NPASS Compound

Structure

CID158179 OpenBabel06191715532D 22 21 0 0 0 0 0 0 0 0999 V2000 15.5885 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 3 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 3 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 3 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 3 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.18
Volume:	348.328
LogP:	3.872
LogD:	4.337
LogS:	-4.267
# Rotatable Bonds:	6
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	3.473
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.86
MDCK Permeability:	9.82035999186337e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	80.49483489990234%
Volume Distribution (VD):	-0.579
Pgp-substrate:	0.17771883308887482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.269
CYP2C9-inhibitor:	0.806
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.256
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	11.903
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.98
Carcinogencity:	0.492
Eye Corrosion:	0.982
Eye Irritation:	0.987
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC158179

Natural Product ID:	NPC158179
*Common Name:**	Icosa-5,8,11,14-Tetraynoic Acid
IUPAC Name:	icosa-5,8,11,14-tetraynoic acid
Synonyms:	5,8,11,14-Eicosatetraynoic Acid
Standard InCHIKey:	MGLDCXPLYOWQRP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
SMILES:	CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458328
PubChem CID:	1780
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	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	34
MIC	14
Others	4
Potency	31

Activity Type	# Activity
Individual Protein	42
Organism	36
Others	3
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	28183.8	nM	PMID[528173]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	28183.8	nM	PMID[528174]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	1122.0	nM	PMID[528173]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	15848.9	nM	PMID[528173]
NPT1387	Individual Protein	Genome polyprotein	Hepatitis C virus	IC50	=	46301.0	nM	PMID[528173]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	631.0	nM	PMID[528173]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	79432.8	nM	PMID[528176]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	10000.0	nM	PMID[528174]
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	IC50	>	108803.0	nM	PMID[528173]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	28183.8	nM	PMID[528174]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[528173]
NPT1498	Individual Protein	Dual specificity protein phosphatase 6	Rattus norvegicus	IC50	=	832.0	nM	PMID[528173]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	19952.6	nM	PMID[528173]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	56234.1	nM	PMID[528174]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	441.49	nM	PMID[528173]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	25118.9	nM	PMID[528173]
NPT2570	Individual Protein	Protein-tyrosine phosphatase LC-PTP	Homo sapiens	IC50	=	15400.0	nM	PMID[528177]
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	3162.3	nM	PMID[528173]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	28183.8	nM	PMID[528173]
NPT1224	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase liver	Homo sapiens	IC50	>	100000.0	nM	PMID[528177]
NPT58	Individual Protein	Bloom syndrome protein	Homo sapiens	Potency	=	12589.3	nM	PMID[528173]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	1122.0	nM	PMID[528173]
NPT1498	Individual Protein	Dual specificity protein phosphatase 6	Rattus norvegicus	IC50	=	25100.0	nM	PMID[528177]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	2238.7	nM	PMID[528173]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	10691.0	nM	PMID[528173]
NPT1039	Individual Protein	Envelope glycoprotein gp160	Human immunodeficiency virus 1	IC50	=	11900.0	nM	PMID[528173]
NPT3725	Individual Protein	Eukaryotic translation initiation factor 4E	Mus musculus	IC50	n.a.	32130.0	nM	PMID[528173]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[528173]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	3981.1	nM	PMID[528173]
NPT1498	Individual Protein	Dual specificity protein phosphatase 6	Rattus norvegicus	IC50	=	30400.0	nM	PMID[528177]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[528178]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	30131.3	nM	PMID[528173]
NPT1632	Individual Protein	Monocarboxylate transporter 2	Rattus norvegicus	Activity	=	125.0	%	PMID[528179]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[528173]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1995.3	nM	PMID[528173]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[528174]
NPT1040	Individual Protein	Human immunodeficiency virus type 1 Tat protein	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	IC50	n.a.	2379.0	nM	PMID[528173]
NPT2	Others	Unspecified		Inhibition	=	95.0	%	PMID[528171]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	8100.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	63300.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	4500.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	4000.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31700.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	5000.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	42200.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	1700.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2000.0	nM	PMID[528172]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	IC50	=	2900.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3500.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5300.0	nM	PMID[528172]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	IC50	=	5400.0	nM	PMID[528172]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IC50	=	6700.0	nM	PMID[528172]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	IC50	=	8400.0	nM	PMID[528172]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	10000.0	nM	PMID[528172]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	13300.0	nM	PMID[528172]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IC50	=	14200.0	nM	PMID[528172]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	15800.0	nM	PMID[528172]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	21.1	uM	PMID[528172]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	21100.0	nM	PMID[528172]
NPT186	Organism	Candida tropicalis	Candida tropicalis	IC50	=	27700.0	nM	PMID[528172]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	31700.0	nM	PMID[528172]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	31700.0	nM	PMID[528172]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	63300.0	nM	PMID[528172]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	84500.0	nM	PMID[528172]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IC50	=	100000.0	nM	PMID[528172]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC50	>	168900.0	nM	PMID[528172]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	168900.0	nM	PMID[528172]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IC50	>	168900.0	nM	PMID[528172]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PMID[528173]
NPT2	Others	Unspecified		IC50	>	12500.0	nM	PMID[528173]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	12589.3	nM	PMID[528175]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	25118.9	nM	PMID[528173]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[528174]
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	28183.8	nM	PMID[528173]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	8912.5	nM	PMID[528173]
NPT706	Individual Protein	Monocarboxylate transporter 1	Rattus norvegicus	Activity	=	117.0	%	PMID[528179]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	3400.0	nM	PMID[528180]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	100000.0	nM	PMID[528180]
NPT2	Others	Unspecified		IC50	n.a.	860.0	nM	PMID[528173]

☑ 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 NPC158179 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	1733
0.1-0.2	22103
0.2-0.3	13039
0.3-0.4	4678
0.4-0.5	760
0.5-0.6	246
0.6-0.7	96
0.7-0.8	31
0.8-0.85	4
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC73245
0.8947	High Similarity	NPC103286
0.8947	High Similarity	NPC163746
0.8718	High Similarity	NPC301528
0.8718	High Similarity	NPC129972
0.8718	High Similarity	NPC71317
0.85	High Similarity	NPC19305
0.85	High Similarity	NPC255837
0.8293	Intermediate Similarity	NPC8219
0.7941	Intermediate Similarity	NPC174368
0.7778	Intermediate Similarity	NPC175342
0.7561	Intermediate Similarity	NPC196924
0.7561	Intermediate Similarity	NPC307783
0.7561	Intermediate Similarity	NPC149184
0.7561	Intermediate Similarity	NPC171736
0.7561	Intermediate Similarity	NPC216630
0.7561	Intermediate Similarity	NPC209970
0.7556	Intermediate Similarity	NPC304162
0.75	Intermediate Similarity	NPC201844
0.75	Intermediate Similarity	NPC3531
0.75	Intermediate Similarity	NPC279026
0.75	Intermediate Similarity	NPC261080
0.75	Intermediate Similarity	NPC154186
0.75	Intermediate Similarity	NPC301696
0.75	Intermediate Similarity	NPC14227
0.75	Intermediate Similarity	NPC301585
0.75	Intermediate Similarity	NPC113928
0.7381	Intermediate Similarity	NPC67462
0.7297	Intermediate Similarity	NPC328710
0.7297	Intermediate Similarity	NPC18224
0.7234	Intermediate Similarity	NPC470410
0.7234	Intermediate Similarity	NPC470412
0.7234	Intermediate Similarity	NPC284212
0.7209	Intermediate Similarity	NPC74845
0.7179	Intermediate Similarity	NPC155263
0.7143	Intermediate Similarity	NPC325452
0.7143	Intermediate Similarity	NPC248763
0.7111	Intermediate Similarity	NPC42304
0.7105	Intermediate Similarity	NPC127142
0.7105	Intermediate Similarity	NPC7814
0.7073	Intermediate Similarity	NPC214610
0.7073	Intermediate Similarity	NPC183424
0.7073	Intermediate Similarity	NPC118968
0.7073	Intermediate Similarity	NPC294085
0.7059	Intermediate Similarity	NPC149209
0.7	Intermediate Similarity	NPC252843
0.7	Intermediate Similarity	NPC109026
0.6923	Remote Similarity	NPC317203
0.6889	Remote Similarity	NPC30195
0.6889	Remote Similarity	NPC12438
0.6875	Remote Similarity	NPC100096
0.6875	Remote Similarity	NPC470411
0.6875	Remote Similarity	NPC28205
0.6842	Remote Similarity	NPC125575
0.6842	Remote Similarity	NPC286695
0.6829	Remote Similarity	NPC268826
0.675	Remote Similarity	NPC154642
0.675	Remote Similarity	NPC80396
0.675	Remote Similarity	NPC134782
0.6739	Remote Similarity	NPC21844
0.6739	Remote Similarity	NPC328497
0.6739	Remote Similarity	NPC324004
0.6735	Remote Similarity	NPC129458
0.6735	Remote Similarity	NPC18357
0.6667	Remote Similarity	NPC473863
0.6667	Remote Similarity	NPC55023
0.6667	Remote Similarity	NPC57499
0.6667	Remote Similarity	NPC154396
0.6667	Remote Similarity	NPC274290
0.66	Remote Similarity	NPC10081
0.66	Remote Similarity	NPC225066
0.6596	Remote Similarity	NPC91495
0.6596	Remote Similarity	NPC324793
0.6596	Remote Similarity	NPC477878
0.6596	Remote Similarity	NPC106872
0.6585	Remote Similarity	NPC206924
0.6579	Remote Similarity	NPC12904
0.6579	Remote Similarity	NPC280532
0.6538	Remote Similarity	NPC179764
0.6538	Remote Similarity	NPC187777
0.6522	Remote Similarity	NPC314679
0.6522	Remote Similarity	NPC117572
0.6512	Remote Similarity	NPC12156
0.6512	Remote Similarity	NPC161097
0.6512	Remote Similarity	NPC28598
0.65	Remote Similarity	NPC156630
0.6486	Remote Similarity	NPC122768
0.6486	Remote Similarity	NPC104195
0.6486	Remote Similarity	NPC61066
0.6486	Remote Similarity	NPC151140
0.6458	Remote Similarity	NPC149821
0.6458	Remote Similarity	NPC5413
0.6429	Remote Similarity	NPC325454
0.6429	Remote Similarity	NPC54980
0.6429	Remote Similarity	NPC22903
0.6429	Remote Similarity	NPC38930
0.6429	Remote Similarity	NPC305660
0.6429	Remote Similarity	NPC201622
0.641	Remote Similarity	NPC322892
0.64	Remote Similarity	NPC303765
0.6364	Remote Similarity	NPC474361
0.6346	Remote Similarity	NPC54766
0.6346	Remote Similarity	NPC45626
0.6341	Remote Similarity	NPC80641
0.6327	Remote Similarity	NPC90904
0.6327	Remote Similarity	NPC59051
0.6296	Remote Similarity	NPC329819
0.6279	Remote Similarity	NPC219536
0.6279	Remote Similarity	NPC80234
0.6279	Remote Similarity	NPC81263
0.6279	Remote Similarity	NPC31551
0.625	Remote Similarity	NPC200618
0.625	Remote Similarity	NPC131770
0.625	Remote Similarity	NPC207292
0.6222	Remote Similarity	NPC289686
0.6222	Remote Similarity	NPC203531
0.6222	Remote Similarity	NPC236579
0.62	Remote Similarity	NPC48162
0.619	Remote Similarity	NPC317945
0.619	Remote Similarity	NPC14608
0.6154	Remote Similarity	NPC40965
0.6136	Remote Similarity	NPC149299
0.6136	Remote Similarity	NPC40597
0.6136	Remote Similarity	NPC250028
0.6136	Remote Similarity	NPC165533
0.6136	Remote Similarity	NPC256163
0.6122	Remote Similarity	NPC26253
0.6111	Remote Similarity	NPC230726
0.6111	Remote Similarity	NPC225929
0.6111	Remote Similarity	NPC314668
0.6098	Remote Similarity	NPC155872
0.6087	Remote Similarity	NPC317128
0.6078	Remote Similarity	NPC161366
0.6078	Remote Similarity	NPC92114
0.6053	Remote Similarity	NPC292641
0.6053	Remote Similarity	NPC248139
0.6	Remote Similarity	NPC267817
0.6	Remote Similarity	NPC53541
0.5962	Remote Similarity	NPC72722
0.5962	Remote Similarity	NPC294548
0.5962	Remote Similarity	NPC1813
0.5962	Remote Similarity	NPC36061
0.5962	Remote Similarity	NPC321062
0.5962	Remote Similarity	NPC139029
0.5962	Remote Similarity	NPC70387
0.5957	Remote Similarity	NPC287231
0.5957	Remote Similarity	NPC47363
0.5957	Remote Similarity	NPC469781
0.5918	Remote Similarity	NPC180534
0.5909	Remote Similarity	NPC223249
0.5897	Remote Similarity	NPC198126
0.5897	Remote Similarity	NPC320981
0.5882	Remote Similarity	NPC181153
0.587	Remote Similarity	NPC310220
0.587	Remote Similarity	NPC144829
0.5854	Remote Similarity	NPC307027
0.5854	Remote Similarity	NPC286498
0.5849	Remote Similarity	NPC322461
0.5849	Remote Similarity	NPC424
0.5849	Remote Similarity	NPC25417
0.5849	Remote Similarity	NPC87394
0.5849	Remote Similarity	NPC87564
0.5849	Remote Similarity	NPC261831
0.5849	Remote Similarity	NPC32467
0.5849	Remote Similarity	NPC320588
0.5849	Remote Similarity	NPC23155
0.5849	Remote Similarity	NPC154245
0.5849	Remote Similarity	NPC88966
0.5849	Remote Similarity	NPC85813
0.5849	Remote Similarity	NPC6095
0.5849	Remote Similarity	NPC281972
0.5849	Remote Similarity	NPC469937
0.5849	Remote Similarity	NPC289979
0.5849	Remote Similarity	NPC290563
0.5849	Remote Similarity	NPC53463
0.5833	Remote Similarity	NPC308301
0.5833	Remote Similarity	NPC28246
0.5833	Remote Similarity	NPC166287
0.5814	Remote Similarity	NPC128996
0.5789	Remote Similarity	NPC235242
0.5789	Remote Similarity	NPC236709
0.5778	Remote Similarity	NPC240109
0.5769	Remote Similarity	NPC281245
0.5763	Remote Similarity	NPC226592
0.5745	Remote Similarity	NPC270796
0.5745	Remote Similarity	NPC76051
0.5745	Remote Similarity	NPC319680
0.5745	Remote Similarity	NPC323974
0.5741	Remote Similarity	NPC477984
0.5741	Remote Similarity	NPC474672
0.5714	Remote Similarity	NPC196442
0.5714	Remote Similarity	NPC168052
0.5714	Remote Similarity	NPC301398
0.5714	Remote Similarity	NPC289344
0.5714	Remote Similarity	NPC249754
0.5714	Remote Similarity	NPC191084
0.5714	Remote Similarity	NPC316685
0.5714	Remote Similarity	NPC223374
0.5714	Remote Similarity	NPC250870
0.5714	Remote Similarity	NPC86545

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 NPC158179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	2178
0.1-0.2	5101
0.2-0.3	1232
0.3-0.4	406
0.4-0.5	158
0.5-0.6	54
0.6-0.7	13
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD9635	Discontinued
0.7561	Intermediate Similarity	NPD2270	Approved
0.75	Intermediate Similarity	NPD9448	Phase 2
0.75	Intermediate Similarity	NPD633	Phase 3
0.75	Intermediate Similarity	NPD9450	Approved
0.75	Intermediate Similarity	NPD77	Approved
0.7105	Intermediate Similarity	NPD8857	Approved
0.7073	Intermediate Similarity	NPD9655	Approved
0.7045	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3206	Approved
0.6596	Remote Similarity	NPD2266	Phase 2
0.6522	Remote Similarity	NPD4222	Approved
0.6522	Remote Similarity	NPD634	Phase 3
0.65	Remote Similarity	NPD9447	Approved
0.6458	Remote Similarity	NPD3173	Approved
0.619	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.617	Remote Similarity	NPD39	Approved
0.6078	Remote Similarity	NPD3186	Phase 1
0.6053	Remote Similarity	NPD62	Approved
0.5962	Remote Similarity	NPD3172	Approved
0.5957	Remote Similarity	NPD2699	Approved
0.5918	Remote Similarity	NPD622	Approved
0.5897	Remote Similarity	NPD8590	Approved
0.5897	Remote Similarity	NPD8618	Approved
0.5882	Remote Similarity	NPD8201	Phase 2
0.5882	Remote Similarity	NPD8615	Phase 2
0.5882	Remote Similarity	NPD8616	Clinical (unspecified phase)
0.587	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3194	Approved
0.5849	Remote Similarity	NPD3195	Phase 2
0.5849	Remote Similarity	NPD3196	Approved
0.5849	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3730	Approved
0.5849	Remote Similarity	NPD4266	Approved
0.5849	Remote Similarity	NPD3728	Approved
0.5833	Remote Similarity	NPD9431	Approved
0.5833	Remote Similarity	NPD9430	Approved
0.5833	Remote Similarity	NPD3174	Discontinued
0.5789	Remote Similarity	NPD8593	Approved
0.5789	Remote Similarity	NPD8594	Approved
0.5745	Remote Similarity	NPD5326	Phase 3
0.5745	Remote Similarity	NPD9019	Approved
0.5652	Remote Similarity	NPD9116	Phase 1
0.5641	Remote Similarity	NPD8619	Approved
0.5641	Remote Similarity	NPD8617	Approved
0.56	Remote Similarity	NPD6125	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