NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	365.91
Volume:	254.538
LogP:	2.628
LogD:	2.184
LogS:	-3.226
# Rotatable Bonds:	1
TPSA:	68.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.256
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.927
MDCK Permeability:	1.2381096894387156e-05
Pgp-inhibitor:	0.598
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.512
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.682
Plasma Protein Binding (PPB):	96.96837615966797%
Volume Distribution (VD):	1.104
Pgp-substrate:	4.5890936851501465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.74
CYP1A2-substrate:	0.763
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.876
CYP2D6-substrate:	0.767
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	2.548
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.852
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.597
Carcinogencity:	0.115
Eye Corrosion:	0.004
Eye Irritation:	0.224
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC280297

Natural Product ID:	NPC280297
*Common Name:**	4-(5,6-Dibromo-1H-Indol-3-Yl)Pyrimidin-2-Amine
IUPAC Name:	4-(5,6-dibromo-1H-indol-3-yl)pyrimidin-2-amine
Synonyms:
Standard InCHIKey:	BYGIRSJUNICQIC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H8Br2N4/c13-8-3-6-7(5-17-11(6)4-9(8)14)10-1-2-16-12(15)18-10/h1-5,17H,(H2,15,16,18)
SMILES:	Brc1cc2[nH]cc(c2cc1Br)c1cc[nH]c(=N)n1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL296271
PubChem CID:	10044516
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
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	South Georgia Islands, South Atlantic	n.a.	PMID[15026054]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748381]
NPO25046	Aplidium meridianum	Species	Polyclinidae	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	8

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Others	1
Protein Complex	2
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	2000.0	nM	PMID[526251]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	1800.0	nM	PMID[526251]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	200.0	nM	PMID[526251]
NPT6311	Cell Line	LMM3 cell line		IC50	=	1400.0	nM	PMID[526251]
NPT1570	Protein Complex	Cyclin-dependent kinase 1/cyclin B	Homo sapiens	IC50	=	20000.0	nM	PMID[526251]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	=	20000.0	nM	PMID[526251]
NPT321	Protein Family	cAMP-dependent protein kinase (PKA)	Homo sapiens	IC50	=	3200.0	nM	PMID[526251]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[526251]

☑ 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 NPC280297 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	3053
0.1-0.2	18203
0.2-0.3	14813
0.3-0.4	2709
0.4-0.5	1913
0.5-0.6	1427
0.6-0.7	456
0.7-0.8	110
0.8-0.85	7
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.949	High Similarity	NPC280864
0.949	High Similarity	NPC17751
0.9182	High Similarity	NPC149265
0.8981	High Similarity	NPC232798
0.8861	High Similarity	NPC141926
0.8805	High Similarity	NPC34844
0.8662	High Similarity	NPC316069
0.8662	High Similarity	NPC143872
0.8647	High Similarity	NPC307191
0.8512	High Similarity	NPC477611
0.8485	Intermediate Similarity	NPC247987
0.8434	Intermediate Similarity	NPC274229
0.8418	Intermediate Similarity	NPC473342
0.8418	Intermediate Similarity	NPC477166
0.8418	Intermediate Similarity	NPC304187
0.8418	Intermediate Similarity	NPC477167
0.8284	Intermediate Similarity	NPC97343
0.8235	Intermediate Similarity	NPC82331
0.8229	Intermediate Similarity	NPC108011
0.821	Intermediate Similarity	NPC2272
0.8198	Intermediate Similarity	NPC474958
0.8153	Intermediate Similarity	NPC125746
0.8144	Intermediate Similarity	NPC122141
0.8089	Intermediate Similarity	NPC96102
0.8081	Intermediate Similarity	NPC64055
0.8066	Intermediate Similarity	NPC188821
0.8066	Intermediate Similarity	NPC474180
0.8038	Intermediate Similarity	NPC84911
0.8038	Intermediate Similarity	NPC105127
0.7975	Intermediate Similarity	NPC261195
0.7975	Intermediate Similarity	NPC29886
0.7937	Intermediate Similarity	NPC110126
0.7937	Intermediate Similarity	NPC73767
0.7929	Intermediate Similarity	NPC470204
0.7898	Intermediate Similarity	NPC276540
0.7898	Intermediate Similarity	NPC233050
0.7892	Intermediate Similarity	NPC474389
0.7888	Intermediate Similarity	NPC469783
0.7888	Intermediate Similarity	NPC279081
0.7888	Intermediate Similarity	NPC469768
0.7888	Intermediate Similarity	NPC469779
0.7888	Intermediate Similarity	NPC469780
0.7888	Intermediate Similarity	NPC469761
0.7888	Intermediate Similarity	NPC469767
0.7888	Intermediate Similarity	NPC469784
0.7882	Intermediate Similarity	NPC470203
0.7874	Intermediate Similarity	NPC288074
0.784	Intermediate Similarity	NPC469766
0.7834	Intermediate Similarity	NPC82295
0.7809	Intermediate Similarity	NPC275292
0.7809	Intermediate Similarity	NPC243381
0.7802	Intermediate Similarity	NPC231536
0.7791	Intermediate Similarity	NPC190296
0.7778	Intermediate Similarity	NPC230002
0.7758	Intermediate Similarity	NPC288838
0.7746	Intermediate Similarity	NPC109447
0.7713	Intermediate Similarity	NPC166209
0.7713	Intermediate Similarity	NPC77241
0.7713	Intermediate Similarity	NPC13456
0.7713	Intermediate Similarity	NPC269203
0.7711	Intermediate Similarity	NPC469811
0.7697	Intermediate Similarity	NPC314372
0.7697	Intermediate Similarity	NPC204141
0.7697	Intermediate Similarity	NPC159856
0.7674	Intermediate Similarity	NPC225018
0.7672	Intermediate Similarity	NPC52909
0.7672	Intermediate Similarity	NPC94211
0.7672	Intermediate Similarity	NPC475935
0.7665	Intermediate Similarity	NPC321911
0.766	Intermediate Similarity	NPC268744
0.766	Intermediate Similarity	NPC153123
0.766	Intermediate Similarity	NPC475914
0.766	Intermediate Similarity	NPC220797
0.766	Intermediate Similarity	NPC201266
0.766	Intermediate Similarity	NPC474318
0.7658	Intermediate Similarity	NPC22079
0.7651	Intermediate Similarity	NPC63545
0.7641	Intermediate Similarity	NPC128084
0.7624	Intermediate Similarity	NPC110158
0.7619	Intermediate Similarity	NPC205254
0.7619	Intermediate Similarity	NPC303820
0.7619	Intermediate Similarity	NPC23420
0.7619	Intermediate Similarity	NPC53947
0.7619	Intermediate Similarity	NPC106771
0.7605	Intermediate Similarity	NPC471957
0.7605	Intermediate Similarity	NPC179787
0.7605	Intermediate Similarity	NPC201380
0.7558	Intermediate Similarity	NPC206819
0.7558	Intermediate Similarity	NPC318065
0.7543	Intermediate Similarity	NPC49217
0.7529	Intermediate Similarity	NPC325903
0.7515	Intermediate Similarity	NPC24678
0.7515	Intermediate Similarity	NPC105818
0.7514	Intermediate Similarity	NPC279918
0.75	Intermediate Similarity	NPC316811
0.7471	Intermediate Similarity	NPC216713
0.7471	Intermediate Similarity	NPC470823
0.7471	Intermediate Similarity	NPC282231
0.7427	Intermediate Similarity	NPC469765
0.7427	Intermediate Similarity	NPC25008
0.7427	Intermediate Similarity	NPC469760
0.7427	Intermediate Similarity	NPC73952
0.7427	Intermediate Similarity	NPC469786
0.7427	Intermediate Similarity	NPC200214
0.7427	Intermediate Similarity	NPC259644
0.7427	Intermediate Similarity	NPC469763
0.7423	Intermediate Similarity	NPC325252
0.7407	Intermediate Similarity	NPC179701
0.74	Intermediate Similarity	NPC477114
0.7399	Intermediate Similarity	NPC286427
0.7399	Intermediate Similarity	NPC216643
0.7398	Intermediate Similarity	NPC80596
0.7394	Intermediate Similarity	NPC88315
0.7384	Intermediate Similarity	NPC211572
0.7384	Intermediate Similarity	NPC80597
0.7384	Intermediate Similarity	NPC212376
0.7384	Intermediate Similarity	NPC75540
0.7384	Intermediate Similarity	NPC70922
0.7382	Intermediate Similarity	NPC477004
0.7371	Intermediate Similarity	NPC253687
0.7368	Intermediate Similarity	NPC262898
0.7362	Intermediate Similarity	NPC198988
0.7356	Intermediate Similarity	NPC56765
0.7356	Intermediate Similarity	NPC92796
0.7356	Intermediate Similarity	NPC41257
0.7356	Intermediate Similarity	NPC135141
0.7348	Intermediate Similarity	NPC473380
0.7348	Intermediate Similarity	NPC240088
0.7345	Intermediate Similarity	NPC49954
0.7345	Intermediate Similarity	NPC54988
0.7345	Intermediate Similarity	NPC474561
0.7341	Intermediate Similarity	NPC469785
0.7337	Intermediate Similarity	NPC470703
0.7317	Intermediate Similarity	NPC218268
0.7303	Intermediate Similarity	NPC63751
0.7299	Intermediate Similarity	NPC469762
0.7299	Intermediate Similarity	NPC236711
0.7296	Intermediate Similarity	NPC250361
0.7292	Intermediate Similarity	NPC237414
0.7288	Intermediate Similarity	NPC195507
0.7288	Intermediate Similarity	NPC2165
0.7286	Intermediate Similarity	NPC470702
0.7286	Intermediate Similarity	NPC473218
0.7284	Intermediate Similarity	NPC101165
0.7267	Intermediate Similarity	NPC470233
0.7263	Intermediate Similarity	NPC194411
0.7232	Intermediate Similarity	NPC90723
0.7232	Intermediate Similarity	NPC317105
0.7222	Intermediate Similarity	NPC470498
0.7216	Intermediate Similarity	NPC215584
0.7216	Intermediate Similarity	NPC44773
0.7216	Intermediate Similarity	NPC131718
0.7213	Intermediate Similarity	NPC265710
0.7205	Intermediate Similarity	NPC473762
0.7192	Intermediate Similarity	NPC475736
0.7186	Intermediate Similarity	NPC88097
0.7179	Intermediate Similarity	NPC473761
0.7174	Intermediate Similarity	NPC16659
0.7169	Intermediate Similarity	NPC150259
0.716	Intermediate Similarity	NPC473587
0.7159	Intermediate Similarity	NPC230869
0.7158	Intermediate Similarity	NPC59269
0.7152	Intermediate Similarity	NPC41174
0.7151	Intermediate Similarity	NPC160105
0.7143	Intermediate Similarity	NPC37423
0.7143	Intermediate Similarity	NPC115611
0.7143	Intermediate Similarity	NPC59084
0.7143	Intermediate Similarity	NPC2949
0.7143	Intermediate Similarity	NPC275305
0.7135	Intermediate Similarity	NPC311276
0.7135	Intermediate Similarity	NPC194640
0.7122	Intermediate Similarity	NPC474195
0.7117	Intermediate Similarity	NPC475428
0.7107	Intermediate Similarity	NPC470505
0.7107	Intermediate Similarity	NPC46358
0.7101	Intermediate Similarity	NPC473868
0.7101	Intermediate Similarity	NPC63157
0.7073	Intermediate Similarity	NPC475450
0.7073	Intermediate Similarity	NPC179365
0.7065	Intermediate Similarity	NPC248454
0.7065	Intermediate Similarity	NPC68354
0.7047	Intermediate Similarity	NPC222018
0.7047	Intermediate Similarity	NPC242209
0.7039	Intermediate Similarity	NPC40779
0.7039	Intermediate Similarity	NPC102423
0.703	Intermediate Similarity	NPC473930
0.7027	Intermediate Similarity	NPC176199
0.7027	Intermediate Similarity	NPC215795
0.7027	Intermediate Similarity	NPC11126
0.7017	Intermediate Similarity	NPC201700
0.6995	Remote Similarity	NPC314603
0.6995	Remote Similarity	NPC477610
0.6986	Remote Similarity	NPC474196
0.6985	Remote Similarity	NPC82053
0.6977	Remote Similarity	NPC470440
0.6966	Remote Similarity	NPC475990
0.6964	Remote Similarity	NPC251722
0.6964	Remote Similarity	NPC314102
0.6957	Remote Similarity	NPC27740
0.6954	Remote Similarity	NPC37548

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 NPC280297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	621
0.1-0.2	1099
0.2-0.3	1659
0.3-0.4	2250
0.4-0.5	1784
0.5-0.6	1258
0.6-0.7	440
0.7-0.8	39
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
0.8089	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1722	Approved
0.7937	Intermediate Similarity	NPD786	Approved
0.7879	Intermediate Similarity	NPD3100	Discontinued
0.756	Intermediate Similarity	NPD1183	Approved
0.7528	Intermediate Similarity	NPD4128	Approved
0.7515	Intermediate Similarity	NPD2172	Phase 1
0.75	Intermediate Similarity	NPD2069	Approved
0.75	Intermediate Similarity	NPD2071	Approved
0.75	Intermediate Similarity	NPD2068	Approved
0.75	Intermediate Similarity	NPD2070	Approved
0.7427	Intermediate Similarity	NPD2837	Discontinued
0.7378	Intermediate Similarity	NPD1262	Discovery
0.7253	Intermediate Similarity	NPD4181	Approved
0.7239	Intermediate Similarity	NPD1995	Approved
0.7239	Intermediate Similarity	NPD1994	Approved
0.7239	Intermediate Similarity	NPD1993	Approved
0.7232	Intermediate Similarity	NPD3323	Discontinued
0.7228	Intermediate Similarity	NPD1895	Discontinued
0.7216	Intermediate Similarity	NPD1403	Approved
0.7216	Intermediate Similarity	NPD1404	Approved
0.7175	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1248	Discontinued
0.7143	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD991	Phase 2
0.7135	Intermediate Similarity	NPD1708	Approved
0.7135	Intermediate Similarity	NPD1707	Approved
0.7111	Intermediate Similarity	NPD2641	Approved
0.7111	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2640	Approved
0.7104	Intermediate Similarity	NPD4075	Phase 2
0.7097	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3505	Approved
0.7065	Intermediate Similarity	NPD3506	Approved
0.7056	Intermediate Similarity	NPD2639	Approved
0.7056	Intermediate Similarity	NPD2642	Approved
0.7033	Intermediate Similarity	NPD3609	Approved
0.7033	Intermediate Similarity	NPD3610	Approved
0.7027	Intermediate Similarity	NPD4076	Approved
0.7027	Intermediate Similarity	NPD4079	Approved
0.7018	Intermediate Similarity	NPD5254	Discontinued
0.7017	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6595	Phase 3
0.6963	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD439	Approved
0.6961	Remote Similarity	NPD438	Approved
0.6959	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5065	Approved
0.6952	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2150	Discontinued
0.694	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6828	Phase 2
0.6933	Remote Similarity	NPD1598	Discontinued
0.6914	Remote Similarity	NPD4462	Approved
0.6914	Remote Similarity	NPD4463	Approved
0.691	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3476	Approved
0.6909	Remote Similarity	NPD3475	Approved
0.6898	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4547	Phase 3
0.6882	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD482	Approved
0.686	Remote Similarity	NPD4047	Discontinued
0.686	Remote Similarity	NPD2006	Phase 2
0.6859	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3961	Discontinued
0.6857	Remote Similarity	NPD2430	Phase 2
0.6848	Remote Similarity	NPD3654	Approved
0.6848	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1683	Approved
0.6831	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2119	Approved
0.6829	Remote Similarity	NPD2118	Approved
0.6828	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2367	Phase 2
0.6825	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6217	Discontinued
0.6793	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5436	Phase 1
0.6791	Remote Similarity	NPD2144	Approved
0.6786	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3385	Approved
0.6786	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.676	Remote Similarity	NPD473	Clinical (unspecified phase)
0.676	Remote Similarity	NPD2580	Discontinued
0.6755	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1917	Discontinued
0.6739	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5105	Approved
0.6737	Remote Similarity	NPD5106	Approved
0.6722	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1313	Approved
0.6719	Remote Similarity	NPD706	Phase 1
0.6704	Remote Similarity	NPD2165	Phase 1
0.6704	Remote Similarity	NPD975	Approved
0.6704	Remote Similarity	NPD977	Approved
0.6704	Remote Similarity	NPD976	Approved
0.6702	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4029	Approved
0.6686	Remote Similarity	NPD4028	Approved
0.6686	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4030	Approved
0.6684	Remote Similarity	NPD3038	Discontinued
0.6684	Remote Similarity	NPD2928	Phase 2
0.6684	Remote Similarity	NPD8431	Approved
0.6667	Remote Similarity	NPD9583	Approved
0.6667	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3113	Approved
0.6667	Remote Similarity	NPD3112	Approved
0.6667	Remote Similarity	NPD3115	Approved
0.6667	Remote Similarity	NPD6664	Approved
0.6667	Remote Similarity	NPD3114	Approved
0.6667	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2094	Phase 2
0.6649	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2095	Phase 2
0.6649	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2092	Phase 2
0.6633	Remote Similarity	NPD4615	Phase 2
0.6632	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD2793	Discontinued
0.6615	Remote Similarity	NPD2096	Phase 2
0.6615	Remote Similarity	NPD2091	Phase 2
0.6614	Remote Similarity	NPD7111	Discontinued
0.6612	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD715	Phase 3
0.6599	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.659	Remote Similarity	NPD680	Discontinued
0.6589	Remote Similarity	NPD4890	Phase 2
0.6588	Remote Similarity	NPD3944	Approved
0.6588	Remote Similarity	NPD3942	Approved
0.6584	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1327	Discontinued
0.6579	Remote Similarity	NPD8386	Phase 2
0.6564	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD268	Approved
0.6564	Remote Similarity	NPD271	Approved
0.6559	Remote Similarity	NPD4638	Approved
0.6559	Remote Similarity	NPD4639	Approved
0.6559	Remote Similarity	NPD4640	Approved
0.6554	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD9357	Approved
0.6543	Remote Similarity	NPD750	Phase 2
0.6537	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1027	Approved
0.6536	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1030	Approved
0.6522	Remote Similarity	NPD9396	Approved
0.6522	Remote Similarity	NPD5315	Discontinued
0.6522	Remote Similarity	NPD9392	Approved
0.6512	Remote Similarity	NPD1255	Approved
0.6512	Remote Similarity	NPD1253	Approved
0.6512	Remote Similarity	NPD1254	Approved
0.6512	Remote Similarity	NPD1256	Approved
0.651	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3015	Discontinued
0.65	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5730	Phase 2
0.6492	Remote Similarity	NPD40	Phase 2
0.6488	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7619	Phase 3
0.6482	Remote Similarity	NPD7618	Phase 3
0.6471	Remote Similarity	NPD2333	Discontinued
0.6471	Remote Similarity	NPD803	Phase 1
0.6464	Remote Similarity	NPD3339	Approved
0.6462	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.645	Remote Similarity	NPD947	Approved
0.645	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.644	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1326	Approved
0.6436	Remote Similarity	NPD1325	Approved
0.6432	Remote Similarity	NPD1015	Phase 2
0.6432	Remote Similarity	NPD1016	Phase 2
0.6425	Remote Similarity	NPD2189	Approved
0.6425	Remote Similarity	NPD2187	Approved
0.6425	Remote Similarity	NPD1661	Suspended
0.6421	Remote Similarity	NPD3799	Suspended
0.6418	Remote Similarity	NPD2880	Discontinued
0.6418	Remote Similarity	NPD7948	Phase 1
0.6417	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1227	Phase 2
0.6408	Remote Similarity	NPD2008	Discontinued
0.64	Remote Similarity	NPD2072	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