NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	513.71
Volume:	286.682
LogP:	5.336
LogD:	2.57
LogS:	-4.859
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	2.646
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	1.675082603469491e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.901
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	100.96964263916016%
Volume Distribution (VD):	2.185
Pgp-substrate:	5.272346496582031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.769
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.449
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	0.426
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.162
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.92
Carcinogencity:	0.245
Eye Corrosion:	0.076
Eye Irritation:	0.962
Respiratory Toxicity:	0.809

Download Data

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

Natural Product: NPC196371

Natural Product ID:	NPC196371
*Common Name:**	3,6-Dibromo-2-(3,5-Dibromo-2-Hydroxyphenoxy)Phenol
IUPAC Name:	3,6-dibromo-2-(3,5-dibromo-2-hydroxyphenoxy)phenol
Synonyms:
Standard InCHIKey:	SFRUBLKYXLNPMS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H6Br4O3/c13-5-3-8(16)10(17)9(4-5)19-12-7(15)2-1-6(14)11(12)18/h1-4,17-18H
SMILES:	Brc1cc(Br)c(c(c1)Oc1c(Br)ccc(c1O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374039
PubChem CID:	16115952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers [CHEMONTID:0001845] Bromodiphenyl ethers

*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
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10075800]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10650102]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17311456]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	Mandapam Coast, Tamilnadu, India	n.a.	PMID[22704923]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9463111]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16323	Umbilicaria proboscidea	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16684	Alibertia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17673	Dysidea herbacea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4863	Dioscorea futschauensis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13746	Achillea leptophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13321	Viguiera cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1793	Uvaria mocoli	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17210	Dorstenia barnimiana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9044	Rubia ustulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13985	Oxybasis urbica	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16204	Zieria chevalieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17991	Sedum forsterianum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7857	Verbascum georgicum	Species	Scrophulariaceae	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
Others	4

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	7.0	mm	PMID[481464]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	13.0	mm	PMID[481464]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	20.0	mm	PMID[481464]
NPT27	Others	Unspecified		IC50	>	15.0	ug.mL-1	PMID[481464]

☑ 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 NPC196371 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	946
0.1-0.2	7102
0.2-0.3	13609
0.3-0.4	5412
0.4-0.5	9950
0.5-0.6	4974
0.6-0.7	640
0.7-0.8	11
0.8-0.85	8
0.85-0.9	11
0.9-0.95	5
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC47769
0.9826	High Similarity	NPC25134
0.9826	High Similarity	NPC64130
0.9826	High Similarity	NPC97157
0.9826	High Similarity	NPC175520
0.9826	High Similarity	NPC295879
0.9826	High Similarity	NPC159866
0.9823	High Similarity	NPC86007
0.9823	High Similarity	NPC44270
0.9739	High Similarity	NPC40302
0.9739	High Similarity	NPC474375
0.9739	High Similarity	NPC137922
0.9735	High Similarity	NPC104124
0.9652	High Similarity	NPC153580
0.9652	High Similarity	NPC299939
0.9652	High Similarity	NPC226737
0.9573	High Similarity	NPC197576
0.9573	High Similarity	NPC68350
0.9573	High Similarity	NPC81149
0.9573	High Similarity	NPC131940
0.9573	High Similarity	NPC230013
0.9565	High Similarity	NPC41232
0.9565	High Similarity	NPC63317
0.9483	High Similarity	NPC170824
0.9402	High Similarity	NPC173511
0.9402	High Similarity	NPC88733
0.9391	High Similarity	NPC191194
0.8966	High Similarity	NPC162294
0.8898	High Similarity	NPC71186
0.888	High Similarity	NPC178301
0.8879	High Similarity	NPC221301
0.8862	High Similarity	NPC45728
0.88	High Similarity	NPC222684
0.88	High Similarity	NPC206183
0.8729	High Similarity	NPC264379
0.8407	Intermediate Similarity	NPC319933
0.8222	Intermediate Similarity	NPC8577
0.816	Intermediate Similarity	NPC235166
0.811	Intermediate Similarity	NPC163019
0.811	Intermediate Similarity	NPC1744
0.7672	Intermediate Similarity	NPC314803
0.7478	Intermediate Similarity	NPC475466
0.7447	Intermediate Similarity	NPC286337
0.7397	Intermediate Similarity	NPC152947
0.7357	Intermediate Similarity	NPC271942
0.7328	Intermediate Similarity	NPC114325
0.7259	Intermediate Similarity	NPC13004
0.7168	Intermediate Similarity	NPC252149
0.7164	Intermediate Similarity	NPC236265
0.7143	Intermediate Similarity	NPC245386
0.7077	Intermediate Similarity	NPC86947
0.7	Intermediate Similarity	NPC303011
0.6991	Remote Similarity	NPC319826
0.6985	Remote Similarity	NPC220311
0.697	Remote Similarity	NPC38483
0.6947	Remote Similarity	NPC151617
0.6947	Remote Similarity	NPC76915
0.6935	Remote Similarity	NPC307875
0.6923	Remote Similarity	NPC318429
0.6889	Remote Similarity	NPC219444
0.6884	Remote Similarity	NPC474147
0.6884	Remote Similarity	NPC473708
0.6866	Remote Similarity	NPC205213
0.6857	Remote Similarity	NPC11449
0.6857	Remote Similarity	NPC226493
0.6857	Remote Similarity	NPC160081
0.6846	Remote Similarity	NPC94217
0.6842	Remote Similarity	NPC125306
0.6842	Remote Similarity	NPC214289
0.6838	Remote Similarity	NPC84606
0.6838	Remote Similarity	NPC473572
0.6838	Remote Similarity	NPC474169
0.6818	Remote Similarity	NPC9248
0.6815	Remote Similarity	NPC127389
0.6815	Remote Similarity	NPC290451
0.6812	Remote Similarity	NPC43706
0.681	Remote Similarity	NPC206876
0.6806	Remote Similarity	NPC213471
0.6797	Remote Similarity	NPC473358
0.6786	Remote Similarity	NPC85049
0.6769	Remote Similarity	NPC33244
0.6769	Remote Similarity	NPC471488
0.6765	Remote Similarity	NPC229213
0.6741	Remote Similarity	NPC205850
0.6735	Remote Similarity	NPC89341
0.6728	Remote Similarity	NPC469979
0.6719	Remote Similarity	NPC7097
0.6719	Remote Similarity	NPC36108
0.6719	Remote Similarity	NPC54543
0.6719	Remote Similarity	NPC233731
0.6719	Remote Similarity	NPC246358
0.6712	Remote Similarity	NPC160932
0.6693	Remote Similarity	NPC124712
0.6692	Remote Similarity	NPC293619
0.6691	Remote Similarity	NPC145780
0.6691	Remote Similarity	NPC134219
0.6687	Remote Similarity	NPC110454
0.6687	Remote Similarity	NPC126128
0.6687	Remote Similarity	NPC298981
0.6687	Remote Similarity	NPC473462
0.6687	Remote Similarity	NPC207819
0.6667	Remote Similarity	NPC228972
0.6667	Remote Similarity	NPC213414
0.6667	Remote Similarity	NPC74478
0.6667	Remote Similarity	NPC122792
0.6667	Remote Similarity	NPC50782
0.6667	Remote Similarity	NPC474535
0.6645	Remote Similarity	NPC473608
0.6644	Remote Similarity	NPC156356
0.6644	Remote Similarity	NPC168680
0.6643	Remote Similarity	NPC122359
0.6643	Remote Similarity	NPC78061
0.6643	Remote Similarity	NPC159987
0.6642	Remote Similarity	NPC105147
0.6642	Remote Similarity	NPC228875
0.6642	Remote Similarity	NPC470626
0.6642	Remote Similarity	NPC126216
0.6641	Remote Similarity	NPC471495
0.6637	Remote Similarity	NPC204932
0.6626	Remote Similarity	NPC226001
0.6624	Remote Similarity	NPC475697
0.6622	Remote Similarity	NPC250597
0.6619	Remote Similarity	NPC194519
0.6619	Remote Similarity	NPC3221
0.6619	Remote Similarity	NPC142776
0.6619	Remote Similarity	NPC87113
0.6618	Remote Similarity	NPC307253
0.6615	Remote Similarity	NPC8547
0.6615	Remote Similarity	NPC156840
0.6615	Remote Similarity	NPC173746
0.6615	Remote Similarity	NPC139617
0.6615	Remote Similarity	NPC195873
0.6615	Remote Similarity	NPC257124
0.6615	Remote Similarity	NPC78918
0.6614	Remote Similarity	NPC41594
0.66	Remote Similarity	NPC109346
0.6597	Remote Similarity	NPC303993
0.6594	Remote Similarity	NPC105999
0.6593	Remote Similarity	NPC117759
0.6593	Remote Similarity	NPC281298
0.6593	Remote Similarity	NPC310338
0.6582	Remote Similarity	NPC38980
0.6577	Remote Similarity	NPC184632
0.6571	Remote Similarity	NPC134431
0.6571	Remote Similarity	NPC304630
0.6571	Remote Similarity	NPC178284
0.6571	Remote Similarity	NPC156854
0.6571	Remote Similarity	NPC58607
0.6571	Remote Similarity	NPC191037
0.6571	Remote Similarity	NPC17837
0.6566	Remote Similarity	NPC214188
0.6566	Remote Similarity	NPC74618
0.6566	Remote Similarity	NPC301941
0.6564	Remote Similarity	NPC225130
0.6547	Remote Similarity	NPC137117
0.6547	Remote Similarity	NPC48990
0.6547	Remote Similarity	NPC114901
0.6547	Remote Similarity	NPC293701
0.6544	Remote Similarity	NPC247364
0.6544	Remote Similarity	NPC227217
0.6544	Remote Similarity	NPC61516
0.6544	Remote Similarity	NPC117780
0.6544	Remote Similarity	NPC56214
0.6544	Remote Similarity	NPC474146
0.6544	Remote Similarity	NPC95614
0.6544	Remote Similarity	NPC10932
0.6544	Remote Similarity	NPC232084
0.6544	Remote Similarity	NPC232316
0.6544	Remote Similarity	NPC165133
0.6544	Remote Similarity	NPC242885
0.6538	Remote Similarity	NPC471487
0.6532	Remote Similarity	NPC307039
0.6532	Remote Similarity	NPC132725
0.6525	Remote Similarity	NPC111247
0.6525	Remote Similarity	NPC50368
0.6525	Remote Similarity	NPC118787
0.6525	Remote Similarity	NPC183181
0.6525	Remote Similarity	NPC470699
0.6525	Remote Similarity	NPC41706
0.6525	Remote Similarity	NPC319625
0.6525	Remote Similarity	NPC210355
0.6525	Remote Similarity	NPC147821
0.6525	Remote Similarity	NPC292056
0.6525	Remote Similarity	NPC163332
0.6522	Remote Similarity	NPC296202
0.6522	Remote Similarity	NPC47790
0.651	Remote Similarity	NPC474851
0.651	Remote Similarity	NPC474850
0.6496	Remote Similarity	NPC207613
0.6496	Remote Similarity	NPC109083
0.6496	Remote Similarity	NPC189844
0.6496	Remote Similarity	NPC14007
0.6496	Remote Similarity	NPC224814
0.6496	Remote Similarity	NPC60962
0.6496	Remote Similarity	NPC269843
0.6493	Remote Similarity	NPC79844
0.6489	Remote Similarity	NPC55300
0.6484	Remote Similarity	NPC232654
0.6483	Remote Similarity	NPC471328
0.6483	Remote Similarity	NPC163560

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 NPC196371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	659
0.1-0.2	1512
0.2-0.3	3171
0.3-0.4	2228
0.4-0.5	1209
0.5-0.6	349
0.6-0.7	21
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
0.7328	Intermediate Similarity	NPD9296	Approved
0.7107	Intermediate Similarity	NPD291	Approved
0.6923	Remote Similarity	NPD9365	Approved
0.6866	Remote Similarity	NPD915	Approved
0.6615	Remote Similarity	NPD228	Approved
0.6614	Remote Similarity	NPD968	Approved
0.6589	Remote Similarity	NPD556	Approved
0.6471	Remote Similarity	NPD9295	Approved
0.6364	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD9299	Approved
0.6328	Remote Similarity	NPD9501	Approved
0.6328	Remote Similarity	NPD9244	Approved
0.6308	Remote Similarity	NPD9552	Approved
0.6308	Remote Similarity	NPD290	Approved
0.6301	Remote Similarity	NPD1558	Phase 1
0.6294	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9094	Approved
0.619	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1613	Approved
0.6136	Remote Similarity	NPD2684	Approved
0.6121	Remote Similarity	NPD4010	Discontinued
0.6115	Remote Similarity	NPD1798	Approved
0.6115	Remote Similarity	NPD1797	Approved
0.6096	Remote Similarity	NPD3027	Phase 3
0.6049	Remote Similarity	NPD2296	Approved
0.6043	Remote Similarity	NPD1548	Phase 1
0.6029	Remote Similarity	NPD5283	Phase 1
0.6018	Remote Similarity	NPD9087	Approved
0.5971	Remote Similarity	NPD1103	Approved
0.5971	Remote Similarity	NPD1102	Approved
0.5971	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5846	Approved
0.5957	Remote Similarity	NPD6516	Phase 2
0.5956	Remote Similarity	NPD7843	Approved
0.5948	Remote Similarity	NPD9088	Approved
0.5942	Remote Similarity	NPD6671	Approved
0.5887	Remote Similarity	NPD1357	Approved
0.5874	Remote Similarity	NPD1610	Phase 2
0.5874	Remote Similarity	NPD1091	Approved
0.5874	Remote Similarity	NPD1535	Discovery
0.5857	Remote Similarity	NPD5536	Phase 2
0.5854	Remote Similarity	NPD4288	Approved
0.5852	Remote Similarity	NPD3022	Approved
0.5852	Remote Similarity	NPD3021	Approved
0.585	Remote Similarity	NPD9494	Approved
0.5833	Remote Similarity	NPD1481	Phase 2
0.5827	Remote Similarity	NPD191	Approved
0.5827	Remote Similarity	NPD7157	Approved
0.5822	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD1318	Phase 2
0.5816	Remote Similarity	NPD7534	Approved
0.5816	Remote Similarity	NPD7533	Approved
0.5804	Remote Similarity	NPD155	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD6583	Phase 3
0.5793	Remote Similarity	NPD6582	Phase 2
0.5789	Remote Similarity	NPD9697	Approved
0.5762	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD4060	Phase 1
0.5762	Remote Similarity	NPD3620	Phase 2
0.575	Remote Similarity	NPD9089	Approved
0.5743	Remote Similarity	NPD2250	Discontinued
0.5733	Remote Similarity	NPD3144	Approved
0.5733	Remote Similarity	NPD3145	Approved
0.5725	Remote Similarity	NPD821	Approved
0.5725	Remote Similarity	NPD5535	Approved
0.5714	Remote Similarity	NPD1169	Approved
0.5714	Remote Similarity	NPD1203	Approved
0.5705	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD1894	Discontinued
0.5703	Remote Similarity	NPD2933	Approved
0.5703	Remote Similarity	NPD2934	Approved
0.5695	Remote Similarity	NPD2674	Phase 3
0.5685	Remote Similarity	NPD2983	Phase 2
0.5685	Remote Similarity	NPD2982	Phase 2
0.5676	Remote Similarity	NPD6584	Phase 3
0.5667	Remote Similarity	NPD9093	Approved
0.5667	Remote Similarity	NPD7095	Approved
0.5659	Remote Similarity	NPD2860	Approved
0.5659	Remote Similarity	NPD2859	Approved
0.5655	Remote Similarity	NPD422	Phase 1
0.5646	Remote Similarity	NPD3225	Approved
0.5638	Remote Similarity	NPD2861	Phase 2
0.5638	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.5629	Remote Similarity	NPD6798	Discontinued
0.5625	Remote Similarity	NPD1511	Approved
0.5621	Remote Similarity	NPD447	Suspended
0.5616	Remote Similarity	NPD2235	Phase 2
0.5616	Remote Similarity	NPD2981	Phase 2
0.5616	Remote Similarity	NPD1608	Approved
0.5616	Remote Similarity	NPD2231	Phase 2
0.5612	Remote Similarity	NPD769	Approved
0.5608	Remote Similarity	NPD2797	Approved
0.5608	Remote Similarity	NPD9549	Phase 2
0.56	Remote Similarity	NPD4908	Phase 1

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