NPASS Natural Product

Natural Product: NPC329165

Natural Product ID:	NPC329165
Common Name:	Monophosphothiamine
IUPAC Name:	2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl dihydrogen phosphate
Synonyms:	Monophosphothiamine
Molecular Formula:	C12H17N4O4PS
Standard InCHIKey:	HZSAJDVWZRBGIF-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)/p+1
Canonical SMILES:	Cc1[n+](csc1CCOP(=O)(O)O)Cc1cnc([nH]c1=N)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO1797	Homo sapiens	Species	Hominidae	Eukaryota	PMID[12111441]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	PMID[19425150]
NPO21658	Saccharomyces cerevisiae	Species	Saccharomycetaceae	Eukaryota	PMID[24678285]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	PMID[21988831]

Biological Activity

Activity Type	# Activity
Potency	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	22387.2	nM	PubChem BioAssay data set
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency		3981.1	nM	PubChem BioAssay data set
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency		7208	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 NPC329165 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	154
0.1-0.2	20539
0.2-0.3	6678
0.3-0.4	2515
0.4-0.5	975
0.5-0.6	22
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC317197
0.9923	High Similarity	NPC320833
0.9167	High Similarity	NPC125076
0.9167	High Similarity	NPC189436
0.9167	High Similarity	NPC150950
0.6894	Remote Similarity	NPC162460

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	1226
0.2-0.3	3134
0.3-0.4	3200
0.4-0.5	1397
0.5-0.6	82
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD807	Approved
0.9167	High Similarity	NPD808	Approved
0.6875	Remote Similarity	NPD6121	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3966	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3877	Approved
0.625	Remote Similarity	NPD3876	Approved
0.6241	Remote Similarity	NPD9402	Discontinued
0.5882	Remote Similarity	NPD9104	Approved
0.581	Remote Similarity	NPD3332	Approved
0.581	Remote Similarity	NPD3333	Approved
0.5602	Remote Similarity	NPD954	Phase 1

Structure

CID329165 OpenBabel06191716202D 22 23 0 0 0 0 0 0 0 0999 V2000 4.6637 1.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3520 0.8703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8205 1.6392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1160 3.2215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3364 3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5430 1.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9250 2.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8385 3.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9431 4.0349 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6295 1.0514 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6476 2.4526 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2024 2.8147 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 2.5933 2.6456 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 20 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 16 2 0 0 0 0 7 22 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 M CHG 1 16 1 M END $$$$

External Identifiers

PubChem CID	1131
ChEMBL	CHEMBL1236378
ZINC

Physicochemical Properties

Molecular Weight:	345.08
ALogP:	-2.3106
MLogP:	1.68
XLogP:	-0.588
# Rotatable Bonds:	10
Polar Surface Area:	156.93
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	22

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