NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	129.06
Volume:	144.922
LogP:	1.996
LogD:	1.999
LogS:	-1.272
# Rotatable Bonds:	0
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	1.348
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.223
MDCK Permeability:	3.2253821700578555e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	85.0159683227539%
Volume Distribution (VD):	1.7
Pgp-substrate:	15.11986255645752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.601
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.426
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.764
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	5.328
Half-life (T1/2):	0.544

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.696
AMES Toxicity:	0.562
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.686
Carcinogencity:	0.447
Eye Corrosion:	0.525
Eye Irritation:	0.993
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC46358

Natural Product ID:	NPC46358
*Common Name:**	Quinoline
IUPAC Name:	quinoline
Synonyms:	1-Benzazine; Quinoline
Standard InCHIKey:	SMWDFEZZVXVKRB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
SMILES:	c1ccc2c(c1)nccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL14474
PubChem CID:	7047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives

*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
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11045	Paederia scandens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11045	Paederia scandens	Species	Rubiaceae	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
NPO21556	NPC46358	n.a.	Sclerotia	0.330 ± 0.120	n.a.	n.a.	%	PMID[20527951]

☑ 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
Ki	2
Others	47
Potency	13

Activity Type	# Activity
Cell Line	2
Individual Protein	13
NON-MOLECULAR	3
ORGANISM	12
Others	31
SINGLE PROTEIN	3
Tissue	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Ki	>	1000000.0	nM	PMID[517496]
NPT2963	Individual Protein	Renal sodium-dependent phosphate transport protein 1	Rattus norvegicus	Activity	=	56.0	%	PMID[517500]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	DA release	=	0.5	%	PMID[517501]
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	DA release	=	23.0	%	PMID[517501]
NPT2966	Individual Protein	T-complex protein 1 subunit beta	Macaaca fascicularis	Potency	n.a.	100000.0	nM	PMID[517512]
NPT1182	Cell Line	J774.A1	Mus musculus	CC50	>	100000.0	nM	PMID[517516]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	100000.0	nM	PMID[517516]
NPT2742	Individual Protein	Aldehyde oxidase	Homo sapiens	K	=	3.6	n.a.	PMID[517522]
NPT2932	Individual Protein	Aldehyde oxidase	Rattus norvegicus	K	=	3.6	n.a.	PMID[517522]
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	61901.3	nM	PubChem BioAssay data set
NPT35	Others	n.a.		pKa	=	4.94	n.a.	PMID[517494]
NPT35	Others	n.a.		Log S	=	-1.3	n.a.	PMID[517495]
NPT27	Others	Unspecified		Log k'w	=	1.56	n.a.	PMID[517497]
NPT35	Others	n.a.		LogP	=	1.85	n.a.	PMID[517497]
NPT35	Others	n.a.		LogP	=	2.03	n.a.	PMID[517497]
NPT27	Others	Unspecified		pKa	=	4.9	n.a.	PMID[517498]
NPT35	Others	n.a.		LogD	=	2.03	n.a.	PMID[517499]
NPT22420	ORGANISM	Rana pipiens	Rana pipiens	Log MBC	=	0.3	n.a.	PMID[517502]
NPT35	Others	n.a.		LogP	=	2.04	n.a.	PMID[517503]
NPT35	Others	n.a.		pKa	=	4.81	n.a.	PMID[517503]
NPT2964	Others	Ferriprotoporphyrin IX	Plasmodium falciparum	Log K	<	2.5	n.a.	PMID[517504]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[517504]
NPT35	Others	n.a.		Log PNalk	=	1.26	n.a.	PMID[517506]
NPT27	Others	Unspecified		log Ks	=	2.12	n.a.	PMID[517507]
NPT35	Others	n.a.		LogD	=	1.99	n.a.	PMID[517508]
NPT35	Others	n.a.		LogD	=	0.97	n.a.	PMID[517508]
NPT35	Others	n.a.		pKa	=	4.85	n.a.	PMID[517509]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	37650.5	nM	PMID[517510]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[517511]
NPT699	Individual Protein	UDP-glucuronosyltransferase 1-10	Homo sapiens	Activity	=	156.0	pm/min/mg	PMID[517513]
NPT695	Individual Protein	UDP-glucuronosyltransferase 1-8	Homo sapiens	Activity	=	54.0	pm/min/mg	PMID[517513]
NPT35	Others	n.a.		Ratio	=	1.4	n.a.	PMID[517514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1.97	n.a.	PMID[517514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	2.42	n.a.	PMID[517514]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	0.98	n.a.	PMID[517514]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.8	nmol	PMID[517514]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.77	nmol	PMID[517514]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	0.73	nmol	PMID[517514]
NPT35	Others	n.a.		LogD	=	2.03	n.a.	PMID[517515]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	50000.0	nM	PMID[517516]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[517511]
NPT35	Others	n.a.		LogP	=	2.03	n.a.	PMID[517517]
NPT35	Others	n.a.		LogP	=	2.04	n.a.	PMID[517517]
NPT35	Others	n.a.		LogD7.4	n.a.	2.09	n.a.	PMID[517518]
NPT27	Others	Unspecified		Km	=	212000.0	nM	PMID[517520]
NPT27	Others	Unspecified		Vmax	=	246.0	pmol/min/ml	PMID[517520]
NPT27	Others	Unspecified		Ratio	=	1.2	n.a.	PMID[517520]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	5000.0	nM	PMID[517521]
NPT26935	SINGLE PROTEIN	Aldehyde oxidase 1	Cavia porcellus	K	=	3.6	n.a.	PMID[517522]
NPT26544	SINGLE PROTEIN	Neutrophil cytosol factor 1	Homo sapiens	Ki	>	2000000.0	nM	PMID[517523]
NPT26544	SINGLE PROTEIN	Neutrophil cytosol factor 1	Homo sapiens	Rmax	<	20.0	%	PMID[517523]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	80.2	%	PMID[517525]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	42.4	%	PMID[517525]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	83.6	%	PMID[517525]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	64.5	%	PMID[517525]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	55.2	%	PMID[517525]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	58.2	%	PMID[517525]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[517526]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[517526]
NPT2	Others	Unspecified		Potency	n.a.	9810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	39057.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	3466.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55169.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17446.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17299	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54704.4	nM	PubChem BioAssay data set

☑ 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 NPC46358 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	2267
0.1-0.2	14289
0.2-0.3	16494
0.3-0.4	4658
0.4-0.5	2099
0.5-0.6	1666
0.6-0.7	826
0.7-0.8	298
0.8-0.85	74
0.85-0.9	22
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9076	High Similarity	NPC91958
0.9076	High Similarity	NPC143603
0.8992	High Similarity	NPC251722
0.8992	High Similarity	NPC314102
0.8923	High Similarity	NPC169433
0.8908	High Similarity	NPC148140
0.8898	High Similarity	NPC82295
0.8833	High Similarity	NPC81561
0.876	High Similarity	NPC54102
0.876	High Similarity	NPC162689
0.8672	High Similarity	NPC282398
0.8626	High Similarity	NPC29886
0.8626	High Similarity	NPC261195
0.8626	High Similarity	NPC96102
0.8618	High Similarity	NPC215519
0.8605	High Similarity	NPC256893
0.8561	High Similarity	NPC150259
0.8561	High Similarity	NPC84911
0.8561	High Similarity	NPC105127
0.8559	High Similarity	NPC27802
0.8525	High Similarity	NPC297486
0.8525	High Similarity	NPC240136
0.8525	High Similarity	NPC471402
0.8467	Intermediate Similarity	NPC63545
0.8462	Intermediate Similarity	NPC231655
0.8462	Intermediate Similarity	NPC76540
0.8433	Intermediate Similarity	NPC73767
0.8433	Intermediate Similarity	NPC110126
0.8406	Intermediate Similarity	NPC470111
0.8406	Intermediate Similarity	NPC179787
0.8406	Intermediate Similarity	NPC201380
0.8406	Intermediate Similarity	NPC469811
0.84	Intermediate Similarity	NPC48564
0.84	Intermediate Similarity	NPC182570
0.84	Intermediate Similarity	NPC265605
0.837	Intermediate Similarity	NPC279081
0.837	Intermediate Similarity	NPC469784
0.837	Intermediate Similarity	NPC469767
0.837	Intermediate Similarity	NPC469779
0.837	Intermediate Similarity	NPC469768
0.837	Intermediate Similarity	NPC230002
0.837	Intermediate Similarity	NPC469761
0.837	Intermediate Similarity	NPC469780
0.837	Intermediate Similarity	NPC469783
0.8346	Intermediate Similarity	NPC476322
0.8346	Intermediate Similarity	NPC122718
0.8345	Intermediate Similarity	NPC321911
0.8309	Intermediate Similarity	NPC469766
0.8286	Intermediate Similarity	NPC40070
0.8281	Intermediate Similarity	NPC146373
0.8281	Intermediate Similarity	NPC166424
0.8281	Intermediate Similarity	NPC245244
0.8261	Intermediate Similarity	NPC86288
0.8248	Intermediate Similarity	NPC190296
0.8217	Intermediate Similarity	NPC476140
0.8203	Intermediate Similarity	NPC27740
0.8201	Intermediate Similarity	NPC143872
0.8201	Intermediate Similarity	NPC288838
0.8169	Intermediate Similarity	NPC325903
0.8162	Intermediate Similarity	NPC315348
0.8162	Intermediate Similarity	NPC32002
0.8162	Intermediate Similarity	NPC316811
0.8134	Intermediate Similarity	NPC198988
0.8129	Intermediate Similarity	NPC285731
0.8129	Intermediate Similarity	NPC314372
0.8129	Intermediate Similarity	NPC159856
0.8125	Intermediate Similarity	NPC290094
0.8115	Intermediate Similarity	NPC235843
0.8103	Intermediate Similarity	NPC83987
0.8074	Intermediate Similarity	NPC325252
0.8071	Intermediate Similarity	NPC316069
0.8056	Intermediate Similarity	NPC476464
0.8047	Intermediate Similarity	NPC41174
0.8045	Intermediate Similarity	NPC101165
0.803	Intermediate Similarity	NPC476131
0.8029	Intermediate Similarity	NPC104483
0.8028	Intermediate Similarity	NPC53947
0.8014	Intermediate Similarity	NPC471957
0.8	Intermediate Similarity	NPC236711
0.7986	Intermediate Similarity	NPC20144
0.7972	Intermediate Similarity	NPC470233
0.797	Intermediate Similarity	NPC22079
0.797	Intermediate Similarity	NPC69914
0.7945	Intermediate Similarity	NPC477591
0.7945	Intermediate Similarity	NPC293487
0.7945	Intermediate Similarity	NPC56765
0.7939	Intermediate Similarity	NPC250361
0.7939	Intermediate Similarity	NPC202957
0.7939	Intermediate Similarity	NPC169625
0.7917	Intermediate Similarity	NPC138842
0.7907	Intermediate Similarity	NPC329825
0.7902	Intermediate Similarity	NPC105818
0.7902	Intermediate Similarity	NPC24678
0.7899	Intermediate Similarity	NPC88097
0.7891	Intermediate Similarity	NPC122141
0.7891	Intermediate Similarity	NPC44773
0.7891	Intermediate Similarity	NPC215584
0.7891	Intermediate Similarity	NPC470204
0.7883	Intermediate Similarity	NPC125746
0.7877	Intermediate Similarity	NPC129721
0.7847	Intermediate Similarity	NPC470823
0.7847	Intermediate Similarity	NPC216713
0.7842	Intermediate Similarity	NPC59084
0.7842	Intermediate Similarity	NPC2949
0.7838	Intermediate Similarity	NPC225018
0.7838	Intermediate Similarity	NPC470203
0.7838	Intermediate Similarity	NPC478185
0.782	Intermediate Similarity	NPC473762
0.782	Intermediate Similarity	NPC89490
0.7808	Intermediate Similarity	NPC51054
0.7793	Intermediate Similarity	NPC25008
0.7793	Intermediate Similarity	NPC141926
0.7793	Intermediate Similarity	NPC469760
0.7793	Intermediate Similarity	NPC469763
0.7793	Intermediate Similarity	NPC469786
0.7793	Intermediate Similarity	NPC73952
0.7793	Intermediate Similarity	NPC469765
0.7793	Intermediate Similarity	NPC200214
0.7793	Intermediate Similarity	NPC259644
0.7786	Intermediate Similarity	NPC473868
0.7786	Intermediate Similarity	NPC63157
0.7785	Intermediate Similarity	NPC90723
0.7785	Intermediate Similarity	NPC478182
0.7785	Intermediate Similarity	NPC317105
0.7785	Intermediate Similarity	NPC478184
0.7778	Intermediate Similarity	NPC324611
0.7761	Intermediate Similarity	NPC473587
0.7761	Intermediate Similarity	NPC329896
0.7761	Intermediate Similarity	NPC475090
0.7761	Intermediate Similarity	NPC475105
0.7755	Intermediate Similarity	NPC286427
0.7755	Intermediate Similarity	NPC216643
0.7744	Intermediate Similarity	NPC471313
0.7744	Intermediate Similarity	NPC471311
0.774	Intermediate Similarity	NPC75540
0.774	Intermediate Similarity	NPC211572
0.774	Intermediate Similarity	NPC70922
0.774	Intermediate Similarity	NPC34844
0.774	Intermediate Similarity	NPC80597
0.774	Intermediate Similarity	NPC212376
0.7733	Intermediate Similarity	NPC274229
0.7714	Intermediate Similarity	NPC115611
0.7704	Intermediate Similarity	NPC475428
0.7703	Intermediate Similarity	NPC206819
0.7703	Intermediate Similarity	NPC41257
0.7703	Intermediate Similarity	NPC318065
0.7703	Intermediate Similarity	NPC92796
0.7703	Intermediate Similarity	NPC135141
0.7687	Intermediate Similarity	NPC469785
0.7682	Intermediate Similarity	NPC478183
0.7682	Intermediate Similarity	NPC56233
0.7681	Intermediate Similarity	NPC218268
0.7651	Intermediate Similarity	NPC279918
0.7647	Intermediate Similarity	NPC475450
0.7647	Intermediate Similarity	NPC179365
0.7635	Intermediate Similarity	NPC469762
0.7627	Intermediate Similarity	NPC213774
0.7622	Intermediate Similarity	NPC470440
0.7622	Intermediate Similarity	NPC204141
0.76	Intermediate Similarity	NPC282231
0.7591	Intermediate Similarity	NPC473930
0.7584	Intermediate Similarity	NPC230869
0.7582	Intermediate Similarity	NPC97343
0.7582	Intermediate Similarity	NPC473764
0.7582	Intermediate Similarity	NPC32534
0.7582	Intermediate Similarity	NPC314940
0.7582	Intermediate Similarity	NPC91895
0.7578	Intermediate Similarity	NPC476566
0.755	Intermediate Similarity	NPC265100
0.7533	Intermediate Similarity	NPC131718
0.7532	Intermediate Similarity	NPC82331
0.7518	Intermediate Similarity	NPC471322
0.7517	Intermediate Similarity	NPC21605
0.75	Intermediate Similarity	NPC17751
0.75	Intermediate Similarity	NPC65408
0.75	Intermediate Similarity	NPC280864
0.7483	Intermediate Similarity	NPC242116
0.7467	Intermediate Similarity	NPC80681
0.7465	Intermediate Similarity	NPC284635
0.7465	Intermediate Similarity	NPC238499
0.7451	Intermediate Similarity	NPC49954
0.7451	Intermediate Similarity	NPC474561
0.7451	Intermediate Similarity	NPC54988
0.7436	Intermediate Similarity	NPC297034
0.7436	Intermediate Similarity	NPC471579
0.7434	Intermediate Similarity	NPC311276
0.7434	Intermediate Similarity	NPC40779
0.7434	Intermediate Similarity	NPC102423
0.7422	Intermediate Similarity	NPC143156
0.7419	Intermediate Similarity	NPC201634
0.7415	Intermediate Similarity	NPC33421
0.7413	Intermediate Similarity	NPC60553
0.7413	Intermediate Similarity	NPC476454
0.7403	Intermediate Similarity	NPC201700
0.7403	Intermediate Similarity	NPC63751
0.7389	Intermediate Similarity	NPC150048
0.7389	Intermediate Similarity	NPC474958
0.7389	Intermediate Similarity	NPC280852
0.7389	Intermediate Similarity	NPC203754
0.7386	Intermediate Similarity	NPC42372

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 NPC46358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	582
0.1-0.2	962
0.2-0.3	957
0.3-0.4	2156
0.4-0.5	2178
0.5-0.6	1505
0.6-0.7	621
0.7-0.8	150
0.8-0.85	31
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.888	High Similarity	NPD2119	Approved
0.888	High Similarity	NPD2118	Approved
0.888	High Similarity	NPD991	Phase 2
0.888	High Similarity	NPD992	Clinical (unspecified phase)
0.8722	High Similarity	NPD1722	Approved
0.8672	High Similarity	NPD3476	Approved
0.8672	High Similarity	NPD715	Phase 3
0.8672	High Similarity	NPD3475	Approved
0.8657	High Similarity	NPD2006	Phase 2
0.8626	High Similarity	NPD198	Clinical (unspecified phase)
0.8504	High Similarity	NPD9583	Approved
0.8492	Intermediate Similarity	NPD9357	Approved
0.8473	Intermediate Similarity	NPD4029	Approved
0.8473	Intermediate Similarity	NPD3944	Approved
0.8473	Intermediate Similarity	NPD4028	Approved
0.8473	Intermediate Similarity	NPD4030	Approved
0.8473	Intermediate Similarity	NPD3942	Approved
0.8462	Intermediate Similarity	NPD9098	Phase 3
0.8462	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD786	Approved
0.8406	Intermediate Similarity	NPD1661	Suspended
0.8406	Intermediate Similarity	NPD4547	Phase 3
0.84	Intermediate Similarity	NPD271	Approved
0.84	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD268	Approved
0.8345	Intermediate Similarity	NPD2430	Phase 2
0.8333	Intermediate Similarity	NPD3385	Approved
0.8321	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD1598	Discontinued
0.8169	Intermediate Similarity	NPD2837	Discontinued
0.8168	Intermediate Similarity	NPD3654	Approved
0.8162	Intermediate Similarity	NPD2075	Approved
0.8162	Intermediate Similarity	NPD2070	Approved
0.8162	Intermediate Similarity	NPD2071	Approved
0.8162	Intermediate Similarity	NPD2072	Approved
0.8162	Intermediate Similarity	NPD2073	Approved
0.8162	Intermediate Similarity	NPD2069	Approved
0.8162	Intermediate Similarity	NPD2068	Approved
0.8162	Intermediate Similarity	NPD2074	Approved
0.8112	Intermediate Similarity	NPD2165	Phase 1
0.8085	Intermediate Similarity	NPD3100	Discontinued
0.8085	Intermediate Similarity	NPD1183	Approved
0.8085	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD9396	Approved
0.808	Intermediate Similarity	NPD9392	Approved
0.8074	Intermediate Similarity	NPD1253	Approved
0.8074	Intermediate Similarity	NPD1254	Approved
0.8074	Intermediate Similarity	NPD1256	Approved
0.8074	Intermediate Similarity	NPD1255	Approved
0.8065	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD3112	Approved
0.8056	Intermediate Similarity	NPD3113	Approved
0.8056	Intermediate Similarity	NPD3115	Approved
0.8056	Intermediate Similarity	NPD3114	Approved
0.803	Intermediate Similarity	NPD947	Approved
0.8015	Intermediate Similarity	NPD45	Approved
0.8015	Intermediate Similarity	NPD6554	Approved
0.8	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1995	Approved
0.7985	Intermediate Similarity	NPD1993	Approved
0.7985	Intermediate Similarity	NPD1994	Approved
0.7967	Intermediate Similarity	NPD4824	Approved
0.7967	Intermediate Similarity	NPD4823	Approved
0.7917	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1251	Discontinued
0.7902	Intermediate Similarity	NPD2172	Phase 1
0.7891	Intermediate Similarity	NPD9705	Discontinued
0.7891	Intermediate Similarity	NPD112	Approved
0.7857	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5315	Discontinued
0.7838	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD7469	Discontinued
0.7785	Intermediate Similarity	NPD3323	Discontinued
0.7769	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4703	Approved
0.7762	Intermediate Similarity	NPD4702	Approved
0.7755	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD975	Approved
0.774	Intermediate Similarity	NPD976	Approved
0.774	Intermediate Similarity	NPD977	Approved
0.7737	Intermediate Similarity	NPD2142	Approved
0.7737	Intermediate Similarity	NPD2140	Approved
0.7737	Intermediate Similarity	NPD2141	Approved
0.7733	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2720	Phase 1
0.7721	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD2896	Discontinued
0.7692	Intermediate Similarity	NPD1683	Approved
0.7687	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1561	Phase 2
0.7632	Intermediate Similarity	NPD2640	Approved
0.7632	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2641	Approved
0.7632	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4047	Discontinued
0.76	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD792	Discontinued
0.7552	Intermediate Similarity	NPD3813	Approved
0.7552	Intermediate Similarity	NPD4509	Discontinued
0.7551	Intermediate Similarity	NPD3339	Approved
0.7533	Intermediate Similarity	NPD1404	Approved
0.7533	Intermediate Similarity	NPD1403	Approved
0.7532	Intermediate Similarity	NPD3116	Approved
0.7532	Intermediate Similarity	NPD3117	Approved
0.7532	Intermediate Similarity	NPD3609	Approved
0.7532	Intermediate Similarity	NPD3610	Approved
0.7532	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD803	Phase 1
0.75	Intermediate Similarity	NPD200	Phase 2
0.75	Intermediate Similarity	NPD201	Phase 2
0.7484	Intermediate Similarity	NPD7216	Approved
0.7484	Intermediate Similarity	NPD7217	Approved
0.7483	Intermediate Similarity	NPD4510	Discontinued
0.7467	Intermediate Similarity	NPD5418	Discontinued
0.745	Intermediate Similarity	NPD2580	Discontinued
0.7436	Intermediate Similarity	NPD5065	Approved
0.7436	Intermediate Similarity	NPD9690	Approved
0.7431	Intermediate Similarity	NPD5254	Discontinued
0.7426	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD9598	Discontinued
0.7417	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2333	Discontinued
0.7403	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4640	Approved
0.7403	Intermediate Similarity	NPD4639	Approved
0.7403	Intermediate Similarity	NPD4638	Approved
0.74	Intermediate Similarity	NPD6497	Approved
0.74	Intermediate Similarity	NPD2581	Approved
0.74	Intermediate Similarity	NPD2582	Approved
0.7389	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1262	Discovery
0.7368	Intermediate Similarity	NPD5400	Approved
0.7365	Intermediate Similarity	NPD2882	Phase 1
0.7361	Intermediate Similarity	NPD3717	Discontinued
0.7355	Intermediate Similarity	NPD5436	Phase 1
0.7351	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5255	Approved
0.7342	Intermediate Similarity	NPD7111	Discontinued
0.7342	Intermediate Similarity	NPD4181	Approved
0.7338	Intermediate Similarity	NPD2642	Approved
0.7338	Intermediate Similarity	NPD2639	Approved
0.7333	Intermediate Similarity	NPD2150	Discontinued
0.7329	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9207	Approved
0.7319	Intermediate Similarity	NPD9206	Approved
0.7297	Intermediate Similarity	NPD2466	Phase 3
0.7297	Intermediate Similarity	NPD2465	Approved
0.7297	Intermediate Similarity	NPD2462	Phase 3
0.7296	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5862	Discovery
0.7285	Intermediate Similarity	NPD4326	Phase 2
0.7278	Intermediate Similarity	NPD3348	Phase 2
0.7267	Intermediate Similarity	NPD2809	Approved
0.7267	Intermediate Similarity	NPD6285	Phase 2
0.7255	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6771	Discontinued
0.725	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3262	Approved
0.7248	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6158	Phase 2
0.7246	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5787	Discontinued
0.7231	Intermediate Similarity	NPD60	Approved
0.723	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9284	Approved
0.7226	Intermediate Similarity	NPD9080	Approved
0.7218	Intermediate Similarity	NPD4811	Discontinued
0.7215	Intermediate Similarity	NPD4128	Approved
0.7208	Intermediate Similarity	NPD3583	Phase 2
0.7203	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1917	Discontinued
0.7197	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4463	Approved
0.7181	Intermediate Similarity	NPD4462	Approved
0.7179	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5020	Approved
0.717	Intermediate Similarity	NPD2771	Approved
0.717	Intermediate Similarity	NPD4075	Phase 2
0.717	Intermediate Similarity	NPD5100	Phase 3
0.7162	Intermediate Similarity	NPD1270	Approved
0.7162	Intermediate Similarity	NPD2110	Approved
0.7161	Intermediate Similarity	NPD1313	Approved
0.7161	Intermediate Similarity	NPD2782	Approved
0.7161	Intermediate Similarity	NPD2780	Approved
0.716	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD750	Phase 2
0.7152	Intermediate Similarity	NPD1328	Approved
0.7152	Intermediate Similarity	NPD409	Clinical (unspecified phase)

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