NPASS Compound

Structure

NPC469717 OpenBabel07101718192D 38 42 0 0 1 0 0 0 0 0999 V2000 -2.5316 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1896 4.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5497 1.8080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9316 2.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6201 0.5392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6361 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8271 1.9890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6018 5.4726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0323 -0.2699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1407 4.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 2.1701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 1.5823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0812 0.0392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0812 1.0392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1896 6.2816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9497 4.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2722 1.6269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 3.4791 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 0.3982 5.4726 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -7.3413 -1.2209 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.2722 -0.5486 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8806 7.2327 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.1555 4.4302 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0323 1.3482 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3587 1.2202 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8452 3.3903 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4343 2.6701 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1407 5.9726 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 3.1701 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 -3.8632 4.7916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3767 2.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 11 1 0 0 0 0 2 9 1 0 0 0 0 2 12 2 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 10 2 0 0 0 0 5 29 1 0 0 0 0 6 13 2 0 0 0 0 6 32 1 0 0 0 0 7 3 1 6 0 0 0 7 8 1 0 0 0 0 8 4 1 1 0 0 0 8 14 1 0 0 0 0 9 18 2 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 16 2 0 0 0 0 11 34 1 0 0 0 0 12 19 1 0 0 0 0 12 33 1 0 0 0 0 13 35 1 0 0 0 0 14 13 1 6 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 36 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 18 33 1 0 0 0 0 19 31 1 0 0 0 0 19 37 2 0 0 0 0 20 30 2 3 0 0 0 20 38 1 0 0 0 0 21 27 2 0 0 0 0 21 32 1 0 0 0 0 21 35 1 0 0 0 0 22 28 2 0 0 0 0 22 34 1 0 0 0 0 22 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	773.87
Volume:	524.604
LogP:	1.152
LogD:	2.555
LogS:	-3.628
# Rotatable Bonds:	9
TPSA:	200.64
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	5.286
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.882
MDCK Permeability:	1.6646466974634677e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	99.21581268310547%
Volume Distribution (VD):	0.633
Pgp-substrate:	4.084418773651123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.018
CYP2C9-inhibitor:	0.679
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	2.388
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.987
Human Hepatotoxicity (H-HT):	0.997
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.641
Carcinogencity:	0.358
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC469717

Natural Product ID:	NPC469717
*Common Name:**	Dibromoageliferin
IUPAC Name:	N-[[(4R,5R,6S)-2-amino-4-(2-amino-1H-imidazol-5-yl)-6-[[(3,4-dibromo-1H-pyrrole-2-carbonyl)amino]methyl]-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl]methyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
Synonyms:	Dibromoageliferin
Standard InCHIKey:	GJJKGKKNMPQKHM-WFEFGEHDSA-N
Standard InCHI:	InChI=1S/C22H22Br4N10O2/c23-9-2-12(33-18(9)26)19(37)31-4-8-7(3-30-20(38)17-15(25)10(24)5-29-17)1-11-16(36-22(28)34-11)14(8)13-6-32-21(27)35-13/h2,5-8,14,29,33H,1,3-4H2,(H,30,38)(H,31,37)(H3,27,32,35)(H3,28,34,36)/t7-,8-,14-/m1/s1
SMILES:	C1C(C(C(C2=C1NC(=N2)N)C3=CN=C(N3)N)CNC(=O)C4=CC(=C(N4)Br)Br)CNC(=O)C5=C(C(=CN5)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162476
PubChem CID:	44584345
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332839]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562840]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19209898]
NPO32675	agelas sp.	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584409]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.08	ug.mL-1	PMID[502050]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.16	ug.mL-1	PMID[502050]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.7	ug.mL-1	PMID[502050]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[502050]

☑ 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 NPC469717 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	806
0.1-0.2	11719
0.2-0.3	20040
0.3-0.4	4927
0.4-0.5	2823
0.5-0.6	1909
0.6-0.7	434
0.7-0.8	24
0.8-0.85	6
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9119	High Similarity	NPC136957
0.9119	High Similarity	NPC19696
0.9016	High Similarity	NPC475286
0.9016	High Similarity	NPC174281
0.886	High Similarity	NPC19342
0.8769	High Similarity	NPC476526
0.8769	High Similarity	NPC48117
0.8769	High Similarity	NPC329765
0.855	High Similarity	NPC9635
0.8549	High Similarity	NPC111566
0.8505	High Similarity	NPC310633
0.848	Intermediate Similarity	NPC476524
0.8359	Intermediate Similarity	NPC63571
0.8265	Intermediate Similarity	NPC476527
0.8213	Intermediate Similarity	NPC476525
0.7789	Intermediate Similarity	NPC184932
0.7789	Intermediate Similarity	NPC472861
0.7704	Intermediate Similarity	NPC54214
0.7639	Intermediate Similarity	NPC66642
0.763	Intermediate Similarity	NPC469716
0.7629	Intermediate Similarity	NPC206148
0.7573	Intermediate Similarity	NPC210123
0.7537	Intermediate Similarity	NPC469814
0.7487	Intermediate Similarity	NPC271927
0.745	Intermediate Similarity	NPC37268
0.7437	Intermediate Similarity	NPC469976
0.7416	Intermediate Similarity	NPC476414
0.7413	Intermediate Similarity	NPC136441
0.74	Intermediate Similarity	NPC80528
0.7389	Intermediate Similarity	NPC40530
0.7389	Intermediate Similarity	NPC314281
0.7368	Intermediate Similarity	NPC476413
0.7325	Intermediate Similarity	NPC156003
0.7309	Intermediate Similarity	NPC475736
0.7286	Intermediate Similarity	NPC474696
0.7273	Intermediate Similarity	NPC476418
0.7273	Intermediate Similarity	NPC73687
0.7264	Intermediate Similarity	NPC28096
0.7264	Intermediate Similarity	NPC476421
0.7264	Intermediate Similarity	NPC227489
0.7192	Intermediate Similarity	NPC97106
0.7178	Intermediate Similarity	NPC226835
0.7129	Intermediate Similarity	NPC46022
0.7129	Intermediate Similarity	NPC112489
0.71	Intermediate Similarity	NPC162268
0.7093	Intermediate Similarity	NPC474195
0.7089	Intermediate Similarity	NPC188821
0.7089	Intermediate Similarity	NPC474180
0.7056	Intermediate Similarity	NPC33229
0.7054	Intermediate Similarity	NPC282247
0.7043	Intermediate Similarity	NPC474196
0.7037	Intermediate Similarity	NPC474389
0.7023	Intermediate Similarity	NPC77061
0.7	Intermediate Similarity	NPC473376
0.7	Intermediate Similarity	NPC473706
0.699	Remote Similarity	NPC52110
0.6987	Remote Similarity	NPC17487
0.6987	Remote Similarity	NPC201831
0.6985	Remote Similarity	NPC475870
0.6978	Remote Similarity	NPC470703
0.6977	Remote Similarity	NPC46811
0.6958	Remote Similarity	NPC477109
0.6958	Remote Similarity	NPC477107
0.6958	Remote Similarity	NPC477108
0.6933	Remote Similarity	NPC470702
0.6933	Remote Similarity	NPC473218
0.6919	Remote Similarity	NPC311282
0.6905	Remote Similarity	NPC270834
0.6889	Remote Similarity	NPC82370
0.6884	Remote Similarity	NPC304187
0.6884	Remote Similarity	NPC477166
0.6883	Remote Similarity	NPC243633
0.6883	Remote Similarity	NPC175150
0.6881	Remote Similarity	NPC171317
0.6877	Remote Similarity	NPC117980
0.6855	Remote Similarity	NPC475746
0.6851	Remote Similarity	NPC69843
0.6849	Remote Similarity	NPC477004
0.6845	Remote Similarity	NPC302647
0.6826	Remote Similarity	NPC168209
0.6816	Remote Similarity	NPC27296
0.6816	Remote Similarity	NPC212742
0.6814	Remote Similarity	NPC320968
0.6812	Remote Similarity	NPC472285
0.681	Remote Similarity	NPC16659
0.6804	Remote Similarity	NPC131887
0.68	Remote Similarity	NPC474236
0.6794	Remote Similarity	NPC240088
0.6794	Remote Similarity	NPC473380
0.6784	Remote Similarity	NPC469715
0.6776	Remote Similarity	NPC17059
0.6762	Remote Similarity	NPC265710
0.6761	Remote Similarity	NPC476423
0.6761	Remote Similarity	NPC471536
0.6758	Remote Similarity	NPC74153
0.6754	Remote Similarity	NPC54744
0.6751	Remote Similarity	NPC470323
0.6744	Remote Similarity	NPC213629
0.6732	Remote Similarity	NPC474383
0.6711	Remote Similarity	NPC471194
0.6711	Remote Similarity	NPC471193
0.6709	Remote Similarity	NPC229893
0.6705	Remote Similarity	NPC77101
0.6701	Remote Similarity	NPC260041
0.67	Remote Similarity	NPC109158
0.6697	Remote Similarity	NPC473821
0.6695	Remote Similarity	NPC474357
0.6667	Remote Similarity	NPC477114
0.6667	Remote Similarity	NPC166209
0.6667	Remote Similarity	NPC13456
0.6667	Remote Similarity	NPC77241
0.6667	Remote Similarity	NPC72956
0.6667	Remote Similarity	NPC269203
0.6653	Remote Similarity	NPC935
0.6653	Remote Similarity	NPC63031
0.6653	Remote Similarity	NPC267078
0.6652	Remote Similarity	NPC50562
0.6652	Remote Similarity	NPC272174
0.6651	Remote Similarity	NPC94752
0.6651	Remote Similarity	NPC473342
0.6651	Remote Similarity	NPC477167
0.665	Remote Similarity	NPC2414
0.6638	Remote Similarity	NPC153980
0.6638	Remote Similarity	NPC6865
0.6637	Remote Similarity	NPC52909
0.6637	Remote Similarity	NPC94211
0.6637	Remote Similarity	NPC475935
0.6636	Remote Similarity	NPC228835
0.6627	Remote Similarity	NPC74619
0.6623	Remote Similarity	NPC471192
0.6623	Remote Similarity	NPC177996
0.6623	Remote Similarity	NPC67658
0.6623	Remote Similarity	NPC147983
0.6622	Remote Similarity	NPC220797
0.6622	Remote Similarity	NPC474318
0.6622	Remote Similarity	NPC153123
0.6622	Remote Similarity	NPC201266
0.6622	Remote Similarity	NPC475914
0.6622	Remote Similarity	NPC268744
0.6617	Remote Similarity	NPC472260
0.6601	Remote Similarity	NPC142688
0.6594	Remote Similarity	NPC54981
0.6592	Remote Similarity	NPC106771
0.6592	Remote Similarity	NPC303820
0.6592	Remote Similarity	NPC205254
0.6592	Remote Similarity	NPC23420
0.659	Remote Similarity	NPC209917
0.6588	Remote Similarity	NPC476419
0.6577	Remote Similarity	NPC321939
0.657	Remote Similarity	NPC233380
0.6564	Remote Similarity	NPC54420
0.6558	Remote Similarity	NPC477003
0.6553	Remote Similarity	NPC474896
0.6552	Remote Similarity	NPC36405
0.6532	Remote Similarity	NPC78767
0.6532	Remote Similarity	NPC473814
0.6532	Remote Similarity	NPC262898
0.653	Remote Similarity	NPC476460
0.6529	Remote Similarity	NPC174489
0.6529	Remote Similarity	NPC475635
0.6528	Remote Similarity	NPC150592
0.6525	Remote Similarity	NPC31097
0.6516	Remote Similarity	NPC93390
0.6515	Remote Similarity	NPC279189
0.6515	Remote Similarity	NPC200553
0.6507	Remote Similarity	NPC107077
0.6507	Remote Similarity	NPC223791
0.6507	Remote Similarity	NPC162860
0.6504	Remote Similarity	NPC171393
0.6504	Remote Similarity	NPC295452
0.6504	Remote Similarity	NPC317701
0.6502	Remote Similarity	NPC162002
0.6502	Remote Similarity	NPC473640
0.6489	Remote Similarity	NPC475506
0.6489	Remote Similarity	NPC300183
0.6489	Remote Similarity	NPC471944
0.6486	Remote Similarity	NPC179701
0.648	Remote Similarity	NPC477630
0.648	Remote Similarity	NPC477635
0.6475	Remote Similarity	NPC26641
0.6473	Remote Similarity	NPC293917
0.6473	Remote Similarity	NPC100321
0.6473	Remote Similarity	NPC253687
0.6463	Remote Similarity	NPC116555
0.6463	Remote Similarity	NPC71238
0.646	Remote Similarity	NPC155143
0.6459	Remote Similarity	NPC49217
0.6457	Remote Similarity	NPC63109
0.6455	Remote Similarity	NPC243716
0.6449	Remote Similarity	NPC11126
0.6446	Remote Similarity	NPC89987
0.6442	Remote Similarity	NPC306160
0.6438	Remote Similarity	NPC473628
0.6429	Remote Similarity	NPC64216
0.6426	Remote Similarity	NPC264285
0.6423	Remote Similarity	NPC37152
0.6417	Remote Similarity	NPC323244
0.6414	Remote Similarity	NPC473317
0.6409	Remote Similarity	NPC83111
0.6409	Remote Similarity	NPC475874

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 NPC469717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	902
0.2-0.3	1325
0.3-0.4	2586
0.4-0.5	2083
0.5-0.6	1642
0.6-0.7	270
0.7-0.8	8
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
0.7358	Intermediate Similarity	NPD7459	Phase 2
0.7184	Intermediate Similarity	NPD3178	Discontinued
0.7033	Intermediate Similarity	NPD1096	Discontinued
0.7014	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2289	Phase 3
0.6866	Remote Similarity	NPD2290	Phase 3
0.6784	Remote Similarity	NPD3917	Approved
0.6784	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3918	Approved
0.6781	Remote Similarity	NPD6753	Phase 1
0.6781	Remote Similarity	NPD6752	Phase 1
0.674	Remote Similarity	NPD3915	Approved
0.6729	Remote Similarity	NPD706	Phase 1
0.6725	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7970	Approved
0.6712	Remote Similarity	NPD5017	Discontinued
0.6695	Remote Similarity	NPD6165	Phase 2
0.6695	Remote Similarity	NPD6164	Phase 2
0.6667	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3353	Approved
0.6623	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2813	Phase 3
0.6595	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1996	Discontinued
0.6522	Remote Similarity	NPD7470	Discontinued
0.6507	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3411	Phase 2
0.6491	Remote Similarity	NPD3410	Approved
0.6485	Remote Similarity	NPD8292	Phase 2
0.6484	Remote Similarity	NPD5686	Approved
0.6484	Remote Similarity	NPD5685	Approved
0.6473	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD460	Discontinued
0.6463	Remote Similarity	NPD2443	Approved
0.6463	Remote Similarity	NPD2442	Approved
0.6452	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD1600	Suspended
0.6435	Remote Similarity	NPD3968	Approved
0.6429	Remote Similarity	NPD6829	Phase 2
0.6426	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2127	Suspended
0.6419	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5426	Phase 3
0.6404	Remote Similarity	NPD5901	Discontinued
0.64	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6999	Discontinued
0.6382	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD2008	Discontinued
0.6368	Remote Similarity	NPD2547	Discontinued
0.636	Remote Similarity	NPD2803	Discontinued
0.6356	Remote Similarity	NPD1623	Approved
0.6351	Remote Similarity	NPD6665	Discontinued
0.6348	Remote Similarity	NPD1506	Discontinued
0.6339	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD5198	Approved
0.6329	Remote Similarity	NPD5199	Approved
0.6325	Remote Similarity	NPD8094	Discontinued
0.6323	Remote Similarity	NPD1173	Approved
0.632	Remote Similarity	NPD7666	Phase 3
0.632	Remote Similarity	NPD7665	Phase 2
0.6318	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD8256	Approved
0.6314	Remote Similarity	NPD5643	Phase 2
0.6314	Remote Similarity	NPD8257	Approved
0.6314	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4558	Phase 2
0.6304	Remote Similarity	NPD7001	Phase 3
0.6304	Remote Similarity	NPD3967	Approved
0.6293	Remote Similarity	NPD2408	Discontinued
0.6293	Remote Similarity	NPD5510	Approved
0.6292	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6458	Discontinued
0.6283	Remote Similarity	NPD1982	Phase 1
0.6282	Remote Similarity	NPD8097	Phase 3
0.6282	Remote Similarity	NPD2411	Approved
0.6282	Remote Similarity	NPD8096	Phase 3
0.6282	Remote Similarity	NPD8093	Discontinued
0.6278	Remote Similarity	NPD3406	Suspended
0.6272	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8106	Phase 2
0.6266	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8349	Phase 1
0.6256	Remote Similarity	NPD2405	Phase 3
0.6244	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7603	Discontinued
0.624	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.624	Remote Similarity	NPD8289	Discontinued
0.6233	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7717	Approved
0.6224	Remote Similarity	NPD7716	Approved
0.6222	Remote Similarity	NPD7619	Phase 3
0.6222	Remote Similarity	NPD7618	Phase 3
0.622	Remote Similarity	NPD7415	Suspended
0.6213	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4376	Phase 3
0.6202	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD6970	Phase 2
0.619	Remote Similarity	NPD8169	Discontinued
0.619	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8098	Approved
0.619	Remote Similarity	NPD8272	Phase 2
0.6189	Remote Similarity	NPD1571	Phase 2
0.6188	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6210	Phase 3
0.6167	Remote Similarity	NPD6664	Approved
0.6167	Remote Similarity	NPD2880	Discontinued
0.6157	Remote Similarity	NPD482	Approved
0.6157	Remote Similarity	NPD4883	Approved
0.6157	Remote Similarity	NPD5065	Approved
0.6157	Remote Similarity	NPD6173	Approved
0.6154	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6137	Remote Similarity	NPD796	Phase 2
0.6136	Remote Similarity	NPD2092	Phase 2
0.6136	Remote Similarity	NPD2095	Phase 2
0.6136	Remote Similarity	NPD2094	Phase 2
0.6136	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5138	Approved
0.6132	Remote Similarity	NPD5140	Approved
0.613	Remote Similarity	NPD7817	Phase 1
0.6129	Remote Similarity	NPD2367	Phase 2
0.6129	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD7168	Phase 3
0.6119	Remote Similarity	NPD6595	Phase 3
0.6113	Remote Similarity	NPD1572	Phase 2
0.6111	Remote Similarity	NPD6376	Discontinued
0.6111	Remote Similarity	NPD4612	Discontinued
0.6111	Remote Similarity	NPD2509	Approved
0.6111	Remote Similarity	NPD4960	Approved
0.6111	Remote Similarity	NPD2510	Approved
0.6111	Remote Similarity	NPD4959	Approved
0.6109	Remote Similarity	NPD2096	Phase 2
0.6109	Remote Similarity	NPD2091	Phase 2
0.6109	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7711	Discontinued
0.6107	Remote Similarity	NPD5461	Discontinued
0.6103	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5827	Discontinued
0.6099	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3961	Discontinued
0.6096	Remote Similarity	NPD5446	Phase 2
0.6094	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6849	Phase 2
0.6091	Remote Similarity	NPD6850	Phase 2
0.6087	Remote Similarity	NPD484	Approved
0.6083	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6470	Phase 3
0.6081	Remote Similarity	NPD6557	Phase 2
0.6079	Remote Similarity	NPD4998	Phase 3
0.6079	Remote Similarity	NPD5853	Phase 3
0.6079	Remote Similarity	NPD5855	Phase 3
0.6079	Remote Similarity	NPD4999	Phase 3
0.6076	Remote Similarity	NPD4852	Phase 2
0.6073	Remote Similarity	NPD5935	Discontinued
0.6071	Remote Similarity	NPD6715	Discontinued
0.607	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.607	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD7781	Approved
0.6057	Remote Similarity	NPD7780	Approved
0.6054	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD3947	Discontinued
0.6052	Remote Similarity	NPD944	Approved
0.6048	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD3439	Approved
0.6044	Remote Similarity	NPD1043	Phase 3
0.6043	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD6459	Phase 2
0.6043	Remote Similarity	NPD5854	Approved
0.6034	Remote Similarity	NPD6268	Phase 1
0.6034	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD1659	Phase 1
0.6031	Remote Similarity	NPD5116	Phase 1
0.6027	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6545	Clinical (unspecified phase)

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