100.0	uM	PMID[486171]

☑ 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 NPC138365 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	360
0.1-0.2	3470
0.2-0.3	13317
0.3-0.4	3340
0.4-0.5	17487
0.5-0.6	4494
0.6-0.7	226
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	NPC29650
0.8521	High Similarity	NPC9373
0.8015	Intermediate Similarity	NPC323948
0.7939	Intermediate Similarity	NPC258992
0.7836	Intermediate Similarity	NPC41801
0.7826	Intermediate Similarity	NPC218323
0.7594	Intermediate Similarity	NPC303370
0.75	Intermediate Similarity	NPC266425
0.7421	Intermediate Similarity	NPC254700
0.7415	Intermediate Similarity	NPC113236
0.7415	Intermediate Similarity	NPC214036
0.7391	Intermediate Similarity	NPC83279
0.7372	Intermediate Similarity	NPC256369
0.7325	Intermediate Similarity	NPC319320
0.7325	Intermediate Similarity	NPC287757
0.731	Intermediate Similarity	NPC471953
0.723	Intermediate Similarity	NPC469808
0.7208	Intermediate Similarity	NPC324081
0.72	Intermediate Similarity	NPC212850
0.72	Intermediate Similarity	NPC189724
0.72	Intermediate Similarity	NPC83289
0.7192	Intermediate Similarity	NPC274732
0.7164	Intermediate Similarity	NPC166837
0.7124	Intermediate Similarity	NPC247298
0.7122	Intermediate Similarity	NPC43275
0.7114	Intermediate Similarity	NPC307682
0.7113	Intermediate Similarity	NPC211218
0.7113	Intermediate Similarity	NPC255253
0.7071	Intermediate Similarity	NPC263835
0.7068	Intermediate Similarity	NPC146530
0.7067	Intermediate Similarity	NPC470707
0.7055	Intermediate Similarity	NPC196026
0.7055	Intermediate Similarity	NPC200555
0.7047	Intermediate Similarity	NPC251454
0.7047	Intermediate Similarity	NPC255817
0.7047	Intermediate Similarity	NPC136330
0.7047	Intermediate Similarity	NPC73883
0.7047	Intermediate Similarity	NPC277042
0.7047	Intermediate Similarity	NPC230698
0.7047	Intermediate Similarity	NPC196609
0.7047	Intermediate Similarity	NPC205178
0.7032	Intermediate Similarity	NPC296085
0.7032	Intermediate Similarity	NPC245974
0.7031	Intermediate Similarity	NPC175298
0.7023	Intermediate Similarity	NPC109637
0.702	Intermediate Similarity	NPC476989
0.702	Intermediate Similarity	NPC231572
0.7013	Intermediate Similarity	NPC244338
0.7	Intermediate Similarity	NPC77992
0.7	Intermediate Similarity	NPC99078
0.6986	Remote Similarity	NPC283079
0.698	Remote Similarity	NPC103947
0.698	Remote Similarity	NPC328419
0.698	Remote Similarity	NPC94280
0.698	Remote Similarity	NPC159150
0.698	Remote Similarity	NPC45783
0.698	Remote Similarity	NPC193673
0.698	Remote Similarity	NPC167096
0.6959	Remote Similarity	NPC118419
0.6957	Remote Similarity	NPC301163
0.6957	Remote Similarity	NPC37302
0.6954	Remote Similarity	NPC220923
0.6954	Remote Similarity	NPC252107
0.6951	Remote Similarity	NPC314861
0.6946	Remote Similarity	NPC164608
0.6944	Remote Similarity	NPC95733
0.6944	Remote Similarity	NPC62101
0.6933	Remote Similarity	NPC472923
0.6933	Remote Similarity	NPC11147
0.6933	Remote Similarity	NPC96406
0.6923	Remote Similarity	NPC13755
0.6923	Remote Similarity	NPC71629
0.6918	Remote Similarity	NPC186898
0.6918	Remote Similarity	NPC474852
0.6917	Remote Similarity	NPC326447
0.6914	Remote Similarity	NPC231862
0.6897	Remote Similarity	NPC476249
0.6897	Remote Similarity	NPC29477
0.6892	Remote Similarity	NPC257390
0.6887	Remote Similarity	NPC145446
0.6887	Remote Similarity	NPC137172
0.6883	Remote Similarity	NPC266741
0.6871	Remote Similarity	NPC191863
0.6871	Remote Similarity	NPC133470
0.6871	Remote Similarity	NPC289776
0.6866	Remote Similarity	NPC151530
0.6866	Remote Similarity	NPC157473
0.6859	Remote Similarity	NPC189908
0.6857	Remote Similarity	NPC185738
0.6857	Remote Similarity	NPC280001
0.6848	Remote Similarity	NPC473502
0.6846	Remote Similarity	NPC217574
0.6842	Remote Similarity	NPC95366
0.6842	Remote Similarity	NPC248505
0.6839	Remote Similarity	NPC81026
0.6839	Remote Similarity	NPC473804
0.6824	Remote Similarity	NPC181905
0.6821	Remote Similarity	NPC209195
0.6821	Remote Similarity	NPC13826
0.6821	Remote Similarity	NPC315542
0.6818	Remote Similarity	NPC179686
0.6815	Remote Similarity	NPC309982
0.6809	Remote Similarity	NPC277460
0.6803	Remote Similarity	NPC251571
0.68	Remote Similarity	NPC169766
0.6795	Remote Similarity	NPC119569
0.6795	Remote Similarity	NPC80928
0.6795	Remote Similarity	NPC16188
0.6792	Remote Similarity	NPC182119
0.6791	Remote Similarity	NPC176971
0.6786	Remote Similarity	NPC248670
0.6786	Remote Similarity	NPC19290
0.6784	Remote Similarity	NPC32064
0.6783	Remote Similarity	NPC473051
0.6783	Remote Similarity	NPC473050
0.6776	Remote Similarity	NPC313694
0.6776	Remote Similarity	NPC242159
0.6772	Remote Similarity	NPC473491
0.677	Remote Similarity	NPC58661
0.677	Remote Similarity	NPC476580
0.6768	Remote Similarity	NPC57105
0.6767	Remote Similarity	NPC2518
0.6766	Remote Similarity	NPC196091
0.6755	Remote Similarity	NPC303993
0.6755	Remote Similarity	NPC274441
0.675	Remote Similarity	NPC39431
0.6746	Remote Similarity	NPC158277
0.6746	Remote Similarity	NPC279871
0.6738	Remote Similarity	NPC311737
0.6738	Remote Similarity	NPC38458
0.6738	Remote Similarity	NPC469954
0.6735	Remote Similarity	NPC301713
0.6733	Remote Similarity	NPC470392
0.6732	Remote Similarity	NPC193528
0.673	Remote Similarity	NPC470019
0.673	Remote Similarity	NPC233702
0.6716	Remote Similarity	NPC128730
0.6715	Remote Similarity	NPC473809
0.6714	Remote Similarity	NPC296526
0.6713	Remote Similarity	NPC321133
0.6713	Remote Similarity	NPC252817
0.6711	Remote Similarity	NPC52029
0.6711	Remote Similarity	NPC35961
0.6711	Remote Similarity	NPC237227
0.6711	Remote Similarity	NPC195749
0.6707	Remote Similarity	NPC186617
0.669	Remote Similarity	NPC220698
0.669	Remote Similarity	NPC471315
0.669	Remote Similarity	NPC471314
0.6689	Remote Similarity	NPC172403
0.6689	Remote Similarity	NPC132308
0.6689	Remote Similarity	NPC297584
0.6687	Remote Similarity	NPC169742
0.6686	Remote Similarity	NPC473748
0.6667	Remote Similarity	NPC109083
0.6667	Remote Similarity	NPC60962
0.6667	Remote Similarity	NPC174629
0.6667	Remote Similarity	NPC471568
0.6667	Remote Similarity	NPC269843
0.6667	Remote Similarity	NPC473693
0.6667	Remote Similarity	NPC471877
0.6667	Remote Similarity	NPC113457
0.6667	Remote Similarity	NPC82963
0.6667	Remote Similarity	NPC224814
0.6667	Remote Similarity	NPC471581
0.6667	Remote Similarity	NPC268317
0.6667	Remote Similarity	NPC189844
0.6667	Remote Similarity	NPC14007
0.6667	Remote Similarity	NPC250476
0.6646	Remote Similarity	NPC57512
0.6645	Remote Similarity	NPC284855
0.6645	Remote Similarity	NPC282477
0.6644	Remote Similarity	NPC155838
0.6642	Remote Similarity	NPC474272
0.6629	Remote Similarity	NPC138083
0.6629	Remote Similarity	NPC313886
0.6628	Remote Similarity	NPC194671
0.6628	Remote Similarity	NPC269750
0.6625	Remote Similarity	NPC153644
0.6623	Remote Similarity	NPC471316
0.6623	Remote Similarity	NPC214869
0.6623	Remote Similarity	NPC208022
0.6623	Remote Similarity	NPC213471
0.6623	Remote Similarity	NPC318862
0.6621	Remote Similarity	NPC251259
0.6617	Remote Similarity	NPC300166
0.6617	Remote Similarity	NPC84325
0.6614	Remote Similarity	NPC259134
0.6614	Remote Similarity	NPC8002
0.6614	Remote Similarity	NPC99886
0.6614	Remote Similarity	NPC177844
0.6611	Remote Similarity	NPC198401
0.6607	Remote Similarity	NPC315388
0.6605	Remote Similarity	NPC256689
0.6605	Remote Similarity	NPC476568
0.6605	Remote Similarity	NPC123011
0.6604	Remote Similarity	NPC132771
0.6601	Remote Similarity	NPC196708
0.6601	Remote Similarity	NPC180647
0.66	Remote Similarity	NPC120251

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 NPC138365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	744
0.2-0.3	955
0.3-0.4	1371
0.4-0.5	3769
0.5-0.6	1943
0.6-0.7	144
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
0.9191	High Similarity	NPD5481	Discontinued
0.8296	Intermediate Similarity	NPD4993	Discontinued
0.7682	Intermediate Similarity	NPD7131	Phase 3
0.7417	Intermediate Similarity	NPD3281	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3596	Phase 2
0.7365	Intermediate Similarity	NPD1725	Approved
0.732	Intermediate Similarity	NPD2335	Discontinued
0.7319	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6580	Approved
0.7299	Intermediate Similarity	NPD6581	Approved
0.7292	Intermediate Similarity	NPD5746	Approved
0.7255	Intermediate Similarity	NPD5297	Approved
0.7246	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5745	Approved
0.7181	Intermediate Similarity	NPD3260	Discontinued
0.7125	Intermediate Similarity	NPD5967	Approved
0.7124	Intermediate Similarity	NPD2219	Phase 1
0.7122	Intermediate Similarity	NPD2594	Approved
0.7122	Intermediate Similarity	NPD2595	Approved
0.7113	Intermediate Similarity	NPD6582	Phase 2
0.7113	Intermediate Similarity	NPD6539	Approved
0.7113	Intermediate Similarity	NPD6543	Approved
0.7113	Intermediate Similarity	NPD6540	Phase 3
0.7113	Intermediate Similarity	NPD6583	Phase 3
0.7113	Intermediate Similarity	NPD6542	Approved
0.708	Intermediate Similarity	NPD2557	Approved
0.7051	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2492	Phase 1
0.7035	Intermediate Similarity	NPD4515	Suspended
0.7007	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3311	Phase 1
0.7	Intermediate Similarity	NPD3312	Phase 1
0.7	Intermediate Similarity	NPD7317	Phase 3
0.6966	Remote Similarity	NPD7018	Phase 2
0.6966	Remote Similarity	NPD6584	Phase 3
0.6944	Remote Similarity	NPD6538	Approved
0.6944	Remote Similarity	NPD6541	Approved
0.6944	Remote Similarity	NPD2922	Phase 1
0.6933	Remote Similarity	NPD8031	Discontinued
0.6933	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3368	Phase 2
0.6928	Remote Similarity	NPD2388	Discontinued
0.6917	Remote Similarity	NPD3134	Approved
0.6914	Remote Similarity	NPD7318	Phase 3
0.6909	Remote Similarity	NPD7485	Phase 3
0.6909	Remote Similarity	NPD7484	Phase 3
0.6901	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7294	Phase 1
0.6892	Remote Similarity	NPD5718	Phase 2
0.6883	Remote Similarity	NPD5289	Phase 2
0.6882	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1358	Approved
0.6857	Remote Similarity	NPD5536	Phase 2
0.6852	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2987	Approved
0.6849	Remote Similarity	NPD2990	Approved
0.6846	Remote Similarity	NPD7265	Discontinued
0.6846	Remote Similarity	NPD2245	Discovery
0.6845	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4357	Discontinued
0.6813	Remote Similarity	NPD2312	Discontinued
0.681	Remote Similarity	NPD2415	Discontinued
0.68	Remote Similarity	NPD4157	Discontinued
0.6795	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5689	Approved
0.6776	Remote Similarity	NPD5688	Approved
0.6776	Remote Similarity	NPD743	Approved
0.6772	Remote Similarity	NPD4123	Phase 3
0.6766	Remote Similarity	NPD5183	Approved
0.6766	Remote Similarity	NPD5186	Approved
0.6761	Remote Similarity	NPD6382	Discontinued
0.6755	Remote Similarity	NPD4618	Approved
0.6755	Remote Similarity	NPD4622	Approved
0.6753	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5756	Phase 2
0.6748	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7810	Phase 3
0.674	Remote Similarity	NPD7811	Phase 3
0.6739	Remote Similarity	NPD5535	Approved
0.6732	Remote Similarity	NPD6380	Phase 1
0.6731	Remote Similarity	NPD2086	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2085	Suspended
0.6713	Remote Similarity	NPD2668	Approved
0.6713	Remote Similarity	NPD2667	Approved
0.6711	Remote Similarity	NPD6179	Discontinued
0.6711	Remote Similarity	NPD5163	Phase 2
0.6707	Remote Similarity	NPD6063	Approved
0.6705	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3140	Approved
0.6689	Remote Similarity	NPD3142	Approved
0.6687	Remote Similarity	NPD6862	Phase 2
0.6685	Remote Similarity	NPD3802	Phase 3
0.6667	Remote Similarity	NPD3447	Discontinued
0.6667	Remote Similarity	NPD2460	Phase 3
0.6667	Remote Similarity	NPD3793	Phase 3
0.6667	Remote Similarity	NPD2458	Approved
0.6667	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2459	Approved
0.6667	Remote Similarity	NPD6364	Approved
0.6667	Remote Similarity	NPD7608	Discontinued
0.6667	Remote Similarity	NPD44	Approved
0.6667	Remote Similarity	NPD3421	Phase 3
0.6667	Remote Similarity	NPD5847	Phase 1
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD2592	Discontinued
0.6647	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5295	Discontinued
0.6644	Remote Similarity	NPD4129	Approved
0.6644	Remote Similarity	NPD1420	Approved
0.6644	Remote Similarity	NPD3685	Discontinued
0.6644	Remote Similarity	NPD1421	Approved
0.6644	Remote Similarity	NPD1669	Approved
0.6642	Remote Similarity	NPD5451	Approved
0.6628	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4205	Phase 3
0.6625	Remote Similarity	NPD7303	Discontinued
0.6624	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7291	Discontinued
0.6608	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2888	Approved
0.6607	Remote Similarity	NPD2890	Approved
0.6607	Remote Similarity	NPD2516	Approved
0.6607	Remote Similarity	NPD2017	Approved
0.6607	Remote Similarity	NPD2889	Approved
0.6605	Remote Similarity	NPD3769	Discontinued
0.6603	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3054	Approved
0.6601	Remote Similarity	NPD3052	Approved
0.6592	Remote Similarity	NPD4372	Phase 1
0.6592	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6297	Approved
0.6588	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3627	Approved
0.6584	Remote Similarity	NPD1670	Discontinued
0.6584	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7263	Phase 2
0.6577	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2486	Discontinued
0.657	Remote Similarity	NPD3965	Phase 1
0.6568	Remote Similarity	NPD2517	Approved
0.6564	Remote Similarity	NPD4678	Approved
0.6564	Remote Similarity	NPD4675	Approved
0.6562	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3985	Discontinued
0.6562	Remote Similarity	NPD8149	Discontinued
0.6562	Remote Similarity	NPD3146	Approved
0.6558	Remote Similarity	NPD7119	Phase 2
0.6556	Remote Similarity	NPD5110	Phase 2
0.6556	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5111	Phase 2
0.6556	Remote Similarity	NPD5109	Approved
0.6554	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4098	Discontinued
0.6554	Remote Similarity	NPD4434	Approved
0.6554	Remote Similarity	NPD3567	Approved
0.6554	Remote Similarity	NPD3568	Approved
0.6552	Remote Similarity	NPD3294	Phase 2
0.6548	Remote Similarity	NPD5677	Discontinued
0.6545	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5267	Discontinued
0.6541	Remote Similarity	NPD6511	Phase 1
0.6541	Remote Similarity	NPD6510	Phase 1
0.6538	Remote Similarity	NPD3656	Approved
0.6534	Remote Similarity	NPD6851	Approved
0.6534	Remote Similarity	NPD6853	Approved
0.6533	Remote Similarity	NPD2985	Phase 3
0.6533	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3444	Approved
0.6528	Remote Similarity	NPD3445	Approved
0.6528	Remote Similarity	NPD3443	Approved
0.6524	Remote Similarity	NPD7110	Phase 1
0.6524	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4435	Approved
0.6513	Remote Similarity	NPD3531	Approved
0.6513	Remote Similarity	NPD3532	Approved
0.6513	Remote Similarity	NPD1423	Approved
0.6513	Remote Similarity	NPD7477	Discontinued
0.6513	Remote Similarity	NPD3530	Approved
0.651	Remote Similarity	NPD7905	Discontinued
0.6509	Remote Similarity	NPD6379	Discontinued
0.6509	Remote Similarity	NPD7126	Discontinued
0.6506	Remote Similarity	NPD3556	Approved
0.6506	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1012	Discontinued
0.6506	Remote Similarity	NPD3557	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