NPASS Compound

Structure

NPC476423 OpenBabel07101718232D 23 23 0 0 1 0 0 0 0 0999 V2000 -1.4264 -3.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 -1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3305 -2.0345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7953 -0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7428 -1.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4046 -3.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7210 -2.1684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0737 -2.7036 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 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 -2.7136 -4.3978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3901 -1.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0300 -3.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 -3.3727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 18 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 14 1 0 0 0 0 8 19 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 20 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	451.96
Volume:	333.473
LogP:	1.309
LogD:	0.745
LogS:	-2.636
# Rotatable Bonds:	9
TPSA:	108.63
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	3.406
Fsp3:	0.5
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:	-5.686
MDCK Permeability:	1.7648038920015097e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.633
20% Bioavailability (F20%):	0.372
30% Bioavailability (F30%):	0.143

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	86.82575225830078%
Volume Distribution (VD):	0.223
Pgp-substrate:	21.893877029418945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.694
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	4.31
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.613
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.347
Skin Sensitization:	0.058
Carcinogencity:	0.283
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC476423

Natural Product ID:	NPC476423
*Common Name:**	Agelanin B
IUPAC Name:	3-acetyl-6-[(4,5-dibromo-1-methylpyrrole-2-carbonyl)amino]-3-hydroxyhexanoic acid
Synonyms:
Standard InCHIKey:	HHNVUTCHBCYOOP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H18Br2N2O5/c1-8(19)14(23,7-11(20)21)4-3-5-17-13(22)10-6-9(15)12(16)18(10)2/h6,23H,3-5,7H2,1-2H3,(H,17,22)(H,20,21)
SMILES:	OC(=O)CC(C(=O)C)(CCCNC(=O)c1cc(c(n1C)Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL599318
PubChem CID:	46231990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000389] Keto acids and derivatives [CHEMONTID:0001415] Medium-chain keto acids and derivatives

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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
MIC	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	92.8	%	PMID[492897]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	44000.0	nM	PMID[492897]

☑ 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 NPC476423 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	268
0.1-0.2	4566
0.2-0.3	18459
0.3-0.4	13398
0.4-0.5	3340
0.5-0.6	2224
0.6-0.7	399
0.7-0.8	39
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8727	High Similarity	NPC27296
0.8363	Intermediate Similarity	NPC474383
0.7989	Intermediate Similarity	NPC476418
0.7886	Intermediate Similarity	NPC306160
0.7849	Intermediate Similarity	NPC474236
0.7841	Intermediate Similarity	NPC2414
0.7647	Intermediate Similarity	NPC260041
0.7582	Intermediate Similarity	NPC97106
0.75	Intermediate Similarity	NPC112489
0.7487	Intermediate Similarity	NPC476413
0.7487	Intermediate Similarity	NPC476524
0.7486	Intermediate Similarity	NPC37268
0.7448	Intermediate Similarity	NPC476414
0.7432	Intermediate Similarity	NPC80528
0.7407	Intermediate Similarity	NPC46022
0.7374	Intermediate Similarity	NPC473706
0.7365	Intermediate Similarity	NPC150592
0.7351	Intermediate Similarity	NPC136441
0.733	Intermediate Similarity	NPC109158
0.732	Intermediate Similarity	NPC46811
0.7313	Intermediate Similarity	NPC476525
0.7302	Intermediate Similarity	NPC469814
0.7287	Intermediate Similarity	NPC184932
0.7287	Intermediate Similarity	NPC472861
0.7283	Intermediate Similarity	NPC227489
0.7283	Intermediate Similarity	NPC226835
0.7283	Intermediate Similarity	NPC28096
0.7283	Intermediate Similarity	NPC476421
0.7202	Intermediate Similarity	NPC20021
0.7198	Intermediate Similarity	NPC206148
0.7158	Intermediate Similarity	NPC233380
0.712	Intermediate Similarity	NPC474696
0.7079	Intermediate Similarity	NPC52110
0.7005	Intermediate Similarity	NPC54214
0.7005	Intermediate Similarity	NPC19342
0.6968	Remote Similarity	NPC271927
0.6961	Remote Similarity	NPC298288
0.6959	Remote Similarity	NPC111566
0.6935	Remote Similarity	NPC77061
0.6923	Remote Similarity	NPC310633
0.6919	Remote Similarity	NPC73687
0.6915	Remote Similarity	NPC136957
0.6915	Remote Similarity	NPC469976
0.6915	Remote Similarity	NPC19696
0.6872	Remote Similarity	NPC63571
0.6857	Remote Similarity	NPC50562
0.685	Remote Similarity	NPC476526
0.685	Remote Similarity	NPC48117
0.685	Remote Similarity	NPC329765
0.6847	Remote Similarity	NPC9635
0.6831	Remote Similarity	NPC142688
0.6825	Remote Similarity	NPC67658
0.6816	Remote Similarity	NPC174281
0.6816	Remote Similarity	NPC475286
0.6761	Remote Similarity	NPC469717
0.6758	Remote Similarity	NPC472260
0.6749	Remote Similarity	NPC477004
0.6735	Remote Similarity	NPC311282
0.6734	Remote Similarity	NPC243716
0.6733	Remote Similarity	NPC262898
0.6683	Remote Similarity	NPC179701
0.6667	Remote Similarity	NPC186068
0.6649	Remote Similarity	NPC74357
0.6648	Remote Similarity	NPC472288
0.6636	Remote Similarity	NPC243633
0.6636	Remote Similarity	NPC175150
0.6634	Remote Similarity	NPC202812
0.6633	Remote Similarity	NPC209917
0.6629	Remote Similarity	NPC291517
0.6602	Remote Similarity	NPC471944
0.6593	Remote Similarity	NPC100726
0.6574	Remote Similarity	NPC168209
0.657	Remote Similarity	NPC469716
0.6566	Remote Similarity	NPC133003
0.6548	Remote Similarity	NPC270834
0.6546	Remote Similarity	NPC476419
0.6531	Remote Similarity	NPC314281
0.6531	Remote Similarity	NPC182940
0.6531	Remote Similarity	NPC40530
0.6528	Remote Similarity	NPC475736
0.652	Remote Similarity	NPC102592
0.652	Remote Similarity	NPC79356
0.6517	Remote Similarity	NPC324091
0.6515	Remote Similarity	NPC470003
0.6505	Remote Similarity	NPC33229
0.6485	Remote Similarity	NPC210123
0.6482	Remote Similarity	NPC474258
0.6477	Remote Similarity	NPC302647
0.6452	Remote Similarity	NPC251391
0.6443	Remote Similarity	NPC288074
0.6439	Remote Similarity	NPC472293
0.6432	Remote Similarity	NPC46895
0.6432	Remote Similarity	NPC473878
0.6432	Remote Similarity	NPC471655
0.6432	Remote Similarity	NPC228835
0.6432	Remote Similarity	NPC477003
0.6425	Remote Similarity	NPC293917
0.6418	Remote Similarity	NPC473946
0.6417	Remote Similarity	NPC209362
0.6413	Remote Similarity	NPC105811
0.641	Remote Similarity	NPC181081
0.641	Remote Similarity	NPC469529
0.6409	Remote Similarity	NPC129412
0.6409	Remote Similarity	NPC58268
0.6409	Remote Similarity	NPC101130
0.6409	Remote Similarity	NPC114033
0.6408	Remote Similarity	NPC78767
0.6408	Remote Similarity	NPC473814
0.6396	Remote Similarity	NPC55772
0.6396	Remote Similarity	NPC11126
0.6396	Remote Similarity	NPC219336
0.6395	Remote Similarity	NPC66642
0.6393	Remote Similarity	NPC467188
0.639	Remote Similarity	NPC93390
0.6382	Remote Similarity	NPC159125
0.6378	Remote Similarity	NPC123906
0.6373	Remote Similarity	NPC472292
0.6372	Remote Similarity	NPC284888
0.6372	Remote Similarity	NPC469715
0.6368	Remote Similarity	NPC476527
0.6368	Remote Similarity	NPC94752
0.6368	Remote Similarity	NPC235684
0.6364	Remote Similarity	NPC61011
0.6364	Remote Similarity	NPC91179
0.6351	Remote Similarity	NPC477043
0.6349	Remote Similarity	NPC213914
0.6346	Remote Similarity	NPC237414
0.6346	Remote Similarity	NPC472296
0.6346	Remote Similarity	NPC192674
0.6346	Remote Similarity	NPC472297
0.6345	Remote Similarity	NPC183662
0.6345	Remote Similarity	NPC15573
0.6345	Remote Similarity	NPC217372
0.6341	Remote Similarity	NPC472210
0.6341	Remote Similarity	NPC269886
0.6341	Remote Similarity	NPC88315
0.6341	Remote Similarity	NPC472295
0.6341	Remote Similarity	NPC247735
0.6341	Remote Similarity	NPC81802
0.6337	Remote Similarity	NPC472323
0.633	Remote Similarity	NPC75135
0.6327	Remote Similarity	NPC63031
0.6324	Remote Similarity	NPC129909
0.6321	Remote Similarity	NPC109447
0.6321	Remote Similarity	NPC82053
0.6321	Remote Similarity	NPC41717
0.6318	Remote Similarity	NPC474195
0.6318	Remote Similarity	NPC295158
0.6313	Remote Similarity	NPC64661
0.6313	Remote Similarity	NPC195704
0.6313	Remote Similarity	NPC14448
0.6313	Remote Similarity	NPC126709
0.6313	Remote Similarity	NPC248041
0.6313	Remote Similarity	NPC167200
0.6313	Remote Similarity	NPC98156
0.6313	Remote Similarity	NPC292434
0.6313	Remote Similarity	NPC283219
0.6313	Remote Similarity	NPC200397
0.6313	Remote Similarity	NPC138596
0.631	Remote Similarity	NPC70406
0.6308	Remote Similarity	NPC478158
0.6308	Remote Similarity	NPC472070
0.6308	Remote Similarity	NPC273532
0.6305	Remote Similarity	NPC175474
0.6302	Remote Similarity	NPC274981
0.63	Remote Similarity	NPC470205
0.6298	Remote Similarity	NPC477041
0.6298	Remote Similarity	NPC477044
0.6296	Remote Similarity	NPC207020
0.6294	Remote Similarity	NPC267885
0.6294	Remote Similarity	NPC151635
0.6291	Remote Similarity	NPC270918
0.6284	Remote Similarity	NPC322064
0.6283	Remote Similarity	NPC470680
0.6283	Remote Similarity	NPC100104
0.6283	Remote Similarity	NPC14288
0.6281	Remote Similarity	NPC477042
0.6281	Remote Similarity	NPC234403
0.628	Remote Similarity	NPC292361
0.6275	Remote Similarity	NPC268966
0.6275	Remote Similarity	NPC154339
0.6274	Remote Similarity	NPC473376
0.6274	Remote Similarity	NPC88115
0.6268	Remote Similarity	NPC474767
0.6263	Remote Similarity	NPC14113
0.6263	Remote Similarity	NPC84827
0.6263	Remote Similarity	NPC83774
0.6263	Remote Similarity	NPC145885
0.6262	Remote Similarity	NPC267343
0.6261	Remote Similarity	NPC478141
0.6257	Remote Similarity	NPC23215
0.6256	Remote Similarity	NPC17059
0.625	Remote Similarity	NPC214142
0.625	Remote Similarity	NPC71236
0.6244	Remote Similarity	NPC469938
0.6244	Remote Similarity	NPC110500
0.6244	Remote Similarity	NPC149155
0.6244	Remote Similarity	NPC476460
0.6244	Remote Similarity	NPC203468
0.6239	Remote Similarity	NPC322135

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 NPC476423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	560
0.2-0.3	1396
0.3-0.4	2650
0.4-0.5	2966
0.5-0.6	1330
0.6-0.7	91
0.7-0.8	3
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
0.7107	Intermediate Similarity	NPD2290	Phase 3
0.7107	Intermediate Similarity	NPD2289	Phase 3
0.7011	Intermediate Similarity	NPD1631	Approved
0.6973	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1573	Approved
0.6952	Remote Similarity	NPD1575	Approved
0.6931	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1096	Discontinued
0.6848	Remote Similarity	NPD1630	Approved
0.6839	Remote Similarity	NPD3178	Discontinued
0.6682	Remote Similarity	NPD6173	Approved
0.6649	Remote Similarity	NPD1587	Approved
0.6635	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD1643	Phase 3
0.6559	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7727	Phase 2
0.6505	Remote Similarity	NPD6248	Phase 2
0.6505	Remote Similarity	NPD6249	Phase 2
0.6495	Remote Similarity	NPD1586	Approved
0.6468	Remote Similarity	NPD4334	Discontinued
0.6462	Remote Similarity	NPD4520	Approved
0.6456	Remote Similarity	NPD7459	Phase 2
0.6452	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD750	Phase 2
0.6442	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7817	Phase 1
0.6432	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4315	Phase 2
0.6364	Remote Similarity	NPD5017	Discontinued
0.6351	Remote Similarity	NPD8115	Approved
0.6351	Remote Similarity	NPD8114	Approved
0.6351	Remote Similarity	NPD3947	Discontinued
0.6346	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD3968	Approved
0.6303	Remote Similarity	NPD5487	Phase 1
0.6301	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.63	Remote Similarity	NPD2095	Phase 2
0.63	Remote Similarity	NPD2092	Phase 2
0.63	Remote Similarity	NPD2094	Phase 2
0.6294	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5809	Phase 3
0.6269	Remote Similarity	NPD2096	Phase 2
0.6269	Remote Similarity	NPD2091	Phase 2
0.6262	Remote Similarity	NPD7232	Discontinued
0.6261	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD482	Approved
0.6244	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7716	Approved
0.6233	Remote Similarity	NPD7717	Approved
0.6227	Remote Similarity	NPD7878	Phase 2
0.6223	Remote Similarity	NPD510	Phase 1
0.622	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3411	Phase 2
0.6215	Remote Similarity	NPD3410	Approved
0.6207	Remote Similarity	NPD5444	Phase 1
0.62	Remote Similarity	NPD5898	Approved
0.62	Remote Similarity	NPD5899	Approved
0.62	Remote Similarity	NPD5897	Approved
0.619	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD721	Approved
0.6184	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6206	Phase 1
0.6168	Remote Similarity	NPD7568	Phase 1
0.6168	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3967	Approved
0.6161	Remote Similarity	NPD2912	Approved
0.6161	Remote Similarity	NPD2911	Approved
0.6157	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4602	Approved
0.6146	Remote Similarity	NPD1657	Approved
0.6143	Remote Similarity	NPD6261	Phase 3
0.6141	Remote Similarity	NPD5020	Approved
0.6139	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD6665	Discontinued
0.6127	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6987	Phase 1
0.6114	Remote Similarity	NPD7308	Discontinued
0.6111	Remote Similarity	NPD6376	Discontinued
0.6111	Remote Similarity	NPD6487	Approved
0.6111	Remote Similarity	NPD6486	Approved
0.6109	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD1996	Discontinued
0.6098	Remote Similarity	NPD4948	Discontinued
0.6093	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD4601	Approved
0.6085	Remote Similarity	NPD4600	Approved
0.6083	Remote Similarity	NPD5834	Phase 3
0.6083	Remote Similarity	NPD5835	Phase 3
0.6077	Remote Similarity	NPD7944	Discontinued
0.6075	Remote Similarity	NPD6176	Phase 1
0.6073	Remote Similarity	NPD7605	Discovery
0.6073	Remote Similarity	NPD5866	Approved
0.607	Remote Similarity	NPD3078	Approved
0.607	Remote Similarity	NPD3076	Approved
0.607	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.607	Remote Similarity	NPD3077	Approved
0.607	Remote Similarity	NPD3079	Approved
0.6059	Remote Similarity	NPD3318	Approved
0.6059	Remote Similarity	NPD3319	Phase 1
0.6059	Remote Similarity	NPD3320	Approved
0.6056	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD5088	Discontinued
0.6047	Remote Similarity	NPD8169	Discontinued
0.6047	Remote Similarity	NPD5901	Discontinued
0.6047	Remote Similarity	NPD3380	Phase 3
0.6047	Remote Similarity	NPD3379	Phase 2
0.6045	Remote Similarity	NPD1781	Discontinued
0.6041	Remote Similarity	NPD2844	Phase 3
0.604	Remote Similarity	NPD3927	Phase 2
0.604	Remote Similarity	NPD3989	Phase 3
0.6039	Remote Similarity	NPD5685	Approved
0.6039	Remote Similarity	NPD5686	Approved
0.603	Remote Similarity	NPD4524	Discontinued
0.6029	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD7187	Phase 2
0.6027	Remote Similarity	NPD6210	Phase 3
0.6019	Remote Similarity	NPD1952	Discontinued
0.6018	Remote Similarity	NPD7970	Approved
0.6018	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1031	Discontinued
0.601	Remote Similarity	NPD3990	Phase 3
0.601	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD5510	Approved
0.6	Remote Similarity	NPD7618	Phase 3
0.6	Remote Similarity	NPD7619	Phase 3
0.6	Remote Similarity	NPD4883	Approved
0.5991	Remote Similarity	NPD3353	Approved
0.5991	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD272	Approved
0.5982	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5505	Discontinued
0.5973	Remote Similarity	NPD8356	Approved
0.5972	Remote Similarity	NPD4848	Phase 1
0.5971	Remote Similarity	NPD3315	Phase 3
0.5971	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4091	Approved
0.5969	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD8289	Discontinued
0.5962	Remote Similarity	NPD3425	Discontinued
0.5961	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5953	Remote Similarity	NPD3774	Approved
0.5953	Remote Similarity	NPD3775	Approved
0.5953	Remote Similarity	NPD3773	Approved
0.5952	Remote Similarity	NPD460	Discontinued
0.5952	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7482	Phase 2
0.5951	Remote Similarity	NPD7483	Phase 2
0.5949	Remote Similarity	NPD2511	Approved
0.5948	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD6752	Phase 1
0.5947	Remote Similarity	NPD6753	Phase 1
0.5946	Remote Similarity	NPD4897	Phase 2
0.5941	Remote Similarity	NPD4092	Approved
0.5933	Remote Similarity	NPD2336	Approved
0.5928	Remote Similarity	NPD7573	Discontinued
0.5928	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3777	Phase 3
0.5924	Remote Similarity	NPD200	Phase 2
0.5924	Remote Similarity	NPD201	Phase 2
0.5917	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD7777	Approved
0.5915	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD53	Approved
0.5915	Remote Similarity	NPD4397	Phase 1
0.5915	Remote Similarity	NPD7778	Approved
0.5913	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7887	Approved
0.5913	Remote Similarity	NPD7888	Approved
0.5907	Remote Similarity	NPD2061	Approved
0.5902	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD8098	Approved
0.5899	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD7853	Phase 2
0.5896	Remote Similarity	NPD6226	Phase 3
0.5895	Remote Similarity	NPD979	Approved
0.5895	Remote Similarity	NPD3263	Phase 3
0.5893	Remote Similarity	NPD6218	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