NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.87
Volume:	163.011
LogP:	2.518
LogD:	1.5
LogS:	-2.529
# Rotatable Bonds:	1
TPSA:	42.23
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.858
Synthetic Accessibility Score:	2.756
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	2.0535295334411785e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.356
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.432

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.424
Plasma Protein Binding (PPB):	93.55357360839844%
Volume Distribution (VD):	0.431
Pgp-substrate:	14.507240295410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	2.1
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.578
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.316
Carcinogencity:	0.817
Eye Corrosion:	0.091
Eye Irritation:	0.975
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC109158

Natural Product ID:	NPC109158
*Common Name:**	Methyl-4,5-Dibromocarboxylic Acid
IUPAC Name:	4,5-dibromo-1-methylpyrrole-2-carboxylic acid
Synonyms:	Methyl-4,5-Dibromocarboxylic Acid
Standard InCHIKey:	OZAXVWIMCAEERV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H5Br2NO2/c1-9-4(6(10)11)2-3(7)5(9)8/h2H,1H3,(H,10,11)
SMILES:	Brc1c(Br)cc(n1C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598918
PubChem CID:	12897106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002554] Pyrrole carboxylic acids and derivatives [CHEMONTID:0002555] Pyrrole carboxylic acids [CHEMONTID:0002557] Pyrrole 2-carboxylic acids

*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	=	87.8	%	PMID[558635]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	71000.0	nM	PMID[558635]

☑ 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 NPC109158 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	914
0.1-0.2	10341
0.2-0.3	17025
0.3-0.4	9247
0.4-0.5	3117
0.5-0.6	1823
0.6-0.7	197
0.7-0.8	27
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC298288
0.8986	High Similarity	NPC52110
0.8506	High Similarity	NPC142688
0.8101	Intermediate Similarity	NPC27296
0.7975	Intermediate Similarity	NPC33229
0.775	Intermediate Similarity	NPC474236
0.7744	Intermediate Similarity	NPC474383
0.7707	Intermediate Similarity	NPC302159
0.7662	Intermediate Similarity	NPC85443
0.75	Intermediate Similarity	NPC13432
0.7451	Intermediate Similarity	NPC150592
0.7421	Intermediate Similarity	NPC260041
0.7365	Intermediate Similarity	NPC476418
0.7348	Intermediate Similarity	NPC77061
0.733	Intermediate Similarity	NPC476423
0.7273	Intermediate Similarity	NPC20021
0.7273	Intermediate Similarity	NPC469814
0.7262	Intermediate Similarity	NPC306160
0.7251	Intermediate Similarity	NPC273532
0.7246	Intermediate Similarity	NPC473706
0.7209	Intermediate Similarity	NPC80528
0.7182	Intermediate Similarity	NPC476413
0.7176	Intermediate Similarity	NPC41717
0.7168	Intermediate Similarity	NPC97106
0.7152	Intermediate Similarity	NPC312860
0.7143	Intermediate Similarity	NPC476414
0.7089	Intermediate Similarity	NPC472288
0.7078	Intermediate Similarity	NPC71236
0.7039	Intermediate Similarity	NPC241025
0.7	Intermediate Similarity	NPC112489
0.6994	Remote Similarity	NPC167400
0.6941	Remote Similarity	NPC322644
0.6933	Remote Similarity	NPC159630
0.6933	Remote Similarity	NPC230085
0.6932	Remote Similarity	NPC136441
0.6919	Remote Similarity	NPC46811
0.6918	Remote Similarity	NPC328029
0.6906	Remote Similarity	NPC46022
0.6905	Remote Similarity	NPC263455
0.6857	Remote Similarity	NPC253810
0.6857	Remote Similarity	NPC226835
0.6842	Remote Similarity	NPC57398
0.6836	Remote Similarity	NPC476419
0.6796	Remote Similarity	NPC207851
0.678	Remote Similarity	NPC37268
0.677	Remote Similarity	NPC114310
0.6761	Remote Similarity	NPC227489
0.6761	Remote Similarity	NPC28096
0.6761	Remote Similarity	NPC476421
0.6761	Remote Similarity	NPC302647
0.67	Remote Similarity	NPC469717
0.6685	Remote Similarity	NPC472861
0.6685	Remote Similarity	NPC184932
0.6667	Remote Similarity	NPC206148
0.6646	Remote Similarity	NPC291517
0.6632	Remote Similarity	NPC472284
0.663	Remote Similarity	NPC317010
0.6607	Remote Similarity	NPC112741
0.659	Remote Similarity	NPC113812
0.6579	Remote Similarity	NPC141454
0.6576	Remote Similarity	NPC311282
0.6576	Remote Similarity	NPC295158
0.6559	Remote Similarity	NPC75544
0.6554	Remote Similarity	NPC470894
0.6543	Remote Similarity	NPC23215
0.6534	Remote Similarity	NPC2414
0.6532	Remote Similarity	NPC116573
0.6503	Remote Similarity	NPC29702
0.6497	Remote Similarity	NPC474696
0.648	Remote Similarity	NPC472287
0.648	Remote Similarity	NPC54214
0.648	Remote Similarity	NPC472286
0.6453	Remote Similarity	NPC107287
0.644	Remote Similarity	NPC179701
0.6436	Remote Similarity	NPC83111
0.6406	Remote Similarity	NPC262898
0.6395	Remote Similarity	NPC472260
0.6378	Remote Similarity	NPC165599
0.6375	Remote Similarity	NPC313823
0.6374	Remote Similarity	NPC286195
0.6354	Remote Similarity	NPC271927
0.6332	Remote Similarity	NPC476524
0.6322	Remote Similarity	NPC75135
0.6311	Remote Similarity	NPC54066
0.6303	Remote Similarity	NPC200397
0.6303	Remote Similarity	NPC98156
0.6303	Remote Similarity	NPC292434
0.6303	Remote Similarity	NPC64661
0.6303	Remote Similarity	NPC14448
0.6303	Remote Similarity	NPC167200
0.6303	Remote Similarity	NPC138596
0.6303	Remote Similarity	NPC195704
0.6298	Remote Similarity	NPC249614
0.629	Remote Similarity	NPC159125
0.6281	Remote Similarity	NPC321428
0.6276	Remote Similarity	NPC9635
0.6263	Remote Similarity	NPC472259
0.6256	Remote Similarity	NPC123395
0.625	Remote Similarity	NPC475870
0.625	Remote Similarity	NPC192306
0.6243	Remote Similarity	NPC278434
0.6238	Remote Similarity	NPC82370
0.6231	Remote Similarity	NPC82053
0.6225	Remote Similarity	NPC50562
0.6221	Remote Similarity	NPC257142
0.6218	Remote Similarity	NPC93390
0.6214	Remote Similarity	NPC174576
0.6205	Remote Similarity	NPC248782
0.62	Remote Similarity	NPC244741
0.6195	Remote Similarity	NPC67658
0.6193	Remote Similarity	NPC471944
0.619	Remote Similarity	NPC111566
0.619	Remote Similarity	NPC63571
0.6178	Remote Similarity	NPC144381
0.6178	Remote Similarity	NPC469489
0.6169	Remote Similarity	NPC476525
0.6166	Remote Similarity	NPC230403
0.6158	Remote Similarity	NPC310633
0.6154	Remote Similarity	NPC78767
0.6154	Remote Similarity	NPC473814
0.6146	Remote Similarity	NPC210123
0.6141	Remote Similarity	NPC303225
0.6139	Remote Similarity	NPC325297
0.6127	Remote Similarity	NPC100726
0.6126	Remote Similarity	NPC209917
0.6126	Remote Similarity	NPC221873
0.6122	Remote Similarity	NPC474916
0.6121	Remote Similarity	NPC322488
0.612	Remote Similarity	NPC158129
0.6118	Remote Similarity	NPC129412
0.6118	Remote Similarity	NPC114033
0.6118	Remote Similarity	NPC101130
0.6118	Remote Similarity	NPC58268
0.6114	Remote Similarity	NPC284348
0.6111	Remote Similarity	NPC73687
0.6111	Remote Similarity	NPC212125
0.6111	Remote Similarity	NPC98864
0.6103	Remote Similarity	NPC109922
0.6102	Remote Similarity	NPC74357
0.6098	Remote Similarity	NPC89508
0.6096	Remote Similarity	NPC40530
0.6096	Remote Similarity	NPC314281
0.6091	Remote Similarity	NPC103361
0.6087	Remote Similarity	NPC472285
0.6087	Remote Similarity	NPC288074
0.6082	Remote Similarity	NPC88315
0.6073	Remote Similarity	NPC473946
0.6067	Remote Similarity	NPC212742
0.6062	Remote Similarity	NPC114974
0.6059	Remote Similarity	NPC286529
0.6059	Remote Similarity	NPC77582
0.6059	Remote Similarity	NPC12831
0.6059	Remote Similarity	NPC302717
0.6059	Remote Similarity	NPC59839
0.6059	Remote Similarity	NPC129753
0.6059	Remote Similarity	NPC209281
0.6059	Remote Similarity	NPC244087
0.6059	Remote Similarity	NPC205604
0.6059	Remote Similarity	NPC48171
0.6059	Remote Similarity	NPC74928
0.6059	Remote Similarity	NPC169308
0.6059	Remote Similarity	NPC3698
0.6059	Remote Similarity	NPC97230
0.6053	Remote Similarity	NPC282103
0.6053	Remote Similarity	NPC474258
0.6051	Remote Similarity	NPC135950
0.6049	Remote Similarity	NPC118940
0.6049	Remote Similarity	NPC207020
0.6043	Remote Similarity	NPC248041
0.6043	Remote Similarity	NPC126709
0.6021	Remote Similarity	NPC160381
0.602	Remote Similarity	NPC132539
0.6019	Remote Similarity	NPC243633
0.6019	Remote Similarity	NPC175150
0.6012	Remote Similarity	NPC306397
0.6012	Remote Similarity	NPC165370
0.601	Remote Similarity	NPC312645
0.6	Remote Similarity	NPC473821
0.6	Remote Similarity	NPC19342
0.6	Remote Similarity	NPC146418
0.6	Remote Similarity	NPC285923
0.5991	Remote Similarity	NPC229893
0.5989	Remote Similarity	NPC219848
0.5988	Remote Similarity	NPC151489
0.5977	Remote Similarity	NPC220523
0.5969	Remote Similarity	NPC202812
0.5968	Remote Similarity	NPC186068
0.5968	Remote Similarity	NPC469938
0.5966	Remote Similarity	NPC473878
0.5959	Remote Similarity	NPC183805
0.5957	Remote Similarity	NPC233050
0.5957	Remote Similarity	NPC219336
0.5957	Remote Similarity	NPC283219
0.5957	Remote Similarity	NPC276540
0.5957	Remote Similarity	NPC256268
0.5956	Remote Similarity	NPC109447
0.5955	Remote Similarity	NPC209362
0.5952	Remote Similarity	NPC168209
0.5949	Remote Similarity	NPC469961
0.5947	Remote Similarity	NPC243058

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 NPC109158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	956
0.2-0.3	1242
0.3-0.4	3011
0.4-0.5	2764
0.5-0.6	858
0.6-0.7	46
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
0.7257	Intermediate Similarity	NPD3178	Discontinued
0.7059	Intermediate Similarity	NPD1631	Approved
0.7044	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD9075	Approved
0.6994	Remote Similarity	NPD9074	Approved
0.6882	Remote Similarity	NPD1630	Approved
0.68	Remote Similarity	NPD1573	Approved
0.68	Remote Similarity	NPD1575	Approved
0.6748	Remote Similarity	NPD107	Approved
0.6667	Remote Similarity	NPD1587	Approved
0.663	Remote Similarity	NPD1643	Phase 3
0.6607	Remote Similarity	NPD9271	Approved
0.6592	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1096	Discontinued
0.65	Remote Similarity	NPD1586	Approved
0.6448	Remote Similarity	NPD6452	Discontinued
0.6424	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4948	Discontinued
0.6413	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD2290	Phase 3
0.6354	Remote Similarity	NPD2289	Phase 3
0.6343	Remote Similarity	NPD820	Phase 3
0.631	Remote Similarity	NPD5020	Approved
0.6264	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD772	Phase 3
0.6175	Remote Similarity	NPD750	Phase 2
0.6154	Remote Similarity	NPD1996	Discontinued
0.6134	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5866	Approved
0.6114	Remote Similarity	NPD510	Phase 1
0.6111	Remote Similarity	NPD9284	Approved
0.6105	Remote Similarity	NPD3315	Phase 3
0.61	Remote Similarity	NPD5901	Discontinued
0.607	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD4520	Approved
0.6054	Remote Similarity	NPD158	Discontinued
0.6041	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6665	Discontinued
0.6031	Remote Similarity	NPD981	Phase 2
0.602	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD9080	Approved
0.6011	Remote Similarity	NPD2844	Phase 3
0.6009	Remote Similarity	NPD5891	Approved
0.6	Remote Similarity	NPD721	Approved
0.5981	Remote Similarity	NPD1623	Approved
0.5976	Remote Similarity	NPD1031	Discontinued
0.596	Remote Similarity	NPD7459	Phase 2
0.5959	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.595	Remote Similarity	NPD5017	Discontinued
0.5949	Remote Similarity	NPD9243	Approved
0.5946	Remote Similarity	NPD485	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3947	Discontinued
0.5941	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5809	Phase 3
0.5936	Remote Similarity	NPD749	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4805	Approved
0.5926	Remote Similarity	NPD9510	Approved
0.5922	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD1173	Approved
0.5902	Remote Similarity	NPD2915	Discontinued
0.5889	Remote Similarity	NPD4326	Phase 2
0.5882	Remote Similarity	NPD9506	Approved
0.5882	Remote Similarity	NPD482	Approved
0.5879	Remote Similarity	NPD53	Approved
0.5879	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD7778	Approved
0.5879	Remote Similarity	NPD7777	Approved
0.5873	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD1649	Discontinued
0.587	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1352	Discontinued
0.5862	Remote Similarity	NPD6987	Phase 1
0.5845	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5897	Approved
0.5842	Remote Similarity	NPD5898	Approved
0.5842	Remote Similarity	NPD5899	Approved
0.5821	Remote Similarity	NPD484	Approved
0.5814	Remote Similarity	NPD4804	Approved
0.5811	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.581	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD7180	Phase 3
0.5771	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD6999	Discontinued
0.5771	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD1499	Phase 3
0.5769	Remote Similarity	NPD5255	Approved
0.5765	Remote Similarity	NPD272	Approved
0.5765	Remote Similarity	NPD5316	Approved
0.5764	Remote Similarity	NPD2779	Approved
0.5762	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5088	Discontinued
0.576	Remote Similarity	NPD3259	Approved
0.5756	Remote Similarity	NPD7001	Phase 3
0.5755	Remote Similarity	NPD7878	Phase 2
0.5744	Remote Similarity	NPD9364	Phase 2
0.5744	Remote Similarity	NPD9363	Approved
0.5744	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD8097	Phase 3
0.5742	Remote Similarity	NPD8096	Phase 3
0.5736	Remote Similarity	NPD2336	Approved
0.5736	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4602	Approved
0.5728	Remote Similarity	NPD6369	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD6209	Approved
0.5721	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4334	Discontinued
0.5714	Remote Similarity	NPD3243	Approved
0.5707	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD944	Approved
0.5699	Remote Similarity	NPD2137	Approved
0.5699	Remote Similarity	NPD2094	Phase 2
0.5699	Remote Similarity	NPD2095	Phase 2
0.5699	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD2092	Phase 2
0.5699	Remote Similarity	NPD2138	Approved
0.5694	Remote Similarity	NPD7470	Discontinued
0.5694	Remote Similarity	NPD6173	Approved
0.5684	Remote Similarity	NPD5104	Approved
0.5684	Remote Similarity	NPD5471	Phase 3
0.5683	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD604	Clinical (unspecified phase)
0.568	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD5003	Discontinued
0.567	Remote Similarity	NPD2096	Phase 2
0.567	Remote Similarity	NPD2091	Phase 2
0.5667	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD852	Discontinued
0.5665	Remote Similarity	NPD2896	Discontinued
0.5663	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.5661	Remote Similarity	NPD4524	Discontinued
0.5661	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6733	Discontinued
0.5657	Remote Similarity	NPD1592	Phase 3
0.5648	Remote Similarity	NPD9362	Approved
0.5646	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4397	Phase 1
0.5634	Remote Similarity	NPD1591	Approved
0.5631	Remote Similarity	NPD8098	Approved
0.5628	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD5827	Discontinued
0.5628	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD4315	Phase 2
0.5628	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD3288	Approved
0.5625	Remote Similarity	NPD3525	Discontinued
0.5622	Remote Similarity	NPD2307	Discontinued
0.5622	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD2778	Approved
0.5613	Remote Similarity	NPD1638	Discovery
0.5613	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5611	Remote Similarity	NPD1467	Approved
0.5611	Remote Similarity	NPD1867	Approved
0.5611	Remote Similarity	NPD1466	Phase 3
0.5607	Remote Similarity	NPD5533	Discontinued
0.5606	Remote Similarity	NPD2564	Approved
0.5606	Remote Similarity	NPD2565	Phase 2
0.5604	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD7568	Phase 1
0.5604	Remote Similarity	NPD4862	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