NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	271.18
Volume:	284.128
LogP:	0.321
LogD:	0.68
LogS:	-2.166
# Rotatable Bonds:	5
TPSA:	89.72
# H-Bond Aceptor:	5
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.039
Fsp3:	0.4
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:	-5.653
MDCK Permeability:	3.3810217701102374e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.533
20% Bioavailability (F20%):	0.447
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	22.188232421875%
Volume Distribution (VD):	2.226
Pgp-substrate:	70.86429595947266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.275
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	8.454
Half-life (T1/2):	0.595

ADMET: Toxicity

hERG Blockers:	0.569
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.688
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.337
Carcinogencity:	0.133
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC204141

Natural Product ID:	NPC204141
*Common Name:**	Trypargine
IUPAC Name:	2-[3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propyl]guanidine
Synonyms:	Trypargine
Standard InCHIKey:	NMPAXZOTIQZCEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H21N5/c16-15(17)19-8-3-6-13-14-11(7-9-18-13)10-4-1-2-5-12(10)20-14/h1-2,4-5,13,18,20H,3,6-9H2,(H4,16,17,19)
SMILES:	NC(=N)NCCCC1NCCc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492608
PubChem CID:	14162516
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
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10346975]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	Far-Eastern	n.a.	PMID[11754612]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12608864]
NPO33386	Eudistoma sp.	Species	n.a.	n.a.	n.a.	Korean	n.a.	PMID[18247569]
NPO21841	African frog	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO28445	Juniperus taiwaniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21841	African frog	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28445	Juniperus taiwaniana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	16.9	mg.kg-1	PMID[543862]

☑ 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 NPC204141 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	1225
0.1-0.2	14719
0.2-0.3	17261
0.3-0.4	3957
0.4-0.5	2524
0.5-0.6	1726
0.6-0.7	916
0.7-0.8	296
0.8-0.85	63
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.927	High Similarity	NPC325252
0.9128	High Similarity	NPC247987
0.9122	High Similarity	NPC470204
0.9071	High Similarity	NPC88097
0.9065	High Similarity	NPC125746
0.906	High Similarity	NPC470203
0.9058	High Similarity	NPC198988
0.8993	High Similarity	NPC218268
0.8828	High Similarity	NPC143872
0.8742	High Similarity	NPC122141
0.8741	High Similarity	NPC115611
0.8681	High Similarity	NPC473868
0.8681	High Similarity	NPC63157
0.8633	High Similarity	NPC22079
0.8611	High Similarity	NPC59084
0.8611	High Similarity	NPC2949
0.8514	High Similarity	NPC469811
0.8503	High Similarity	NPC470440
0.8478	Intermediate Similarity	NPC250361
0.8462	Intermediate Similarity	NPC96102
0.8456	Intermediate Similarity	NPC321911
0.8446	Intermediate Similarity	NPC63545
0.8431	Intermediate Similarity	NPC474880
0.8431	Intermediate Similarity	NPC475990
0.8431	Intermediate Similarity	NPC221786
0.8414	Intermediate Similarity	NPC73767
0.8403	Intermediate Similarity	NPC84911
0.8403	Intermediate Similarity	NPC105127
0.8389	Intermediate Similarity	NPC179787
0.8389	Intermediate Similarity	NPC201380
0.8389	Intermediate Similarity	NPC21605
0.8357	Intermediate Similarity	NPC473762
0.8356	Intermediate Similarity	NPC469783
0.8356	Intermediate Similarity	NPC469784
0.8356	Intermediate Similarity	NPC469779
0.8356	Intermediate Similarity	NPC469761
0.8356	Intermediate Similarity	NPC469780
0.8356	Intermediate Similarity	NPC469767
0.8356	Intermediate Similarity	NPC469768
0.8355	Intermediate Similarity	NPC476297
0.8355	Intermediate Similarity	NPC476219
0.8333	Intermediate Similarity	NPC307191
0.8333	Intermediate Similarity	NPC29886
0.8333	Intermediate Similarity	NPC261195
0.8321	Intermediate Similarity	NPC41174
0.831	Intermediate Similarity	NPC475450
0.8299	Intermediate Similarity	NPC469766
0.8298	Intermediate Similarity	NPC473587
0.8289	Intermediate Similarity	NPC232798
0.8289	Intermediate Similarity	NPC325903
0.8288	Intermediate Similarity	NPC110126
0.8278	Intermediate Similarity	NPC33421
0.8258	Intermediate Similarity	NPC229173
0.8239	Intermediate Similarity	NPC475428
0.8231	Intermediate Similarity	NPC279081
0.8231	Intermediate Similarity	NPC284635
0.8205	Intermediate Similarity	NPC225018
0.8182	Intermediate Similarity	NPC82295
0.8182	Intermediate Similarity	NPC179365
0.8133	Intermediate Similarity	NPC314372
0.8125	Intermediate Similarity	NPC473930
0.8121	Intermediate Similarity	NPC190296
0.8108	Intermediate Similarity	NPC230002
0.8101	Intermediate Similarity	NPC280864
0.8101	Intermediate Similarity	NPC17751
0.8079	Intermediate Similarity	NPC288838
0.8077	Intermediate Similarity	NPC56765
0.805	Intermediate Similarity	NPC49217
0.8039	Intermediate Similarity	NPC53947
0.8038	Intermediate Similarity	NPC271797
0.8038	Intermediate Similarity	NPC21174
0.8037	Intermediate Similarity	NPC240088
0.8037	Intermediate Similarity	NPC473380
0.8013	Intermediate Similarity	NPC159856
0.8013	Intermediate Similarity	NPC236711
0.8	Intermediate Similarity	NPC20144
0.7988	Intermediate Similarity	NPC265710
0.7974	Intermediate Similarity	NPC2272
0.7974	Intermediate Similarity	NPC37548
0.7956	Intermediate Similarity	NPC81561
0.795	Intermediate Similarity	NPC474897
0.7939	Intermediate Similarity	NPC16659
0.7925	Intermediate Similarity	NPC317105
0.7922	Intermediate Similarity	NPC24678
0.7922	Intermediate Similarity	NPC105818
0.7908	Intermediate Similarity	NPC471957
0.7908	Intermediate Similarity	NPC114209
0.7904	Intermediate Similarity	NPC108011
0.7888	Intermediate Similarity	NPC317430
0.7883	Intermediate Similarity	NPC148140
0.7871	Intermediate Similarity	NPC470233
0.7848	Intermediate Similarity	NPC206819
0.7848	Intermediate Similarity	NPC41257
0.7848	Intermediate Similarity	NPC318065
0.7829	Intermediate Similarity	NPC242556
0.7821	Intermediate Similarity	NPC200214
0.7821	Intermediate Similarity	NPC73952
0.7821	Intermediate Similarity	NPC469763
0.7821	Intermediate Similarity	NPC469760
0.7821	Intermediate Similarity	NPC469786
0.7821	Intermediate Similarity	NPC259644
0.7821	Intermediate Similarity	NPC469765
0.7821	Intermediate Similarity	NPC25008
0.7812	Intermediate Similarity	NPC90723
0.78	Intermediate Similarity	NPC312092
0.78	Intermediate Similarity	NPC104483
0.7785	Intermediate Similarity	NPC216643
0.7785	Intermediate Similarity	NPC286427
0.7771	Intermediate Similarity	NPC211572
0.7771	Intermediate Similarity	NPC470507
0.7771	Intermediate Similarity	NPC80597
0.7771	Intermediate Similarity	NPC70922
0.7771	Intermediate Similarity	NPC212376
0.7771	Intermediate Similarity	NPC38736
0.7771	Intermediate Similarity	NPC75540
0.777	Intermediate Similarity	NPC54102
0.777	Intermediate Similarity	NPC162689
0.7764	Intermediate Similarity	NPC274229
0.7758	Intermediate Similarity	NPC280852
0.7758	Intermediate Similarity	NPC474958
0.7756	Intermediate Similarity	NPC470823
0.7756	Intermediate Similarity	NPC216713
0.7744	Intermediate Similarity	NPC161861
0.7744	Intermediate Similarity	NPC472123
0.7742	Intermediate Similarity	NPC187951
0.7736	Intermediate Similarity	NPC135141
0.7736	Intermediate Similarity	NPC92796
0.7722	Intermediate Similarity	NPC469785
0.7722	Intermediate Similarity	NPC285469
0.7707	Intermediate Similarity	NPC141926
0.7697	Intermediate Similarity	NPC280297
0.7692	Intermediate Similarity	NPC40070
0.7692	Intermediate Similarity	NPC148592
0.7688	Intermediate Similarity	NPC215584
0.7688	Intermediate Similarity	NPC279918
0.7688	Intermediate Similarity	NPC44773
0.7683	Intermediate Similarity	NPC82331
0.7677	Intermediate Similarity	NPC470111
0.7677	Intermediate Similarity	NPC477134
0.7673	Intermediate Similarity	NPC469762
0.766	Intermediate Similarity	NPC215519
0.7658	Intermediate Similarity	NPC34844
0.764	Intermediate Similarity	NPC282231
0.7628	Intermediate Similarity	NPC124005
0.7625	Intermediate Similarity	NPC300238
0.7622	Intermediate Similarity	NPC46358
0.7622	Intermediate Similarity	NPC97343
0.7619	Intermediate Similarity	NPC469896
0.7607	Intermediate Similarity	NPC474561
0.7607	Intermediate Similarity	NPC49954
0.7607	Intermediate Similarity	NPC160105
0.7605	Intermediate Similarity	NPC183662
0.7605	Intermediate Similarity	NPC217372
0.7605	Intermediate Similarity	NPC15573
0.7588	Intermediate Similarity	NPC21429
0.7588	Intermediate Similarity	NPC472294
0.7586	Intermediate Similarity	NPC477166
0.7586	Intermediate Similarity	NPC473342
0.7586	Intermediate Similarity	NPC304187
0.7586	Intermediate Similarity	NPC477167
0.7569	Intermediate Similarity	NPC27740
0.7568	Intermediate Similarity	NPC101165
0.7562	Intermediate Similarity	NPC299594
0.7561	Intermediate Similarity	NPC63751
0.756	Intermediate Similarity	NPC219336
0.755	Intermediate Similarity	NPC314102
0.755	Intermediate Similarity	NPC251722
0.755	Intermediate Similarity	NPC150259
0.7546	Intermediate Similarity	NPC2165
0.7546	Intermediate Similarity	NPC195507
0.7531	Intermediate Similarity	NPC16667
0.7529	Intermediate Similarity	NPC470205
0.7515	Intermediate Similarity	NPC194411
0.75	Intermediate Similarity	NPC141612
0.75	Intermediate Similarity	NPC141353
0.75	Intermediate Similarity	NPC109447
0.75	Intermediate Similarity	NPC316069
0.75	Intermediate Similarity	NPC54988
0.75	Intermediate Similarity	NPC17273
0.75	Intermediate Similarity	NPC135601
0.7485	Intermediate Similarity	NPC317054
0.7485	Intermediate Similarity	NPC311276
0.7485	Intermediate Similarity	NPC329688
0.7485	Intermediate Similarity	NPC189812
0.7469	Intermediate Similarity	NPC131718
0.7456	Intermediate Similarity	NPC11126
0.7448	Intermediate Similarity	NPC122718
0.7443	Intermediate Similarity	NPC188821
0.7443	Intermediate Similarity	NPC474180
0.7438	Intermediate Similarity	NPC207726
0.7438	Intermediate Similarity	NPC471458
0.7427	Intermediate Similarity	NPC139291
0.7427	Intermediate Similarity	NPC472108
0.7425	Intermediate Similarity	NPC477611
0.7425	Intermediate Similarity	NPC314603
0.7407	Intermediate Similarity	NPC230869
0.7397	Intermediate Similarity	NPC245244
0.7397	Intermediate Similarity	NPC166424
0.7397	Intermediate Similarity	NPC146373
0.7396	Intermediate Similarity	NPC59269

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 NPC204141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	913
0.2-0.3	987
0.3-0.4	1912
0.4-0.5	2212
0.5-0.6	1893
0.6-0.7	670
0.7-0.8	146
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD1722	Approved
0.8621	High Similarity	NPD4637	Clinical (unspecified phase)
0.8543	High Similarity	NPD2150	Discontinued
0.8542	High Similarity	NPD786	Approved
0.8531	High Similarity	NPD1262	Discovery
0.8471	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6828	Phase 2
0.8462	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1683	Approved
0.8356	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4181	Approved
0.8212	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5254	Discontinued
0.8137	Intermediate Similarity	NPD4128	Approved
0.8121	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4047	Discontinued
0.8092	Intermediate Similarity	NPD3100	Discontinued
0.8069	Intermediate Similarity	NPD3385	Approved
0.8052	Intermediate Similarity	NPD2837	Discontinued
0.8039	Intermediate Similarity	NPD4463	Approved
0.8039	Intermediate Similarity	NPD4462	Approved
0.8	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1313	Approved
0.7949	Intermediate Similarity	NPD2927	Phase 3
0.7939	Intermediate Similarity	NPD5962	Phase 2
0.7925	Intermediate Similarity	NPD3323	Discontinued
0.7922	Intermediate Similarity	NPD2172	Phase 1
0.7917	Intermediate Similarity	NPD3654	Approved
0.7892	Intermediate Similarity	NPD1895	Discontinued
0.7879	Intermediate Similarity	NPD8386	Phase 2
0.7875	Intermediate Similarity	NPD509	Phase 3
0.784	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD991	Phase 2
0.7771	Intermediate Similarity	NPD5730	Phase 2
0.7771	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD40	Phase 2
0.7764	Intermediate Similarity	NPD1002	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1248	Discontinued
0.7683	Intermediate Similarity	NPD3609	Approved
0.7683	Intermediate Similarity	NPD3610	Approved
0.7683	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD680	Discontinued
0.7679	Intermediate Similarity	NPD1708	Approved
0.7679	Intermediate Similarity	NPD1707	Approved
0.7676	Intermediate Similarity	NPD5787	Discontinued
0.7671	Intermediate Similarity	NPD947	Approved
0.7669	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2641	Approved
0.7669	Intermediate Similarity	NPD2640	Approved
0.766	Intermediate Similarity	NPD4811	Discontinued
0.7657	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1255	Approved
0.76	Intermediate Similarity	NPD1256	Approved
0.76	Intermediate Similarity	NPD1253	Approved
0.76	Intermediate Similarity	NPD1254	Approved
0.7597	Intermediate Similarity	NPD5671	Approved
0.759	Intermediate Similarity	NPD5065	Approved
0.7578	Intermediate Similarity	NPD1403	Approved
0.7578	Intermediate Similarity	NPD1404	Approved
0.7572	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6554	Approved
0.755	Intermediate Similarity	NPD45	Approved
0.7547	Intermediate Similarity	NPD6285	Phase 2
0.7529	Intermediate Similarity	NPD4441	Phase 2
0.7515	Intermediate Similarity	NPD1325	Approved
0.7515	Intermediate Similarity	NPD1326	Approved
0.7515	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2880	Discontinued
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD7111	Discontinued
0.75	Intermediate Similarity	NPD3475	Approved
0.7485	Intermediate Similarity	NPD3799	Suspended
0.7455	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4547	Phase 3
0.745	Intermediate Similarity	NPD1251	Discontinued
0.7439	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7709	Discontinued
0.7427	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2006	Phase 2
0.7417	Intermediate Similarity	NPD4880	Discontinued
0.7415	Intermediate Similarity	NPD2118	Approved
0.7415	Intermediate Similarity	NPD1598	Discontinued
0.7415	Intermediate Similarity	NPD2119	Approved
0.7412	Intermediate Similarity	NPD6595	Phase 3
0.7405	Intermediate Similarity	NPD2430	Phase 2
0.7399	Intermediate Similarity	NPD2793	Discontinued
0.7399	Intermediate Similarity	NPD2591	Phase 2
0.7399	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1950	Approved
0.7397	Intermediate Similarity	NPD1949	Approved
0.7394	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2642	Approved
0.7394	Intermediate Similarity	NPD6794	Approved
0.7394	Intermediate Similarity	NPD2639	Approved
0.7391	Intermediate Similarity	NPD2580	Discontinued
0.7362	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4075	Phase 2
0.7329	Intermediate Similarity	NPD976	Approved
0.7329	Intermediate Similarity	NPD975	Approved
0.7329	Intermediate Similarity	NPD977	Approved
0.7326	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6664	Approved
0.7317	Intermediate Similarity	NPD2480	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5473	Discontinued
0.731	Intermediate Similarity	NPD1561	Phase 2
0.7305	Intermediate Similarity	NPD5436	Phase 1
0.7299	Intermediate Similarity	NPD706	Phase 1
0.7297	Intermediate Similarity	NPD2442	Approved
0.7297	Intermediate Similarity	NPD2443	Approved
0.7296	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3505	Approved
0.7294	Intermediate Similarity	NPD3506	Approved
0.7289	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1215	Discontinued
0.7288	Intermediate Similarity	NPD4615	Phase 2
0.7284	Intermediate Similarity	NPD3112	Approved
0.7284	Intermediate Similarity	NPD3114	Approved
0.7284	Intermediate Similarity	NPD3115	Approved
0.7284	Intermediate Similarity	NPD3113	Approved
0.7284	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5138	Approved
0.7273	Intermediate Similarity	NPD5140	Approved
0.7267	Intermediate Similarity	NPD715	Phase 3
0.7267	Intermediate Similarity	NPD1917	Discontinued
0.7261	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3961	Discontinued
0.7251	Intermediate Similarity	NPD4079	Approved
0.7251	Intermediate Similarity	NPD1327	Discontinued
0.7251	Intermediate Similarity	NPD4076	Approved
0.725	Intermediate Similarity	NPD3833	Phase 3
0.725	Intermediate Similarity	NPD1030	Approved
0.725	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3835	Phase 3
0.725	Intermediate Similarity	NPD1027	Approved
0.7246	Intermediate Similarity	NPD2333	Discontinued
0.7244	Intermediate Similarity	NPD1592	Phase 3
0.7243	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4029	Approved
0.7237	Intermediate Similarity	NPD4028	Approved
0.7237	Intermediate Similarity	NPD4030	Approved
0.7229	Intermediate Similarity	NPD1333	Phase 3
0.7229	Intermediate Similarity	NPD2915	Discontinued
0.7226	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2165	Phase 1
0.7222	Intermediate Similarity	NPD3830	Phase 1
0.7219	Intermediate Similarity	NPD809	Discontinued
0.7219	Intermediate Similarity	NPD803	Phase 1
0.7213	Intermediate Similarity	NPD3015	Discontinued
0.7212	Intermediate Similarity	NPD1015	Phase 2
0.7212	Intermediate Similarity	NPD1016	Phase 2
0.7209	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7618	Phase 3
0.7207	Intermediate Similarity	NPD7619	Phase 3
0.7193	Intermediate Similarity	NPD2144	Approved
0.719	Intermediate Similarity	NPD2140	Approved
0.719	Intermediate Similarity	NPD2141	Approved
0.719	Intermediate Similarity	NPD2142	Approved
0.7182	Intermediate Similarity	NPD6469	Phase 3
0.7182	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7006	Approved
0.7176	Intermediate Similarity	NPD482	Approved
0.7175	Intermediate Similarity	NPD1043	Phase 3
0.7169	Intermediate Similarity	NPD404	Discontinued
0.7168	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4509	Discontinued
0.7151	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2465	Approved
0.7143	Intermediate Similarity	NPD2462	Phase 3
0.7143	Intermediate Similarity	NPD2466	Phase 3
0.7143	Intermediate Similarity	NPD5021	Discontinued
0.7135	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4326	Phase 2
0.7133	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5106	Approved
0.7126	Intermediate Similarity	NPD5105	Approved
0.7126	Intermediate Similarity	NPD3889	Approved
0.7125	Intermediate Similarity	NPD1661	Suspended
0.7124	Intermediate Similarity	NPD3942	Approved
0.7124	Intermediate Similarity	NPD3944	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