NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.87
Volume:	163.011
LogP:	2.542
LogD:	2.623
LogS:	-3.347
# Rotatable Bonds:	2
TPSA:	42.09
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	2.717
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	1.821250953071285e-05
Pgp-inhibitor:	0.239
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	94.542724609375%
Volume Distribution (VD):	0.6
Pgp-substrate:	14.16892147064209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.547
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.683
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.68
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	3.621
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.652
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.285
Skin Sensitization:	0.274
Carcinogencity:	0.795
Eye Corrosion:	0.158
Eye Irritation:	0.989
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC142688

Natural Product ID:	NPC142688
*Common Name:**	Methyl 4,5-Dibromo-1H-Pyrrole-2-Carboxylate
IUPAC Name:	methyl 4,5-dibromo-1H-pyrrole-2-carboxylate
Synonyms:
Standard InCHIKey:	ISQWCRSAYRXYRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H5Br2NO2/c1-11-6(10)4-2-3(7)5(8)9-4/h2,9H,1H3
SMILES:	COC(=O)c1[nH]c(c(c1)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL391386
PubChem CID:	324097
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002554] Pyrrole carboxylic 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
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[11170659]
NPO27012	Laurencia pannosa	Species	Rhodomelaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[11374951]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502329]
NPO27072	Monochaetum vulcanicum	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165161]
NPO40426	Agelas oroides enoyl	Strain	Agelasidae	Eukaryota	Tubers	n.a.	n.a.	PMID[17765547]
NPO17223	Agelas oroides	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32072810]
NPO27725	Artemisia vestita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27725	Artemisia vestita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27773	Rhododendron ovatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27725	Artemisia vestita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27012	Laurencia pannosa	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22488	Leptosphaeria oraemaris	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27569	Archangelica officinalis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27648	Cereus aethiops	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27688	Aeonium goochiae	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27707	Soja hispida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20208	Rhinogobius brunneus	Species	Gobiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17223	Agelas oroides	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16500	Byssochlamys spectabilis	Species	Thermoascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27072	Monochaetum vulcanicum	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27773	Rhododendron ovatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27262	Dryopteris inaequalis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27191	Schistochila appendiculata	Species	Schistochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27725	Artemisia vestita	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7497	Guatteria blepharophylla	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27740	Alcantara ekmaniana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26895	Baccharis bigelovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11140	Coprinopsis cinerea	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1333	Individual Protein	Enoyl-acyl-carrier protein reductase	Plasmodium falciparum	IC50	>	100.0	ug.mL-1	PMID[533702]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90.0	ug.mL-1	PMID[533702]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50.0	ug.mL-1	PMID[533702]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	13.3	ug.mL-1	PMID[533702]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	30.0	ug.mL-1	PMID[533702]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30.0	ug.mL-1	PMID[533702]

☑ 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 NPC142688 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	1102
0.1-0.2	10953
0.2-0.3	16287
0.3-0.4	9644
0.4-0.5	2858
0.5-0.6	1617
0.6-0.7	201
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC52110
0.9133	High Similarity	NPC298288
0.8506	High Similarity	NPC109158
0.8121	Intermediate Similarity	NPC150592
0.8065	Intermediate Similarity	NPC260041
0.7933	Intermediate Similarity	NPC20021
0.791	Intermediate Similarity	NPC77061
0.7826	Intermediate Similarity	NPC33229
0.7799	Intermediate Similarity	NPC13432
0.7515	Intermediate Similarity	NPC27296
0.7394	Intermediate Similarity	NPC474236
0.7384	Intermediate Similarity	NPC80528
0.7193	Intermediate Similarity	NPC474383
0.7081	Intermediate Similarity	NPC85443
0.7035	Intermediate Similarity	NPC206148
0.7011	Intermediate Similarity	NPC470894
0.7	Intermediate Similarity	NPC195704
0.7	Intermediate Similarity	NPC64661
0.7	Intermediate Similarity	NPC200397
0.7	Intermediate Similarity	NPC292434
0.7	Intermediate Similarity	NPC98156
0.7	Intermediate Similarity	NPC138596
0.7	Intermediate Similarity	NPC14448
0.7	Intermediate Similarity	NPC167200
0.6982	Remote Similarity	NPC75135
0.6937	Remote Similarity	NPC23215
0.6937	Remote Similarity	NPC291517
0.6936	Remote Similarity	NPC306160
0.6936	Remote Similarity	NPC476418
0.6927	Remote Similarity	NPC132539
0.6919	Remote Similarity	NPC473706
0.6897	Remote Similarity	NPC2414
0.6891	Remote Similarity	NPC82053
0.6885	Remote Similarity	NPC160381
0.6869	Remote Similarity	NPC50562
0.6854	Remote Similarity	NPC37268
0.6834	Remote Similarity	NPC67658
0.6831	Remote Similarity	NPC476423
0.6826	Remote Similarity	NPC302159
0.6788	Remote Similarity	NPC101130
0.6788	Remote Similarity	NPC114033
0.6788	Remote Similarity	NPC129412
0.6788	Remote Similarity	NPC58268
0.6776	Remote Similarity	NPC469814
0.6769	Remote Similarity	NPC321428
0.6758	Remote Similarity	NPC472861
0.6758	Remote Similarity	NPC184932
0.6727	Remote Similarity	NPC129753
0.6727	Remote Similarity	NPC169308
0.6727	Remote Similarity	NPC205604
0.6727	Remote Similarity	NPC286529
0.6727	Remote Similarity	NPC302717
0.6727	Remote Similarity	NPC209281
0.6727	Remote Similarity	NPC244087
0.6727	Remote Similarity	NPC59839
0.6727	Remote Similarity	NPC74928
0.6727	Remote Similarity	NPC3698
0.6727	Remote Similarity	NPC12831
0.6727	Remote Similarity	NPC97230
0.6727	Remote Similarity	NPC48171
0.6727	Remote Similarity	NPC77582
0.6683	Remote Similarity	NPC118940
0.665	Remote Similarity	NPC89508
0.6649	Remote Similarity	NPC141454
0.6648	Remote Similarity	NPC226835
0.6648	Remote Similarity	NPC54214
0.6614	Remote Similarity	NPC476413
0.6601	Remote Similarity	NPC469717
0.6588	Remote Similarity	NPC112741
0.6579	Remote Similarity	NPC476414
0.6575	Remote Similarity	NPC97106
0.6573	Remote Similarity	NPC474696
0.6566	Remote Similarity	NPC266249
0.6561	Remote Similarity	NPC138370
0.6557	Remote Similarity	NPC233050
0.6557	Remote Similarity	NPC276540
0.6556	Remote Similarity	NPC28096
0.6556	Remote Similarity	NPC302647
0.6556	Remote Similarity	NPC227489
0.6556	Remote Similarity	NPC476421
0.6553	Remote Similarity	NPC175150
0.6553	Remote Similarity	NPC243633
0.6552	Remote Similarity	NPC312645
0.6538	Remote Similarity	NPC136441
0.6538	Remote Similarity	NPC286195
0.6535	Remote Similarity	NPC477979
0.6531	Remote Similarity	NPC165599
0.6524	Remote Similarity	NPC111566
0.6524	Remote Similarity	NPC112489
0.6524	Remote Similarity	NPC63571
0.6522	Remote Similarity	NPC71236
0.6508	Remote Similarity	NPC469489
0.6502	Remote Similarity	NPC36405
0.65	Remote Similarity	NPC123839
0.6489	Remote Similarity	NPC310633
0.6488	Remote Similarity	NPC168209
0.6486	Remote Similarity	NPC275292
0.6486	Remote Similarity	NPC243381
0.6482	Remote Similarity	NPC476525
0.648	Remote Similarity	NPC470509
0.6461	Remote Similarity	NPC73687
0.6441	Remote Similarity	NPC322644
0.6437	Remote Similarity	NPC107287
0.6436	Remote Similarity	NPC46022
0.6429	Remote Similarity	NPC271927
0.6429	Remote Similarity	NPC9635
0.641	Remote Similarity	NPC103361
0.6406	Remote Similarity	NPC88315
0.6404	Remote Similarity	NPC39500
0.639	Remote Similarity	NPC223189
0.6389	Remote Similarity	NPC41717
0.6374	Remote Similarity	NPC273532
0.6373	Remote Similarity	NPC135950
0.6373	Remote Similarity	NPC46811
0.6359	Remote Similarity	NPC476419
0.635	Remote Similarity	NPC244741
0.6347	Remote Similarity	NPC472288
0.6332	Remote Similarity	NPC473239
0.6321	Remote Similarity	NPC19342
0.6304	Remote Similarity	NPC186068
0.63	Remote Similarity	NPC300156
0.6296	Remote Similarity	NPC311282
0.6293	Remote Similarity	NPC118228
0.6284	Remote Similarity	NPC249614
0.6283	Remote Similarity	NPC221873
0.628	Remote Similarity	NPC174576
0.628	Remote Similarity	NPC184408
0.6271	Remote Similarity	NPC169586
0.6269	Remote Similarity	NPC4687
0.6256	Remote Similarity	NPC179701
0.625	Remote Similarity	NPC83111
0.625	Remote Similarity	NPC312860
0.6244	Remote Similarity	NPC123395
0.6238	Remote Similarity	NPC476524
0.6238	Remote Similarity	NPC39679
0.6237	Remote Similarity	NPC230403
0.6225	Remote Similarity	NPC187501
0.6224	Remote Similarity	NPC262898
0.6221	Remote Similarity	NPC230085
0.6221	Remote Similarity	NPC159630
0.6211	Remote Similarity	NPC474258
0.6207	Remote Similarity	NPC325297
0.6198	Remote Similarity	NPC209917
0.6197	Remote Similarity	NPC192712
0.6196	Remote Similarity	NPC469976
0.6188	Remote Similarity	NPC8104
0.6183	Remote Similarity	NPC84347
0.617	Remote Similarity	NPC469896
0.6162	Remote Similarity	NPC136957
0.6162	Remote Similarity	NPC19696
0.6161	Remote Similarity	NPC144452
0.6154	Remote Similarity	NPC192306
0.6154	Remote Similarity	NPC115232
0.6146	Remote Similarity	NPC87413
0.6146	Remote Similarity	NPC278434
0.6146	Remote Similarity	NPC473946
0.6145	Remote Similarity	NPC116573
0.6126	Remote Similarity	NPC282103
0.6126	Remote Similarity	NPC241025
0.6124	Remote Similarity	NPC263455
0.6111	Remote Similarity	NPC267853
0.6111	Remote Similarity	NPC315062
0.6108	Remote Similarity	NPC253810
0.6103	Remote Similarity	NPC469961
0.61	Remote Similarity	NPC471944
0.6095	Remote Similarity	NPC328029
0.6092	Remote Similarity	NPC167400
0.6091	Remote Similarity	NPC79356
0.6091	Remote Similarity	NPC48117
0.6091	Remote Similarity	NPC102592
0.6091	Remote Similarity	NPC476526
0.6091	Remote Similarity	NPC329765
0.6083	Remote Similarity	NPC244897
0.608	Remote Similarity	NPC220408
0.6073	Remote Similarity	NPC207851
0.6073	Remote Similarity	NPC110158
0.6071	Remote Similarity	NPC247735
0.6071	Remote Similarity	NPC472295
0.6071	Remote Similarity	NPC472210
0.6071	Remote Similarity	NPC81802
0.6071	Remote Similarity	NPC269886
0.607	Remote Similarity	NPC469716
0.6068	Remote Similarity	NPC82370
0.6066	Remote Similarity	NPC233380
0.6061	Remote Similarity	NPC475286
0.6061	Remote Similarity	NPC174281
0.6061	Remote Similarity	NPC313823
0.6059	Remote Similarity	NPC472287
0.6059	Remote Similarity	NPC472286
0.6059	Remote Similarity	NPC45190
0.6058	Remote Similarity	NPC116238
0.6056	Remote Similarity	NPC51388
0.6056	Remote Similarity	NPC475870
0.6039	Remote Similarity	NPC207020
0.6037	Remote Similarity	NPC260434
0.6033	Remote Similarity	NPC109447
0.6029	Remote Similarity	NPC74969
0.6029	Remote Similarity	NPC3207
0.6029	Remote Similarity	NPC249583
0.6027	Remote Similarity	NPC316411

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 NPC142688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	1051
0.2-0.3	1298
0.3-0.4	3111
0.4-0.5	2821
0.5-0.6	548
0.6-0.7	26
0.7-0.8	1
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
0.7135	Intermediate Similarity	NPD3178	Discontinued
0.67	Remote Similarity	NPD1996	Discontinued
0.6588	Remote Similarity	NPD9271	Approved
0.6364	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.633	Remote Similarity	NPD1096	Discontinued
0.6328	Remote Similarity	NPD820	Phase 3
0.631	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5003	Discontinued
0.6292	Remote Similarity	NPD1630	Approved
0.6235	Remote Similarity	NPD107	Approved
0.6219	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD1631	Approved
0.6172	Remote Similarity	NPD6770	Approved
0.6169	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD2565	Phase 2
0.6166	Remote Similarity	NPD2564	Approved
0.6161	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4506	Discontinued
0.6124	Remote Similarity	NPD5632	Approved
0.6111	Remote Similarity	NPD772	Phase 3
0.6105	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD9243	Approved
0.6092	Remote Similarity	NPD9075	Approved
0.6092	Remote Similarity	NPD9074	Approved
0.6089	Remote Similarity	NPD3947	Discontinued
0.6087	Remote Similarity	NPD2844	Phase 3
0.6078	Remote Similarity	NPD2509	Approved
0.6078	Remote Similarity	NPD2510	Approved
0.6067	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD1575	Approved
0.5968	Remote Similarity	NPD565	Phase 2
0.5968	Remote Similarity	NPD1573	Approved
0.5957	Remote Similarity	NPD1586	Approved
0.5952	Remote Similarity	NPD3394	Approved
0.5952	Remote Similarity	NPD3393	Approved
0.5952	Remote Similarity	NPD3389	Approved
0.5928	Remote Similarity	NPD5891	Approved
0.592	Remote Similarity	NPD2778	Approved
0.5919	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5475	Discontinued
0.5913	Remote Similarity	NPD7470	Discontinued
0.5907	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD1623	Approved
0.5896	Remote Similarity	NPD569	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD2915	Discontinued
0.5885	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD5866	Approved
0.5882	Remote Similarity	NPD6176	Phase 1
0.5877	Remote Similarity	NPD8160	Phase 2
0.5871	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD7946	Pre-registration
0.5864	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD1587	Approved
0.5857	Remote Similarity	NPD3945	Discontinued
0.5854	Remote Similarity	NPD5901	Discontinued
0.5842	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2779	Approved
0.5829	Remote Similarity	NPD1592	Phase 3
0.5824	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD2920	Discontinued
0.5797	Remote Similarity	NPD3371	Approved
0.5789	Remote Similarity	NPD482	Approved
0.5789	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD1801	Approved
0.5787	Remote Similarity	NPD1802	Approved
0.5778	Remote Similarity	NPD3835	Phase 3
0.5778	Remote Similarity	NPD3833	Phase 3
0.5762	Remote Similarity	NPD5416	Discontinued
0.5761	Remote Similarity	NPD2213	Approved
0.5761	Remote Similarity	NPD2214	Approved
0.5758	Remote Similarity	NPD4499	Approved
0.5755	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD1638	Discovery
0.5755	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD1643	Phase 3
0.5735	Remote Similarity	NPD8097	Phase 3
0.5735	Remote Similarity	NPD8096	Phase 3
0.5733	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5913	Phase 3
0.5728	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5482	Discontinued
0.5714	Remote Similarity	NPD7853	Phase 2
0.5701	Remote Similarity	NPD5479	Discontinued
0.57	Remote Similarity	NPD8282	Approved
0.57	Remote Similarity	NPD56	Approved
0.57	Remote Similarity	NPD4376	Phase 3
0.57	Remote Similarity	NPD8283	Approved
0.5694	Remote Similarity	NPD7180	Phase 3
0.5684	Remote Similarity	NPD485	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7994	Phase 2
0.5681	Remote Similarity	NPD2547	Discontinued
0.5677	Remote Similarity	NPD5104	Approved
0.5676	Remote Similarity	NPD7688	Phase 1
0.5659	Remote Similarity	NPD4500	Approved
0.5659	Remote Similarity	NPD4501	Approved
0.5659	Remote Similarity	NPD484	Approved
0.5659	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4948	Discontinued
0.5657	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.565	Remote Similarity	NPD5020	Approved
0.565	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6974	Phase 3
0.5648	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD1591	Approved
0.5628	Remote Similarity	NPD1534	Approved
0.5625	Remote Similarity	NPD8098	Approved
0.5622	Remote Similarity	NPD6242	Discontinued
0.5619	Remote Similarity	NPD8423	Phase 2
0.5619	Remote Similarity	NPD8399	Phase 1
0.5616	Remote Similarity	NPD2289	Phase 3
0.5616	Remote Similarity	NPD2290	Phase 3
0.5612	Remote Similarity	NPD2095	Phase 2
0.5612	Remote Similarity	NPD2094	Phase 2
0.5612	Remote Similarity	NPD2092	Phase 2
0.5608	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD1867	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data