NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	401.91
Volume:	291.497
LogP:	3.685
LogD:	3.034
LogS:	-3.567
# Rotatable Bonds:	3
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	2.542
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	1.5463308955077082e-05
Pgp-inhibitor:	0.847
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	99.57783508300781%
Volume Distribution (VD):	0.708
Pgp-substrate:	0.6984591484069824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.811
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.51
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.452
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.495
CYP3A4-inhibitor:	0.127
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	4.087
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.424
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.462
Skin Sensitization:	0.965
Carcinogencity:	0.077
Eye Corrosion:	0.036
Eye Irritation:	0.943
Respiratory Toxicity:	0.062

Download Data

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

Natural Product: NPC38483

Natural Product ID:	NPC38483
*Common Name:**	1,2-Bis(3-Bromo-4,5-Dihydroxyphenyl)Ethane
IUPAC Name:	3-bromo-5-[2-(3-bromo-4,5-dihydroxyphenyl)ethyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	IFYFPCNWTZBOEQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12Br2O4/c15-9-3-7(5-11(17)13(9)19)1-2-8-4-10(16)14(20)12(18)6-8/h3-6,17-20H,1-2H2
SMILES:	C(Cc1cc(c(c(c1)O)O)Br)c1cc(c(c(c1)O)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241792
PubChem CID:	44437166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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	=	19640.0	nM	PMID[524744]

☑ 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 NPC38483 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	543
0.1-0.2	2566
0.2-0.3	11344
0.3-0.4	9288
0.4-0.5	7347
0.5-0.6	8638
0.6-0.7	2626
0.7-0.8	292
0.8-0.85	32
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC220311
0.9098	High Similarity	NPC474614
0.8934	High Similarity	NPC13004
0.8908	High Similarity	NPC136543
0.888	High Similarity	NPC300678
0.8839	High Similarity	NPC471495
0.881	High Similarity	NPC163560
0.881	High Similarity	NPC471328
0.881	High Similarity	NPC244890
0.88	High Similarity	NPC43613
0.874	High Similarity	NPC312155
0.8718	High Similarity	NPC79844
0.8689	High Similarity	NPC137117
0.8684	High Similarity	NPC473358
0.8655	High Similarity	NPC117759
0.8607	High Similarity	NPC84606
0.8605	High Similarity	NPC224663
0.8596	High Similarity	NPC54543
0.856	High Similarity	NPC150929
0.8538	High Similarity	NPC156356
0.8525	High Similarity	NPC219444
0.8525	High Similarity	NPC229213
0.8482	Intermediate Similarity	NPC471511
0.8473	Intermediate Similarity	NPC160932
0.8455	Intermediate Similarity	NPC474169
0.8455	Intermediate Similarity	NPC473572
0.845	Intermediate Similarity	NPC245386
0.843	Intermediate Similarity	NPC474146
0.8374	Intermediate Similarity	NPC47790
0.8346	Intermediate Similarity	NPC118794
0.8346	Intermediate Similarity	NPC89341
0.832	Intermediate Similarity	NPC142776
0.8254	Intermediate Similarity	NPC43706
0.8246	Intermediate Similarity	NPC239291
0.8214	Intermediate Similarity	NPC223393
0.8203	Intermediate Similarity	NPC85049
0.8189	Intermediate Similarity	NPC474147
0.8189	Intermediate Similarity	NPC473708
0.8162	Intermediate Similarity	NPC109346
0.814	Intermediate Similarity	NPC160081
0.814	Intermediate Similarity	NPC226493
0.812	Intermediate Similarity	NPC254833
0.812	Intermediate Similarity	NPC271942
0.812	Intermediate Similarity	NPC228343
0.8062	Intermediate Similarity	NPC474536
0.8051	Intermediate Similarity	NPC174096
0.8051	Intermediate Similarity	NPC147634
0.8051	Intermediate Similarity	NPC226401
0.8051	Intermediate Similarity	NPC471487
0.8051	Intermediate Similarity	NPC79793
0.8051	Intermediate Similarity	NPC120982
0.8043	Intermediate Similarity	NPC88896
0.8036	Intermediate Similarity	NPC109955
0.8	Intermediate Similarity	NPC471488
0.7983	Intermediate Similarity	NPC257430
0.7983	Intermediate Similarity	NPC268032
0.7983	Intermediate Similarity	NPC187583
0.7983	Intermediate Similarity	NPC179002
0.7966	Intermediate Similarity	NPC55617
0.7966	Intermediate Similarity	NPC62258
0.7966	Intermediate Similarity	NPC473372
0.7934	Intermediate Similarity	NPC94217
0.7923	Intermediate Similarity	NPC105702
0.792	Intermediate Similarity	NPC471486
0.7881	Intermediate Similarity	NPC233835
0.7872	Intermediate Similarity	NPC7398
0.7869	Intermediate Similarity	NPC50782
0.7857	Intermediate Similarity	NPC274678
0.7851	Intermediate Similarity	NPC471485
0.7851	Intermediate Similarity	NPC33244
0.7851	Intermediate Similarity	NPC76400
0.7845	Intermediate Similarity	NPC120719
0.7833	Intermediate Similarity	NPC297657
0.7826	Intermediate Similarity	NPC110764
0.7795	Intermediate Similarity	NPC296202
0.7787	Intermediate Similarity	NPC120280
0.7759	Intermediate Similarity	NPC196479
0.7744	Intermediate Similarity	NPC303011
0.7731	Intermediate Similarity	NPC105727
0.7731	Intermediate Similarity	NPC34864
0.7731	Intermediate Similarity	NPC114392
0.7731	Intermediate Similarity	NPC58427
0.7724	Intermediate Similarity	NPC472893
0.7721	Intermediate Similarity	NPC168680
0.7717	Intermediate Similarity	NPC7830
0.7712	Intermediate Similarity	NPC477814
0.771	Intermediate Similarity	NPC214553
0.7699	Intermediate Similarity	NPC107522
0.7692	Intermediate Similarity	NPC12278
0.7674	Intermediate Similarity	NPC213414
0.7652	Intermediate Similarity	NPC131587
0.7647	Intermediate Similarity	NPC176527
0.7638	Intermediate Similarity	NPC227976
0.7626	Intermediate Similarity	NPC184632
0.76	Intermediate Similarity	NPC277588
0.76	Intermediate Similarity	NPC145023
0.76	Intermediate Similarity	NPC293619
0.76	Intermediate Similarity	NPC610
0.76	Intermediate Similarity	NPC200988
0.76	Intermediate Similarity	NPC175799
0.7597	Intermediate Similarity	NPC105999
0.7594	Intermediate Similarity	NPC473724
0.7589	Intermediate Similarity	NPC45040
0.7551	Intermediate Similarity	NPC474535
0.7542	Intermediate Similarity	NPC52087
0.754	Intermediate Similarity	NPC470626
0.754	Intermediate Similarity	NPC144343
0.754	Intermediate Similarity	NPC86198
0.752	Intermediate Similarity	NPC299252
0.752	Intermediate Similarity	NPC61062
0.752	Intermediate Similarity	NPC277394
0.75	Intermediate Similarity	NPC152947
0.75	Intermediate Similarity	NPC475697
0.7481	Intermediate Similarity	NPC474135
0.748	Intermediate Similarity	NPC191866
0.748	Intermediate Similarity	NPC70084
0.748	Intermediate Similarity	NPC51698
0.748	Intermediate Similarity	NPC470214
0.748	Intermediate Similarity	NPC471179
0.748	Intermediate Similarity	NPC109371
0.748	Intermediate Similarity	NPC470215
0.746	Intermediate Similarity	NPC278652
0.7459	Intermediate Similarity	NPC222084
0.7458	Intermediate Similarity	NPC477802
0.7458	Intermediate Similarity	NPC477801
0.7456	Intermediate Similarity	NPC151715
0.7456	Intermediate Similarity	NPC76938
0.7456	Intermediate Similarity	NPC128062
0.7445	Intermediate Similarity	NPC199089
0.7424	Intermediate Similarity	NPC134219
0.7422	Intermediate Similarity	NPC472071
0.7422	Intermediate Similarity	NPC34634
0.7422	Intermediate Similarity	NPC227217
0.7422	Intermediate Similarity	NPC475245
0.7422	Intermediate Similarity	NPC95614
0.7422	Intermediate Similarity	NPC165133
0.7422	Intermediate Similarity	NPC232316
0.7422	Intermediate Similarity	NPC56214
0.7422	Intermediate Similarity	NPC242885
0.7422	Intermediate Similarity	NPC265454
0.7422	Intermediate Similarity	NPC117780
0.7419	Intermediate Similarity	NPC59387
0.7417	Intermediate Similarity	NPC1786
0.7417	Intermediate Similarity	NPC1075
0.7417	Intermediate Similarity	NPC294902
0.7414	Intermediate Similarity	NPC32674
0.7395	Intermediate Similarity	NPC30506
0.7395	Intermediate Similarity	NPC79672
0.7391	Intermediate Similarity	NPC32714
0.7391	Intermediate Similarity	NPC26244
0.7388	Intermediate Similarity	NPC99280
0.7388	Intermediate Similarity	NPC474091
0.7388	Intermediate Similarity	NPC478071
0.7368	Intermediate Similarity	NPC122359
0.7368	Intermediate Similarity	NPC159987
0.7368	Intermediate Similarity	NPC78061
0.7364	Intermediate Similarity	NPC98305
0.7364	Intermediate Similarity	NPC470414
0.7364	Intermediate Similarity	NPC24125
0.7364	Intermediate Similarity	NPC207613
0.736	Intermediate Similarity	NPC115803
0.735	Intermediate Similarity	NPC92730
0.7344	Intermediate Similarity	NPC281298
0.7344	Intermediate Similarity	NPC217174
0.7344	Intermediate Similarity	NPC141791
0.7344	Intermediate Similarity	NPC268572
0.7344	Intermediate Similarity	NPC310338
0.7344	Intermediate Similarity	NPC176893
0.7344	Intermediate Similarity	NPC263386
0.7333	Intermediate Similarity	NPC38980
0.7333	Intermediate Similarity	NPC475735
0.7333	Intermediate Similarity	NPC11449
0.7328	Intermediate Similarity	NPC132271
0.7328	Intermediate Similarity	NPC292730
0.7328	Intermediate Similarity	NPC473388
0.7328	Intermediate Similarity	NPC216520
0.7328	Intermediate Similarity	NPC82664
0.7323	Intermediate Similarity	NPC86947
0.7313	Intermediate Similarity	NPC55113
0.7308	Intermediate Similarity	NPC473853
0.7308	Intermediate Similarity	NPC324571
0.7308	Intermediate Similarity	NPC38996
0.7308	Intermediate Similarity	NPC184651
0.7308	Intermediate Similarity	NPC113865
0.7308	Intermediate Similarity	NPC343720
0.7308	Intermediate Similarity	NPC470212
0.7308	Intermediate Similarity	NPC237667
0.7308	Intermediate Similarity	NPC312675
0.7308	Intermediate Similarity	NPC160380
0.7308	Intermediate Similarity	NPC262156
0.7308	Intermediate Similarity	NPC54872
0.7308	Intermediate Similarity	NPC39029
0.7288	Intermediate Similarity	NPC294741
0.7287	Intermediate Similarity	NPC180207
0.728	Intermediate Similarity	NPC264558
0.728	Intermediate Similarity	NPC148969
0.7273	Intermediate Similarity	NPC19149
0.7273	Intermediate Similarity	NPC54765
0.7266	Intermediate Similarity	NPC122009
0.7266	Intermediate Similarity	NPC275519

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 NPC38483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	475
0.1-0.2	1101
0.2-0.3	2141
0.3-0.4	3054
0.4-0.5	1549
0.5-0.6	698
0.6-0.7	118
0.7-0.8	12
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.812	Intermediate Similarity	NPD3022	Approved
0.812	Intermediate Similarity	NPD3021	Approved
0.7391	Intermediate Similarity	NPD2859	Approved
0.7391	Intermediate Similarity	NPD2860	Approved
0.735	Intermediate Similarity	NPD3020	Approved
0.7304	Intermediate Similarity	NPD2934	Approved
0.7304	Intermediate Similarity	NPD2933	Approved
0.7258	Intermediate Similarity	NPD228	Approved
0.725	Intermediate Similarity	NPD9244	Approved
0.72	Intermediate Similarity	NPD9377	Approved
0.72	Intermediate Similarity	NPD9379	Approved
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.704	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD844	Approved
0.6934	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD288	Approved
0.6889	Remote Similarity	NPD5310	Approved
0.6889	Remote Similarity	NPD5311	Approved
0.6884	Remote Similarity	NPD3027	Phase 3
0.6875	Remote Similarity	NPD5283	Phase 1
0.686	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3053	Approved
0.6838	Remote Similarity	NPD3055	Approved
0.6815	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD111	Approved
0.6767	Remote Similarity	NPD9381	Approved
0.6767	Remote Similarity	NPD9384	Approved
0.6763	Remote Similarity	NPD9718	Approved
0.6741	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1613	Approved
0.6738	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD943	Approved
0.6714	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4010	Discontinued
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6667	Remote Similarity	NPD1809	Phase 2
0.6642	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3062	Approved
0.662	Remote Similarity	NPD3059	Approved
0.662	Remote Similarity	NPD3061	Approved
0.6585	Remote Similarity	NPD3028	Approved
0.6569	Remote Similarity	NPD9622	Approved
0.6562	Remote Similarity	NPD4750	Phase 3
0.6562	Remote Similarity	NPD1792	Phase 2
0.6544	Remote Similarity	NPD3092	Approved
0.6538	Remote Similarity	NPD7635	Approved
0.6528	Remote Similarity	NPD5314	Approved
0.6519	Remote Similarity	NPD2286	Discontinued
0.6507	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3620	Phase 2
0.6503	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1558	Phase 1
0.65	Remote Similarity	NPD9569	Approved
0.65	Remote Similarity	NPD845	Approved
0.6493	Remote Similarity	NPD3091	Approved
0.6489	Remote Similarity	NPD2229	Approved
0.6489	Remote Similarity	NPD2234	Approved
0.6489	Remote Similarity	NPD2228	Approved
0.6475	Remote Similarity	NPD3094	Phase 2
0.6457	Remote Similarity	NPD1445	Approved
0.6457	Remote Similarity	NPD1444	Approved
0.6449	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4093	Discontinued
0.6438	Remote Similarity	NPD1169	Approved
0.6429	Remote Similarity	NPD9619	Approved
0.6429	Remote Similarity	NPD9620	Approved
0.6429	Remote Similarity	NPD9621	Approved
0.6408	Remote Similarity	NPD9536	Phase 1
0.6408	Remote Similarity	NPD9537	Phase 1
0.6397	Remote Similarity	NPD3019	Approved
0.6397	Remote Similarity	NPD2932	Approved
0.6397	Remote Similarity	NPD4059	Approved
0.6389	Remote Similarity	NPD826	Approved
0.6389	Remote Similarity	NPD825	Approved
0.6377	Remote Similarity	NPD9269	Phase 2
0.6357	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7266	Discontinued
0.6349	Remote Similarity	NPD9500	Approved
0.6345	Remote Similarity	NPD275	Approved
0.6345	Remote Similarity	NPD274	Approved
0.6329	Remote Similarity	NPD2296	Approved
0.6328	Remote Similarity	NPD968	Approved
0.6319	Remote Similarity	NPD259	Phase 1
0.6301	Remote Similarity	NPD823	Approved
0.6301	Remote Similarity	NPD817	Approved
0.6299	Remote Similarity	NPD9608	Approved
0.6299	Remote Similarity	NPD9610	Approved
0.6296	Remote Similarity	NPD5536	Phase 2
0.6277	Remote Similarity	NPD3095	Discontinued
0.6277	Remote Similarity	NPD1751	Approved
0.6276	Remote Similarity	NPD4060	Phase 1
0.6269	Remote Similarity	NPD6671	Approved
0.625	Remote Similarity	NPD598	Approved
0.625	Remote Similarity	NPD601	Approved
0.625	Remote Similarity	NPD597	Approved
0.6233	Remote Similarity	NPD555	Phase 2
0.6231	Remote Similarity	NPD2684	Approved
0.6226	Remote Similarity	NPD4288	Approved
0.6225	Remote Similarity	NPD8166	Discontinued
0.6218	Remote Similarity	NPD9094	Approved
0.6212	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2674	Phase 3
0.6207	Remote Similarity	NPD1136	Approved
0.6207	Remote Similarity	NPD1132	Approved
0.6207	Remote Similarity	NPD1130	Approved
0.6204	Remote Similarity	NPD1357	Approved
0.6197	Remote Similarity	NPD6584	Phase 3
0.6194	Remote Similarity	NPD497	Approved
0.6194	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD1201	Approved
0.6187	Remote Similarity	NPD1610	Phase 2
0.6183	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7095	Approved
0.6165	Remote Similarity	NPD7843	Approved
0.6159	Remote Similarity	NPD4589	Approved
0.6159	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9494	Approved
0.6154	Remote Similarity	NPD2861	Phase 2
0.6148	Remote Similarity	NPD7157	Approved
0.6144	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD3845	Phase 1
0.6131	Remote Similarity	NPD1548	Phase 1
0.6131	Remote Similarity	NPD5303	Approved
0.6131	Remote Similarity	NPD5304	Approved
0.6127	Remote Similarity	NPD1470	Approved
0.6122	Remote Similarity	NPD230	Phase 1
0.6119	Remote Similarity	NPD498	Approved
0.6119	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD496	Approved
0.6119	Remote Similarity	NPD495	Approved
0.6107	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD2420	Approved
0.6104	Remote Similarity	NPD2421	Approved
0.6104	Remote Similarity	NPD1511	Approved
0.6099	Remote Similarity	NPD2983	Phase 2
0.6099	Remote Similarity	NPD2982	Phase 2
0.6087	Remote Similarity	NPD9268	Approved
0.6078	Remote Similarity	NPD6190	Approved
0.6074	Remote Similarity	NPD475	Phase 2
0.6074	Remote Similarity	NPD1793	Approved
0.6074	Remote Similarity	NPD1791	Approved
0.6074	Remote Similarity	NPD9618	Approved
0.6074	Remote Similarity	NPD9614	Approved
0.6071	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1535	Discovery
0.6071	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD9570	Approved
0.6065	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5451	Approved
0.6056	Remote Similarity	NPD1283	Approved
0.6053	Remote Similarity	NPD3060	Approved
0.6048	Remote Similarity	NPD9296	Approved
0.6045	Remote Similarity	NPD5535	Approved
0.6043	Remote Similarity	NPD6516	Phase 2
0.6043	Remote Similarity	NPD5846	Approved
0.6042	Remote Similarity	NPD5736	Approved
0.6042	Remote Similarity	NPD3018	Phase 2
0.6032	Remote Similarity	NPD9273	Approved
0.6029	Remote Similarity	NPD256	Approved
0.6029	Remote Similarity	NPD709	Approved
0.6029	Remote Similarity	NPD255	Approved
0.6028	Remote Similarity	NPD1481	Phase 2
0.6028	Remote Similarity	NPD2981	Phase 2
0.6027	Remote Similarity	NPD3145	Approved
0.6027	Remote Similarity	NPD5109	Approved
0.6027	Remote Similarity	NPD5110	Phase 2
0.6027	Remote Similarity	NPD3144	Approved
0.6027	Remote Similarity	NPD5111	Phase 2
0.6026	Remote Similarity	NPD1512	Approved
0.6014	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1164	Approved
0.6	Remote Similarity	NPD4908	Phase 1
0.6	Remote Similarity	NPD3023	Approved
0.6	Remote Similarity	NPD3026	Approved
0.6	Remote Similarity	NPD3847	Discontinued
0.5986	Remote Similarity	NPD4659	Approved
0.5986	Remote Similarity	NPD6583	Phase 3
0.5986	Remote Similarity	NPD1669	Approved
0.5986	Remote Similarity	NPD6582	Phase 2
0.5985	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD9087	Approved
0.5972	Remote Similarity	NPD2195	Approved
0.5972	Remote Similarity	NPD2194	Approved
0.5971	Remote Similarity	NPD3025	Approved
0.5971	Remote Similarity	NPD1651	Approved
0.5971	Remote Similarity	NPD3024	Approved
0.5962	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3645	Discontinued
0.5959	Remote Similarity	NPD5156	Approved
0.5959	Remote Similarity	NPD5155	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