NPASS Natural Product

Natural Product: NPC109188

Natural Product ID:	NPC109188
Common Name:	Azaribine
IUPAC Name:	[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(3,5-dioxo-1,2,4-triazin-2-yl)oxolan-2-yl]methyl acetate
Synonyms:	Azaribine; CB-304; Triazure
Molecular Formula:	C14H17N3O9
Standard InCHIKey:	QQOBRRFOVWGIMD-OJAKKHQRSA-N
Standard InCHI:	InChI=1S/C14H17N3O9/c1-6(18)23-5-9-11(24-7(2)19)12(25-8(3)20)13(26-9)17-14(22)16-10(21)4-15-17/h4,9,11-13H,5H2,1-3H3,(H,16,21,22)/t9-,11-,12-,13-/m1/s1
Canonical SMILES:	CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1ncc(nc1=O)O)COC(=O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30360	Bacillus methanolicus	Species	Bacillidae	Eukaryota				PMID[25518943]
NPO30360	Bacillus methanolicus	Species	Bacillidae	Eukaryota				PMID[26366644]

Biological Activity

Activity Type	# Activity
AC50	2
IC50	1
Potency	42

Activity Type	# Activity
Cell Line	1
Individual Protein	14
Others	28
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	562.3	nM	PubChem BioAssay data set
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	2930.9	nM	PubChem BioAssay data set
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	=	398107.2	nM	PubChem BioAssay data set
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	2511.9	nM	PubChem BioAssay data set
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	89125.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		IC50	=	9792	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency		259.3	nM	PubChem BioAssay data set
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency		23109.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		11.2	nM	PubChem BioAssay data set
NPT71	Cell Line	HEK293	Homo sapiens	Potency		730.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1299.5	nM	PubChem BioAssay data set
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency		9992.4	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		326.4	nM	PubChem BioAssay data set
NPT10	Individual Protein	Geminin	Homo sapiens	Potency		6513.1	nM	PubChem BioAssay data set
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency		1000	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		4109.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		366.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		10593.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		21136	nM	PubChem BioAssay data set
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency		31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		8485.2	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency		5353.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1883.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1584.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		119.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		841.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		943.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		0.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		2683.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1059.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1995.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1678.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		5308	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		23710.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1333.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		4730.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		2131.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		7497.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		1496	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		AC50		12589.3	nM	PubChem BioAssay data set

Similar Natural Products 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 NPC109188 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	158
0.1-0.2	10569
0.2-0.3	16598
0.3-0.4	2952
0.4-0.5	507
0.5-0.6	83
0.6-0.7	19
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7841	Intermediate Similarity	NPC319753
0.7273	Intermediate Similarity	NPC329077
0.7	Intermediate Similarity	NPC325902
0.6735	Remote Similarity	NPC171116
0.6667	Remote Similarity	NPC325723
0.6598	Remote Similarity	NPC89051
0.6598	Remote Similarity	NPC43246
0.6531	Remote Similarity	NPC163352
0.6531	Remote Similarity	NPC210456
0.64	Remote Similarity	NPC315063
0.6311	Remote Similarity	NPC36985
0.6311	Remote Similarity	NPC17892
0.6289	Remote Similarity	NPC106780
0.625	Remote Similarity	NPC283698
0.625	Remote Similarity	NPC73765
0.6224	Remote Similarity	NPC71339
0.6224	Remote Similarity	NPC112842
0.6196	Remote Similarity	NPC315806
0.6095	Remote Similarity	NPC317639
0.6019	Remote Similarity	NPC324390
0.6	Remote Similarity	NPC324516
0.6	Remote Similarity	NPC318166
0.5962	Remote Similarity	NPC322594
0.5962	Remote Similarity	NPC327344
0.5962	Remote Similarity	NPC320249
0.5877	Remote Similarity	NPC155087
0.5877	Remote Similarity	NPC149843
0.5841	Remote Similarity	NPC329277
0.5726	Remote Similarity	NPC325750
0.5684	Remote Similarity	NPC126186
0.5678	Remote Similarity	NPC478024

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC109188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	76
0.1-0.2	2471
0.2-0.3	5236
0.3-0.4	991
0.4-0.5	280
0.5-0.6	81
0.6-0.7	24
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1331	Approved
0.7766	Intermediate Similarity	NPD1686	Approved
0.6598	Remote Similarity	NPD9580	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD9581	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD1385	Discontinued
0.6458	Remote Similarity	NPD9559	Phase 1
0.64	Remote Similarity	NPD755	Phase 3
0.6389	Remote Similarity	NPD4743	Phase 2
0.625	Remote Similarity	NPD9639	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9558	Phase 3
0.625	Remote Similarity	NPD9556	Approved
0.6224	Remote Similarity	NPD280	Approved
0.62	Remote Similarity	NPD1760	Approved
0.6196	Remote Similarity	NPD9653	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD9560	Approved
0.6186	Remote Similarity	NPD9561	Approved
0.6176	Remote Similarity	NPD9565	Discontinued
0.6162	Remote Similarity	NPD9557	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD9546	Phase 2
0.6117	Remote Similarity	NPD251	Approved
0.61	Remote Similarity	NPD240	Phase 3
0.6078	Remote Similarity	NPD841	Approved
0.6064	Remote Similarity	NPD9407	Approved
0.6061	Remote Similarity	NPD9533	Phase 2
0.604	Remote Similarity	NPD241	Discontinued
0.602	Remote Similarity	NPD2691	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD9429	Discontinued
0.5941	Remote Similarity	NPD9562	Discovery
0.5941	Remote Similarity	NPD170	Approved
0.59	Remote Similarity	NPD239	Phase 2
0.59	Remote Similarity	NPD238	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD3128	Phase 3
0.5841	Remote Similarity	NPD3129	Phase 3
0.5833	Remote Similarity	NPD502	Approved
0.58	Remote Similarity	NPD9529	Phase 1
0.58	Remote Similarity	NPD882	Phase 2
0.58	Remote Similarity	NPD883	Phase 2
0.578	Remote Similarity	NPD3121	Phase 2
0.578	Remote Similarity	NPD5789	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD9405	Approved
0.5741	Remote Similarity	NPD762	Discontinued
0.5727	Remote Similarity	NPD223	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1061	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD1706	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6943	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD1804	Phase 2
0.5641	Remote Similarity	NPD1805	Phase 2
0.5625	Remote Similarity	NPD7651	Approved

Structure

CID109188 OpenBabel06191715462D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.3664 2.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6243 2.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1465 -2.1720 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 -2.3554 2.6160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7731 3.3205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0310 1.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9385 -1.1939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 C 0 0 2 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 -2.4487 0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1853 4.1295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0255 1.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6817 -0.5248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 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 -1.7677 3.4250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4432 0.7319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 -0.8849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 10 1 0 0 0 0 4 15 2 0 0 0 0 5 23 1 0 0 0 0 6 18 2 0 0 0 0 6 23 1 0 0 0 0 7 19 2 0 0 0 0 7 24 1 0 0 0 0 8 20 2 0 0 0 0 8 25 1 0 0 0 0 9 5 1 1 0 0 0 9 11 1 0 0 0 0 9 26 1 0 0 0 0 10 16 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 6 0 0 0 12 13 1 0 0 0 0 12 25 1 6 0 0 0 13 17 1 1 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	16574
ChEMBL	CHEMBL515914
ZINC

Physicochemical Properties

Molecular Weight:	371.10
ALogP:	-0.723
MLogP:	1.68
XLogP:	-0.251
# Rotatable Bonds:	12
Polar Surface Area:	153.39
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	26

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