NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.97
Volume:	205.432
LogP:	2.049
LogD:	1.674
LogS:	-2.126
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.491
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	2.0926741854054853e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	97.96894073486328%
Volume Distribution (VD):	0.268
Pgp-substrate:	2.574859142303467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.519
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.218
CYP2C9-substrate:	0.441
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.352
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	2.062
Half-life (T1/2):	0.911

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.262
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.576
Skin Sensitization:	0.956
Carcinogencity:	0.716
Eye Corrosion:	0.349
Eye Irritation:	0.951
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC117759

Natural Product ID:	NPC117759
*Common Name:**	(E)-4-(3-Bromo-4,5-Dihydroxyphenyl)But-3-En-2-One
IUPAC Name:	(E)-4-(3-bromo-4,5-dihydroxyphenyl)but-3-en-2-one
Synonyms:
Standard InCHIKey:	MYKFZEDOPLREOR-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C10H9BrO3/c1-6(12)2-3-7-4-8(11)10(14)9(13)5-7/h2-5,13-14H,1H3/b3-2+
SMILES:	CC(=O)/C=C/c1cc(c(c(c1)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240090
PubChem CID:	44437164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic 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
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17765551]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18088100]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18324823]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21875052]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	9670.0	nM	PMID[481462]

☑ 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 NPC117759 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	321
0.1-0.2	3041
0.2-0.3	9405
0.3-0.4	10639
0.4-0.5	6833
0.5-0.6	9816
0.6-0.7	2378
0.7-0.8	242
0.8-0.85	17
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC142776
0.8655	High Similarity	NPC38483
0.8649	High Similarity	NPC79672
0.8559	High Similarity	NPC79844
0.8525	High Similarity	NPC229213
0.8482	Intermediate Similarity	NPC52087
0.8455	Intermediate Similarity	NPC474169
0.8455	Intermediate Similarity	NPC473572
0.8443	Intermediate Similarity	NPC136543
0.8413	Intermediate Similarity	NPC214553
0.824	Intermediate Similarity	NPC137117
0.8175	Intermediate Similarity	NPC220311
0.8174	Intermediate Similarity	NPC19149
0.8174	Intermediate Similarity	NPC294902
0.8174	Intermediate Similarity	NPC1075
0.8174	Intermediate Similarity	NPC1786
0.813	Intermediate Similarity	NPC474146
0.811	Intermediate Similarity	NPC43706
0.808	Intermediate Similarity	NPC47790
0.8062	Intermediate Similarity	NPC474536
0.8062	Intermediate Similarity	NPC85049
0.8047	Intermediate Similarity	NPC473708
0.8047	Intermediate Similarity	NPC474147
0.8018	Intermediate Similarity	NPC107522
0.8015	Intermediate Similarity	NPC474135
0.8	Intermediate Similarity	NPC226493
0.8	Intermediate Similarity	NPC160081
0.7984	Intermediate Similarity	NPC150929
0.7983	Intermediate Similarity	NPC226250
0.7983	Intermediate Similarity	NPC297657
0.797	Intermediate Similarity	NPC199089
0.7955	Intermediate Similarity	NPC471328
0.7941	Intermediate Similarity	NPC250597
0.7923	Intermediate Similarity	NPC474614
0.7917	Intermediate Similarity	NPC51698
0.7881	Intermediate Similarity	NPC471495
0.7879	Intermediate Similarity	NPC300678
0.7876	Intermediate Similarity	NPC109955
0.7869	Intermediate Similarity	NPC50782
0.7851	Intermediate Similarity	NPC95381
0.7838	Intermediate Similarity	NPC181709
0.7807	Intermediate Similarity	NPC131587
0.7803	Intermediate Similarity	NPC43613
0.7787	Intermediate Similarity	NPC33749
0.7787	Intermediate Similarity	NPC328593
0.7787	Intermediate Similarity	NPC261453
0.7769	Intermediate Similarity	NPC13004
0.7759	Intermediate Similarity	NPC196479
0.775	Intermediate Similarity	NPC473358
0.7742	Intermediate Similarity	NPC150919
0.7739	Intermediate Similarity	NPC223393
0.7724	Intermediate Similarity	NPC233669
0.7724	Intermediate Similarity	NPC474967
0.7705	Intermediate Similarity	NPC76400
0.7692	Intermediate Similarity	NPC120719
0.7687	Intermediate Similarity	NPC244890
0.7687	Intermediate Similarity	NPC163560
0.7672	Intermediate Similarity	NPC110764
0.7661	Intermediate Similarity	NPC277394
0.7661	Intermediate Similarity	NPC281277
0.7661	Intermediate Similarity	NPC299252
0.7661	Intermediate Similarity	NPC61062
0.7642	Intermediate Similarity	NPC217472
0.763	Intermediate Similarity	NPC312155
0.763	Intermediate Similarity	NPC245386
0.7626	Intermediate Similarity	NPC184632
0.7623	Intermediate Similarity	NPC131530
0.7606	Intermediate Similarity	NPC178097
0.76	Intermediate Similarity	NPC65791
0.76	Intermediate Similarity	NPC39793
0.7578	Intermediate Similarity	NPC7830
0.7563	Intermediate Similarity	NPC477814
0.7552	Intermediate Similarity	NPC473608
0.7544	Intermediate Similarity	NPC257182
0.7542	Intermediate Similarity	NPC471511
0.7542	Intermediate Similarity	NPC12278
0.754	Intermediate Similarity	NPC203124
0.754	Intermediate Similarity	NPC164706
0.754	Intermediate Similarity	NPC70744
0.754	Intermediate Similarity	NPC107588
0.754	Intermediate Similarity	NPC309434
0.754	Intermediate Similarity	NPC137537
0.754	Intermediate Similarity	NPC272471
0.7536	Intermediate Similarity	NPC160932
0.7521	Intermediate Similarity	NPC54543
0.7519	Intermediate Similarity	NPC296202
0.7519	Intermediate Similarity	NPC105702
0.7518	Intermediate Similarity	NPC224663
0.75	Intermediate Similarity	NPC14007
0.75	Intermediate Similarity	NPC189844
0.75	Intermediate Similarity	NPC109083
0.75	Intermediate Similarity	NPC60962
0.75	Intermediate Similarity	NPC269843
0.75	Intermediate Similarity	NPC224814
0.7479	Intermediate Similarity	NPC239291
0.7464	Intermediate Similarity	NPC156356
0.7462	Intermediate Similarity	NPC84606
0.746	Intermediate Similarity	NPC278652
0.7459	Intermediate Similarity	NPC222084
0.7458	Intermediate Similarity	NPC477802
0.7458	Intermediate Similarity	NPC477801
0.7456	Intermediate Similarity	NPC32977
0.7456	Intermediate Similarity	NPC81010
0.7429	Intermediate Similarity	NPC89341
0.7422	Intermediate Similarity	NPC202474
0.7419	Intermediate Similarity	NPC59387
0.7419	Intermediate Similarity	NPC264558
0.7419	Intermediate Similarity	NPC148969
0.7414	Intermediate Similarity	NPC201967
0.7405	Intermediate Similarity	NPC213414
0.7402	Intermediate Similarity	NPC275519
0.7391	Intermediate Similarity	NPC286006
0.7385	Intermediate Similarity	NPC219444
0.7385	Intermediate Similarity	NPC286573
0.7385	Intermediate Similarity	NPC114298
0.7377	Intermediate Similarity	NPC233731
0.7377	Intermediate Similarity	NPC246358
0.7377	Intermediate Similarity	NPC228343
0.7377	Intermediate Similarity	NPC7097
0.7377	Intermediate Similarity	NPC36108
0.7377	Intermediate Similarity	NPC254833
0.7373	Intermediate Similarity	NPC94343
0.7368	Intermediate Similarity	NPC78061
0.7368	Intermediate Similarity	NPC122359
0.7368	Intermediate Similarity	NPC159987
0.7364	Intermediate Similarity	NPC470848
0.7364	Intermediate Similarity	NPC470849
0.7364	Intermediate Similarity	NPC204466
0.7364	Intermediate Similarity	NPC158949
0.7364	Intermediate Similarity	NPC227976
0.7355	Intermediate Similarity	NPC176527
0.735	Intermediate Similarity	NPC130193
0.7344	Intermediate Similarity	NPC141791
0.7344	Intermediate Similarity	NPC100395
0.7344	Intermediate Similarity	NPC263386
0.7344	Intermediate Similarity	NPC241634
0.7338	Intermediate Similarity	NPC271942
0.7328	Intermediate Similarity	NPC106659
0.7328	Intermediate Similarity	NPC238810
0.7328	Intermediate Similarity	NPC164778
0.7328	Intermediate Similarity	NPC160900
0.7328	Intermediate Similarity	NPC257976
0.7328	Intermediate Similarity	NPC18984
0.7328	Intermediate Similarity	NPC242372
0.7328	Intermediate Similarity	NPC4181
0.7328	Intermediate Similarity	NPC229084
0.7308	Intermediate Similarity	NPC70752
0.7305	Intermediate Similarity	NPC118794
0.7302	Intermediate Similarity	NPC278102
0.7295	Intermediate Similarity	NPC105727
0.7295	Intermediate Similarity	NPC233835
0.7295	Intermediate Similarity	NPC114392
0.7295	Intermediate Similarity	NPC34864
0.7295	Intermediate Similarity	NPC58427
0.7293	Intermediate Similarity	NPC134219
0.7288	Intermediate Similarity	NPC253746
0.7287	Intermediate Similarity	NPC2058
0.7287	Intermediate Similarity	NPC180207
0.7273	Intermediate Similarity	NPC312404
0.7273	Intermediate Similarity	NPC273686
0.7273	Intermediate Similarity	NPC109346
0.7266	Intermediate Similarity	NPC212743
0.7258	Intermediate Similarity	NPC470355
0.7258	Intermediate Similarity	NPC78918
0.7258	Intermediate Similarity	NPC156840
0.7258	Intermediate Similarity	NPC173746
0.7258	Intermediate Similarity	NPC257124
0.7258	Intermediate Similarity	NPC8547
0.7258	Intermediate Similarity	NPC139617
0.7252	Intermediate Similarity	NPC86900
0.7236	Intermediate Similarity	NPC62258
0.7236	Intermediate Similarity	NPC55617
0.7236	Intermediate Similarity	NPC473372
0.7231	Intermediate Similarity	NPC294361
0.7231	Intermediate Similarity	NPC236520
0.7227	Intermediate Similarity	NPC472585
0.7222	Intermediate Similarity	NPC294941
0.7218	Intermediate Similarity	NPC197832
0.7213	Intermediate Similarity	NPC34715
0.7209	Intermediate Similarity	NPC299406
0.7207	Intermediate Similarity	NPC248817
0.7207	Intermediate Similarity	NPC150837
0.7206	Intermediate Similarity	NPC11449
0.72	Intermediate Similarity	NPC231717
0.7197	Intermediate Similarity	NPC105999
0.7197	Intermediate Similarity	NPC306100
0.7188	Intermediate Similarity	NPC280001
0.7188	Intermediate Similarity	NPC610
0.7188	Intermediate Similarity	NPC200988
0.7188	Intermediate Similarity	NPC175799
0.7188	Intermediate Similarity	NPC145023
0.7185	Intermediate Similarity	NPC55113
0.7177	Intermediate Similarity	NPC79793
0.7177	Intermediate Similarity	NPC120982
0.7177	Intermediate Similarity	NPC471487
0.7177	Intermediate Similarity	NPC147634
0.7177	Intermediate Similarity	NPC226401
0.7177	Intermediate Similarity	NPC174096
0.7176	Intermediate Similarity	NPC147654
0.7172	Intermediate Similarity	NPC88896

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 NPC117759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1187
0.2-0.3	2024
0.3-0.4	3244
0.4-0.5	1583
0.5-0.6	662
0.6-0.7	105
0.7-0.8	5
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
0.7377	Intermediate Similarity	NPD3021	Approved
0.7377	Intermediate Similarity	NPD3022	Approved
0.7328	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD9244	Approved
0.7117	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD9377	Approved
0.7063	Intermediate Similarity	NPD9379	Approved
0.6985	Remote Similarity	NPD9494	Approved
0.6905	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2934	Approved
0.6864	Remote Similarity	NPD2933	Approved
0.686	Remote Similarity	NPD1242	Phase 1
0.6807	Remote Similarity	NPD2859	Approved
0.6807	Remote Similarity	NPD2860	Approved
0.6807	Remote Similarity	NPD844	Approved
0.6794	Remote Similarity	NPD5536	Phase 2
0.6777	Remote Similarity	NPD3020	Approved
0.675	Remote Similarity	NPD288	Approved
0.6741	Remote Similarity	NPD9269	Phase 2
0.6738	Remote Similarity	NPD943	Approved
0.6721	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6643	Remote Similarity	NPD9718	Approved
0.6642	Remote Similarity	NPD9381	Approved
0.6642	Remote Similarity	NPD9384	Approved
0.6573	Remote Similarity	NPD230	Phase 1
0.6569	Remote Similarity	NPD9622	Approved
0.6552	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD846	Approved
0.6532	Remote Similarity	NPD940	Approved
0.6522	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9569	Approved
0.6496	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3055	Approved
0.6475	Remote Similarity	NPD3053	Approved
0.6466	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7266	Discontinued
0.6444	Remote Similarity	NPD1357	Approved
0.6444	Remote Similarity	NPD9268	Approved
0.6443	Remote Similarity	NPD8166	Discontinued
0.6434	Remote Similarity	NPD259	Phase 1
0.6433	Remote Similarity	NPD2296	Approved
0.6429	Remote Similarity	NPD9620	Approved
0.6429	Remote Similarity	NPD9621	Approved
0.6429	Remote Similarity	NPD9619	Approved
0.6408	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1358	Approved
0.6403	Remote Similarity	NPD5310	Approved
0.6403	Remote Similarity	NPD5311	Approved
0.6397	Remote Similarity	NPD3019	Approved
0.6397	Remote Similarity	NPD2932	Approved
0.6393	Remote Similarity	NPD1809	Phase 2
0.6389	Remote Similarity	NPD826	Approved
0.6389	Remote Similarity	NPD825	Approved
0.637	Remote Similarity	NPD9545	Approved
0.6364	Remote Similarity	NPD845	Approved
0.6356	Remote Similarity	NPD9094	Approved
0.6349	Remote Similarity	NPD9500	Approved
0.6345	Remote Similarity	NPD274	Approved
0.6345	Remote Similarity	NPD555	Phase 2
0.6345	Remote Similarity	NPD275	Approved
0.6328	Remote Similarity	NPD1445	Approved
0.6328	Remote Similarity	NPD3134	Approved
0.6328	Remote Similarity	NPD1444	Approved
0.6311	Remote Similarity	NPD9296	Approved
0.6299	Remote Similarity	NPD9608	Approved
0.6299	Remote Similarity	NPD9610	Approved
0.6294	Remote Similarity	NPD3027	Phase 3
0.6294	Remote Similarity	NPD9537	Phase 1
0.6294	Remote Similarity	NPD9536	Phase 1
0.6277	Remote Similarity	NPD4626	Approved
0.625	Remote Similarity	NPD598	Approved
0.625	Remote Similarity	NPD3145	Approved
0.625	Remote Similarity	NPD3144	Approved
0.625	Remote Similarity	NPD601	Approved
0.625	Remote Similarity	NPD597	Approved
0.6241	Remote Similarity	NPD5283	Phase 1
0.6231	Remote Similarity	NPD9266	Approved
0.6231	Remote Similarity	NPD74	Approved
0.6224	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD9493	Approved
0.6207	Remote Similarity	NPD1136	Approved
0.6207	Remote Similarity	NPD1132	Approved
0.6207	Remote Similarity	NPD1130	Approved
0.6207	Remote Similarity	NPD2674	Phase 3
0.6204	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD3092	Approved
0.6187	Remote Similarity	NPD1201	Approved
0.6184	Remote Similarity	NPD6190	Approved
0.6183	Remote Similarity	NPD4750	Phase 3
0.6183	Remote Similarity	NPD1792	Phase 2
0.6164	Remote Similarity	NPD1558	Phase 1
0.6154	Remote Similarity	NPD9264	Approved
0.6154	Remote Similarity	NPD9267	Approved
0.6154	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9263	Approved
0.6148	Remote Similarity	NPD256	Approved
0.6148	Remote Similarity	NPD255	Approved
0.6138	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD3091	Approved
0.6127	Remote Similarity	NPD1470	Approved
0.6126	Remote Similarity	NPD9087	Approved
0.6122	Remote Similarity	NPD447	Suspended
0.6119	Remote Similarity	NPD2228	Approved
0.6119	Remote Similarity	NPD1241	Discontinued
0.6119	Remote Similarity	NPD2229	Approved
0.6119	Remote Similarity	NPD2234	Approved
0.6107	Remote Similarity	NPD2684	Approved
0.6104	Remote Similarity	NPD1511	Approved
0.6098	Remote Similarity	NPD4010	Discontinued
0.609	Remote Similarity	NPD711	Discontinued
0.6074	Remote Similarity	NPD9618	Approved
0.6074	Remote Similarity	NPD9614	Approved
0.6071	Remote Similarity	NPD422	Phase 1
0.6067	Remote Similarity	NPD9570	Approved
0.6063	Remote Similarity	NPD3028	Approved
0.6061	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD3062	Approved
0.6054	Remote Similarity	NPD3061	Approved
0.6054	Remote Similarity	NPD1613	Approved
0.6054	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD3620	Phase 2
0.6054	Remote Similarity	NPD3059	Approved
0.6053	Remote Similarity	NPD9088	Approved
0.6045	Remote Similarity	NPD7635	Approved
0.6043	Remote Similarity	NPD4059	Approved
0.6032	Remote Similarity	NPD9273	Approved
0.6031	Remote Similarity	NPD2342	Discontinued
0.6031	Remote Similarity	NPD290	Approved
0.6029	Remote Similarity	NPD6671	Approved
0.6026	Remote Similarity	NPD1512	Approved
0.6025	Remote Similarity	NPD4288	Approved
0.6014	Remote Similarity	NPD3094	Phase 2
0.6014	Remote Similarity	NPD1164	Approved
0.6013	Remote Similarity	NPD3455	Phase 2
0.6013	Remote Similarity	NPD824	Approved
0.6	Remote Similarity	NPD3496	Discontinued
0.6	Remote Similarity	NPD1169	Approved
0.5986	Remote Similarity	NPD1755	Approved
0.5985	Remote Similarity	NPD9568	Approved
0.5973	Remote Similarity	NPD823	Approved
0.5973	Remote Similarity	NPD5314	Approved
0.5973	Remote Similarity	NPD817	Approved
0.5971	Remote Similarity	NPD5691	Approved
0.5971	Remote Similarity	NPD4093	Discontinued
0.5956	Remote Similarity	NPD1793	Approved
0.5956	Remote Similarity	NPD1791	Approved
0.5954	Remote Similarity	NPD968	Approved
0.5949	Remote Similarity	NPD1653	Approved
0.5946	Remote Similarity	NPD4060	Phase 1
0.5942	Remote Similarity	NPD9616	Approved
0.5942	Remote Similarity	NPD9613	Approved
0.5942	Remote Similarity	NPD9615	Approved
0.5931	Remote Similarity	NPD5736	Approved
0.5929	Remote Similarity	NPD2286	Discontinued
0.5929	Remote Similarity	NPD1751	Approved
0.5926	Remote Similarity	NPD7843	Approved
0.5912	Remote Similarity	NPD7157	Approved
0.5901	Remote Similarity	NPD1934	Approved
0.5899	Remote Similarity	NPD316	Approved
0.5897	Remote Similarity	NPD4357	Discontinued
0.5894	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.589	Remote Similarity	NPD3882	Suspended
0.5887	Remote Similarity	NPD3026	Approved
0.5887	Remote Similarity	NPD3023	Approved
0.5878	Remote Similarity	NPD9697	Approved
0.5874	Remote Similarity	NPD2982	Phase 2
0.5874	Remote Similarity	NPD2983	Phase 2
0.5874	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD2801	Approved
0.5864	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.586	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD1651	Approved
0.5857	Remote Similarity	NPD3024	Approved
0.5857	Remote Similarity	NPD3025	Approved
0.5855	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD2935	Discontinued
0.5854	Remote Similarity	NPD9258	Approved
0.5854	Remote Similarity	NPD9256	Approved
0.5852	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.585	Remote Similarity	NPD7095	Approved
0.5847	Remote Similarity	NPD9089	Approved
0.5846	Remote Similarity	NPD9261	Approved
0.5839	Remote Similarity	NPD475	Phase 2
0.5839	Remote Similarity	NPD9281	Approved
0.5839	Remote Similarity	NPD1240	Approved
0.5833	Remote Similarity	NPD1283	Approved
0.5827	Remote Similarity	NPD317	Approved
0.5827	Remote Similarity	NPD16	Approved
0.5827	Remote Similarity	NPD856	Approved
0.5827	Remote Similarity	NPD318	Approved
0.5826	Remote Similarity	NPD9294	Approved
0.5817	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD3095	Discontinued
0.5816	Remote Similarity	NPD1778	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