NPASS Natural Product

Natural Product: NPC4668

Natural Product ID:	NPC4668
Common Name:	Guvacine
IUPAC Name:	1,2,3,6-tetrahydropyridin-1-ium-5-carboxylate
Synonyms:	Guvacine
Molecular Formula:	C6H9NO2
Standard InCHIKey:	QTDZOWFRBNTPQR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
Canonical SMILES:	OC(=O)C1=CCCNC1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	fruit	Phytochemistry,1998,48(3): 581-582
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota		TCMSP*
NPO29577	Arecae semen	NA	NA	NA		TCMSP*
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota		TM-MC*
NPO5949	Pericarpium arecae	NA	NA	NA		TCMID*
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota		TCMID*
NPO6483	Semen arecae preparata	NA	NA	NA		TCMID*
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota		TCMID*

Biological Activity

Activity Type	# Activity
IC50	35
Others	3
Potency	7

Activity Type	# Activity
Individual Protein	39
Organism	5
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	4920	nM	2985785
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Inhibition	=	27	%	2985785
NPT806	Individual Protein	Glutamate decarboxylase 67 kDa isoform	Rattus norvegicus	Inhibition	=	0	%	2985785
NPT807	Individual Protein	Gamma-amino-N-butyrate transaminase	Rattus norvegicus	Inhibition	=	7	%	2985785
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	7300	nM	1433224
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	=	12000	nM	10639282
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	32000	nM	10639282
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	29000	nM	10639282
NPT808	Individual Protein	GABA transporter 1	Homo sapiens	IC50	=	14000	nM	8057281
NPT809	Individual Protein	GABA transporter 2	Rattus norvegicus	IC50	=	58000	nM	8057281
NPT810	Individual Protein	GABA transporter 3	Homo sapiens	IC50	=	119000	nM	8057281
NPT811	Individual Protein	Betaine transporter	Homo sapiens	IC50	=	1870000	nM	8057281
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2650	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	1680	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2900	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2260	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2660	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	1760	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	1870	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2790	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	1910	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2770	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	1850	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2590	nM	15509161
NPT812	Individual Protein	GABA transporter 1	Rattus norvegicus	IC50	=	2560	nM	15509161
NPT813	Individual Protein	GABA transporter 1	Mus musculus	IC50	=	13489.63	nM	18395300
NPT814	Individual Protein	GABA transporter 2	Mus musculus	IC50	=	489778.82	nM	18395300
NPT815	Individual Protein	GABA transporter 3	Mus musculus	IC50	=	25703.96	nM	18395300
NPT816	Individual Protein	GABA transporter 4	Mus musculus	IC50	=	25703.96	nM	18395300
NPT810	Individual Protein	GABA transporter 3	Homo sapiens	IC50	=	110000	nM	20219271
NPT817	Individual Protein	GABA transporter 2	Homo sapiens	IC50	=	66000	nM	20219271
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT242	Individual Protein	Dopamine D1 receptor	Homo sapiens	Potency		1458	nM	PubChem BioAssay data set
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency		891.3	nM	PubChem BioAssay data set
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency		37933	nM	PubChem BioAssay data set
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency		5972.8	nM	PubChem BioAssay data set
NPT813	Individual Protein	GABA transporter 1	Mus musculus	IC50	=	12589.25	nM	23336362
NPT813	Individual Protein	GABA transporter 1	Mus musculus	IC50	=	14000	nM	23336362
NPT104	Individual Protein	Cerebroside-sulfatase	Homo sapiens	Potency		13.5	nM	PubChem BioAssay data set
NPT813	Individual Protein	GABA transporter 1	Mus musculus	IC50	=	20900	nM	26706177
NPT814	Individual Protein	GABA transporter 2	Mus musculus	IC50	>	1000000	nM	26706177
NPT815	Individual Protein	GABA transporter 3	Mus musculus	IC50	=	72400	nM	26706177
NPT816	Individual Protein	GABA transporter 4	Mus musculus	IC50	=	114800	nM	26706177

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 NPC4668 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	37
0.1-0.2	3085
0.2-0.3	20107
0.3-0.4	6604
0.4-0.5	955
0.5-0.6	89
0.6-0.7	5
0.7-0.8	2
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133758
0.8906	High Similarity	NPC98329
0.8906	High Similarity	NPC7392
0.8852	High Similarity	NPC305973
0.8594	High Similarity	NPC112312
0.7576	Intermediate Similarity	NPC14437
0.7576	Intermediate Similarity	NPC270412
0.6842	Remote Similarity	NPC122471
0.6757	Remote Similarity	NPC133700
0.6747	Remote Similarity	NPC202056
0.64	Remote Similarity	NPC90782
0.6389	Remote Similarity	NPC66789
0.5938	Remote Similarity	NPC87137
0.5909	Remote Similarity	NPC221467
0.5823	Remote Similarity	NPC126293
0.5821	Remote Similarity	NPC43053
0.5758	Remote Similarity	NPC137419
0.5758	Remote Similarity	NPC122212
0.5738	Remote Similarity	NPC8270
0.5645	Remote Similarity	NPC221250
0.5634	Remote Similarity	NPC51846
0.5625	Remote Similarity	NPC6963
0.5625	Remote Similarity	NPC304079
0.56	Remote Similarity	NPC77891

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	38
0.1-0.2	1206
0.2-0.3	5604
0.3-0.4	2103
0.4-0.5	190
0.5-0.6	18
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD9137	Approved
0.7576	Intermediate Similarity	NPD9418	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD2905	Discontinued
0.5823	Remote Similarity	NPD9354	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD9355	Approved

Structure

External Identifiers

PubChem CID	40468028;3532
ChEMBL	CHEMBL76768
ZINC

Physicochemical Properties

Molecular Weight:	127.06
ALogP:	-0.6528
MLogP:	1.79
XLogP:	0.041
# Rotatable Bonds:	2
Polar Surface Area:	49.33
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	9

Download Data

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