NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.1
Volume:	213.91
LogP:	3.204
LogD:	3.148
LogS:	-3.188
# Rotatable Bonds:	1
TPSA:	28.68
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	2.103
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.791
MDCK Permeability:	2.1276160623528995e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	90.2994155883789%
Volume Distribution (VD):	2.027
Pgp-substrate:	5.385348796844482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.331
CYP2C9-inhibitor:	0.413
CYP2C9-substrate:	0.742
CYP2D6-inhibitor:	0.834
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.637
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	3.873
Half-life (T1/2):	0.387

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.811
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.877
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.601
Carcinogencity:	0.375
Eye Corrosion:	0.032
Eye Irritation:	0.952
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC201380

Natural Product ID:	NPC201380
*Common Name:**	Sid56317899
IUPAC Name:	1-ethyl-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	YTQRHYCHEIXUIU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H12N2/c1-2-11-13-10(7-8-14-11)9-5-3-4-6-12(9)15-13/h3-8,15H,2H2,1H3
SMILES:	CCc1c2c(ccn1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL441986
PubChem CID:	5324325
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
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791472]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO40256	Orthoscuticella ventricosa	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31961680]
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	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
AC50	1
EC50	2
IC50	12
MIC	6
Others	5
Potency	7

Activity Type	# Activity
Cell Line	4
Individual Protein	8
Organism	11
Others	6
Protein Complex	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	25.0	ug.mL-1	PMID[465749]
NPT168	Cell Line	P388	Mus musculus	IC50	>	12.5	ug.mL-1	PMID[465751]
NPT4044	Individual Protein	Short transient receptor potential channel 4	Mus musculus	EC50	n.a.	2985.3	nM	PMID[465752]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[465752]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[465752]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[465752]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[465752]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	30.2	%	PMID[465754]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	35.0	%	PMID[465755]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	40000.0	nM	PMID[465755]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	IC50	=	250034.54	nM	PMID[465744]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	IC50	=	250034.54	nM	PMID[465745]
NPT996	Protein Complex	GABA-A receptor; anion channel	Homo sapiens	IC50	=	251188.64	nM	PMID[465746]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	IC50	=	250000.0	nM	PMID[465747]
NPT2	Others	Unspecified		IC50	=	251188.64	nM	PMID[465748]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	120.0	ug	PMID[465749]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7.5	ug	PMID[465749]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[465749]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.9	ug	PMID[465749]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	1.9	ug	PMID[465749]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	30.0	ug	PMID[465749]
NPT2	Others	Unspecified		IC50	=	251188.64	nM	PMID[465750]
NPT20	Organism	Candida albicans	Candida albicans	MID	=	1.9	ug ml-1	PMID[465751]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MID	=	7.5	ug ml-1	PMID[465751]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MID	=	1.9	ug ml-1	PMID[465751]
NPT2	Others	Unspecified		EC50	>	50000.0	nM	PMID[465752]
NPT2	Others	Unspecified		IC50	=	123290.0	nM	PMID[465752]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[465752]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	AC50	=	5668.0	nM	PMID[465752]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	56234.1	nM	PMID[465752]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[465752]
NPT2	Others	Unspecified		IC50	=	251188.64	nM	PMID[465753]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18000.0	nM	PMID[465755]

☑ 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 NPC201380 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	1188
0.1-0.2	13903
0.2-0.3	18202
0.3-0.4	4345
0.4-0.5	1756
0.5-0.6	1651
0.6-0.7	1019
0.7-0.8	459
0.8-0.85	106
0.85-0.9	45
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179787
0.9928	High Similarity	NPC63545
0.9928	High Similarity	NPC321911
0.9856	High Similarity	NPC469811
0.958	High Similarity	NPC325903
0.9517	High Similarity	NPC236711
0.9286	High Similarity	NPC115611
0.9257	High Similarity	NPC122141
0.9257	High Similarity	NPC470204
0.9209	High Similarity	NPC84911
0.9195	High Similarity	NPC470203
0.9137	High Similarity	NPC96102
0.9137	High Similarity	NPC29886
0.9137	High Similarity	NPC261195
0.9133	High Similarity	NPC317105
0.9078	High Similarity	NPC73767
0.9078	High Similarity	NPC110126
0.9073	High Similarity	NPC274229
0.9071	High Similarity	NPC105127
0.9065	High Similarity	NPC198988
0.9034	High Similarity	NPC470111
0.9014	High Similarity	NPC469784
0.9014	High Similarity	NPC469768
0.9014	High Similarity	NPC469761
0.9014	High Similarity	NPC469783
0.9014	High Similarity	NPC469779
0.9014	High Similarity	NPC469780
0.9014	High Similarity	NPC469767
0.9	High Similarity	NPC325252
0.8966	High Similarity	NPC288838
0.8961	High Similarity	NPC82331
0.8951	High Similarity	NPC469766
0.8912	High Similarity	NPC53947
0.8896	High Similarity	NPC97343
0.8889	High Similarity	NPC190296
0.8881	High Similarity	NPC279081
0.8851	High Similarity	NPC470233
0.8849	High Similarity	NPC82295
0.879	High Similarity	NPC474958
0.879	High Similarity	NPC280852
0.8767	High Similarity	NPC314372
0.875	High Similarity	NPC215584
0.875	High Similarity	NPC230002
0.875	High Similarity	NPC284635
0.875	High Similarity	NPC44773
0.8707	High Similarity	NPC143872
0.8693	High Similarity	NPC225018
0.8681	High Similarity	NPC88097
0.8649	High Similarity	NPC471957
0.8643	High Similarity	NPC22079
0.8639	High Similarity	NPC159856
0.8571	High Similarity	NPC191415
0.8562	High Similarity	NPC56765
0.8562	High Similarity	NPC477591
0.8533	High Similarity	NPC105818
0.8533	High Similarity	NPC24678
0.8533	High Similarity	NPC40070
0.8516	High Similarity	NPC478184
0.8514	High Similarity	NPC470440
0.8497	Intermediate Similarity	NPC216643
0.8493	Intermediate Similarity	NPC59084
0.8493	Intermediate Similarity	NPC2949
0.8489	Intermediate Similarity	NPC250361
0.8487	Intermediate Similarity	NPC476219
0.8487	Intermediate Similarity	NPC476297
0.8477	Intermediate Similarity	NPC470823
0.8472	Intermediate Similarity	NPC218268
0.8466	Intermediate Similarity	NPC284678
0.8457	Intermediate Similarity	NPC307191
0.8442	Intermediate Similarity	NPC135141
0.8442	Intermediate Similarity	NPC92796
0.8442	Intermediate Similarity	NPC293487
0.844	Intermediate Similarity	NPC473587
0.8435	Intermediate Similarity	NPC473868
0.8435	Intermediate Similarity	NPC63157
0.8421	Intermediate Similarity	NPC469786
0.8421	Intermediate Similarity	NPC469763
0.8421	Intermediate Similarity	NPC469760
0.8421	Intermediate Similarity	NPC469765
0.8421	Intermediate Similarity	NPC25008
0.8421	Intermediate Similarity	NPC259644
0.8421	Intermediate Similarity	NPC73952
0.8421	Intermediate Similarity	NPC141926
0.8421	Intermediate Similarity	NPC200214
0.8414	Intermediate Similarity	NPC314102
0.8414	Intermediate Similarity	NPC251722
0.8406	Intermediate Similarity	NPC46358
0.8405	Intermediate Similarity	NPC102755
0.8405	Intermediate Similarity	NPC48938
0.8397	Intermediate Similarity	NPC90723
0.8397	Intermediate Similarity	NPC478182
0.8389	Intermediate Similarity	NPC204141
0.838	Intermediate Similarity	NPC475428
0.8377	Intermediate Similarity	NPC286427
0.8375	Intermediate Similarity	NPC471579
0.8369	Intermediate Similarity	NPC473762
0.8366	Intermediate Similarity	NPC34844
0.8366	Intermediate Similarity	NPC70922
0.8366	Intermediate Similarity	NPC211572
0.8366	Intermediate Similarity	NPC212376
0.8366	Intermediate Similarity	NPC75540
0.8366	Intermediate Similarity	NPC80597
0.8355	Intermediate Similarity	NPC216713
0.8333	Intermediate Similarity	NPC41174
0.8323	Intermediate Similarity	NPC206819
0.8323	Intermediate Similarity	NPC41257
0.8323	Intermediate Similarity	NPC318065
0.8322	Intermediate Similarity	NPC475450
0.8322	Intermediate Similarity	NPC179365
0.8288	Intermediate Similarity	NPC150259
0.8253	Intermediate Similarity	NPC62749
0.8217	Intermediate Similarity	NPC478185
0.8217	Intermediate Similarity	NPC282231
0.8214	Intermediate Similarity	NPC231536
0.8194	Intermediate Similarity	NPC469785
0.8187	Intermediate Similarity	NPC91895
0.8176	Intermediate Similarity	NPC478183
0.8176	Intermediate Similarity	NPC56233
0.8163	Intermediate Similarity	NPC125746
0.8158	Intermediate Similarity	NPC21605
0.8153	Intermediate Similarity	NPC229173
0.8153	Intermediate Similarity	NPC279918
0.8141	Intermediate Similarity	NPC469762
0.8138	Intermediate Similarity	NPC473930
0.8125	Intermediate Similarity	NPC282398
0.8108	Intermediate Similarity	NPC169433
0.8092	Intermediate Similarity	NPC316069
0.8089	Intermediate Similarity	NPC475990
0.8089	Intermediate Similarity	NPC221786
0.8089	Intermediate Similarity	NPC474880
0.8085	Intermediate Similarity	NPC27740
0.8075	Intermediate Similarity	NPC32534
0.8063	Intermediate Similarity	NPC474561
0.8063	Intermediate Similarity	NPC49954
0.8052	Intermediate Similarity	NPC33421
0.805	Intermediate Similarity	NPC311276
0.8043	Intermediate Similarity	NPC91958
0.8038	Intermediate Similarity	NPC131718
0.8037	Intermediate Similarity	NPC317054
0.8024	Intermediate Similarity	NPC108011
0.8013	Intermediate Similarity	NPC20144
0.8012	Intermediate Similarity	NPC63751
0.8012	Intermediate Similarity	NPC324149
0.8	Intermediate Similarity	NPC280864
0.8	Intermediate Similarity	NPC17751
0.7975	Intermediate Similarity	NPC230869
0.7975	Intermediate Similarity	NPC477611
0.7965	Intermediate Similarity	NPC326422
0.7963	Intermediate Similarity	NPC194411
0.795	Intermediate Similarity	NPC160105
0.795	Intermediate Similarity	NPC54988
0.795	Intermediate Similarity	NPC49217
0.7937	Intermediate Similarity	NPC40779
0.7937	Intermediate Similarity	NPC149265
0.7914	Intermediate Similarity	NPC470498
0.7908	Intermediate Similarity	NPC86288
0.7908	Intermediate Similarity	NPC285731
0.7902	Intermediate Similarity	NPC245244
0.7902	Intermediate Similarity	NPC166424
0.7902	Intermediate Similarity	NPC146373
0.7901	Intermediate Similarity	NPC201700
0.7899	Intermediate Similarity	NPC148140
0.7892	Intermediate Similarity	NPC11126
0.7892	Intermediate Similarity	NPC12649
0.7872	Intermediate Similarity	NPC182570
0.7872	Intermediate Similarity	NPC48564
0.7872	Intermediate Similarity	NPC265605
0.7857	Intermediate Similarity	NPC478186
0.7853	Intermediate Similarity	NPC474897
0.7844	Intermediate Similarity	NPC314919
0.7842	Intermediate Similarity	NPC81561
0.7841	Intermediate Similarity	NPC237414
0.7831	Intermediate Similarity	NPC240088
0.7831	Intermediate Similarity	NPC59269
0.7831	Intermediate Similarity	NPC473380
0.7826	Intermediate Similarity	NPC271797
0.7826	Intermediate Similarity	NPC21174
0.7826	Intermediate Similarity	NPC102423
0.7826	Intermediate Similarity	NPC194640
0.7818	Intermediate Similarity	NPC275305
0.7818	Intermediate Similarity	NPC37423
0.7815	Intermediate Similarity	NPC104483
0.7815	Intermediate Similarity	NPC312092
0.7797	Intermediate Similarity	NPC19872
0.7797	Intermediate Similarity	NPC176538
0.7786	Intermediate Similarity	NPC54102
0.7786	Intermediate Similarity	NPC162689
0.7786	Intermediate Similarity	NPC143603
0.7784	Intermediate Similarity	NPC265710
0.7784	Intermediate Similarity	NPC265576
0.7765	Intermediate Similarity	NPC308931
0.7765	Intermediate Similarity	NPC15102
0.7765	Intermediate Similarity	NPC99939
0.7758	Intermediate Similarity	NPC314603
0.7756	Intermediate Similarity	NPC37548
0.7756	Intermediate Similarity	NPC2272
0.7753	Intermediate Similarity	NPC232727
0.774	Intermediate Similarity	NPC476167
0.7738	Intermediate Similarity	NPC24864
0.7738	Intermediate Similarity	NPC16659

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 NPC201380 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	487
0.1-0.2	891
0.2-0.3	984
0.3-0.4	2201
0.4-0.5	2021
0.5-0.6	1560
0.6-0.7	762
0.7-0.8	212
0.8-0.85	26
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.922	High Similarity	NPD1722	Approved
0.9137	High Similarity	NPD198	Clinical (unspecified phase)
0.9078	High Similarity	NPD786	Approved
0.8919	High Similarity	NPD2837	Discontinued
0.8716	High Similarity	NPD3100	Discontinued
0.8716	High Similarity	NPD4374	Clinical (unspecified phase)
0.8643	High Similarity	NPD715	Phase 3
0.8571	High Similarity	NPD1853	Clinical (unspecified phase)
0.8533	High Similarity	NPD2172	Phase 1
0.8516	High Similarity	NPD3323	Discontinued
0.8503	High Similarity	NPD4637	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD4547	Phase 3
0.8378	Intermediate Similarity	NPD2006	Phase 2
0.8367	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2430	Phase 2
0.8322	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD991	Phase 2
0.8252	Intermediate Similarity	NPD3476	Approved
0.8252	Intermediate Similarity	NPD3475	Approved
0.825	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD976	Approved
0.8247	Intermediate Similarity	NPD975	Approved
0.8247	Intermediate Similarity	NPD977	Approved
0.8239	Intermediate Similarity	NPD2641	Approved
0.8239	Intermediate Similarity	NPD2640	Approved
0.8232	Intermediate Similarity	NPD1895	Discontinued
0.8212	Intermediate Similarity	NPD1683	Approved
0.8207	Intermediate Similarity	NPD3385	Approved
0.82	Intermediate Similarity	NPD5254	Discontinued
0.8171	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2119	Approved
0.8169	Intermediate Similarity	NPD2118	Approved
0.816	Intermediate Similarity	NPD4181	Approved
0.8153	Intermediate Similarity	NPD1403	Approved
0.8153	Intermediate Similarity	NPD1404	Approved
0.8141	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3609	Approved
0.8137	Intermediate Similarity	NPD3610	Approved
0.8133	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1262	Discovery
0.8037	Intermediate Similarity	NPD4128	Approved
0.8037	Intermediate Similarity	NPD5065	Approved
0.8012	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD9583	Approved
0.7959	Intermediate Similarity	NPD4030	Approved
0.7959	Intermediate Similarity	NPD4029	Approved
0.7959	Intermediate Similarity	NPD4028	Approved
0.795	Intermediate Similarity	NPD2639	Approved
0.795	Intermediate Similarity	NPD2642	Approved
0.7945	Intermediate Similarity	NPD803	Phase 1
0.7935	Intermediate Similarity	NPD4463	Approved
0.7935	Intermediate Similarity	NPD4462	Approved
0.7931	Intermediate Similarity	NPD3654	Approved
0.7922	Intermediate Similarity	NPD1661	Suspended
0.7901	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD268	Approved
0.7872	Intermediate Similarity	NPD271	Approved
0.787	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1254	Approved
0.7852	Intermediate Similarity	NPD1255	Approved
0.7852	Intermediate Similarity	NPD1253	Approved
0.7852	Intermediate Similarity	NPD1256	Approved
0.7848	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2580	Discontinued
0.7844	Intermediate Similarity	NPD6595	Phase 3
0.784	Intermediate Similarity	NPD1248	Discontinued
0.7838	Intermediate Similarity	NPD3944	Approved
0.7838	Intermediate Similarity	NPD3942	Approved
0.7832	Intermediate Similarity	NPD9357	Approved
0.78	Intermediate Similarity	NPD6554	Approved
0.78	Intermediate Similarity	NPD45	Approved
0.7799	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2333	Discontinued
0.7785	Intermediate Similarity	NPD2165	Phase 1
0.7784	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1313	Approved
0.7778	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4075	Phase 2
0.775	Intermediate Similarity	NPD5418	Discontinued
0.7746	Intermediate Similarity	NPD9598	Discontinued
0.7744	Intermediate Similarity	NPD5436	Phase 1
0.7736	Intermediate Similarity	NPD3115	Approved
0.7736	Intermediate Similarity	NPD3112	Approved
0.7736	Intermediate Similarity	NPD3114	Approved
0.7736	Intermediate Similarity	NPD3113	Approved
0.7725	Intermediate Similarity	NPD3506	Approved
0.7725	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3505	Approved
0.7719	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9392	Approved
0.7714	Intermediate Similarity	NPD9396	Approved
0.7698	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1708	Approved
0.7692	Intermediate Similarity	NPD1707	Approved
0.7687	Intermediate Similarity	NPD947	Approved
0.7679	Intermediate Similarity	NPD4079	Approved
0.7679	Intermediate Similarity	NPD4076	Approved
0.7674	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1598	Discontinued
0.7665	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD5315	Discontinued
0.7647	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5105	Approved
0.7647	Intermediate Similarity	NPD5106	Approved
0.7628	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7111	Discontinued
0.7619	Intermediate Similarity	NPD2144	Approved
0.7616	Intermediate Similarity	NPD2793	Discontinued
0.7616	Intermediate Similarity	NPD3378	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7619	Phase 3
0.7614	Intermediate Similarity	NPD7618	Phase 3
0.7605	Intermediate Similarity	NPD482	Approved
0.7586	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD2068	Approved
0.7582	Intermediate Similarity	NPD2071	Approved
0.7582	Intermediate Similarity	NPD2072	Approved
0.7582	Intermediate Similarity	NPD2073	Approved
0.7582	Intermediate Similarity	NPD2070	Approved
0.7582	Intermediate Similarity	NPD2074	Approved
0.7582	Intermediate Similarity	NPD2069	Approved
0.7582	Intermediate Similarity	NPD2075	Approved
0.7572	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3961	Discontinued
0.7571	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1561	Phase 2
0.7558	Intermediate Similarity	NPD1227	Phase 2
0.7546	Intermediate Similarity	NPD1015	Phase 2
0.7546	Intermediate Similarity	NPD1016	Phase 2
0.7545	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5962	Phase 2
0.7528	Intermediate Similarity	NPD2880	Discontinued
0.7516	Intermediate Similarity	NPD2150	Discontinued
0.7516	Intermediate Similarity	NPD7469	Discontinued
0.7516	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2478	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6217	Discontinued
0.75	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3038	Discontinued
0.7485	Intermediate Similarity	NPD6828	Phase 2
0.7472	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7394	Phase 2
0.7471	Intermediate Similarity	NPD8431	Approved
0.7468	Intermediate Similarity	NPD4702	Approved
0.7468	Intermediate Similarity	NPD4703	Approved
0.7458	Intermediate Similarity	NPD3485	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3348	Phase 2
0.7455	Intermediate Similarity	NPD2720	Phase 1
0.7455	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD509	Phase 3
0.7455	Intermediate Similarity	NPD1333	Phase 3
0.7448	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3419	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4047	Discontinued
0.7427	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3015	Discontinued
0.7414	Intermediate Similarity	NPD4902	Discontinued
0.7407	Intermediate Similarity	NPD2927	Phase 3
0.7399	Intermediate Similarity	NPD6178	Phase 3
0.7399	Intermediate Similarity	NPD4957	Phase 2
0.7391	Intermediate Similarity	NPD3339	Approved
0.7381	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3835	Phase 3
0.7375	Intermediate Similarity	NPD1029	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1030	Approved
0.7375	Intermediate Similarity	NPD1027	Approved
0.7375	Intermediate Similarity	NPD3833	Phase 3
0.7368	Intermediate Similarity	NPD1327	Discontinued
0.7363	Intermediate Similarity	NPD4318	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4326	Phase 2
0.7353	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1251	Discontinued
0.7351	Intermediate Similarity	NPD809	Discontinued
0.7341	Intermediate Similarity	NPD2094	Phase 2
0.7341	Intermediate Similarity	NPD2092	Phase 2
0.7341	Intermediate Similarity	NPD2095	Phase 2
0.7337	Intermediate Similarity	NPD750	Phase 2
0.7333	Intermediate Similarity	NPD5462	Discontinued
0.7333	Intermediate Similarity	NPD6771	Discontinued
0.732	Intermediate Similarity	NPD4880	Discontinued
0.7314	Intermediate Similarity	NPD706	Phase 1
0.7312	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1183	Approved
0.7303	Intermediate Similarity	NPD1995	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