NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.09
Volume:	215.971
LogP:	0.985
LogD:	1.433
LogS:	-2.82
# Rotatable Bonds:	1
TPSA:	68.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.879
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:	-4.923
MDCK Permeability:	6.003799171594437e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.647
30% Bioavailability (F30%):	0.273

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.576
Plasma Protein Binding (PPB):	85.93883514404297%
Volume Distribution (VD):	1.031
Pgp-substrate:	20.564971923828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.325
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.415
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	7.995
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.758
AMES Toxicity:	0.763
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.368
Carcinogencity:	0.593
Eye Corrosion:	0.006
Eye Irritation:	0.758
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC125746

Natural Product ID:	NPC125746
*Common Name:**	4-(1H-Indol-2-Yl)Pyrimidin-2-Amine
IUPAC Name:	4-(1H-indol-2-yl)pyrimidin-2-amine
Synonyms:
Standard InCHIKey:	DMIMDIGPBYDVRA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10N4/c13-12-14-6-5-10(16-12)11-7-8-3-1-2-4-9(8)15-11/h1-7,15H,(H2,13,14,16)
SMILES:	N=c1[nH]ccc(n1)c1cc2c([nH]1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL50226
PubChem CID:	10965763
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	6

Activity Type	# Activity
Individual Protein	2
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	=	420000.0	nM	PMID[488793]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	420000.0	nM	PMID[488794]
NPT1570	Protein Complex	Cyclin-dependent kinase 1/cyclin B	Homo sapiens	IC50	=	140000.0	nM	PMID[488793]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	=	130000.0	nM	PMID[488793]
NPT321	Protein Family	cAMP-dependent protein kinase (PKA)	Homo sapiens	IC50	=	500000.0	nM	PMID[488793]
NPT2	Others	Unspecified		IC50	=	1000000.0	nM	PMID[488793]

☑ 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 NPC125746 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	2298
0.1-0.2	15423
0.2-0.3	17178
0.3-0.4	3097
0.4-0.5	1934
0.5-0.6	1607
0.6-0.7	869
0.7-0.8	234
0.8-0.85	41
0.85-0.9	11
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC143872
0.9091	High Similarity	NPC22079
0.9085	High Similarity	NPC232798
0.9065	High Similarity	NPC204141
0.8776	High Similarity	NPC122141
0.8769	High Similarity	NPC41174
0.8759	High Similarity	NPC325252
0.8759	High Similarity	NPC96102
0.8741	High Similarity	NPC82295
0.8696	High Similarity	NPC84911
0.8696	High Similarity	NPC105127
0.8686	High Similarity	NPC198988
0.8647	High Similarity	NPC250361
0.8623	High Similarity	NPC261195
0.8623	High Similarity	NPC218268
0.8623	High Similarity	NPC29886
0.86	High Similarity	NPC17751
0.86	High Similarity	NPC280864
0.8571	High Similarity	NPC110126
0.8571	High Similarity	NPC73767
0.8523	High Similarity	NPC470204
0.8519	High Similarity	NPC473762
0.8511	High Similarity	NPC469779
0.8511	High Similarity	NPC469783
0.8511	High Similarity	NPC469780
0.8511	High Similarity	NPC469784
0.8511	High Similarity	NPC469767
0.8511	High Similarity	NPC469761
0.8511	High Similarity	NPC279081
0.8511	High Similarity	NPC469768
0.8467	Intermediate Similarity	NPC470203
0.8456	Intermediate Similarity	NPC473587
0.8451	Intermediate Similarity	NPC469766
0.844	Intermediate Similarity	NPC88097
0.8394	Intermediate Similarity	NPC475428
0.8392	Intermediate Similarity	NPC190296
0.838	Intermediate Similarity	NPC115611
0.838	Intermediate Similarity	NPC59084
0.838	Intermediate Similarity	NPC2949
0.838	Intermediate Similarity	NPC230002
0.8345	Intermediate Similarity	NPC288838
0.8333	Intermediate Similarity	NPC179365
0.8333	Intermediate Similarity	NPC475450
0.8322	Intermediate Similarity	NPC473868
0.8322	Intermediate Similarity	NPC63157
0.8289	Intermediate Similarity	NPC247987
0.8288	Intermediate Similarity	NPC469811
0.8276	Intermediate Similarity	NPC314372
0.8276	Intermediate Similarity	NPC159856
0.8273	Intermediate Similarity	NPC473930
0.8231	Intermediate Similarity	NPC321911
0.8224	Intermediate Similarity	NPC225018
0.8219	Intermediate Similarity	NPC63545
0.8176	Intermediate Similarity	NPC53947
0.8163	Intermediate Similarity	NPC471957
0.8163	Intermediate Similarity	NPC179787
0.8163	Intermediate Similarity	NPC201380
0.8153	Intermediate Similarity	NPC280297
0.8151	Intermediate Similarity	NPC470440
0.8108	Intermediate Similarity	NPC37548
0.8092	Intermediate Similarity	NPC318065
0.8092	Intermediate Similarity	NPC206819
0.8092	Intermediate Similarity	NPC475990
0.8082	Intermediate Similarity	NPC242556
0.8067	Intermediate Similarity	NPC325903
0.8065	Intermediate Similarity	NPC49217
0.8054	Intermediate Similarity	NPC24678
0.8054	Intermediate Similarity	NPC105818
0.8054	Intermediate Similarity	NPC148592
0.8041	Intermediate Similarity	NPC21605
0.8039	Intermediate Similarity	NPC279918
0.8	Intermediate Similarity	NPC216713
0.8	Intermediate Similarity	NPC284635
0.8	Intermediate Similarity	NPC470823
0.7987	Intermediate Similarity	NPC282231
0.7987	Intermediate Similarity	NPC2272
0.7973	Intermediate Similarity	NPC316069
0.7947	Intermediate Similarity	NPC469765
0.7947	Intermediate Similarity	NPC200214
0.7947	Intermediate Similarity	NPC469763
0.7947	Intermediate Similarity	NPC141926
0.7947	Intermediate Similarity	NPC25008
0.7947	Intermediate Similarity	NPC73952
0.7947	Intermediate Similarity	NPC469786
0.7947	Intermediate Similarity	NPC469760
0.7947	Intermediate Similarity	NPC259644
0.7933	Intermediate Similarity	NPC33421
0.7931	Intermediate Similarity	NPC312092
0.7908	Intermediate Similarity	NPC216643
0.7908	Intermediate Similarity	NPC286427
0.7895	Intermediate Similarity	NPC70922
0.7895	Intermediate Similarity	NPC80597
0.7895	Intermediate Similarity	NPC38736
0.7895	Intermediate Similarity	NPC75540
0.7895	Intermediate Similarity	NPC212376
0.7895	Intermediate Similarity	NPC211572
0.7895	Intermediate Similarity	NPC148140
0.7895	Intermediate Similarity	NPC34844
0.7895	Intermediate Similarity	NPC470507
0.7883	Intermediate Similarity	NPC46358
0.7867	Intermediate Similarity	NPC187951
0.7867	Intermediate Similarity	NPC124005
0.7857	Intermediate Similarity	NPC41257
0.7857	Intermediate Similarity	NPC135141
0.7857	Intermediate Similarity	NPC474880
0.7857	Intermediate Similarity	NPC221786
0.7857	Intermediate Similarity	NPC56765
0.7857	Intermediate Similarity	NPC92796
0.7843	Intermediate Similarity	NPC469785
0.7843	Intermediate Similarity	NPC141353
0.7843	Intermediate Similarity	NPC285469
0.7836	Intermediate Similarity	NPC81561
0.7834	Intermediate Similarity	NPC54988
0.7834	Intermediate Similarity	NPC49954
0.7834	Intermediate Similarity	NPC474561
0.7826	Intermediate Similarity	NPC240088
0.7826	Intermediate Similarity	NPC473380
0.7817	Intermediate Similarity	NPC101165
0.78	Intermediate Similarity	NPC114209
0.7792	Intermediate Similarity	NPC236711
0.7792	Intermediate Similarity	NPC469762
0.7791	Intermediate Similarity	NPC307191
0.7785	Intermediate Similarity	NPC63751
0.7778	Intermediate Similarity	NPC476219
0.7778	Intermediate Similarity	NPC162689
0.7778	Intermediate Similarity	NPC476297
0.7778	Intermediate Similarity	NPC54102
0.777	Intermediate Similarity	NPC20144
0.7763	Intermediate Similarity	NPC470233
0.7736	Intermediate Similarity	NPC194411
0.7707	Intermediate Similarity	NPC317105
0.7707	Intermediate Similarity	NPC90723
0.7698	Intermediate Similarity	NPC27740
0.7692	Intermediate Similarity	NPC215584
0.7692	Intermediate Similarity	NPC131718
0.7692	Intermediate Similarity	NPC44773
0.7692	Intermediate Similarity	NPC229173
0.7688	Intermediate Similarity	NPC470498
0.7682	Intermediate Similarity	NPC477134
0.7671	Intermediate Similarity	NPC150259
0.7669	Intermediate Similarity	NPC265710
0.7664	Intermediate Similarity	NPC215519
0.7662	Intermediate Similarity	NPC471458
0.7643	Intermediate Similarity	NPC16667
0.7635	Intermediate Similarity	NPC238499
0.7628	Intermediate Similarity	NPC230869
0.7622	Intermediate Similarity	NPC16659
0.7616	Intermediate Similarity	NPC129042
0.7613	Intermediate Similarity	NPC184476
0.761	Intermediate Similarity	NPC160105
0.7607	Intermediate Similarity	NPC59269
0.7595	Intermediate Similarity	NPC311276
0.7595	Intermediate Similarity	NPC194640
0.7594	Intermediate Similarity	NPC314141
0.7593	Intermediate Similarity	NPC275305
0.7593	Intermediate Similarity	NPC37423
0.7588	Intermediate Similarity	NPC477166
0.7588	Intermediate Similarity	NPC473342
0.7588	Intermediate Similarity	NPC304187
0.7588	Intermediate Similarity	NPC477167
0.7568	Intermediate Similarity	NPC104483
0.7564	Intermediate Similarity	NPC299594
0.7548	Intermediate Similarity	NPC207726
0.7547	Intermediate Similarity	NPC274229
0.7531	Intermediate Similarity	NPC477611
0.75	Intermediate Similarity	NPC248454
0.75	Intermediate Similarity	NPC282398
0.75	Intermediate Similarity	NPC68354
0.7484	Intermediate Similarity	NPC21174
0.7484	Intermediate Similarity	NPC40779
0.7484	Intermediate Similarity	NPC102423
0.7484	Intermediate Similarity	NPC149265
0.7484	Intermediate Similarity	NPC271797
0.7468	Intermediate Similarity	NPC473320
0.7457	Intermediate Similarity	NPC242209
0.7455	Intermediate Similarity	NPC215795
0.7455	Intermediate Similarity	NPC176199
0.7455	Intermediate Similarity	NPC11126
0.7453	Intermediate Similarity	NPC201700
0.7447	Intermediate Similarity	NPC122718
0.7432	Intermediate Similarity	NPC314102
0.7432	Intermediate Similarity	NPC251722
0.7423	Intermediate Similarity	NPC314603
0.7407	Intermediate Similarity	NPC474897
0.7407	Intermediate Similarity	NPC280548
0.7407	Intermediate Similarity	NPC97343
0.7405	Intermediate Similarity	NPC67056
0.7405	Intermediate Similarity	NPC300238
0.7394	Intermediate Similarity	NPC245244
0.7394	Intermediate Similarity	NPC166424
0.7394	Intermediate Similarity	NPC146373
0.7391	Intermediate Similarity	NPC109447
0.7381	Intermediate Similarity	NPC21429
0.7381	Intermediate Similarity	NPC108011
0.7375	Intermediate Similarity	NPC472587
0.7375	Intermediate Similarity	NPC271734
0.7372	Intermediate Similarity	NPC281094
0.7362	Intermediate Similarity	NPC6982
0.7362	Intermediate Similarity	NPC82331
0.7351	Intermediate Similarity	NPC277157

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 NPC125746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	551
0.1-0.2	1001
0.2-0.3	1199
0.3-0.4	2075
0.4-0.5	1698
0.5-0.6	1551
0.6-0.7	786
0.7-0.8	256
0.8-0.85	29
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD198	Clinical (unspecified phase)
0.8696	High Similarity	NPD1262	Discovery
0.8611	High Similarity	NPD4374	Clinical (unspecified phase)
0.8582	High Similarity	NPD1722	Approved
0.8571	High Similarity	NPD786	Approved
0.8483	Intermediate Similarity	NPD3100	Discontinued
0.838	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD5254	Discontinued
0.8138	Intermediate Similarity	NPD4047	Discontinued
0.8079	Intermediate Similarity	NPD2150	Discontinued
0.8054	Intermediate Similarity	NPD2172	Phase 1
0.8054	Intermediate Similarity	NPD4462	Approved
0.8054	Intermediate Similarity	NPD4463	Approved
0.8038	Intermediate Similarity	NPD4128	Approved
0.8025	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6828	Phase 2
0.8014	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2837	Discontinued
0.7929	Intermediate Similarity	NPD3654	Approved
0.7852	Intermediate Similarity	NPD1683	Approved
0.7832	Intermediate Similarity	NPD3385	Approved
0.7786	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD991	Phase 2
0.7722	Intermediate Similarity	NPD1248	Discontinued
0.7716	Intermediate Similarity	NPD4181	Approved
0.7707	Intermediate Similarity	NPD3323	Discontinued
0.7692	Intermediate Similarity	NPD1404	Approved
0.7692	Intermediate Similarity	NPD1403	Approved
0.7687	Intermediate Similarity	NPD680	Discontinued
0.7683	Intermediate Similarity	NPD1895	Discontinued
0.7676	Intermediate Similarity	NPD947	Approved
0.766	Intermediate Similarity	NPD1598	Discontinued
0.7651	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1255	Approved
0.7603	Intermediate Similarity	NPD1256	Approved
0.7603	Intermediate Similarity	NPD1254	Approved
0.7603	Intermediate Similarity	NPD1253	Approved
0.7584	Intermediate Similarity	NPD1592	Phase 3
0.7576	Intermediate Similarity	NPD1707	Approved
0.7576	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1708	Approved
0.7562	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2640	Approved
0.7562	Intermediate Similarity	NPD2641	Approved
0.7561	Intermediate Similarity	NPD5730	Phase 2
0.7561	Intermediate Similarity	NPD8386	Phase 2
0.7561	Intermediate Similarity	NPD40	Phase 2
0.7551	Intermediate Similarity	NPD6554	Approved
0.7551	Intermediate Similarity	NPD45	Approved
0.7547	Intermediate Similarity	NPD1313	Approved
0.7546	Intermediate Similarity	NPD4075	Phase 2
0.7533	Intermediate Similarity	NPD2006	Phase 2
0.753	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD2639	Approved
0.75	Intermediate Similarity	NPD2927	Phase 3
0.75	Intermediate Similarity	NPD3505	Approved
0.75	Intermediate Similarity	NPD3506	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.75	Intermediate Similarity	NPD2642	Approved
0.7469	Intermediate Similarity	NPD3610	Approved
0.7469	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3609	Approved
0.7468	Intermediate Similarity	NPD3833	Phase 3
0.7468	Intermediate Similarity	NPD3835	Phase 3
0.7455	Intermediate Similarity	NPD4076	Approved
0.7455	Intermediate Similarity	NPD4079	Approved
0.7453	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1251	Discontinued
0.7438	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD509	Phase 3
0.7438	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4880	Discontinued
0.741	Intermediate Similarity	NPD6595	Phase 3
0.741	Intermediate Similarity	NPD5962	Phase 2
0.7407	Intermediate Similarity	NPD1325	Approved
0.7407	Intermediate Similarity	NPD1326	Approved
0.7389	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5065	Approved
0.7372	Intermediate Similarity	NPD1917	Discontinued
0.7342	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4547	Phase 3
0.7325	Intermediate Similarity	NPD2165	Phase 1
0.7305	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5787	Discontinued
0.7292	Intermediate Similarity	NPD2118	Approved
0.7292	Intermediate Similarity	NPD2119	Approved
0.729	Intermediate Similarity	NPD2430	Phase 2
0.7289	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4811	Discontinued
0.7278	Intermediate Similarity	NPD3114	Approved
0.7278	Intermediate Similarity	NPD3115	Approved
0.7278	Intermediate Similarity	NPD3113	Approved
0.7278	Intermediate Similarity	NPD3112	Approved
0.7273	Intermediate Similarity	NPD482	Approved
0.7273	Intermediate Similarity	NPD2928	Phase 2
0.7267	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3961	Discontinued
0.7246	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5439	Approved
0.7235	Intermediate Similarity	NPD5438	Approved
0.7234	Intermediate Similarity	NPD268	Approved
0.7234	Intermediate Similarity	NPD271	Approved
0.7234	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9583	Approved
0.7219	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6285	Phase 2
0.7212	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9357	Approved
0.7197	Intermediate Similarity	NPD993	Approved
0.7197	Intermediate Similarity	NPD990	Approved
0.7195	Intermediate Similarity	NPD5436	Phase 1
0.7194	Intermediate Similarity	NPD9392	Approved
0.7194	Intermediate Similarity	NPD9396	Approved
0.7193	Intermediate Similarity	NPD706	Phase 1
0.7193	Intermediate Similarity	NPD6217	Discontinued
0.7186	Intermediate Similarity	NPD2144	Approved
0.7183	Intermediate Similarity	NPD1561	Phase 2
0.7178	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2580	Discontinued
0.717	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5140	Approved
0.716	Intermediate Similarity	NPD5138	Approved
0.7159	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD715	Phase 3
0.7135	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5021	Discontinued
0.7124	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7481	Approved
0.7122	Intermediate Similarity	NPD7480	Approved
0.7118	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5105	Approved
0.7118	Intermediate Similarity	NPD5106	Approved
0.7114	Intermediate Similarity	NPD4029	Approved
0.7114	Intermediate Similarity	NPD4030	Approved
0.7114	Intermediate Similarity	NPD4028	Approved
0.7107	Intermediate Similarity	NPD976	Approved
0.7107	Intermediate Similarity	NPD977	Approved
0.7107	Intermediate Similarity	NPD975	Approved
0.7107	Intermediate Similarity	NPD1597	Phase 1
0.7105	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD803	Phase 1
0.7093	Intermediate Similarity	NPD2793	Discontinued
0.709	Intermediate Similarity	NPD477	Phase 1
0.7086	Intermediate Similarity	NPD544	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3038	Discontinued
0.7056	Intermediate Similarity	NPD4511	Phase 1
0.7052	Intermediate Similarity	NPD8431	Approved
0.7039	Intermediate Similarity	NPD3814	Phase 1
0.7032	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7709	Discontinued
0.7022	Intermediate Similarity	NPD6664	Approved
0.7018	Intermediate Similarity	NPD4441	Phase 2
0.7018	Intermediate Similarity	NPD3320	Approved
0.7018	Intermediate Similarity	NPD2095	Phase 2
0.7018	Intermediate Similarity	NPD2092	Phase 2
0.7018	Intermediate Similarity	NPD3319	Phase 1
0.7018	Intermediate Similarity	NPD3318	Approved
0.7018	Intermediate Similarity	NPD2094	Phase 2
0.7012	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1661	Suspended
0.7006	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4294	Phase 2
0.7	Intermediate Similarity	NPD3944	Approved
0.7	Intermediate Similarity	NPD5473	Discontinued
0.7	Intermediate Similarity	NPD3942	Approved
0.6994	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2591	Phase 2
0.6994	Remote Similarity	NPD1016	Phase 2
0.6994	Remote Similarity	NPD1015	Phase 2
0.6989	Remote Similarity	NPD4615	Phase 2
0.6983	Remote Similarity	NPD6469	Phase 3
0.6983	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7111	Discontinued
0.6977	Remote Similarity	NPD2096	Phase 2
0.6977	Remote Similarity	NPD2091	Phase 2
0.6975	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD1043	Phase 3
0.697	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1215	Discontinued

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