NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	267.15
Volume:	278.855
LogP:	1.523
LogD:	1.084
LogS:	-3.042
# Rotatable Bonds:	5
TPSA:	90.58
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	2.417
Fsp3:	0.2
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:	-5.261
MDCK Permeability:	4.3718673623516224e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.383
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.509
Plasma Protein Binding (PPB):	64.34052276611328%
Volume Distribution (VD):	1.996
Pgp-substrate:	30.04302406311035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.428
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.641
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	9.485
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.568
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.706
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.359
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470204

Natural Product ID:	NPC470204
*Common Name:**	2-[3-(9H-Pyrido[3,4-B]Indol-1-Yl)Propyl]Guanidine
IUPAC Name:	2-[3-(9H-pyrido[3,4-b]indol-1-yl)propyl]guanidine
Synonyms:
Standard InCHIKey:	KZIBFBLFUXMPFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H17N5/c16-15(17)19-8-3-6-13-14-11(7-9-18-13)10-4-1-2-5-12(10)20-14/h1-2,4-5,7,9,20H,3,6,8H2,(H4,16,17,19)
SMILES:	C1=CC=C2C(=C1)C3=C(N2)C(=NC=C3)CCCN=C(N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821998
PubChem CID:	54669867
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
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21846091]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26670413]
NPO5690	Pseudodistoma opacum	Species	Pseudoceratinidae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	101000.0	nM	PMID[542967]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	7700.0	nM	PMID[542967]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	130000.0	nM	PMID[542967]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	200000.0	nM	PMID[542967]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	7800.0	nM	PMID[542967]

☑ 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 NPC470204 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	1211
0.1-0.2	14881
0.2-0.3	17772
0.3-0.4	3743
0.4-0.5	1990
0.5-0.6	1597
0.6-0.7	994
0.7-0.8	391
0.8-0.85	73
0.85-0.9	34
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC470203
0.96	High Similarity	NPC122141
0.9388	High Similarity	NPC469811
0.9324	High Similarity	NPC321911
0.932	High Similarity	NPC63545
0.9257	High Similarity	NPC201380
0.9257	High Similarity	NPC179787
0.9139	High Similarity	NPC325903
0.913	High Similarity	NPC307191
0.9122	High Similarity	NPC204141
0.906	High Similarity	NPC143872
0.9032	High Similarity	NPC225018
0.8839	High Similarity	NPC236711
0.8734	High Similarity	NPC317105
0.8725	High Similarity	NPC115611
0.8707	High Similarity	NPC96102
0.8675	High Similarity	NPC108011
0.8658	High Similarity	NPC73767
0.8649	High Similarity	NPC105127
0.8649	High Similarity	NPC84911
0.86	High Similarity	NPC469779
0.86	High Similarity	NPC469767
0.86	High Similarity	NPC469761
0.86	High Similarity	NPC469780
0.86	High Similarity	NPC469784
0.86	High Similarity	NPC469783
0.86	High Similarity	NPC469768
0.8581	High Similarity	NPC29886
0.8581	High Similarity	NPC261195
0.8562	High Similarity	NPC274229
0.8562	High Similarity	NPC288838
0.8543	High Similarity	NPC469766
0.8533	High Similarity	NPC110126
0.8523	High Similarity	NPC125746
0.8516	High Similarity	NPC53947
0.8506	High Similarity	NPC470111
0.8477	Intermediate Similarity	NPC279081
0.8471	Intermediate Similarity	NPC476297
0.8471	Intermediate Similarity	NPC476219
0.8466	Intermediate Similarity	NPC82331
0.8456	Intermediate Similarity	NPC325252
0.8435	Intermediate Similarity	NPC82295
0.8424	Intermediate Similarity	NPC474958
0.8424	Intermediate Similarity	NPC280852
0.8405	Intermediate Similarity	NPC97343
0.8389	Intermediate Similarity	NPC198988
0.8385	Intermediate Similarity	NPC247987
0.8377	Intermediate Similarity	NPC314372
0.8366	Intermediate Similarity	NPC190296
0.8355	Intermediate Similarity	NPC230002
0.8344	Intermediate Similarity	NPC470233
0.8333	Intermediate Similarity	NPC280864
0.8333	Intermediate Similarity	NPC17751
0.8289	Intermediate Similarity	NPC88097
0.8282	Intermediate Similarity	NPC49217
0.8263	Intermediate Similarity	NPC473380
0.8263	Intermediate Similarity	NPC240088
0.8258	Intermediate Similarity	NPC159856
0.8253	Intermediate Similarity	NPC317054
0.825	Intermediate Similarity	NPC216643
0.8235	Intermediate Similarity	NPC284635
0.8214	Intermediate Similarity	NPC265710
0.8212	Intermediate Similarity	NPC218268
0.8199	Intermediate Similarity	NPC135141
0.8199	Intermediate Similarity	NPC56765
0.8199	Intermediate Similarity	NPC92796
0.8166	Intermediate Similarity	NPC16659
0.8165	Intermediate Similarity	NPC105818
0.8165	Intermediate Similarity	NPC24678
0.8153	Intermediate Similarity	NPC471957
0.8148	Intermediate Similarity	NPC215584
0.8148	Intermediate Similarity	NPC44773
0.8144	Intermediate Similarity	NPC471579
0.8063	Intermediate Similarity	NPC259644
0.8063	Intermediate Similarity	NPC469786
0.8063	Intermediate Similarity	NPC469760
0.8063	Intermediate Similarity	NPC73952
0.8063	Intermediate Similarity	NPC200214
0.8063	Intermediate Similarity	NPC25008
0.8063	Intermediate Similarity	NPC469763
0.8063	Intermediate Similarity	NPC469765
0.805	Intermediate Similarity	NPC40070
0.8049	Intermediate Similarity	NPC478184
0.8049	Intermediate Similarity	NPC90723
0.8025	Intermediate Similarity	NPC286427
0.8012	Intermediate Similarity	NPC70922
0.8012	Intermediate Similarity	NPC80597
0.8012	Intermediate Similarity	NPC212376
0.8012	Intermediate Similarity	NPC211572
0.8012	Intermediate Similarity	NPC191415
0.8012	Intermediate Similarity	NPC75540
0.8	Intermediate Similarity	NPC2949
0.8	Intermediate Similarity	NPC22079
0.8	Intermediate Similarity	NPC216713
0.8	Intermediate Similarity	NPC59084
0.8	Intermediate Similarity	NPC470823
0.7975	Intermediate Similarity	NPC477591
0.7975	Intermediate Similarity	NPC293487
0.7975	Intermediate Similarity	NPC206819
0.7975	Intermediate Similarity	NPC41257
0.7975	Intermediate Similarity	NPC318065
0.7973	Intermediate Similarity	NPC250361
0.7965	Intermediate Similarity	NPC102755
0.7965	Intermediate Similarity	NPC48938
0.7963	Intermediate Similarity	NPC469785
0.795	Intermediate Similarity	NPC141926
0.7949	Intermediate Similarity	NPC473868
0.7949	Intermediate Similarity	NPC63157
0.7939	Intermediate Similarity	NPC478182
0.7929	Intermediate Similarity	NPC280297
0.7922	Intermediate Similarity	NPC314102
0.7922	Intermediate Similarity	NPC251722
0.7919	Intermediate Similarity	NPC284678
0.7914	Intermediate Similarity	NPC469762
0.7911	Intermediate Similarity	NPC470440
0.7901	Intermediate Similarity	NPC34844
0.7898	Intermediate Similarity	NPC231536
0.7892	Intermediate Similarity	NPC116555
0.7891	Intermediate Similarity	NPC46358
0.787	Intermediate Similarity	NPC477611
0.7867	Intermediate Similarity	NPC473762
0.7866	Intermediate Similarity	NPC475990
0.7866	Intermediate Similarity	NPC300238
0.7866	Intermediate Similarity	NPC221786
0.7866	Intermediate Similarity	NPC474880
0.784	Intermediate Similarity	NPC232798
0.7829	Intermediate Similarity	NPC475450
0.7829	Intermediate Similarity	NPC62749
0.7829	Intermediate Similarity	NPC101165
0.7818	Intermediate Similarity	NPC279918
0.7818	Intermediate Similarity	NPC229173
0.7815	Intermediate Similarity	NPC473587
0.7812	Intermediate Similarity	NPC114209
0.7806	Intermediate Similarity	NPC150259
0.7798	Intermediate Similarity	NPC63751
0.7771	Intermediate Similarity	NPC282231
0.7771	Intermediate Similarity	NPC253687
0.7771	Intermediate Similarity	NPC478185
0.7763	Intermediate Similarity	NPC475428
0.775	Intermediate Similarity	NPC316069
0.7738	Intermediate Similarity	NPC160105
0.7738	Intermediate Similarity	NPC474561
0.7738	Intermediate Similarity	NPC49954
0.7738	Intermediate Similarity	NPC56233
0.7738	Intermediate Similarity	NPC478183
0.7733	Intermediate Similarity	NPC59269
0.7725	Intermediate Similarity	NPC311276
0.7718	Intermediate Similarity	NPC27740
0.7712	Intermediate Similarity	NPC179365
0.7711	Intermediate Similarity	NPC131718
0.7709	Intermediate Similarity	NPC324149
0.7709	Intermediate Similarity	NPC477167
0.7709	Intermediate Similarity	NPC477166
0.7709	Intermediate Similarity	NPC473342
0.7709	Intermediate Similarity	NPC304187
0.7703	Intermediate Similarity	NPC41174
0.7702	Intermediate Similarity	NPC21605
0.7692	Intermediate Similarity	NPC265576
0.767	Intermediate Similarity	NPC99939
0.767	Intermediate Similarity	NPC308931
0.767	Intermediate Similarity	NPC15102
0.7667	Intermediate Similarity	NPC474180
0.7667	Intermediate Similarity	NPC188821
0.7667	Intermediate Similarity	NPC326422
0.7663	Intermediate Similarity	NPC469308
0.7662	Intermediate Similarity	NPC473930
0.7651	Intermediate Similarity	NPC230869
0.7647	Intermediate Similarity	NPC282398
0.7647	Intermediate Similarity	NPC91895
0.7647	Intermediate Similarity	NPC194411
0.7647	Intermediate Similarity	NPC32534
0.7643	Intermediate Similarity	NPC169433
0.7633	Intermediate Similarity	NPC54988
0.7619	Intermediate Similarity	NPC40779
0.7607	Intermediate Similarity	NPC33421
0.7588	Intermediate Similarity	NPC201700
0.7586	Intermediate Similarity	NPC11126
0.7562	Intermediate Similarity	NPC20144
0.7558	Intermediate Similarity	NPC314603
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
0.7543	Intermediate Similarity	NPC314919
0.7528	Intermediate Similarity	NPC94752
0.7515	Intermediate Similarity	NPC102423
0.7515	Intermediate Similarity	NPC194640
0.7515	Intermediate Similarity	NPC149265
0.7514	Intermediate Similarity	NPC275305
0.7514	Intermediate Similarity	NPC37423
0.75	Intermediate Similarity	NPC474389
0.75	Intermediate Similarity	NPC470498
0.7487	Intermediate Similarity	NPC317701
0.7469	Intermediate Similarity	NPC86288
0.7439	Intermediate Similarity	NPC282531
0.7439	Intermediate Similarity	NPC2272
0.7429	Intermediate Similarity	NPC284775
0.7429	Intermediate Similarity	NPC248454
0.7429	Intermediate Similarity	NPC68354

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 NPC470204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	918
0.2-0.3	1045
0.3-0.4	2050
0.4-0.5	1908
0.5-0.6	1659
0.6-0.7	850
0.7-0.8	264
0.8-0.85	14
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD1722	Approved
0.8707	High Similarity	NPD198	Clinical (unspecified phase)
0.8667	High Similarity	NPD4649	Clinical (unspecified phase)
0.8667	High Similarity	NPD1895	Discontinued
0.8658	High Similarity	NPD786	Approved
0.8571	High Similarity	NPD4374	Clinical (unspecified phase)
0.8526	High Similarity	NPD2837	Discontinued
0.8466	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD4181	Approved
0.8366	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3100	Discontinued
0.8323	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4128	Approved
0.8221	Intermediate Similarity	NPD1313	Approved
0.8165	Intermediate Similarity	NPD2172	Phase 1
0.816	Intermediate Similarity	NPD3323	Discontinued
0.8129	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1708	Approved
0.8118	Intermediate Similarity	NPD1707	Approved
0.8098	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1262	Discovery
0.8035	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2793	Discontinued
0.8024	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6828	Phase 2
0.8012	Intermediate Similarity	NPD2333	Discontinued
0.8	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD715	Phase 3
0.7963	Intermediate Similarity	NPD2150	Discontinued
0.7963	Intermediate Similarity	NPD2927	Phase 3
0.7953	Intermediate Similarity	NPD5962	Phase 2
0.7952	Intermediate Similarity	NPD1248	Discontinued
0.7941	Intermediate Similarity	NPD7111	Discontinued
0.7933	Intermediate Similarity	NPD2880	Discontinued
0.7925	Intermediate Similarity	NPD4547	Phase 3
0.7919	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD991	Phase 2
0.7904	Intermediate Similarity	NPD2641	Approved
0.7904	Intermediate Similarity	NPD2640	Approved
0.7901	Intermediate Similarity	NPD977	Approved
0.7901	Intermediate Similarity	NPD976	Approved
0.7901	Intermediate Similarity	NPD975	Approved
0.7898	Intermediate Similarity	NPD2006	Phase 2
0.7892	Intermediate Similarity	NPD1333	Phase 3
0.7885	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1016	Phase 2
0.7879	Intermediate Similarity	NPD1015	Phase 2
0.7877	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2430	Phase 2
0.7865	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1683	Approved
0.7853	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD706	Phase 1
0.7826	Intermediate Similarity	NPD1027	Approved
0.7826	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1030	Approved
0.7824	Intermediate Similarity	NPD5065	Approved
0.7818	Intermediate Similarity	NPD1404	Approved
0.7818	Intermediate Similarity	NPD1403	Approved
0.7811	Intermediate Similarity	NPD3609	Approved
0.7811	Intermediate Similarity	NPD3610	Approved
0.7805	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1327	Discontinued
0.7763	Intermediate Similarity	NPD3476	Approved
0.7763	Intermediate Similarity	NPD3475	Approved
0.7746	Intermediate Similarity	NPD6595	Phase 3
0.7736	Intermediate Similarity	NPD5254	Discontinued
0.7736	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4902	Discontinued
0.7727	Intermediate Similarity	NPD3385	Approved
0.7712	Intermediate Similarity	NPD809	Discontinued
0.7712	Intermediate Similarity	NPD803	Phase 1
0.7709	Intermediate Similarity	NPD4615	Phase 2
0.7701	Intermediate Similarity	NPD2443	Approved
0.7701	Intermediate Similarity	NPD2442	Approved
0.7688	Intermediate Similarity	NPD2008	Discontinued
0.7688	Intermediate Similarity	NPD4023	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD40	Phase 2
0.7688	Intermediate Similarity	NPD5730	Phase 2
0.7684	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2118	Approved
0.7682	Intermediate Similarity	NPD1598	Discontinued
0.7682	Intermediate Similarity	NPD2119	Approved
0.768	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD509	Phase 3
0.7674	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5436	Phase 1
0.7647	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD5462	Discontinued
0.7633	Intermediate Similarity	NPD2642	Approved
0.7633	Intermediate Similarity	NPD2639	Approved
0.7632	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3015	Discontinued
0.7622	Intermediate Similarity	NPD1303	Phase 1
0.7607	Intermediate Similarity	NPD4462	Approved
0.7607	Intermediate Similarity	NPD4463	Approved
0.76	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1661	Suspended
0.7592	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4047	Discontinued
0.756	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5418	Discontinued
0.7541	Intermediate Similarity	NPD3830	Phase 1
0.7539	Intermediate Similarity	NPD2411	Approved
0.753	Intermediate Similarity	NPD2580	Discontinued
0.753	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6721	Phase 1
0.7515	Intermediate Similarity	NPD1917	Discontinued
0.7515	Intermediate Similarity	NPD695	Discontinued
0.75	Intermediate Similarity	NPD4029	Approved
0.75	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4028	Approved
0.75	Intermediate Similarity	NPD4030	Approved
0.7487	Intermediate Similarity	NPD2364	Suspended
0.7486	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7394	Phase 2
0.7485	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD2408	Discontinued
0.7472	Intermediate Similarity	NPD4298	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4075	Phase 2
0.747	Intermediate Similarity	NPD2165	Phase 1
0.7468	Intermediate Similarity	NPD3654	Approved
0.746	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1257	Approved
0.7452	Intermediate Similarity	NPD2142	Approved
0.7452	Intermediate Similarity	NPD2141	Approved
0.7452	Intermediate Similarity	NPD2140	Approved
0.7446	Intermediate Similarity	NPD6664	Approved
0.744	Intermediate Similarity	NPD1042	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7618	Phase 3
0.7432	Intermediate Similarity	NPD7619	Phase 3
0.743	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3505	Approved
0.7429	Intermediate Similarity	NPD3506	Approved
0.7427	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD1215	Discontinued
0.7425	Intermediate Similarity	NPD3112	Approved
0.7425	Intermediate Similarity	NPD3115	Approved
0.7425	Intermediate Similarity	NPD3113	Approved
0.7425	Intermediate Similarity	NPD3114	Approved
0.7425	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1290	Phase 2
0.7419	Intermediate Similarity	NPD6816	Phase 3
0.7416	Intermediate Similarity	NPD5892	Approved
0.7414	Intermediate Similarity	NPD3799	Suspended
0.7405	Intermediate Similarity	NPD6469	Phase 3
0.7405	Intermediate Similarity	NPD6468	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2818	Discontinued
0.74	Intermediate Similarity	NPD9598	Discontinued
0.7389	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3961	Discontinued
0.7389	Intermediate Similarity	NPD3942	Approved
0.7389	Intermediate Similarity	NPD3944	Approved
0.7386	Intermediate Similarity	NPD9583	Approved
0.7386	Intermediate Similarity	NPD4076	Approved
0.7386	Intermediate Similarity	NPD4079	Approved
0.7386	Intermediate Similarity	NPD1893	Phase 2
0.7386	Intermediate Similarity	NPD8386	Phase 2
0.7386	Intermediate Similarity	NPD1892	Phase 2
0.7381	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2445	Approved
0.7377	Intermediate Similarity	NPD2446	Approved
0.7375	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD174	Discontinued
0.7368	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1506	Discontinued
0.736	Intermediate Similarity	NPD5106	Approved
0.736	Intermediate Similarity	NPD5105	Approved
0.736	Intermediate Similarity	NPD4441	Phase 2
0.7358	Intermediate Similarity	NPD45	Approved
0.7358	Intermediate Similarity	NPD6554	Approved
0.7356	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8026	Phase 1
0.7348	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4024	Phase 3
0.7333	Intermediate Similarity	NPD2591	Phase 2
0.7333	Intermediate Similarity	NPD5642	Approved
0.7333	Intermediate Similarity	NPD7026	Phase 2
0.733	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2144	Approved
0.7326	Intermediate Similarity	NPD6794	Approved
0.7322	Intermediate Similarity	NPD3431	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