NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	286.0
Volume:	227.425
LogP:	0.577
LogD:	0.644
LogS:	-2.663
# Rotatable Bonds:	5
TPSA:	92.42
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	2.163
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.935
MDCK Permeability:	1.5749630620121025e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.134

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	82.13491821289062%
Volume Distribution (VD):	0.569
Pgp-substrate:	34.15162658691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.286
CYP2C9-substrate:	0.824
CYP2D6-inhibitor:	0.348
CYP2D6-substrate:	0.355
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	6.263
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.342
AMES Toxicity:	0.191
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.251
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.083
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC474087

Natural Product ID:	NPC474087
*Common Name:**	N1-(3-Bromo-4-Hydroxyphenethyl)Oxalamide
IUPAC Name:	N'-[2-(3-bromo-4-hydroxyphenyl)ethyl]oxamide
Synonyms:
Standard InCHIKey:	JHMFUOWCGIULBS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H11BrN2O3/c11-7-5-6(1-2-8(7)14)3-4-13-10(16)9(12)15/h1-2,5,14H,3-4H2,(H2,12,15)(H,13,16)
SMILES:	NC(=O)C(=O)NCCc1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460763
PubChem CID:	10708395
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 [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	10.0	ug	PMID[566541]

☑ 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 NPC474087 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	217
0.1-0.2	3097
0.2-0.3	13764
0.3-0.4	7763
0.4-0.5	13781
0.5-0.6	3474
0.6-0.7	548
0.7-0.8	48
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8607	High Similarity	NPC59387
0.831	Intermediate Similarity	NPC20755
0.824	Intermediate Similarity	NPC115803
0.8214	Intermediate Similarity	NPC308571
0.7872	Intermediate Similarity	NPC128877
0.777	Intermediate Similarity	NPC469711
0.7676	Intermediate Similarity	NPC197045
0.7643	Intermediate Similarity	NPC243404
0.7541	Intermediate Similarity	NPC125732
0.7429	Intermediate Similarity	NPC474091
0.7413	Intermediate Similarity	NPC470471
0.7376	Intermediate Similarity	NPC257390
0.7376	Intermediate Similarity	NPC475735
0.7348	Intermediate Similarity	NPC10286
0.7348	Intermediate Similarity	NPC213
0.7344	Intermediate Similarity	NPC471495
0.7339	Intermediate Similarity	NPC155847
0.7339	Intermediate Similarity	NPC289381
0.731	Intermediate Similarity	NPC470470
0.7254	Intermediate Similarity	NPC473724
0.7231	Intermediate Similarity	NPC473358
0.7203	Intermediate Similarity	NPC474753
0.7185	Intermediate Similarity	NPC85276
0.7164	Intermediate Similarity	NPC106551
0.7164	Intermediate Similarity	NPC281686
0.7164	Intermediate Similarity	NPC188867
0.7163	Intermediate Similarity	NPC202776
0.7154	Intermediate Similarity	NPC145638
0.7154	Intermediate Similarity	NPC290566
0.7152	Intermediate Similarity	NPC296085
0.7143	Intermediate Similarity	NPC96275
0.7087	Intermediate Similarity	NPC68055
0.7087	Intermediate Similarity	NPC178902
0.7083	Intermediate Similarity	NPC166624
0.7075	Intermediate Similarity	NPC238412
0.7075	Intermediate Similarity	NPC474673
0.7071	Intermediate Similarity	NPC171372
0.7071	Intermediate Similarity	NPC272463
0.7067	Intermediate Similarity	NPC470472
0.7067	Intermediate Similarity	NPC78530
0.7063	Intermediate Similarity	NPC29601
0.7059	Intermediate Similarity	NPC76412
0.7039	Intermediate Similarity	NPC71629
0.7023	Intermediate Similarity	NPC54543
0.7007	Intermediate Similarity	NPC239697
0.7007	Intermediate Similarity	NPC313694
0.7007	Intermediate Similarity	NPC242159
0.6992	Remote Similarity	NPC146422
0.6985	Remote Similarity	NPC137096
0.6978	Remote Similarity	NPC27581
0.6972	Remote Similarity	NPC218323
0.6968	Remote Similarity	NPC47672
0.6943	Remote Similarity	NPC233926
0.6943	Remote Similarity	NPC156311
0.6933	Remote Similarity	NPC474128
0.6923	Remote Similarity	NPC473580
0.6923	Remote Similarity	NPC231705
0.6919	Remote Similarity	NPC248822
0.6918	Remote Similarity	NPC184465
0.6918	Remote Similarity	NPC163810
0.6913	Remote Similarity	NPC476989
0.6901	Remote Similarity	NPC318965
0.6901	Remote Similarity	NPC246591
0.6901	Remote Similarity	NPC110131
0.6884	Remote Similarity	NPC283760
0.6884	Remote Similarity	NPC117759
0.6871	Remote Similarity	NPC71888
0.6871	Remote Similarity	NPC120114
0.687	Remote Similarity	NPC142297
0.6857	Remote Similarity	NPC7830
0.6855	Remote Similarity	NPC469243
0.6828	Remote Similarity	NPC99280
0.6828	Remote Similarity	NPC120251
0.6824	Remote Similarity	NPC109580
0.6818	Remote Similarity	NPC96224
0.6818	Remote Similarity	NPC24101
0.6818	Remote Similarity	NPC153690
0.6812	Remote Similarity	NPC142638
0.6812	Remote Similarity	NPC317784
0.6809	Remote Similarity	NPC296202
0.68	Remote Similarity	NPC40321
0.6779	Remote Similarity	NPC309667
0.6776	Remote Similarity	NPC266741
0.6772	Remote Similarity	NPC107619
0.6767	Remote Similarity	NPC473372
0.6767	Remote Similarity	NPC258056
0.6759	Remote Similarity	NPC325651
0.6757	Remote Similarity	NPC470441
0.675	Remote Similarity	NPC475544
0.6747	Remote Similarity	NPC475688
0.6738	Remote Similarity	NPC268348
0.6736	Remote Similarity	NPC323775
0.6736	Remote Similarity	NPC236347
0.6733	Remote Similarity	NPC48202
0.6732	Remote Similarity	NPC81026
0.6732	Remote Similarity	NPC135349
0.673	Remote Similarity	NPC326349
0.673	Remote Similarity	NPC323336
0.6728	Remote Similarity	NPC223207
0.6727	Remote Similarity	NPC477255
0.6716	Remote Similarity	NPC471487
0.6716	Remote Similarity	NPC474149
0.6714	Remote Similarity	NPC180207
0.6713	Remote Similarity	NPC213414
0.6705	Remote Similarity	NPC80514
0.6704	Remote Similarity	NPC473450
0.6689	Remote Similarity	NPC474473
0.6688	Remote Similarity	NPC56685
0.6688	Remote Similarity	NPC16188
0.6688	Remote Similarity	NPC119569
0.6687	Remote Similarity	NPC290755
0.6687	Remote Similarity	NPC304074
0.6687	Remote Similarity	NPC471771
0.6686	Remote Similarity	NPC77435
0.6686	Remote Similarity	NPC259071
0.6667	Remote Similarity	NPC326966
0.6667	Remote Similarity	NPC326079
0.6667	Remote Similarity	NPC324081
0.6667	Remote Similarity	NPC56634
0.6648	Remote Similarity	NPC65714
0.6644	Remote Similarity	NPC473360
0.6644	Remote Similarity	NPC303993
0.6644	Remote Similarity	NPC271808
0.6643	Remote Similarity	NPC38483
0.6643	Remote Similarity	NPC319950
0.6642	Remote Similarity	NPC94217
0.6642	Remote Similarity	NPC118202
0.6627	Remote Similarity	NPC191557
0.6624	Remote Similarity	NPC233702
0.6623	Remote Similarity	NPC473804
0.6622	Remote Similarity	NPC208757
0.6615	Remote Similarity	NPC327226
0.6606	Remote Similarity	NPC129486
0.6604	Remote Similarity	NPC244509
0.66	Remote Similarity	NPC235633
0.6599	Remote Similarity	NPC135173
0.6596	Remote Similarity	NPC118522
0.6596	Remote Similarity	NPC115627
0.6596	Remote Similarity	NPC169207
0.6594	Remote Similarity	NPC317254
0.6591	Remote Similarity	NPC42383
0.659	Remote Similarity	NPC8093
0.659	Remote Similarity	NPC121571
0.6588	Remote Similarity	NPC475120
0.6582	Remote Similarity	NPC262166
0.6582	Remote Similarity	NPC5194
0.6582	Remote Similarity	NPC226514
0.6582	Remote Similarity	NPC261934
0.6582	Remote Similarity	NPC258222
0.6577	Remote Similarity	NPC267237
0.6575	Remote Similarity	NPC16031
0.6575	Remote Similarity	NPC161593
0.6575	Remote Similarity	NPC78061
0.6575	Remote Similarity	NPC159987
0.6575	Remote Similarity	NPC17374
0.6575	Remote Similarity	NPC122359
0.6575	Remote Similarity	NPC145888
0.657	Remote Similarity	NPC477254
0.6569	Remote Similarity	NPC471488
0.6566	Remote Similarity	NPC274198
0.6566	Remote Similarity	NPC198254
0.6561	Remote Similarity	NPC473491
0.6557	Remote Similarity	NPC175313
0.6556	Remote Similarity	NPC474587
0.6556	Remote Similarity	NPC475132
0.6552	Remote Similarity	NPC142776
0.6549	Remote Similarity	NPC318357
0.6547	Remote Similarity	NPC82963
0.6541	Remote Similarity	NPC475432
0.6536	Remote Similarity	NPC471592
0.6528	Remote Similarity	NPC105999
0.6524	Remote Similarity	NPC63931
0.6522	Remote Similarity	NPC142599
0.6519	Remote Similarity	NPC172046
0.6515	Remote Similarity	NPC304761
0.6515	Remote Similarity	NPC150254
0.6515	Remote Similarity	NPC147000
0.6515	Remote Similarity	NPC226778
0.6513	Remote Similarity	NPC213471
0.6513	Remote Similarity	NPC475293
0.651	Remote Similarity	NPC300020
0.651	Remote Similarity	NPC33338
0.651	Remote Similarity	NPC149379
0.651	Remote Similarity	NPC302171
0.6507	Remote Similarity	NPC322366
0.6504	Remote Similarity	NPC197783
0.6503	Remote Similarity	NPC142577
0.6503	Remote Similarity	NPC136543
0.65	Remote Similarity	NPC311737
0.65	Remote Similarity	NPC476268
0.65	Remote Similarity	NPC38458
0.6497	Remote Similarity	NPC2672
0.6497	Remote Similarity	NPC64066
0.6488	Remote Similarity	NPC475532
0.6486	Remote Similarity	NPC478071
0.6481	Remote Similarity	NPC244336
0.6478	Remote Similarity	NPC202198
0.6475	Remote Similarity	NPC265146
0.6475	Remote Similarity	NPC160179
0.6471	Remote Similarity	NPC150712

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 NPC474087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	753
0.2-0.3	1222
0.3-0.4	2553
0.4-0.5	3098
0.5-0.6	1156
0.6-0.7	209
0.7-0.8	12
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
0.781	Intermediate Similarity	NPD9718	Approved
0.7368	Intermediate Similarity	NPD856	Approved
0.7368	Intermediate Similarity	NPD16	Approved
0.7302	Intermediate Similarity	NPD9610	Approved
0.7302	Intermediate Similarity	NPD9608	Approved
0.7239	Intermediate Similarity	NPD317	Approved
0.7239	Intermediate Similarity	NPD318	Approved
0.7164	Intermediate Similarity	NPD9568	Approved
0.7154	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5311	Approved
0.7071	Intermediate Similarity	NPD5310	Approved
0.7059	Intermediate Similarity	NPD316	Approved
0.705	Intermediate Similarity	NPD2561	Approved
0.705	Intermediate Similarity	NPD2562	Approved
0.6992	Remote Similarity	NPD9377	Approved
0.6992	Remote Similarity	NPD9379	Approved
0.6985	Remote Similarity	NPD9616	Approved
0.6985	Remote Similarity	NPD9613	Approved
0.6985	Remote Similarity	NPD9615	Approved
0.6966	Remote Similarity	NPD2245	Discovery
0.6948	Remote Similarity	NPD7303	Discontinued
0.6901	Remote Similarity	NPD1133	Approved
0.6901	Remote Similarity	NPD1131	Approved
0.6901	Remote Similarity	NPD1135	Approved
0.6901	Remote Similarity	NPD3055	Approved
0.6901	Remote Similarity	NPD1134	Approved
0.6901	Remote Similarity	NPD3053	Approved
0.6901	Remote Similarity	NPD1129	Approved
0.6838	Remote Similarity	NPD255	Approved
0.6838	Remote Similarity	NPD256	Approved
0.6831	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2228	Approved
0.6815	Remote Similarity	NPD2229	Approved
0.6815	Remote Similarity	NPD2234	Approved
0.6786	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9619	Approved
0.6736	Remote Similarity	NPD9621	Approved
0.6736	Remote Similarity	NPD9620	Approved
0.6712	Remote Similarity	NPD3136	Phase 2
0.6689	Remote Similarity	NPD7450	Phase 2
0.6686	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD597	Approved
0.6667	Remote Similarity	NPD601	Approved
0.6667	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD598	Approved
0.6667	Remote Similarity	NPD1445	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6642	Remote Similarity	NPD9618	Approved
0.6642	Remote Similarity	NPD9614	Approved
0.6625	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD829	Discontinued
0.6622	Remote Similarity	NPD6407	Approved
0.6622	Remote Similarity	NPD6405	Approved
0.6622	Remote Similarity	NPD1136	Approved
0.6622	Remote Similarity	NPD1130	Approved
0.6622	Remote Similarity	NPD1132	Approved
0.66	Remote Similarity	NPD5314	Approved
0.6596	Remote Similarity	NPD9384	Approved
0.6596	Remote Similarity	NPD9381	Approved
0.6585	Remote Similarity	NPD8303	Discontinued
0.6577	Remote Similarity	NPD3062	Approved
0.6577	Remote Similarity	NPD3061	Approved
0.6577	Remote Similarity	NPD3059	Approved
0.6575	Remote Similarity	NPD9569	Approved
0.6556	Remote Similarity	NPD3555	Approved
0.6556	Remote Similarity	NPD3553	Approved
0.6556	Remote Similarity	NPD3554	Approved
0.6556	Remote Similarity	NPD3552	Approved
0.6538	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5137	Approved
0.6525	Remote Similarity	NPD4093	Discontinued
0.6524	Remote Similarity	NPD2098	Approved
0.6522	Remote Similarity	NPD1791	Approved
0.6522	Remote Similarity	NPD1793	Approved
0.6519	Remote Similarity	NPD2184	Approved
0.6519	Remote Similarity	NPD1792	Phase 2
0.6519	Remote Similarity	NPD2183	Approved
0.6515	Remote Similarity	NPD309	Approved
0.6515	Remote Similarity	NPD10	Approved
0.6515	Remote Similarity	NPD314	Approved
0.6515	Remote Similarity	NPD315	Approved
0.6515	Remote Similarity	NPD310	Approved
0.6515	Remote Similarity	NPD311	Approved
0.651	Remote Similarity	NPD5745	Approved
0.6507	Remote Similarity	NPD602	Approved
0.6507	Remote Similarity	NPD599	Approved
0.6507	Remote Similarity	NPD858	Approved
0.6507	Remote Similarity	NPD7451	Discontinued
0.6507	Remote Similarity	NPD859	Approved
0.649	Remote Similarity	NPD3054	Approved
0.649	Remote Similarity	NPD2568	Approved
0.649	Remote Similarity	NPD817	Approved
0.649	Remote Similarity	NPD3052	Approved
0.649	Remote Similarity	NPD823	Approved
0.6485	Remote Similarity	NPD1168	Approved
0.6483	Remote Similarity	NPD196	Phase 1
0.6479	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1161	Approved
0.6467	Remote Similarity	NPD4652	Approved
0.6454	Remote Similarity	NPD5304	Approved
0.6454	Remote Similarity	NPD5303	Approved
0.6419	Remote Similarity	NPD4207	Discontinued
0.6414	Remote Similarity	NPD4659	Approved
0.6414	Remote Similarity	NPD9622	Approved
0.6407	Remote Similarity	NPD2017	Approved
0.6407	Remote Similarity	NPD2888	Approved
0.6407	Remote Similarity	NPD2889	Approved
0.6407	Remote Similarity	NPD2890	Approved
0.6405	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD593	Approved
0.6403	Remote Similarity	NPD595	Approved
0.6402	Remote Similarity	NPD2097	Approved
0.64	Remote Similarity	NPD259	Phase 1
0.6376	Remote Similarity	NPD5163	Phase 2
0.6376	Remote Similarity	NPD9537	Phase 1
0.6376	Remote Similarity	NPD9536	Phase 1
0.6376	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5746	Approved
0.6375	Remote Similarity	NPD7131	Phase 3
0.6364	Remote Similarity	NPD1751	Approved
0.6364	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD111	Approved
0.6338	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4103	Phase 2
0.6327	Remote Similarity	NPD1318	Phase 2
0.6323	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD7978	Discontinued
0.6316	Remote Similarity	NPD555	Phase 2
0.6301	Remote Similarity	NPD1755	Approved
0.6299	Remote Similarity	NPD1169	Approved
0.6284	Remote Similarity	NPD258	Approved
0.6284	Remote Similarity	NPD257	Approved
0.6282	Remote Similarity	NPD4256	Phase 2
0.6282	Remote Similarity	NPD4257	Approved
0.6279	Remote Similarity	NPD2933	Approved
0.6279	Remote Similarity	NPD2934	Approved
0.6273	Remote Similarity	NPD7523	Phase 3
0.6266	Remote Similarity	NPD8131	Suspended
0.626	Remote Similarity	NPD9611	Approved
0.626	Remote Similarity	NPD9609	Approved
0.626	Remote Similarity	NPD9612	Approved
0.625	Remote Similarity	NPD2668	Approved
0.625	Remote Similarity	NPD3536	Discontinued
0.625	Remote Similarity	NPD2667	Approved
0.6242	Remote Similarity	NPD2209	Approved
0.6242	Remote Similarity	NPD3060	Approved
0.6242	Remote Similarity	NPD2211	Approved
0.6234	Remote Similarity	NPD6636	Phase 3
0.6231	Remote Similarity	NPD2859	Approved
0.6231	Remote Similarity	NPD2860	Approved
0.6225	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1330	Phase 2
0.6224	Remote Similarity	NPD1759	Phase 1
0.6216	Remote Similarity	NPD1818	Approved
0.6216	Remote Similarity	NPD1817	Approved
0.6216	Remote Similarity	NPD1820	Approved
0.6216	Remote Similarity	NPD1819	Approved
0.6213	Remote Similarity	NPD7484	Phase 3
0.6213	Remote Similarity	NPD7485	Phase 3
0.6203	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5481	Discontinued
0.6185	Remote Similarity	NPD1170	Approved
0.6184	Remote Similarity	NPD1423	Approved
0.6184	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7495	Discontinued
0.6174	Remote Similarity	NPD2194	Approved
0.6174	Remote Similarity	NPD2195	Approved
0.6164	Remote Similarity	NPD4761	Approved
0.6164	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4762	Approved
0.6164	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1519	Approved
0.6154	Remote Similarity	NPD1538	Phase 1
0.6154	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1758	Phase 1
0.6154	Remote Similarity	NPD1537	Approved
0.6154	Remote Similarity	NPD9570	Approved
0.6148	Remote Similarity	NPD9244	Approved
0.6144	Remote Similarity	NPD6346	Approved
0.6136	Remote Similarity	NPD9273	Approved
0.6133	Remote Similarity	NPD3636	Approved
0.6133	Remote Similarity	NPD4208	Discontinued
0.6133	Remote Similarity	NPD3637	Approved
0.6133	Remote Similarity	NPD3635	Approved
0.6131	Remote Similarity	NPD8031	Discontinued
0.6125	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3845	Phase 1
0.6125	Remote Similarity	NPD2120	Phase 2
0.6122	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3072	Approved
0.6122	Remote Similarity	NPD3073	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