NPASS Compound

Structure

NPC476413 OpenBabel07101719122D 28 29 0 0 1 0 0 0 0 0999 V2000 9.4668 1.6317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6974 2.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9482 1.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6456 1.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 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 7.9969 3.7612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9141 4.1596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0923 2.7658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5764 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3430 2.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4621 2.6189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8664 2.8866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.1310 5.1358 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 10.5718 3.5058 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.9796 3.3487 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3949 2.4212 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7615 3.3324 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0138 1.8975 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.0685 2.5489 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5420 1.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4512 2.7662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 1 0 0 0 0 4 18 1 0 0 0 0 5 6 1 0 0 0 0 5 19 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 25 28 1 0 0 0 0 26 28 2 0 0 0 0 27 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	541.96
Volume:	387.413
LogP:	-1.512
LogD:	-0.065
LogS:	-1.809
# Rotatable Bonds:	10
TPSA:	167.91
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	4.049
Fsp3:	0.5
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:	-5.907
MDCK Permeability:	1.3174301784601994e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.968
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	64.87451934814453%
Volume Distribution (VD):	1.365
Pgp-substrate:	50.09191131591797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.609
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.541

ADMET: Excretion

Clearance (CL):	2.548
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.14
Skin Sensitization:	0.134
Carcinogencity:	0.29
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.869

Download Data

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

Natural Product: NPC476413

Natural Product ID:	NPC476413
*Common Name:**	Mauritamide B
IUPAC Name:	2-[[2-amino-4-[3-[(4,5-dibromo-1-methylpyrrole-2-carbonyl)amino]propyl]-5-oxo-1H-imidazol-4-yl]amino]ethanesulfonic acid
Synonyms:
Standard InCHIKey:	SHVQFZJGPQSLPO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H20Br2N6O5S/c1-22-9(7-8(15)10(22)16)11(23)18-4-2-3-14(12(24)20-13(17)21-14)19-5-6-28(25,26)27/h7,19H,2-6H2,1H3,(H,18,23)(H,25,26,27)(H3,17,20,21,24)
SMILES:	CN1C(=CC(=C1Br)Br)C(=O)NCCCC2(C(=O)NC(=N2)N)NCCS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598106
PubChem CID:	46232062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino 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	=	92.5	%	PMID[518313]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	37000.0	nM	PMID[518313]

☑ 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 NPC476413 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	976
0.1-0.2	16091
0.2-0.3	17900
0.3-0.4	3181
0.4-0.5	3352
0.5-0.6	1072
0.6-0.7	79
0.7-0.8	38
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC476414
0.8765	High Similarity	NPC306160
0.8547	High Similarity	NPC476418
0.8398	Intermediate Similarity	NPC469814
0.8315	Intermediate Similarity	NPC97106
0.8272	Intermediate Similarity	NPC469716
0.8167	Intermediate Similarity	NPC136441
0.8125	Intermediate Similarity	NPC206148
0.8011	Intermediate Similarity	NPC112489
0.8	Intermediate Similarity	NPC227489
0.8	Intermediate Similarity	NPC476421
0.8	Intermediate Similarity	NPC46811
0.8	Intermediate Similarity	NPC226835
0.8	Intermediate Similarity	NPC27296
0.8	Intermediate Similarity	NPC28096
0.7914	Intermediate Similarity	NPC46022
0.7901	Intermediate Similarity	NPC54214
0.7857	Intermediate Similarity	NPC80528
0.7784	Intermediate Similarity	NPC474236
0.7701	Intermediate Similarity	NPC184932
0.7701	Intermediate Similarity	NPC472861
0.768	Intermediate Similarity	NPC474383
0.7632	Intermediate Similarity	NPC111566
0.7632	Intermediate Similarity	NPC63571
0.7592	Intermediate Similarity	NPC310633
0.7576	Intermediate Similarity	NPC9635
0.7527	Intermediate Similarity	NPC73687
0.7525	Intermediate Similarity	NPC476524
0.7487	Intermediate Similarity	NPC476423
0.7398	Intermediate Similarity	NPC19342
0.7386	Intermediate Similarity	NPC260041
0.738	Intermediate Similarity	NPC271927
0.7368	Intermediate Similarity	NPC469717
0.7353	Intermediate Similarity	NPC476525
0.734	Intermediate Similarity	NPC37268
0.7322	Intermediate Similarity	NPC473706
0.73	Intermediate Similarity	NPC136957
0.73	Intermediate Similarity	NPC19696
0.7277	Intermediate Similarity	NPC40530
0.7277	Intermediate Similarity	NPC314281
0.7236	Intermediate Similarity	NPC48117
0.7236	Intermediate Similarity	NPC476526
0.7236	Intermediate Similarity	NPC329765
0.7234	Intermediate Similarity	NPC469976
0.72	Intermediate Similarity	NPC475286
0.72	Intermediate Similarity	NPC174281
0.7182	Intermediate Similarity	NPC109158
0.7166	Intermediate Similarity	NPC474696
0.7121	Intermediate Similarity	NPC210123
0.711	Intermediate Similarity	NPC150592
0.6954	Remote Similarity	NPC20021
0.6848	Remote Similarity	NPC52110
0.6828	Remote Similarity	NPC298288
0.6768	Remote Similarity	NPC270834
0.6754	Remote Similarity	NPC2414
0.675	Remote Similarity	NPC476527
0.6652	Remote Similarity	NPC66642
0.6651	Remote Similarity	NPC469715
0.6614	Remote Similarity	NPC142688
0.6575	Remote Similarity	NPC475736
0.6429	Remote Similarity	NPC472288
0.6394	Remote Similarity	NPC474180
0.6394	Remote Similarity	NPC188821
0.6377	Remote Similarity	NPC243716
0.6368	Remote Similarity	NPC472260
0.6368	Remote Similarity	NPC474195
0.6351	Remote Similarity	NPC474389
0.6333	Remote Similarity	NPC77061
0.6326	Remote Similarity	NPC473376
0.6302	Remote Similarity	NPC33229
0.6301	Remote Similarity	NPC263117
0.6301	Remote Similarity	NPC242872
0.6301	Remote Similarity	NPC125181
0.6256	Remote Similarity	NPC474196
0.6188	Remote Similarity	NPC476419
0.6162	Remote Similarity	NPC233380
0.6143	Remote Similarity	NPC50562
0.6141	Remote Similarity	NPC291517
0.6126	Remote Similarity	NPC321939
0.6116	Remote Similarity	NPC67658
0.6099	Remote Similarity	NPC54744
0.6098	Remote Similarity	NPC91179
0.6081	Remote Similarity	NPC320968
0.6078	Remote Similarity	NPC240088
0.6078	Remote Similarity	NPC473380
0.6075	Remote Similarity	NPC262898
0.607	Remote Similarity	NPC476817
0.6054	Remote Similarity	NPC471193
0.6054	Remote Similarity	NPC75726
0.6054	Remote Similarity	NPC110602
0.6054	Remote Similarity	NPC6865
0.6054	Remote Similarity	NPC23215
0.6054	Remote Similarity	NPC153980
0.6054	Remote Similarity	NPC471194
0.6054	Remote Similarity	NPC31385
0.6049	Remote Similarity	NPC265710
0.6048	Remote Similarity	NPC213629
0.6047	Remote Similarity	NPC171317
0.6044	Remote Similarity	NPC71236
0.6034	Remote Similarity	NPC156003
0.603	Remote Similarity	NPC162268
0.6028	Remote Similarity	NPC179701
0.6019	Remote Similarity	NPC477004
0.6019	Remote Similarity	NPC16659
0.601	Remote Similarity	NPC288074
0.601	Remote Similarity	NPC13432
0.6009	Remote Similarity	NPC72956
0.6	Remote Similarity	NPC17059
0.5962	Remote Similarity	NPC477167
0.5962	Remote Similarity	NPC473342
0.5962	Remote Similarity	NPC304187
0.5962	Remote Similarity	NPC477166
0.5957	Remote Similarity	NPC175150
0.5957	Remote Similarity	NPC243633
0.5952	Remote Similarity	NPC94752
0.5946	Remote Similarity	NPC71238
0.5936	Remote Similarity	NPC64661
0.5936	Remote Similarity	NPC98156
0.5936	Remote Similarity	NPC167200
0.5936	Remote Similarity	NPC14448
0.5936	Remote Similarity	NPC195704
0.5936	Remote Similarity	NPC200397
0.5936	Remote Similarity	NPC292434
0.5936	Remote Similarity	NPC138596
0.5933	Remote Similarity	NPC228835
0.5928	Remote Similarity	NPC471191
0.5909	Remote Similarity	NPC475870
0.5905	Remote Similarity	NPC133003
0.5903	Remote Similarity	NPC471192
0.5903	Remote Similarity	NPC147983
0.5903	Remote Similarity	NPC177996
0.59	Remote Similarity	NPC253687
0.5895	Remote Similarity	NPC168209
0.5894	Remote Similarity	NPC11126
0.5892	Remote Similarity	NPC17487
0.5892	Remote Similarity	NPC201831
0.5891	Remote Similarity	NPC109447
0.589	Remote Similarity	NPC98864
0.5885	Remote Similarity	NPC470703
0.5872	Remote Similarity	NPC69843
0.5868	Remote Similarity	NPC477107
0.5868	Remote Similarity	NPC477108
0.5868	Remote Similarity	NPC477109
0.5867	Remote Similarity	NPC54981
0.5862	Remote Similarity	NPC64216
0.5841	Remote Similarity	NPC470702
0.5841	Remote Similarity	NPC473218
0.5833	Remote Similarity	NPC294693
0.5826	Remote Similarity	NPC248782
0.5825	Remote Similarity	NPC186068
0.5825	Remote Similarity	NPC469529
0.5823	Remote Similarity	NPC165743
0.5822	Remote Similarity	NPC209917
0.5812	Remote Similarity	NPC12831
0.5812	Remote Similarity	NPC59839
0.5812	Remote Similarity	NPC74928
0.5812	Remote Similarity	NPC129753
0.5812	Remote Similarity	NPC302717
0.5812	Remote Similarity	NPC209281
0.5812	Remote Similarity	NPC3698
0.5812	Remote Similarity	NPC77582
0.5812	Remote Similarity	NPC48171
0.5812	Remote Similarity	NPC244087
0.5812	Remote Similarity	NPC205604
0.5812	Remote Similarity	NPC169308
0.5812	Remote Similarity	NPC97230
0.5812	Remote Similarity	NPC286529
0.5811	Remote Similarity	NPC88115
0.581	Remote Similarity	NPC159125
0.5799	Remote Similarity	NPC293917
0.5798	Remote Similarity	NPC63279
0.5794	Remote Similarity	NPC268966
0.5781	Remote Similarity	NPC475969
0.5781	Remote Similarity	NPC101130
0.5781	Remote Similarity	NPC114033
0.5781	Remote Similarity	NPC129412
0.5781	Remote Similarity	NPC475859
0.5781	Remote Similarity	NPC58268
0.5781	Remote Similarity	NPC474877
0.5779	Remote Similarity	NPC74357
0.5777	Remote Similarity	NPC64055
0.5774	Remote Similarity	NPC297642
0.5769	Remote Similarity	NPC14849
0.5769	Remote Similarity	NPC19170
0.5764	Remote Similarity	NPC470732
0.5764	Remote Similarity	NPC470731
0.5759	Remote Similarity	NPC54420
0.5755	Remote Similarity	NPC311282
0.5753	Remote Similarity	NPC473640
0.5751	Remote Similarity	NPC327095
0.5751	Remote Similarity	NPC312942
0.575	Remote Similarity	NPC212742
0.5749	Remote Similarity	NPC478030
0.5747	Remote Similarity	NPC475506
0.5746	Remote Similarity	NPC282247
0.5742	Remote Similarity	NPC219336
0.5738	Remote Similarity	NPC470729
0.5738	Remote Similarity	NPC470730
0.5738	Remote Similarity	NPC477176
0.5738	Remote Similarity	NPC477175

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 NPC476413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1058
0.2-0.3	1739
0.3-0.4	2367
0.4-0.5	2924
0.5-0.6	819
0.6-0.7	21
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
0.6995	Remote Similarity	NPD7459	Phase 2
0.657	Remote Similarity	NPD2290	Phase 3
0.657	Remote Similarity	NPD2289	Phase 3
0.6476	Remote Similarity	NPD2405	Phase 3
0.6462	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5686	Approved
0.6408	Remote Similarity	NPD5685	Approved
0.6404	Remote Similarity	NPD1096	Discontinued
0.6364	Remote Similarity	NPD7970	Approved
0.6364	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8169	Discontinued
0.6219	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5017	Discontinued
0.6186	Remote Similarity	NPD7817	Phase 1
0.6183	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD5199	Approved
0.6178	Remote Similarity	NPD5198	Approved
0.6161	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6173	Approved
0.6111	Remote Similarity	NPD4962	Approved
0.6111	Remote Similarity	NPD4963	Approved
0.6091	Remote Similarity	NPD4959	Approved
0.6091	Remote Similarity	NPD4960	Approved
0.6068	Remote Similarity	NPD3178	Discontinued
0.6065	Remote Similarity	NPD4961	Approved
0.6063	Remote Similarity	NPD3968	Approved
0.6052	Remote Similarity	NPD5935	Discontinued
0.6045	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD953	Approved
0.5973	Remote Similarity	NPD3410	Approved
0.5973	Remote Similarity	NPD3411	Phase 2
0.5965	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1745	Approved
0.5955	Remote Similarity	NPD8272	Phase 2
0.5936	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD3967	Approved
0.5928	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD1623	Approved
0.592	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD3856	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD3353	Approved
0.5902	Remote Similarity	NPD1031	Discontinued
0.5901	Remote Similarity	NPD4415	Approved
0.589	Remote Similarity	NPD3891	Phase 2
0.589	Remote Similarity	NPD3890	Phase 2
0.589	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5643	Phase 2
0.5877	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3292	Discontinued
0.5874	Remote Similarity	NPD2443	Approved
0.5874	Remote Similarity	NPD7232	Discontinued
0.5874	Remote Similarity	NPD2442	Approved
0.587	Remote Similarity	NPD6210	Phase 3
0.5867	Remote Similarity	NPD510	Phase 1
0.5865	Remote Similarity	NPD3989	Phase 3
0.5862	Remote Similarity	NPD7717	Approved
0.5862	Remote Similarity	NPD7716	Approved
0.586	Remote Similarity	NPD460	Discontinued
0.5848	Remote Similarity	NPD1600	Suspended
0.5837	Remote Similarity	NPD3990	Phase 3
0.5833	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7727	Phase 2
0.5811	Remote Similarity	NPD8115	Approved
0.5811	Remote Similarity	NPD8114	Approved
0.5806	Remote Similarity	NPD7027	Phase 3
0.5799	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD4091	Approved
0.5792	Remote Similarity	NPD1631	Approved
0.5789	Remote Similarity	NPD2547	Discontinued
0.5785	Remote Similarity	NPD7568	Phase 1
0.5785	Remote Similarity	NPD4904	Approved
0.5783	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.578	Remote Similarity	NPD1952	Discontinued
0.5778	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5510	Approved
0.5772	Remote Similarity	NPD4887	Discontinued
0.5769	Remote Similarity	NPD4092	Approved
0.5767	Remote Similarity	NPD1658	Discontinued
0.5756	Remote Similarity	NPD1573	Approved
0.5756	Remote Similarity	NPD1575	Approved
0.5745	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5744	Remote Similarity	NPD2893	Phase 3
0.5741	Remote Similarity	NPD981	Phase 2
0.574	Remote Similarity	NPD4906	Approved
0.574	Remote Similarity	NPD4905	Approved
0.574	Remote Similarity	NPD2130	Discontinued
0.574	Remote Similarity	NPD4903	Approved
0.5735	Remote Similarity	NPD2137	Approved
0.5735	Remote Similarity	NPD2138	Approved
0.5733	Remote Similarity	NPD6487	Approved
0.5733	Remote Similarity	NPD6486	Approved
0.5727	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6752	Phase 1
0.5726	Remote Similarity	NPD6753	Phase 1
0.5721	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD2367	Phase 2
0.572	Remote Similarity	NPD6164	Phase 2
0.572	Remote Similarity	NPD6165	Phase 2
0.5714	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5709	Remote Similarity	NPD5461	Discontinued
0.5708	Remote Similarity	NPD1174	Phase 2
0.5708	Remote Similarity	NPD2408	Discontinued
0.5701	Remote Similarity	NPD2911	Approved
0.5701	Remote Similarity	NPD2912	Approved
0.57	Remote Similarity	NPD750	Phase 2
0.57	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD3993	Approved
0.5694	Remote Similarity	NPD3992	Approved
0.5694	Remote Similarity	NPD3996	Approved
0.5694	Remote Similarity	NPD3991	Approved
0.5694	Remote Similarity	NPD3995	Approved
0.5694	Remote Similarity	NPD2892	Phase 1
0.5694	Remote Similarity	NPD3994	Approved
0.5694	Remote Similarity	NPD3517	Clinical (unspecified phase)
0.5689	Remote Similarity	NPD1506	Discontinued
0.5681	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD2847	Phase 2
0.5676	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD1657	Approved
0.5673	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD3522	Approved
0.5667	Remote Similarity	NPD3997	Approved
0.5667	Remote Similarity	NPD3999	Approved
0.5667	Remote Similarity	NPD3998	Approved
0.5665	Remote Similarity	NPD6579	Phase 2
0.5659	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD438	Approved
0.5659	Remote Similarity	NPD439	Approved
0.5658	Remote Similarity	NPD3915	Approved
0.5657	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD1630	Approved
0.5644	Remote Similarity	NPD2008	Discontinued
0.564	Remote Similarity	NPD1643	Phase 3
0.5639	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD721	Approved
0.5633	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD3918	Approved
0.5633	Remote Similarity	NPD3917	Approved
0.563	Remote Similarity	NPD7887	Approved
0.563	Remote Similarity	NPD7888	Approved
0.563	Remote Similarity	NPD1571	Phase 2
0.5628	Remote Similarity	NPD2180	Approved
0.5628	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5840	Discontinued
0.5614	Remote Similarity	NPD8261	Discontinued
0.5612	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.5611	Remote Similarity	NPD4364	Phase 1
0.5611	Remote Similarity	NPD4397	Phase 1
0.5609	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD2813	Phase 3
0.5603	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD1250	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD207	Discontinued
0.56	Remote Similarity	NPD3380	Phase 3
0.56	Remote Similarity	NPD3379	Phase 2
0.56	Remote Similarity	NPD6288	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