NPASS Compound

Structure

NPC475635 OpenBabel07101718242D 25 29 0 0 1 0 0 0 0 0999 V2000 2.0519 1.2968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0762 2.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 0.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9105 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3887 2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8887 1.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3887 0.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8887 1.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3887 2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 3 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 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8887 -0.4563 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.4559 2.6353 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 -1.9400 2.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8887 1.2757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7195 2.8849 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 8 1 0 0 0 0 2 20 1 0 0 0 0 3 9 1 0 0 0 0 3 10 2 0 0 0 0 4 9 1 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 12 2 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 21 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	415.0
Volume:	344.374
LogP:	4.489
LogD:	3.317
LogS:	-4.396
# Rotatable Bonds:	2
TPSA:	80.64
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	4.433
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138
MDCK Permeability:	4.114850980840856e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.065
Human Intestinal Absorption (HIA):	0.209
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	98.55674743652344%
Volume Distribution (VD):	0.569
Pgp-substrate:	1.1717495918273926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	4.005
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.593
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.851
Carcinogencity:	0.879
Eye Corrosion:	0.003
Eye Irritation:	0.438
Respiratory Toxicity:	0.66

Download Data

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

Natural Product: NPC475635

Natural Product ID:	NPC475635
*Common Name:**	Makaluvamine F
IUPAC Name:	n.a.
Synonyms:	(-)-Makaluvamine F; Makaluvamine F
Standard InCHIKey:	ZEIRCDSUNJVVPP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14BrN3O2S/c19-10-3-9-4-15(25-14(9)6-13(10)23)22-12-5-11-16-8(1-2-20-11)7-21-17(16)18(12)24/h3,5-7,15,21-23H,1-2,4H2
SMILES:	Brc1cc2CC(Sc2cc1O)NC1=CC2=NCCc3c2c(C1=O)[nH]c3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509890
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001734] Pyrroloquinolines [CHEMONTID:0002829] Pyrrolo[4,3,2-de]quinolines

*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
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	indopacific	n.a.	PMID[12027767]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16180829]
NPO33184	sceptrella sp.	Species	Latrunculiidae	Eukaryota	n.a.	Korean	n.a.	PMID[20055495]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	pohnpeian	n.a.	PMID[8691207]
NPO32549	zyzzya fuliginosa	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9134749]

☑ 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	8
MIC	6
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	5
NON-MOLECULAR	3
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	8900.0	nM	PMID[550515]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	174700.0	nM	PMID[550515]
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC90	=	25000.0	nM	PMID[550516]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	170.0	nM	PMID[550516]
NPT6399	Cell Line	XRS6	Cricetulus griseus	IC50	=	80.0	nM	PMID[550516]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	INH	=	0.1	uM	PMID[550517]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	INH	=	0.25	uM	PMID[550517]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	8300.0	nM	PMID[550517]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	100.0	ug.mL-1	PMID[550515]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	25.0	ug.mL-1	PMID[550515]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[550515]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[550515]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.125	ug.mL-1	PMID[550515]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[550515]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7200.0	nM	PMID[550517]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[550517]

☑ 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 NPC475635 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	550
0.1-0.2	6164
0.2-0.3	11600
0.3-0.4	16686
0.4-0.5	4425
0.5-0.6	2792
0.6-0.7	452
0.7-0.8	25
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.823	Intermediate Similarity	NPC74153
0.8173	Intermediate Similarity	NPC473821
0.7972	Intermediate Similarity	NPC473814
0.7972	Intermediate Similarity	NPC78767
0.7877	Intermediate Similarity	NPC93390
0.7682	Intermediate Similarity	NPC175602
0.7607	Intermediate Similarity	NPC200553
0.7578	Intermediate Similarity	NPC61038
0.7534	Intermediate Similarity	NPC143075
0.7511	Intermediate Similarity	NPC162002
0.7468	Intermediate Similarity	NPC174489
0.7458	Intermediate Similarity	NPC279189
0.7445	Intermediate Similarity	NPC207866
0.7406	Intermediate Similarity	NPC26641
0.7344	Intermediate Similarity	NPC37152
0.7339	Intermediate Similarity	NPC221726
0.7339	Intermediate Similarity	NPC477414
0.7339	Intermediate Similarity	NPC225622
0.7325	Intermediate Similarity	NPC110182
0.7265	Intermediate Similarity	NPC175150
0.7265	Intermediate Similarity	NPC243633
0.711	Intermediate Similarity	NPC477415
0.711	Intermediate Similarity	NPC474259
0.711	Intermediate Similarity	NPC23476
0.7064	Intermediate Similarity	NPC269270
0.7051	Intermediate Similarity	NPC27041
0.7034	Intermediate Similarity	NPC14686
0.7018	Intermediate Similarity	NPC295158
0.6992	Remote Similarity	NPC168209
0.6967	Remote Similarity	NPC97902
0.6936	Remote Similarity	NPC67658
0.6847	Remote Similarity	NPC473628
0.682	Remote Similarity	NPC276657
0.6816	Remote Similarity	NPC268966
0.6816	Remote Similarity	NPC475874
0.6797	Remote Similarity	NPC88115
0.6783	Remote Similarity	NPC106757
0.6777	Remote Similarity	NPC245348
0.6763	Remote Similarity	NPC471655
0.6758	Remote Similarity	NPC79777
0.6758	Remote Similarity	NPC234403
0.6749	Remote Similarity	NPC60006
0.6748	Remote Similarity	NPC207686
0.6738	Remote Similarity	NPC183777
0.6736	Remote Similarity	NPC264285
0.6724	Remote Similarity	NPC469563
0.6723	Remote Similarity	NPC322064
0.6694	Remote Similarity	NPC470501
0.6681	Remote Similarity	NPC50562
0.6667	Remote Similarity	NPC222018
0.6654	Remote Similarity	NPC216369
0.6653	Remote Similarity	NPC220594
0.6653	Remote Similarity	NPC470502
0.6653	Remote Similarity	NPC469562
0.6652	Remote Similarity	NPC473946
0.6639	Remote Similarity	NPC477610
0.6637	Remote Similarity	NPC474258
0.6626	Remote Similarity	NPC16352
0.6623	Remote Similarity	NPC315491
0.6623	Remote Similarity	NPC45459
0.6615	Remote Similarity	NPC475746
0.661	Remote Similarity	NPC80596
0.6604	Remote Similarity	NPC77101
0.6598	Remote Similarity	NPC470503
0.6597	Remote Similarity	NPC219087
0.6595	Remote Similarity	NPC98864
0.6568	Remote Similarity	NPC171787
0.6565	Remote Similarity	NPC272483
0.6562	Remote Similarity	NPC241025
0.656	Remote Similarity	NPC302647
0.656	Remote Similarity	NPC262338
0.6558	Remote Similarity	NPC274981
0.6552	Remote Similarity	NPC213308
0.6549	Remote Similarity	NPC470504
0.6535	Remote Similarity	NPC324149
0.6535	Remote Similarity	NPC99666
0.6533	Remote Similarity	NPC469359
0.6532	Remote Similarity	NPC182940
0.6531	Remote Similarity	NPC167908
0.6529	Remote Similarity	NPC469717
0.6527	Remote Similarity	NPC477413
0.6527	Remote Similarity	NPC128084
0.6525	Remote Similarity	NPC270918
0.6509	Remote Similarity	NPC477004
0.6508	Remote Similarity	NPC15801
0.6504	Remote Similarity	NPC46580
0.6502	Remote Similarity	NPC255110
0.65	Remote Similarity	NPC186068
0.6498	Remote Similarity	NPC469578
0.6495	Remote Similarity	NPC474492
0.6485	Remote Similarity	NPC82370
0.6478	Remote Similarity	NPC202812
0.6468	Remote Similarity	NPC477549
0.6466	Remote Similarity	NPC477044
0.6466	Remote Similarity	NPC477041
0.6463	Remote Similarity	NPC229893
0.6461	Remote Similarity	NPC477609
0.6459	Remote Similarity	NPC178858
0.645	Remote Similarity	NPC179701
0.6443	Remote Similarity	NPC235685
0.6441	Remote Similarity	NPC96890
0.6441	Remote Similarity	NPC477043
0.6432	Remote Similarity	NPC278434
0.6429	Remote Similarity	NPC100726
0.6422	Remote Similarity	NPC227582
0.6422	Remote Similarity	NPC156704
0.6422	Remote Similarity	NPC262898
0.6422	Remote Similarity	NPC77555
0.642	Remote Similarity	NPC472285
0.6417	Remote Similarity	NPC101350
0.6416	Remote Similarity	NPC314002
0.6414	Remote Similarity	NPC82053
0.6409	Remote Similarity	NPC91868
0.6409	Remote Similarity	NPC63971
0.6404	Remote Similarity	NPC209917
0.64	Remote Similarity	NPC220765
0.6398	Remote Similarity	NPC138562
0.6395	Remote Similarity	NPC476143
0.6395	Remote Similarity	NPC248782
0.6395	Remote Similarity	NPC306376
0.6394	Remote Similarity	NPC117980
0.6389	Remote Similarity	NPC470680
0.6389	Remote Similarity	NPC100104
0.6384	Remote Similarity	NPC477042
0.6383	Remote Similarity	NPC471944
0.6379	Remote Similarity	NPC77061
0.6376	Remote Similarity	NPC83111
0.6372	Remote Similarity	NPC204717
0.6368	Remote Similarity	NPC477045
0.6368	Remote Similarity	NPC284775
0.6367	Remote Similarity	NPC74360
0.6364	Remote Similarity	NPC33064
0.6364	Remote Similarity	NPC63109
0.636	Remote Similarity	NPC477608
0.636	Remote Similarity	NPC238242
0.636	Remote Similarity	NPC477607
0.636	Remote Similarity	NPC194740
0.6356	Remote Similarity	NPC220851
0.6352	Remote Similarity	NPC469727
0.6345	Remote Similarity	NPC153467
0.634	Remote Similarity	NPC252338
0.6337	Remote Similarity	NPC237740
0.6336	Remote Similarity	NPC153400
0.6335	Remote Similarity	NPC326363
0.6332	Remote Similarity	NPC477420
0.6332	Remote Similarity	NPC477418
0.6331	Remote Similarity	NPC122436
0.6325	Remote Similarity	NPC131887
0.6325	Remote Similarity	NPC472284
0.6322	Remote Similarity	NPC207020
0.6318	Remote Similarity	NPC469577
0.6318	Remote Similarity	NPC88008
0.6318	Remote Similarity	NPC475410
0.6316	Remote Similarity	NPC473317
0.6316	Remote Similarity	NPC41982
0.6316	Remote Similarity	NPC171171
0.6311	Remote Similarity	NPC271792
0.6311	Remote Similarity	NPC74969
0.6309	Remote Similarity	NPC242209
0.6298	Remote Similarity	NPC237414
0.6295	Remote Similarity	NPC184964
0.6295	Remote Similarity	NPC248454
0.6286	Remote Similarity	NPC477416
0.6283	Remote Similarity	NPC314056
0.6282	Remote Similarity	NPC167710
0.6278	Remote Similarity	NPC74619
0.6275	Remote Similarity	NPC323969
0.6274	Remote Similarity	NPC471536
0.6266	Remote Similarity	NPC294693
0.6266	Remote Similarity	NPC276517
0.6261	Remote Similarity	NPC75498
0.6261	Remote Similarity	NPC134848
0.626	Remote Similarity	NPC284888
0.6255	Remote Similarity	NPC470702
0.6255	Remote Similarity	NPC473218
0.625	Remote Similarity	NPC47190
0.625	Remote Similarity	NPC56170
0.6241	Remote Similarity	NPC478011
0.624	Remote Similarity	NPC125597
0.624	Remote Similarity	NPC309845
0.624	Remote Similarity	NPC476818
0.6235	Remote Similarity	NPC182222
0.6235	Remote Similarity	NPC48317
0.6235	Remote Similarity	NPC325976
0.6234	Remote Similarity	NPC473239
0.6234	Remote Similarity	NPC470500
0.6234	Remote Similarity	NPC470505
0.6234	Remote Similarity	NPC472259
0.6234	Remote Similarity	NPC154339
0.6233	Remote Similarity	NPC247980
0.623	Remote Similarity	NPC470703
0.6229	Remote Similarity	NPC474318
0.6229	Remote Similarity	NPC153123
0.6229	Remote Similarity	NPC268744
0.6229	Remote Similarity	NPC201266
0.6229	Remote Similarity	NPC220797
0.6229	Remote Similarity	NPC475914
0.6228	Remote Similarity	NPC477003
0.6225	Remote Similarity	NPC478141
0.6223	Remote Similarity	NPC304203

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 NPC475635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	741
0.2-0.3	846
0.3-0.4	2243
0.4-0.5	3037
0.5-0.6	1911
0.6-0.7	96
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6798	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3178	Discontinued
0.6623	Remote Similarity	NPD484	Approved
0.6581	Remote Similarity	NPD5901	Discontinued
0.6552	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6173	Approved
0.652	Remote Similarity	NPD4850	Phase 1
0.6518	Remote Similarity	NPD4845	Discontinued
0.6507	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8106	Phase 2
0.6498	Remote Similarity	NPD6376	Discontinued
0.6494	Remote Similarity	NPD7948	Phase 1
0.6489	Remote Similarity	NPD5050	Approved
0.6475	Remote Similarity	NPD6242	Discontinued
0.6461	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD2803	Discontinued
0.6341	Remote Similarity	NPD1996	Discontinued
0.632	Remote Similarity	NPD981	Phase 2
0.6269	Remote Similarity	NPD5817	Discontinued
0.6266	Remote Similarity	NPD3396	Approved
0.6266	Remote Similarity	NPD3395	Approved
0.626	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.625	Remote Similarity	NPD946	Discontinued
0.6215	Remote Similarity	NPD7603	Discontinued
0.6214	Remote Similarity	NPD4417	Approved
0.6213	Remote Similarity	NPD1218	Approved
0.6213	Remote Similarity	NPD1219	Approved
0.6207	Remote Similarity	NPD954	Phase 1
0.6205	Remote Similarity	NPD5065	Approved
0.6193	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.617	Remote Similarity	NPD2290	Phase 3
0.617	Remote Similarity	NPD2289	Phase 3
0.617	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD2509	Approved
0.6157	Remote Similarity	NPD2510	Approved
0.6129	Remote Similarity	NPD2021	Discontinued
0.6125	Remote Similarity	NPD4044	Discontinued
0.6116	Remote Similarity	NPD4865	Approved
0.6113	Remote Similarity	NPD3393	Approved
0.6113	Remote Similarity	NPD3389	Approved
0.6113	Remote Similarity	NPD3394	Approved
0.6111	Remote Similarity	NPD4890	Phase 2
0.6109	Remote Similarity	NPD4511	Phase 1
0.6104	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD8284	Discontinued
0.6092	Remote Similarity	NPD3814	Phase 1
0.6083	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.607	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD482	Approved
0.6058	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD3918	Approved
0.6057	Remote Similarity	NPD3917	Approved
0.6049	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD2853	Approved
0.6039	Remote Similarity	NPD2761	Approved
0.6035	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4906	Approved
0.6033	Remote Similarity	NPD4905	Approved
0.6033	Remote Similarity	NPD4903	Approved
0.603	Remote Similarity	NPD5857	Phase 3
0.6027	Remote Similarity	NPD2781	Approved
0.6024	Remote Similarity	NPD5524	Approved
0.6024	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5523	Approved
0.6017	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD1096	Discontinued
0.6017	Remote Similarity	NPD1038	Approved
0.6017	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD3915	Approved
0.6015	Remote Similarity	NPD6531	Approved
0.6015	Remote Similarity	NPD6530	Approved
0.6009	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD2782	Approved
0.6009	Remote Similarity	NPD2780	Approved
0.6008	Remote Similarity	NPD4904	Approved
0.6008	Remote Similarity	NPD5046	Discontinued
0.6008	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1575	Approved
0.6	Remote Similarity	NPD1573	Approved
0.6	Remote Similarity	NPD5228	Phase 3
0.6	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6205	Discontinued
0.6	Remote Similarity	NPD1235	Phase 3
0.5992	Remote Similarity	NPD5513	Phase 2
0.5992	Remote Similarity	NPD3336	Discovery
0.5991	Remote Similarity	NPD158	Discontinued
0.5984	Remote Similarity	NPD5612	Discontinued
0.5977	Remote Similarity	NPD6825	Phase 1
0.5974	Remote Similarity	NPD2092	Phase 2
0.5974	Remote Similarity	NPD2095	Phase 2
0.5974	Remote Similarity	NPD5105	Approved
0.5974	Remote Similarity	NPD5106	Approved
0.5974	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD2094	Phase 2
0.597	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD2321	Approved
0.5967	Remote Similarity	NPD3947	Discontinued
0.5965	Remote Similarity	NPD1544	Phase 1
0.5961	Remote Similarity	NPD7711	Discontinued
0.596	Remote Similarity	NPD5818	Discontinued
0.596	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6475	Phase 2
0.5955	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7470	Discontinued
0.595	Remote Similarity	NPD8073	Approved
0.5949	Remote Similarity	NPD802	Phase 2
0.5948	Remote Similarity	NPD2096	Phase 2
0.5948	Remote Similarity	NPD2091	Phase 2
0.5947	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.594	Remote Similarity	NPD6276	Discontinued
0.5939	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD4429	Discontinued
0.5936	Remote Similarity	NPD3354	Phase 2
0.5932	Remote Similarity	NPD4949	Discontinued
0.5929	Remote Similarity	NPD4923	Phase 1
0.5927	Remote Similarity	NPD5866	Approved
0.5925	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4558	Phase 2
0.5918	Remote Similarity	NPD4887	Discontinued
0.5915	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5911	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD8356	Approved
0.5904	Remote Similarity	NPD3243	Approved
0.5903	Remote Similarity	NPD3883	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5426	Phase 3
0.5902	Remote Similarity	NPD8272	Phase 2
0.5896	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6044	Discontinued
0.5893	Remote Similarity	NPD7655	Discontinued
0.5893	Remote Similarity	NPD1631	Approved
0.5887	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5884	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6752	Phase 1
0.5882	Remote Similarity	NPD6753	Phase 1
0.588	Remote Similarity	NPD3328	Phase 2
0.5878	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD7994	Phase 2
0.5865	Remote Similarity	NPD3962	Phase 2
0.5865	Remote Similarity	NPD3959	Phase 2
0.5863	Remote Similarity	NPD8093	Discontinued
0.5861	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.5861	Remote Similarity	NPD8072	Approved
0.5858	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6458	Discontinued
0.5846	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD5017	Discontinued
0.5844	Remote Similarity	NPD5259	Phase 3
0.584	Remote Similarity	NPD8094	Discontinued
0.584	Remote Similarity	NPD3250	Phase 1
0.584	Remote Similarity	NPD7853	Phase 2
0.584	Remote Similarity	NPD3006	Discontinued
0.584	Remote Similarity	NPD3288	Approved
0.5836	Remote Similarity	NPD5482	Discontinued
0.5833	Remote Similarity	NPD2123	Phase 3
0.5833	Remote Similarity	NPD4848	Phase 1
0.5833	Remote Similarity	NPD4989	Phase 2
0.5833	Remote Similarity	NPD2893	Phase 3
0.583	Remote Similarity	NPD1659	Phase 1
0.583	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.583	Remote Similarity	NPD604	Clinical (unspecified phase)
0.583	Remote Similarity	NPD5479	Discontinued
0.583	Remote Similarity	NPD3315	Phase 3
0.583	Remote Similarity	NPD5022	Discontinued
0.5827	Remote Similarity	NPD3264	Phase 3
0.5826	Remote Similarity	NPD3825	Phase 3
0.5826	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6999	Discontinued
0.5826	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD1545	Discontinued
0.582	Remote Similarity	NPD6975	Discontinued
0.5819	Remote Similarity	NPD9510	Approved
0.5819	Remote Similarity	NPD1643	Phase 3
0.5815	Remote Similarity	NPD2844	Phase 3
0.5815	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8430	Approved
0.5814	Remote Similarity	NPD8292	Phase 2
0.5808	Remote Similarity	NPD750	Phase 2
0.5806	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD4948	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