NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	187.96
Volume:	128.638
LogP:	1.086
LogD:	1.002
LogS:	-1.651
# Rotatable Bonds:	1
TPSA:	58.88
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	3.103
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.525
MDCK Permeability:	2.7976788260275498e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	65.34260559082031%
Volume Distribution (VD):	0.943
Pgp-substrate:	58.23341751098633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.461
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	5.309
Half-life (T1/2):	0.447

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.679
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.083
Carcinogencity:	0.823
Eye Corrosion:	0.015
Eye Irritation:	0.968
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC20021

Natural Product ID:	NPC20021
*Common Name:**	5-Bromopyrrole-2-Carboxamide
IUPAC Name:	5-bromo-1H-pyrrole-2-carboxamide
Synonyms:
Standard InCHIKey:	IUCIXLJBQZTUQS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5BrN2O/c6-4-2-1-3(8-4)5(7)9/h1-2,8H,(H2,7,9)
SMILES:	c1cc(Br)[nH]c1C(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449714
PubChem CID:	10419997
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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	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	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IC50	=	3.13	ug.mL-1	PMID[513593]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IC50	=	6.25	ug.mL-1	PMID[513593]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	0.78	ug.mL-1	PMID[513593]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	3.13	ug.mL-1	PMID[513593]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	6.25	ug.mL-1	PMID[513593]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	3.13	ug.mL-1	PMID[513593]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	3.13	ug.mL-1	PMID[513593]

☑ 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 NPC20021 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	3115
0.1-0.2	16388
0.2-0.3	16406
0.3-0.4	3059
0.4-0.5	2273
0.5-0.6	1169
0.6-0.7	204
0.7-0.8	67
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC150592
0.9051	High Similarity	NPC260041
0.8389	Intermediate Similarity	NPC206148
0.8231	Intermediate Similarity	NPC474236
0.8212	Intermediate Similarity	NPC2414
0.8121	Intermediate Similarity	NPC27296
0.8027	Intermediate Similarity	NPC52110
0.7949	Intermediate Similarity	NPC80528
0.7933	Intermediate Similarity	NPC142688
0.7908	Intermediate Similarity	NPC306160
0.7908	Intermediate Similarity	NPC476418
0.7885	Intermediate Similarity	NPC54214
0.7872	Intermediate Similarity	NPC23215
0.7872	Intermediate Similarity	NPC291517
0.7857	Intermediate Similarity	NPC474383
0.7817	Intermediate Similarity	NPC200397
0.7817	Intermediate Similarity	NPC195704
0.7817	Intermediate Similarity	NPC98156
0.7817	Intermediate Similarity	NPC292434
0.7817	Intermediate Similarity	NPC167200
0.7817	Intermediate Similarity	NPC64661
0.7817	Intermediate Similarity	NPC138596
0.7817	Intermediate Similarity	NPC14448
0.7785	Intermediate Similarity	NPC37268
0.7778	Intermediate Similarity	NPC473706
0.7724	Intermediate Similarity	NPC12831
0.7724	Intermediate Similarity	NPC48171
0.7724	Intermediate Similarity	NPC169308
0.7724	Intermediate Similarity	NPC129753
0.7724	Intermediate Similarity	NPC286529
0.7724	Intermediate Similarity	NPC244087
0.7724	Intermediate Similarity	NPC77582
0.7724	Intermediate Similarity	NPC302717
0.7724	Intermediate Similarity	NPC205604
0.7724	Intermediate Similarity	NPC59839
0.7724	Intermediate Similarity	NPC74928
0.7724	Intermediate Similarity	NPC97230
0.7724	Intermediate Similarity	NPC209281
0.7724	Intermediate Similarity	NPC3698
0.7658	Intermediate Similarity	NPC28096
0.7658	Intermediate Similarity	NPC227489
0.7658	Intermediate Similarity	NPC476421
0.7658	Intermediate Similarity	NPC226835
0.7576	Intermediate Similarity	NPC63571
0.7564	Intermediate Similarity	NPC73687
0.7551	Intermediate Similarity	NPC114033
0.7551	Intermediate Similarity	NPC101130
0.7551	Intermediate Similarity	NPC129412
0.7551	Intermediate Similarity	NPC58268
0.7546	Intermediate Similarity	NPC472861
0.7546	Intermediate Similarity	NPC184932
0.753	Intermediate Similarity	NPC310633
0.7516	Intermediate Similarity	NPC136441
0.747	Intermediate Similarity	NPC111566
0.7453	Intermediate Similarity	NPC97106
0.7296	Intermediate Similarity	NPC233380
0.7273	Intermediate Similarity	NPC109158
0.7273	Intermediate Similarity	NPC71236
0.7262	Intermediate Similarity	NPC112489
0.7262	Intermediate Similarity	NPC46022
0.7255	Intermediate Similarity	NPC13432
0.7246	Intermediate Similarity	NPC469814
0.7222	Intermediate Similarity	NPC469976
0.7209	Intermediate Similarity	NPC19342
0.7202	Intermediate Similarity	NPC476423
0.7179	Intermediate Similarity	NPC298288
0.7143	Intermediate Similarity	NPC474696
0.707	Intermediate Similarity	NPC33229
0.7047	Intermediate Similarity	NPC472288
0.7022	Intermediate Similarity	NPC9635
0.7006	Intermediate Similarity	NPC19696
0.7006	Intermediate Similarity	NPC136957
0.6988	Remote Similarity	NPC151635
0.6983	Remote Similarity	NPC469716
0.6971	Remote Similarity	NPC46811
0.697	Remote Similarity	NPC271927
0.6954	Remote Similarity	NPC476413
0.6943	Remote Similarity	NPC472260
0.6932	Remote Similarity	NPC329765
0.6932	Remote Similarity	NPC476526
0.6932	Remote Similarity	NPC48117
0.6914	Remote Similarity	NPC476414
0.6893	Remote Similarity	NPC475286
0.6893	Remote Similarity	NPC174281
0.6867	Remote Similarity	NPC252572
0.6849	Remote Similarity	NPC313823
0.6826	Remote Similarity	NPC186068
0.6772	Remote Similarity	NPC471655
0.6768	Remote Similarity	NPC115232
0.6747	Remote Similarity	NPC471943
0.6722	Remote Similarity	NPC477004
0.6705	Remote Similarity	NPC133003
0.6667	Remote Similarity	NPC476527
0.6667	Remote Similarity	NPC76982
0.6647	Remote Similarity	NPC110158
0.6646	Remote Similarity	NPC75135
0.663	Remote Similarity	NPC237414
0.6605	Remote Similarity	NPC74357
0.6579	Remote Similarity	NPC50562
0.6556	Remote Similarity	NPC77061
0.6554	Remote Similarity	NPC324091
0.6545	Remote Similarity	NPC67658
0.6524	Remote Similarity	NPC476524
0.6524	Remote Similarity	NPC476525
0.6519	Remote Similarity	NPC467188
0.6519	Remote Similarity	NPC470440
0.6506	Remote Similarity	NPC274981
0.6474	Remote Similarity	NPC88110
0.6474	Remote Similarity	NPC314281
0.6474	Remote Similarity	NPC40530
0.6457	Remote Similarity	NPC477003
0.6446	Remote Similarity	NPC214106
0.6444	Remote Similarity	NPC188821
0.6444	Remote Similarity	NPC474180
0.6441	Remote Similarity	NPC473946
0.6438	Remote Similarity	NPC100726
0.6437	Remote Similarity	NPC191415
0.6429	Remote Similarity	NPC470509
0.6425	Remote Similarity	NPC210123
0.6424	Remote Similarity	NPC474492
0.642	Remote Similarity	NPC474258
0.641	Remote Similarity	NPC85443
0.64	Remote Similarity	NPC470205
0.64	Remote Similarity	NPC102755
0.64	Remote Similarity	NPC270834
0.6393	Remote Similarity	NPC474389
0.6392	Remote Similarity	NPC469717
0.6379	Remote Similarity	NPC79777
0.6374	Remote Similarity	NPC102592
0.6374	Remote Similarity	NPC79356
0.6374	Remote Similarity	NPC161861
0.6369	Remote Similarity	NPC42372
0.6364	Remote Similarity	NPC21429
0.6364	Remote Similarity	NPC299594
0.6358	Remote Similarity	NPC284775
0.634	Remote Similarity	NPC330326
0.6335	Remote Similarity	NPC105811
0.6333	Remote Similarity	NPC243716
0.6327	Remote Similarity	NPC41174
0.6296	Remote Similarity	NPC2272
0.6292	Remote Similarity	NPC17273
0.6292	Remote Similarity	NPC141612
0.6292	Remote Similarity	NPC135601
0.6287	Remote Similarity	NPC470680
0.6287	Remote Similarity	NPC100104
0.6286	Remote Similarity	NPC477042
0.6286	Remote Similarity	NPC234403
0.6276	Remote Similarity	NPC168209
0.6273	Remote Similarity	NPC316069
0.6272	Remote Similarity	NPC71132
0.627	Remote Similarity	NPC474318
0.627	Remote Similarity	NPC475914
0.627	Remote Similarity	NPC268744
0.627	Remote Similarity	NPC153123
0.627	Remote Similarity	NPC201266
0.627	Remote Similarity	NPC220797
0.6263	Remote Similarity	NPC175150
0.6263	Remote Similarity	NPC243633
0.6258	Remote Similarity	NPC473878
0.625	Remote Similarity	NPC253687
0.6243	Remote Similarity	NPC476460
0.6242	Remote Similarity	NPC209362
0.6237	Remote Similarity	NPC166209
0.6237	Remote Similarity	NPC269203
0.6237	Remote Similarity	NPC13456
0.6237	Remote Similarity	NPC77241
0.6235	Remote Similarity	NPC109447
0.6229	Remote Similarity	NPC233050
0.6229	Remote Similarity	NPC276540
0.6222	Remote Similarity	NPC473666
0.6221	Remote Similarity	NPC262338
0.622	Remote Similarity	NPC70406
0.6218	Remote Similarity	NPC473218
0.6218	Remote Similarity	NPC470702
0.6215	Remote Similarity	NPC117027
0.6213	Remote Similarity	NPC271797
0.6213	Remote Similarity	NPC21174
0.6213	Remote Similarity	NPC271734
0.6203	Remote Similarity	NPC471944
0.6194	Remote Similarity	NPC213774
0.6186	Remote Similarity	NPC470703
0.6184	Remote Similarity	NPC471589
0.6182	Remote Similarity	NPC141926
0.6182	Remote Similarity	NPC232798
0.6182	Remote Similarity	NPC251391
0.6175	Remote Similarity	NPC326422
0.6173	Remote Similarity	NPC302159
0.6171	Remote Similarity	NPC473380
0.6171	Remote Similarity	NPC240088
0.6168	Remote Similarity	NPC213914
0.6162	Remote Similarity	NPC141454
0.6159	Remote Similarity	NPC250361
0.6158	Remote Similarity	NPC275292
0.6158	Remote Similarity	NPC243381
0.6154	Remote Similarity	NPC198988
0.6149	Remote Similarity	NPC293216
0.6145	Remote Similarity	NPC34844
0.6145	Remote Similarity	NPC229055
0.6139	Remote Similarity	NPC104049
0.6138	Remote Similarity	NPC317701

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 NPC20021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	502
0.1-0.2	1139
0.2-0.3	2057
0.3-0.4	2599
0.4-0.5	2250
0.5-0.6	573
0.6-0.7	29
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
0.6943	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD2289	Phase 3
0.6464	Remote Similarity	NPD2290	Phase 3
0.64	Remote Similarity	NPD1031	Discontinued
0.634	Remote Similarity	NPD9100	Approved
0.6307	Remote Similarity	NPD3318	Approved
0.6307	Remote Similarity	NPD3319	Phase 1
0.6307	Remote Similarity	NPD3320	Approved
0.6278	Remote Similarity	NPD5685	Approved
0.6278	Remote Similarity	NPD5686	Approved
0.6266	Remote Similarity	NPD9599	Approved
0.6258	Remote Similarity	NPD272	Approved
0.625	Remote Similarity	NPD3178	Discontinued
0.6243	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1630	Approved
0.6216	Remote Similarity	NPD7459	Phase 2
0.6176	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1631	Approved
0.6111	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5473	Discontinued
0.6089	Remote Similarity	NPD1096	Discontinued
0.6089	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD460	Discontinued
0.6081	Remote Similarity	NPD4811	Discontinued
0.6066	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.604	Remote Similarity	NPD9598	Discontinued
0.6038	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD1592	Phase 3
0.6	Remote Similarity	NPD5787	Discontinued
0.5988	Remote Similarity	NPD180	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD9396	Approved
0.5986	Remote Similarity	NPD9392	Approved
0.5978	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1573	Approved
0.5977	Remote Similarity	NPD1575	Approved
0.5956	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.592	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD198	Clinical (unspecified phase)
0.589	Remote Similarity	NPD9724	Phase 1
0.5876	Remote Similarity	NPD4883	Approved
0.5876	Remote Similarity	NPD1506	Discontinued
0.5876	Remote Similarity	NPD1586	Approved
0.5876	Remote Similarity	NPD482	Approved
0.5875	Remote Similarity	NPD1262	Discovery
0.5875	Remote Similarity	NPD200	Phase 2
0.5875	Remote Similarity	NPD201	Phase 2
0.5866	Remote Similarity	NPD3076	Approved
0.5866	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD3079	Approved
0.5866	Remote Similarity	NPD3078	Approved
0.5866	Remote Similarity	NPD3077	Approved
0.5862	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.586	Remote Similarity	NPD1896	Approved
0.5856	Remote Similarity	NPD1745	Approved
0.5848	Remote Similarity	NPD2213	Approved
0.5848	Remote Similarity	NPD2214	Approved
0.5846	Remote Similarity	NPD6459	Phase 2
0.5845	Remote Similarity	NPD9098	Phase 3
0.5845	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3927	Phase 2
0.5833	Remote Similarity	NPD1619	Phase 3
0.5829	Remote Similarity	NPD2844	Phase 3
0.5828	Remote Similarity	NPD5020	Approved
0.5802	Remote Similarity	NPD786	Approved
0.5789	Remote Similarity	NPD465	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD5017	Discontinued
0.5778	Remote Similarity	NPD1587	Approved
0.5775	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD4922	Phase 2
0.5774	Remote Similarity	NPD3835	Phase 3
0.5774	Remote Similarity	NPD4463	Approved
0.5774	Remote Similarity	NPD4462	Approved
0.5774	Remote Similarity	NPD3833	Phase 3
0.5767	Remote Similarity	NPD1871	Approved
0.5767	Remote Similarity	NPD107	Approved
0.5767	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD2061	Approved
0.5759	Remote Similarity	NPD803	Phase 1
0.5747	Remote Similarity	NPD3583	Phase 2
0.5745	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.574	Remote Similarity	NPD510	Phase 1
0.5736	Remote Similarity	NPD1600	Suspended
0.5736	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD1722	Approved
0.573	Remote Similarity	NPD4524	Discontinued
0.5714	Remote Similarity	NPD5199	Approved
0.5714	Remote Similarity	NPD7619	Phase 3
0.5714	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5198	Approved
0.5714	Remote Similarity	NPD7618	Phase 3
0.5686	Remote Similarity	NPD1561	Phase 2
0.5686	Remote Similarity	NPD1996	Discontinued
0.5685	Remote Similarity	NPD6376	Discontinued
0.5685	Remote Similarity	NPD2443	Approved
0.5685	Remote Similarity	NPD2442	Approved
0.5684	Remote Similarity	NPD4848	Phase 1
0.5683	Remote Similarity	NPD2094	Phase 2
0.5683	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD2095	Phase 2
0.5683	Remote Similarity	NPD2092	Phase 2
0.568	Remote Similarity	NPD7716	Approved
0.568	Remote Similarity	NPD7717	Approved
0.568	Remote Similarity	NPD971	Clinical (unspecified phase)
0.5677	Remote Similarity	NPD2405	Phase 3
0.5676	Remote Similarity	NPD5809	Phase 3
0.5667	Remote Similarity	NPD4075	Phase 2
0.5663	Remote Similarity	NPD2008	Discontinued
0.5663	Remote Similarity	NPD5254	Discontinued
0.5659	Remote Similarity	NPD2481	Approved
0.5659	Remote Similarity	NPD2479	Phase 3
0.5659	Remote Similarity	NPD1618	Phase 2
0.5658	Remote Similarity	NPD1079	Discontinued
0.5655	Remote Similarity	NPD1270	Approved
0.5654	Remote Similarity	NPD1952	Discontinued
0.5652	Remote Similarity	NPD2096	Phase 2
0.5652	Remote Similarity	NPD2091	Phase 2
0.5652	Remote Similarity	NPD7564	Discontinued
0.565	Remote Similarity	NPD1343	Approved
0.5647	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD3961	Discontinued
0.5642	Remote Similarity	NPD3868	Phase 1
0.5641	Remote Similarity	NPD6176	Phase 1
0.5638	Remote Similarity	NPD1658	Discontinued
0.5638	Remote Similarity	NPD269	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD7865	Approved
0.5633	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD9074	Approved
0.5629	Remote Similarity	NPD9075	Approved
0.5628	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2915	Discontinued
0.5625	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1982	Phase 1
0.5621	Remote Similarity	NPD1183	Approved
0.5619	Remote Similarity	NPD7727	Phase 2
0.5619	Remote Similarity	NPD7817	Phase 1
0.5617	Remote Similarity	NPD206	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.561	Remote Similarity	NPD2071	Approved
0.561	Remote Similarity	NPD2069	Approved
0.561	Remote Similarity	NPD2070	Approved
0.561	Remote Similarity	NPD2068	Approved
0.5605	Remote Similarity	NPD1781	Discontinued
0.5602	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5400	Approved
0.56	Remote Similarity	NPD6771	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