NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	340.8
Volume:	199.252
LogP:	4.976
LogD:	3.343
LogS:	-6.858
# Rotatable Bonds:	0
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	3.022
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	1.3354349903238472e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.292
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.673
Plasma Protein Binding (PPB):	100.00696563720703%
Volume Distribution (VD):	5.389
Pgp-substrate:	1.9958382844924927%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.691
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	1.65
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.862
Carcinogencity:	0.68
Eye Corrosion:	0.976
Eye Irritation:	0.993
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC161550

Natural Product ID:	NPC161550
*Common Name:**	4,7-Dibromo-2,3-Dichloroindole
IUPAC Name:	4,7-dibromo-2,3-dichloro-1H-indole
Synonyms:
Standard InCHIKey:	MPEKURMZTPLRQE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H3Br2Cl2N/c9-3-1-2-4(10)7-5(3)6(11)8(12)13-7/h1-2,13H
SMILES:	Clc1[nH]c2c(c1Cl)c(Br)ccc2Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3814584
PubChem CID:	23425158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO8705	Rhodophyllis membranacea	Species	Cystocloniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26756908]
NPO6765	Illicium micranthum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8162	Digitalis thapsi	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8705	Rhodophyllis membranacea	Species	Cystocloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2716	Anemone cylindrica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5321	Anacamptis morio	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25634	Echinothrix calamaris	Species	Diadematidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO505	Agathosma ciliaris	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3320	Sesbania aegyptiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2920	Tagetes elliptica	Species	Asteraceae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28000.0	nM	PMID[540335]
NPT610	Others	Molecular identity unknown		IC50	=	23000.0	nM	PMID[540335]

☑ 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 NPC161550 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	3109
0.1-0.2	16909
0.2-0.3	16315
0.3-0.4	3311
0.4-0.5	1909
0.5-0.6	940
0.6-0.7	188
0.7-0.8	11
0.8-0.85	1
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7468	Intermediate Similarity	NPC316069
0.7375	Intermediate Similarity	NPC2272
0.7279	Intermediate Similarity	NPC41174
0.7239	Intermediate Similarity	NPC141926
0.7239	Intermediate Similarity	NPC232798
0.7195	Intermediate Similarity	NPC34844
0.7143	Intermediate Similarity	NPC149265
0.7086	Intermediate Similarity	NPC250361
0.6993	Remote Similarity	NPC473762
0.6959	Remote Similarity	NPC109447
0.6954	Remote Similarity	NPC280297
0.6948	Remote Similarity	NPC473587
0.6941	Remote Similarity	NPC247987
0.6903	Remote Similarity	NPC22079
0.6903	Remote Similarity	NPC475428
0.6901	Remote Similarity	NPC17751
0.6901	Remote Similarity	NPC274229
0.6901	Remote Similarity	NPC280864
0.6897	Remote Similarity	NPC64055
0.6879	Remote Similarity	NPC474168
0.6859	Remote Similarity	NPC475450
0.6859	Remote Similarity	NPC179365
0.6859	Remote Similarity	NPC82295
0.6815	Remote Similarity	NPC473930
0.68	Remote Similarity	NPC477611
0.6782	Remote Similarity	NPC97343
0.6743	Remote Similarity	NPC82331
0.673	Remote Similarity	NPC198988
0.6687	Remote Similarity	NPC325252
0.6687	Remote Similarity	NPC29886
0.6687	Remote Similarity	NPC218268
0.6687	Remote Similarity	NPC96102
0.6687	Remote Similarity	NPC261195
0.6647	Remote Similarity	NPC115049
0.6646	Remote Similarity	NPC125746
0.6646	Remote Similarity	NPC105127
0.6646	Remote Similarity	NPC84911
0.6629	Remote Similarity	NPC474958
0.661	Remote Similarity	NPC288074
0.6564	Remote Similarity	NPC88097
0.6564	Remote Similarity	NPC73767
0.6564	Remote Similarity	NPC110126
0.6564	Remote Similarity	NPC312092
0.6556	Remote Similarity	NPC233050
0.6556	Remote Similarity	NPC276540
0.6533	Remote Similarity	NPC148140
0.6524	Remote Similarity	NPC469783
0.6524	Remote Similarity	NPC115611
0.6524	Remote Similarity	NPC469779
0.6524	Remote Similarity	NPC2949
0.6524	Remote Similarity	NPC279081
0.6524	Remote Similarity	NPC469761
0.6524	Remote Similarity	NPC469780
0.6524	Remote Similarity	NPC469768
0.6524	Remote Similarity	NPC469767
0.6524	Remote Similarity	NPC469784
0.6524	Remote Similarity	NPC59084
0.6524	Remote Similarity	NPC230002
0.6524	Remote Similarity	NPC284635
0.6517	Remote Similarity	NPC247980
0.649	Remote Similarity	NPC81561
0.6485	Remote Similarity	NPC63157
0.6485	Remote Similarity	NPC469766
0.6485	Remote Similarity	NPC473868
0.6484	Remote Similarity	NPC275292
0.6484	Remote Similarity	NPC307191
0.6484	Remote Similarity	NPC243381
0.6447	Remote Similarity	NPC162689
0.6447	Remote Similarity	NPC54102
0.6446	Remote Similarity	NPC190296
0.6413	Remote Similarity	NPC110158
0.6407	Remote Similarity	NPC242556
0.6369	Remote Similarity	NPC204141
0.6369	Remote Similarity	NPC159856
0.6369	Remote Similarity	NPC314372
0.6369	Remote Similarity	NPC470440
0.6364	Remote Similarity	NPC215519
0.6364	Remote Similarity	NPC162799
0.6359	Remote Similarity	NPC83381
0.6339	Remote Similarity	NPC314919
0.6331	Remote Similarity	NPC143872
0.6331	Remote Similarity	NPC63545
0.6331	Remote Similarity	NPC129042
0.6331	Remote Similarity	NPC288838
0.633	Remote Similarity	NPC231536
0.6328	Remote Similarity	NPC195507
0.6328	Remote Similarity	NPC2165
0.6294	Remote Similarity	NPC469811
0.6294	Remote Similarity	NPC471957
0.6294	Remote Similarity	NPC201380
0.6294	Remote Similarity	NPC477134
0.6294	Remote Similarity	NPC179787
0.6294	Remote Similarity	NPC21605
0.6264	Remote Similarity	NPC476464
0.6257	Remote Similarity	NPC321911
0.6257	Remote Similarity	NPC124005
0.6257	Remote Similarity	NPC187951
0.6257	Remote Similarity	NPC37548
0.6242	Remote Similarity	NPC46358
0.6221	Remote Similarity	NPC105818
0.6221	Remote Similarity	NPC33421
0.6221	Remote Similarity	NPC148592
0.6221	Remote Similarity	NPC53947
0.6221	Remote Similarity	NPC24678
0.6203	Remote Similarity	NPC122718
0.6193	Remote Similarity	NPC6436
0.6193	Remote Similarity	NPC477591
0.6185	Remote Similarity	NPC216713
0.6185	Remote Similarity	NPC470823
0.6178	Remote Similarity	NPC473342
0.6178	Remote Similarity	NPC304187
0.6178	Remote Similarity	NPC477167
0.6178	Remote Similarity	NPC477166
0.615	Remote Similarity	NPC108011
0.6149	Remote Similarity	NPC73952
0.6149	Remote Similarity	NPC469786
0.6149	Remote Similarity	NPC25008
0.6149	Remote Similarity	NPC200214
0.6149	Remote Similarity	NPC259644
0.6149	Remote Similarity	NPC469760
0.6149	Remote Similarity	NPC469765
0.6149	Remote Similarity	NPC469763
0.6149	Remote Similarity	NPC325903
0.6146	Remote Similarity	NPC88315
0.6146	Remote Similarity	NPC474180
0.6146	Remote Similarity	NPC188821
0.6125	Remote Similarity	NPC476140
0.6114	Remote Similarity	NPC212376
0.6114	Remote Similarity	NPC471458
0.6114	Remote Similarity	NPC38736
0.6114	Remote Similarity	NPC80597
0.6114	Remote Similarity	NPC75540
0.6114	Remote Similarity	NPC207726
0.6114	Remote Similarity	NPC70922
0.6114	Remote Similarity	NPC470507
0.6114	Remote Similarity	NPC211572
0.6095	Remote Similarity	NPC476454
0.6087	Remote Similarity	NPC121903
0.6087	Remote Similarity	NPC288785
0.6082	Remote Similarity	NPC222018
0.6082	Remote Similarity	NPC179701
0.608	Remote Similarity	NPC285469
0.608	Remote Similarity	NPC184476
0.608	Remote Similarity	NPC141353
0.608	Remote Similarity	NPC469785
0.6071	Remote Similarity	NPC316811
0.6054	Remote Similarity	NPC293472
0.6051	Remote Similarity	NPC262898
0.6048	Remote Similarity	NPC150259
0.6045	Remote Similarity	NPC299594
0.6045	Remote Similarity	NPC236711
0.6045	Remote Similarity	NPC286427
0.6045	Remote Similarity	NPC469762
0.6045	Remote Similarity	NPC76982
0.6045	Remote Similarity	NPC216643
0.6041	Remote Similarity	NPC77241
0.6041	Remote Similarity	NPC13456
0.6041	Remote Similarity	NPC166209
0.6041	Remote Similarity	NPC269203
0.602	Remote Similarity	NPC474389
0.6011	Remote Similarity	NPC474791
0.6011	Remote Similarity	NPC230869
0.6011	Remote Similarity	NPC41257
0.6011	Remote Similarity	NPC206819
0.6011	Remote Similarity	NPC135141
0.6011	Remote Similarity	NPC474880
0.6011	Remote Similarity	NPC475990
0.6011	Remote Similarity	NPC67056
0.6011	Remote Similarity	NPC56765
0.6011	Remote Similarity	NPC318065
0.6011	Remote Similarity	NPC92796
0.6011	Remote Similarity	NPC221786
0.601	Remote Similarity	NPC94211
0.601	Remote Similarity	NPC316018
0.601	Remote Similarity	NPC314058
0.601	Remote Similarity	NPC475935
0.601	Remote Similarity	NPC315617
0.601	Remote Similarity	NPC52909
0.601	Remote Similarity	NPC316359
0.6	Remote Similarity	NPC470233
0.599	Remote Similarity	NPC268744
0.599	Remote Similarity	NPC153123
0.599	Remote Similarity	NPC475914
0.599	Remote Similarity	NPC220797
0.599	Remote Similarity	NPC474318
0.599	Remote Similarity	NPC237414
0.599	Remote Similarity	NPC201266
0.599	Remote Similarity	NPC477004
0.5978	Remote Similarity	NPC44773
0.5978	Remote Similarity	NPC470204
0.5978	Remote Similarity	NPC215584
0.5978	Remote Similarity	NPC473320
0.5978	Remote Similarity	NPC122141
0.5978	Remote Similarity	NPC229173
0.5978	Remote Similarity	NPC279918
0.5978	Remote Similarity	NPC131718
0.5976	Remote Similarity	NPC315348
0.5976	Remote Similarity	NPC104483
0.5976	Remote Similarity	NPC32002
0.596	Remote Similarity	NPC23420

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 NPC161550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	791
0.1-0.2	967
0.2-0.3	1980
0.3-0.4	2916
0.4-0.5	2031
0.5-0.6	424
0.6-0.7	41
0.7-0.8	0
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
0.6687	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1262	Discovery
0.657	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD786	Approved
0.6524	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4880	Discontinued
0.6485	Remote Similarity	NPD1722	Approved
0.6453	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD5254	Discontinued
0.6384	Remote Similarity	NPD1248	Discontinued
0.6364	Remote Similarity	NPD680	Discontinued
0.6353	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD3654	Approved
0.6301	Remote Similarity	NPD2165	Phase 1
0.6287	Remote Similarity	NPD1592	Phase 3
0.6264	Remote Similarity	NPD3114	Approved
0.6264	Remote Similarity	NPD3112	Approved
0.6264	Remote Similarity	NPD3115	Approved
0.6264	Remote Similarity	NPD3113	Approved
0.6257	Remote Similarity	NPD1183	Approved
0.6257	Remote Similarity	NPD3100	Discontinued
0.6257	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD2172	Phase 1
0.6221	Remote Similarity	NPD4463	Approved
0.6221	Remote Similarity	NPD3833	Phase 3
0.6221	Remote Similarity	NPD4462	Approved
0.6221	Remote Similarity	NPD3835	Phase 3
0.6211	Remote Similarity	NPD947	Approved
0.6203	Remote Similarity	NPD1227	Phase 2
0.6159	Remote Similarity	NPD3385	Approved
0.6154	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2837	Discontinued
0.6135	Remote Similarity	NPD1251	Discontinued
0.6085	Remote Similarity	NPD6217	Discontinued
0.6071	Remote Similarity	NPD2069	Approved
0.6071	Remote Similarity	NPD2070	Approved
0.6071	Remote Similarity	NPD2068	Approved
0.6071	Remote Similarity	NPD2071	Approved
0.6071	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD45	Approved
0.6048	Remote Similarity	NPD6554	Approved
0.6047	Remote Similarity	NPD1683	Approved
0.6021	Remote Similarity	NPD1534	Approved
0.6012	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1253	Approved
0.5988	Remote Similarity	NPD1256	Approved
0.5988	Remote Similarity	NPD1254	Approved
0.5988	Remote Similarity	NPD1255	Approved
0.5978	Remote Similarity	NPD1403	Approved
0.5978	Remote Similarity	NPD1404	Approved
0.5976	Remote Similarity	NPD2075	Approved
0.5976	Remote Similarity	NPD2073	Approved
0.5976	Remote Similarity	NPD2072	Approved
0.5976	Remote Similarity	NPD2074	Approved
0.5944	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD3117	Approved
0.5924	Remote Similarity	NPD3116	Approved
0.5912	Remote Similarity	NPD3323	Discontinued
0.5906	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD1993	Approved
0.5904	Remote Similarity	NPD1994	Approved
0.5904	Remote Similarity	NPD1995	Approved
0.5902	Remote Similarity	NPD1857	Discontinued
0.59	Remote Similarity	NPD5495	Phase 2
0.5879	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD3339	Approved
0.5876	Remote Similarity	NPD4297	Phase 1
0.5875	Remote Similarity	NPD1561	Phase 2
0.5872	Remote Similarity	NPD2006	Phase 2
0.5872	Remote Similarity	NPD4047	Discontinued
0.5867	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD165	Phase 2
0.5847	Remote Similarity	NPD2642	Approved
0.5847	Remote Similarity	NPD2639	Approved
0.5815	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD2641	Approved
0.5815	Remote Similarity	NPD2640	Approved
0.5815	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.581	Remote Similarity	NPD2150	Discontinued
0.5806	Remote Similarity	NPD409	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD991	Phase 2
0.5793	Remote Similarity	NPD992	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD1325	Approved
0.5784	Remote Similarity	NPD1326	Approved
0.5783	Remote Similarity	NPD3476	Approved
0.5783	Remote Similarity	NPD3475	Approved
0.5775	Remote Similarity	NPD1472	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD3609	Approved
0.5753	Remote Similarity	NPD3610	Approved
0.5744	Remote Similarity	NPD6133	Discontinued
0.5743	Remote Similarity	NPD6802	Phase 3
0.5739	Remote Similarity	NPD4547	Phase 3
0.5722	Remote Similarity	NPD7216	Approved
0.5722	Remote Similarity	NPD7217	Approved
0.5707	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD2430	Phase 2
0.5698	Remote Similarity	NPD945	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5065	Approved
0.5691	Remote Similarity	NPD482	Approved
0.5691	Remote Similarity	NPD4128	Approved
0.5677	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.5661	Remote Similarity	NPD4075	Phase 2
0.5661	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5140	Approved
0.5652	Remote Similarity	NPD5138	Approved
0.5648	Remote Similarity	NPD5892	Approved
0.5642	Remote Similarity	NPD3758	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD9583	Approved
0.5632	Remote Similarity	NPD4181	Approved
0.5632	Remote Similarity	NPD3506	Approved
0.5632	Remote Similarity	NPD3505	Approved
0.5632	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD2144	Approved
0.5632	Remote Similarity	NPD2315	Approved
0.5625	Remote Similarity	NPD2301	Approved
0.5625	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD3279	Phase 2
0.5617	Remote Similarity	NPD271	Approved
0.5617	Remote Similarity	NPD270	Clinical (unspecified phase)
0.5617	Remote Similarity	NPD268	Approved
0.561	Remote Similarity	NPD9357	Approved
0.561	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.561	Remote Similarity	NPD1937	Approved
0.5602	Remote Similarity	NPD676	Discontinued
0.5602	Remote Similarity	NPD2119	Approved
0.5602	Remote Similarity	NPD4079	Approved
0.5602	Remote Similarity	NPD8386	Phase 2
0.5602	Remote Similarity	NPD4076	Approved
0.5602	Remote Similarity	NPD2118	Approved
0.56	Remote Similarity	NPD4848	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