NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	261.1
Volume:	265.026
LogP:	0.646
LogD:	1.738
LogS:	-3.143
# Rotatable Bonds:	1
TPSA:	81.21
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	2.89
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:	-5.076
MDCK Permeability:	6.232146915863268e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.353
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.672

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.663
Plasma Protein Binding (PPB):	93.55145263671875%
Volume Distribution (VD):	0.832
Pgp-substrate:	7.809872150421143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.66
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.309
CYP2D6-substrate:	0.681
CYP3A4-inhibitor:	0.469
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	5.792
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.759
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.774
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.747
Carcinogencity:	0.263
Eye Corrosion:	0.004
Eye Irritation:	0.401
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC122141

Natural Product ID:	NPC122141
*Common Name:**	Annomontine
IUPAC Name:	4-(9H-pyrido[3,4-b]indol-1-yl)pyrimidin-2-amine
Synonyms:	Annomontine
Standard InCHIKey:	IUDMZJRPDRCJEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H11N5/c16-15-18-8-6-12(20-15)14-13-10(5-7-17-14)9-3-1-2-4-11(9)19-13/h1-8,19H,(H2,16,18,20)
SMILES:	N=c1[nH]ccc(n1)c1nccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501413
PubChem CID:	5257090
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	trunk bark	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568766]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499336]
NPO30886	Annona foteida	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[16499336]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[18687006]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18687006]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7436	Annona foetida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13370	Annona montana	Species	Annonaceae	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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC50	=	34800.0	nM	PMID[564239]
NPT3631	Organism	Leishmania guyanensis	Leishmania guyanensis	IC50	>	613000.0	nM	PMID[564239]

☑ 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 NPC122141 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	1742
0.1-0.2	15740
0.2-0.3	17559
0.3-0.4	3059
0.4-0.5	1884
0.5-0.6	1584
0.6-0.7	870
0.7-0.8	220
0.8-0.85	19
0.85-0.9	16
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC470204
0.9536	High Similarity	NPC470203
0.9408	High Similarity	NPC225018
0.9388	High Similarity	NPC469811
0.9324	High Similarity	NPC321911
0.932	High Similarity	NPC143872
0.932	High Similarity	NPC63545
0.9267	High Similarity	NPC325903
0.9257	High Similarity	NPC179787
0.9257	High Similarity	NPC201380
0.8854	High Similarity	NPC317105
0.8839	High Similarity	NPC236711
0.878	High Similarity	NPC307191
0.8776	High Similarity	NPC125746
0.8742	High Similarity	NPC204141
0.8725	High Similarity	NPC115611
0.8707	High Similarity	NPC96102
0.8649	High Similarity	NPC105127
0.8649	High Similarity	NPC84911
0.8581	High Similarity	NPC29886
0.8581	High Similarity	NPC261195
0.8562	High Similarity	NPC17751
0.8562	High Similarity	NPC274229
0.8562	High Similarity	NPC280864
0.8562	High Similarity	NPC288838
0.8533	High Similarity	NPC110126
0.8533	High Similarity	NPC73767
0.8477	Intermediate Similarity	NPC469784
0.8477	Intermediate Similarity	NPC469779
0.8477	Intermediate Similarity	NPC279081
0.8477	Intermediate Similarity	NPC469768
0.8477	Intermediate Similarity	NPC469780
0.8477	Intermediate Similarity	NPC469767
0.8477	Intermediate Similarity	NPC469783
0.8477	Intermediate Similarity	NPC469761
0.8456	Intermediate Similarity	NPC325252
0.8435	Intermediate Similarity	NPC82295
0.8424	Intermediate Similarity	NPC280852
0.8421	Intermediate Similarity	NPC469766
0.8405	Intermediate Similarity	NPC97343
0.8397	Intermediate Similarity	NPC53947
0.8389	Intermediate Similarity	NPC198988
0.8387	Intermediate Similarity	NPC470111
0.8385	Intermediate Similarity	NPC478184
0.8366	Intermediate Similarity	NPC190296
0.8355	Intermediate Similarity	NPC230002
0.8355	Intermediate Similarity	NPC284635
0.8354	Intermediate Similarity	NPC82331
0.8354	Intermediate Similarity	NPC476219
0.8344	Intermediate Similarity	NPC470233
0.8343	Intermediate Similarity	NPC108011
0.8313	Intermediate Similarity	NPC474958
0.8313	Intermediate Similarity	NPC293487
0.8289	Intermediate Similarity	NPC88097
0.8261	Intermediate Similarity	NPC44773
0.8261	Intermediate Similarity	NPC215584
0.8258	Intermediate Similarity	NPC159856
0.8258	Intermediate Similarity	NPC314372
0.8253	Intermediate Similarity	NPC471579
0.825	Intermediate Similarity	NPC216643
0.8243	Intermediate Similarity	NPC22079
0.8239	Intermediate Similarity	NPC476297
0.8199	Intermediate Similarity	NPC56765
0.8199	Intermediate Similarity	NPC206819
0.8199	Intermediate Similarity	NPC318065
0.8188	Intermediate Similarity	NPC101165
0.816	Intermediate Similarity	NPC478182
0.8153	Intermediate Similarity	NPC471957
0.8144	Intermediate Similarity	NPC280297
0.8098	Intermediate Similarity	NPC478185
0.8092	Intermediate Similarity	NPC218268
0.8086	Intermediate Similarity	NPC135141
0.8086	Intermediate Similarity	NPC475990
0.8086	Intermediate Similarity	NPC92796
0.8063	Intermediate Similarity	NPC232798
0.8061	Intermediate Similarity	NPC478183
0.8061	Intermediate Similarity	NPC49217
0.805	Intermediate Similarity	NPC24678
0.805	Intermediate Similarity	NPC105818
0.805	Intermediate Similarity	NPC40070
0.8049	Intermediate Similarity	NPC247987
0.8047	Intermediate Similarity	NPC473380
0.8047	Intermediate Similarity	NPC240088
0.8037	Intermediate Similarity	NPC279918
0.8036	Intermediate Similarity	NPC317054
0.8025	Intermediate Similarity	NPC286427
0.8012	Intermediate Similarity	NPC63751
0.8012	Intermediate Similarity	NPC191415
0.8	Intermediate Similarity	NPC216713
0.8	Intermediate Similarity	NPC470823
0.7988	Intermediate Similarity	NPC282231
0.7975	Intermediate Similarity	NPC477591
0.7975	Intermediate Similarity	NPC41257
0.7973	Intermediate Similarity	NPC250361
0.7965	Intermediate Similarity	NPC102755
0.7965	Intermediate Similarity	NPC48938
0.7964	Intermediate Similarity	NPC32534
0.7964	Intermediate Similarity	NPC91895
0.795	Intermediate Similarity	NPC141926
0.795	Intermediate Similarity	NPC469786
0.795	Intermediate Similarity	NPC73952
0.795	Intermediate Similarity	NPC25008
0.795	Intermediate Similarity	NPC469765
0.795	Intermediate Similarity	NPC469763
0.795	Intermediate Similarity	NPC259644
0.795	Intermediate Similarity	NPC200214
0.795	Intermediate Similarity	NPC469760
0.7941	Intermediate Similarity	NPC59269
0.7939	Intermediate Similarity	NPC90723
0.7922	Intermediate Similarity	NPC314102
0.7922	Intermediate Similarity	NPC251722
0.7919	Intermediate Similarity	NPC284678
0.7911	Intermediate Similarity	NPC470440
0.7901	Intermediate Similarity	NPC80597
0.7901	Intermediate Similarity	NPC212376
0.7901	Intermediate Similarity	NPC75540
0.7901	Intermediate Similarity	NPC34844
0.7901	Intermediate Similarity	NPC70922
0.7901	Intermediate Similarity	NPC211572
0.7898	Intermediate Similarity	NPC231536
0.7895	Intermediate Similarity	NPC265710
0.7891	Intermediate Similarity	NPC46358
0.7885	Intermediate Similarity	NPC59084
0.7885	Intermediate Similarity	NPC2949
0.7874	Intermediate Similarity	NPC99939
0.7874	Intermediate Similarity	NPC15102
0.7874	Intermediate Similarity	NPC308931
0.7867	Intermediate Similarity	NPC473762
0.7866	Intermediate Similarity	NPC221786
0.7866	Intermediate Similarity	NPC474880
0.7857	Intermediate Similarity	NPC194411
0.7853	Intermediate Similarity	NPC469785
0.7849	Intermediate Similarity	NPC16659
0.7844	Intermediate Similarity	NPC56233
0.7844	Intermediate Similarity	NPC49954
0.7844	Intermediate Similarity	NPC474561
0.7844	Intermediate Similarity	NPC54988
0.7834	Intermediate Similarity	NPC473868
0.7834	Intermediate Similarity	NPC63157
0.7829	Intermediate Similarity	NPC62749
0.7818	Intermediate Similarity	NPC229173
0.7815	Intermediate Similarity	NPC473587
0.7809	Intermediate Similarity	NPC324149
0.7805	Intermediate Similarity	NPC469762
0.7785	Intermediate Similarity	NPC20144
0.7778	Intermediate Similarity	NPC473930
0.7765	Intermediate Similarity	NPC477611
0.7765	Intermediate Similarity	NPC326422
0.7763	Intermediate Similarity	NPC475428
0.7756	Intermediate Similarity	NPC169433
0.775	Intermediate Similarity	NPC316069
0.7719	Intermediate Similarity	NPC275305
0.7719	Intermediate Similarity	NPC37423
0.7718	Intermediate Similarity	NPC27740
0.7712	Intermediate Similarity	NPC475450
0.7712	Intermediate Similarity	NPC179365
0.7711	Intermediate Similarity	NPC131718
0.7706	Intermediate Similarity	NPC470498
0.7703	Intermediate Similarity	NPC41174
0.7702	Intermediate Similarity	NPC21605
0.7701	Intermediate Similarity	NPC116555
0.7692	Intermediate Similarity	NPC150259
0.7692	Intermediate Similarity	NPC265576
0.7688	Intermediate Similarity	NPC11126
0.7688	Intermediate Similarity	NPC12649
0.7651	Intermediate Similarity	NPC300238
0.7651	Intermediate Similarity	NPC230869
0.7647	Intermediate Similarity	NPC282398
0.7644	Intermediate Similarity	NPC24864
0.764	Intermediate Similarity	NPC478186
0.7633	Intermediate Similarity	NPC160105
0.763	Intermediate Similarity	NPC68354
0.7619	Intermediate Similarity	NPC194640
0.7619	Intermediate Similarity	NPC311276
0.7611	Intermediate Similarity	NPC473342
0.7611	Intermediate Similarity	NPC477166
0.7611	Intermediate Similarity	NPC477167
0.7611	Intermediate Similarity	NPC304187
0.7607	Intermediate Similarity	NPC33421
0.7593	Intermediate Similarity	NPC114209
0.7586	Intermediate Similarity	NPC176199
0.7586	Intermediate Similarity	NPC215795
0.7578	Intermediate Similarity	NPC86288
0.756	Intermediate Similarity	NPC253687
0.7551	Intermediate Similarity	NPC91958
0.755	Intermediate Similarity	NPC146373
0.755	Intermediate Similarity	NPC166424
0.755	Intermediate Similarity	NPC245244
0.7544	Intermediate Similarity	NPC474897
0.7541	Intermediate Similarity	NPC167710
0.7529	Intermediate Similarity	NPC248454
0.7515	Intermediate Similarity	NPC102423
0.7515	Intermediate Similarity	NPC40779
0.7515	Intermediate Similarity	NPC149265
0.7514	Intermediate Similarity	NPC467063
0.7514	Intermediate Similarity	NPC228835
0.7487	Intermediate Similarity	NPC317701
0.7486	Intermediate Similarity	NPC242209
0.7485	Intermediate Similarity	NPC201700
0.7484	Intermediate Similarity	NPC312092

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 NPC122141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	559
0.1-0.2	975
0.2-0.3	1308
0.3-0.4	2121
0.4-0.5	1632
0.5-0.6	1495
0.6-0.7	790
0.7-0.8	237
0.8-0.85	27
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD4374	Clinical (unspecified phase)
0.8792	High Similarity	NPD1722	Approved
0.8707	High Similarity	NPD198	Clinical (unspecified phase)
0.8533	High Similarity	NPD786	Approved
0.8526	High Similarity	NPD2837	Discontinued
0.8452	Intermediate Similarity	NPD3100	Discontinued
0.8443	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD1895	Discontinued
0.8364	Intermediate Similarity	NPD4128	Approved
0.8263	Intermediate Similarity	NPD4181	Approved
0.8242	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD3323	Discontinued
0.8129	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2172	Phase 1
0.8039	Intermediate Similarity	NPD1262	Discovery
0.8024	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6828	Phase 2
0.8012	Intermediate Similarity	NPD977	Approved
0.8012	Intermediate Similarity	NPD976	Approved
0.8012	Intermediate Similarity	NPD975	Approved
0.8	Intermediate Similarity	NPD715	Phase 3
0.7925	Intermediate Similarity	NPD4547	Phase 3
0.7919	Intermediate Similarity	NPD991	Phase 2
0.7919	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD1313	Approved
0.7877	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1683	Approved
0.7848	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1248	Discontinued
0.7829	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD706	Phase 1
0.7824	Intermediate Similarity	NPD5065	Approved
0.7811	Intermediate Similarity	NPD3609	Approved
0.7811	Intermediate Similarity	NPD3610	Approved
0.7805	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1707	Approved
0.7803	Intermediate Similarity	NPD1708	Approved
0.7798	Intermediate Similarity	NPD2640	Approved
0.7798	Intermediate Similarity	NPD2333	Discontinued
0.7798	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2641	Approved
0.7797	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2006	Phase 2
0.7771	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2430	Phase 2
0.7759	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2927	Phase 3
0.7733	Intermediate Similarity	NPD7111	Discontinued
0.7727	Intermediate Similarity	NPD3385	Approved
0.7727	Intermediate Similarity	NPD2793	Discontinued
0.7711	Intermediate Similarity	NPD1403	Approved
0.7711	Intermediate Similarity	NPD1404	Approved
0.7692	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5730	Phase 2
0.7688	Intermediate Similarity	NPD40	Phase 2
0.7682	Intermediate Similarity	NPD1598	Discontinued
0.768	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4075	Phase 2
0.7673	Intermediate Similarity	NPD4047	Discontinued
0.767	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1015	Phase 2
0.7665	Intermediate Similarity	NPD1016	Phase 2
0.7654	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5436	Phase 1
0.7647	Intermediate Similarity	NPD3475	Approved
0.7647	Intermediate Similarity	NPD3476	Approved
0.7644	Intermediate Similarity	NPD6595	Phase 3
0.7644	Intermediate Similarity	NPD5962	Phase 2
0.7637	Intermediate Similarity	NPD2880	Discontinued
0.7636	Intermediate Similarity	NPD2150	Discontinued
0.763	Intermediate Similarity	NPD3505	Approved
0.763	Intermediate Similarity	NPD3506	Approved
0.7625	Intermediate Similarity	NPD5254	Discontinued
0.7622	Intermediate Similarity	NPD1917	Discontinued
0.7597	Intermediate Similarity	NPD803	Phase 1
0.7586	Intermediate Similarity	NPD4079	Approved
0.7586	Intermediate Similarity	NPD4076	Approved
0.7584	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3961	Discontinued
0.7574	Intermediate Similarity	NPD1333	Phase 3
0.7569	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2119	Approved
0.7566	Intermediate Similarity	NPD2118	Approved
0.7545	Intermediate Similarity	NPD5418	Discontinued
0.7544	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2639	Approved
0.7529	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2642	Approved
0.7528	Intermediate Similarity	NPD4902	Discontinued
0.7514	Intermediate Similarity	NPD4615	Phase 2
0.75	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1030	Approved
0.75	Intermediate Similarity	NPD1027	Approved
0.75	Intermediate Similarity	NPD4462	Approved
0.75	Intermediate Similarity	NPD4463	Approved
0.7486	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1327	Discontinued
0.7485	Intermediate Similarity	NPD1661	Suspended
0.7485	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD509	Phase 3
0.7458	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD5462	Discontinued
0.7443	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD3015	Discontinued
0.7432	Intermediate Similarity	NPD7618	Phase 3
0.7432	Intermediate Similarity	NPD7619	Phase 3
0.743	Intermediate Similarity	NPD6217	Discontinued
0.743	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2580	Discontinued
0.7425	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2442	Approved
0.7421	Intermediate Similarity	NPD2443	Approved
0.7409	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2008	Discontinued
0.7405	Intermediate Similarity	NPD1256	Approved
0.7405	Intermediate Similarity	NPD1255	Approved
0.7405	Intermediate Similarity	NPD1253	Approved
0.7405	Intermediate Similarity	NPD6469	Phase 3
0.7405	Intermediate Similarity	NPD1254	Approved
0.7405	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9598	Discontinued
0.7389	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4030	Approved
0.7389	Intermediate Similarity	NPD7394	Phase 2
0.7389	Intermediate Similarity	NPD4029	Approved
0.7389	Intermediate Similarity	NPD4028	Approved
0.7389	Intermediate Similarity	NPD3942	Approved
0.7389	Intermediate Similarity	NPD3944	Approved
0.7386	Intermediate Similarity	NPD9583	Approved
0.7381	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD809	Discontinued
0.7368	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2165	Phase 1
0.7358	Intermediate Similarity	NPD45	Approved
0.7358	Intermediate Similarity	NPD6554	Approved
0.7356	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3654	Approved
0.7355	Intermediate Similarity	NPD947	Approved
0.7351	Intermediate Similarity	NPD6664	Approved
0.7351	Intermediate Similarity	NPD3830	Phase 1
0.7333	Intermediate Similarity	NPD6721	Phase 1
0.733	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3114	Approved
0.7321	Intermediate Similarity	NPD3113	Approved
0.7321	Intermediate Similarity	NPD3115	Approved
0.7321	Intermediate Similarity	NPD3112	Approved
0.7318	Intermediate Similarity	NPD5892	Approved
0.7317	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD482	Approved
0.7305	Intermediate Similarity	NPD1303	Phase 1
0.7305	Intermediate Similarity	NPD695	Discontinued
0.7302	Intermediate Similarity	NPD2364	Suspended
0.7296	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8431	Approved
0.7285	Intermediate Similarity	NPD268	Approved
0.7285	Intermediate Similarity	NPD271	Approved
0.7285	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1227	Phase 2
0.7277	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD1506	Discontinued
0.7273	Intermediate Similarity	NPD3348	Phase 2
0.7273	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2751	Phase 1
0.7268	Intermediate Similarity	NPD2411	Approved
0.7268	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5106	Approved
0.7263	Intermediate Similarity	NPD5105	Approved
0.7255	Intermediate Similarity	NPD9357	Approved
0.7253	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5315	Discontinued
0.7248	Intermediate Similarity	NPD9392	Approved
0.7248	Intermediate Similarity	NPD9396	Approved
0.7246	Intermediate Similarity	NPD1257	Approved
0.7244	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4294	Phase 2
0.7241	Intermediate Similarity	NPD4024	Phase 3
0.7238	Intermediate Similarity	NPD7026	Phase 2
0.7234	Intermediate Similarity	NPD6816	Phase 3
0.7232	Intermediate Similarity	NPD2144	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