Guvacine

Details

• Internal ID: c6567e19-1ec5-4404-8338-e83fb75f2d8f
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: 1,2,3,6-tetrahydropyridine-5-carboxylic acid
• SMILES (Canonical): C1CNCC(=C1)C(=O)O
• SMILES (Isomeric): C1CNCC(=C1)C(=O)O
• InChI: InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
• InChI Key: QTDZOWFRBNTPQR-UHFFFAOYSA-N
• Popularity: 221 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.14 g/mol
• Exact Mass: 127.063328530 g/mol
• Topological Polar Surface Area (TPSA): 49.30 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 498-96-4
• 1,2,5,6-tetrahydropyridine-3-carboxylic acid
• 1,2,5,6-Tetrahydro-3-pyridinecarboxylic acid
• 1,2,5,6-Tetrahydro-pyridine-3-carboxylic acid
• 1,2,5,6-Tetrahydronicotinic acid
• 1,2,3,6-tetrahydropyridine-5-carboxylic acid
• CHEBI:5576
• UNII-41538P325K
• 41538P325K
• MLS000859975
• SMR000326834
• Spectrum_001426
• Tocris-0234
• SpecPlus_000808
• Lopac-G-007
• GUVACINE [MI]
• Spectrum2_001474
• Spectrum3_001511
• Spectrum4_001753
• Spectrum5_000606
• Biomol-NT_000253
• D0U5MF
• D0V7RG
• C10149
• Lopac0_000571
• BSPBio_003181
• KBioGR_002226
• KBioSS_001906
• CHEMBL76768
• DivK1c_006904
• SCHEMBL336053
• SPBio_001427
• BPBio1_000838
• GTPL4691
• BDBM90787
• KBio1_001848
• KBio2_001906
• KBio2_004474
• KBio2_007042
• KBio3_002681
• DTXSID50871702
• cid_11957555
• QTDZOWFRBNTPQR-UHFFFAOYSA-N
• AMY32578
• HY-N2482
• MFCD01365700
• ZINC03872753
• AKOS006282520
• CCG-204660
• DB08848
• SB37356
• SDCCGMLS-0066665.P001
• SDCCGSBI-0050553.P003
• NCGC00015457-01
• NCGC00015457-02
• NCGC00015457-03
• NCGC00015457-04
• NCGC00015457-05
• NCGC00015457-08
• NCGC00024508-01
• NCGC00024508-02
• NCGC00024508-03
• BB 0253172
• CS-0022753
• EN300-261948
• F13202
• 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro
• 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-
• Q15322708

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9400	94.00%
Caco-2	+	0.6494	64.94%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5362	53.62%
OATP2B1 inhibitior	-	0.8497	84.97%
OATP1B1 inhibitior	+	0.9689	96.89%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9550	95.50%
P-glycoprotein inhibitior	-	0.9870	98.70%
P-glycoprotein substrate	-	0.9796	97.96%
CYP3A4 substrate	-	0.7916	79.16%
CYP2C9 substrate	-	0.7867	78.67%
CYP2D6 substrate	-	0.8281	82.81%
CYP3A4 inhibition	-	0.9888	98.88%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9114	91.14%
CYP2D6 inhibition	-	0.9580	95.80%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9813	98.13%
CYP inhibitory promiscuity	-	0.9907	99.07%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6877	68.77%
Eye corrosion	-	0.7726	77.26%
Eye irritation	+	0.9935	99.35%
Skin irritation	+	0.5087	50.87%
Skin corrosion	-	0.8825	88.25%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8444	84.44%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5287	52.87%
skin sensitisation	-	0.7761	77.61%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6122	61.22%
Acute Oral Toxicity (c)	III	0.6101	61.01%
Estrogen receptor binding	-	0.9554	95.54%
Androgen receptor binding	-	0.8714	87.14%
Thyroid receptor binding	-	0.9038	90.38%
Glucocorticoid receptor binding	-	0.9310	93.10%
Aromatase binding	-	0.8821	88.21%
PPAR gamma	-	0.8725	87.25%
Honey bee toxicity	-	0.9451	94.51%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	-	0.8478	84.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1903	P30531	GABA transporter 1	14000 nM	IC50	PMID: 8057281
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.64%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.37%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.00%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.91%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.75%	95.56%

Plants that contains it

• Areca catechu
• Garcinia morella

Cross-Links

• PubChem: 3532
• NPASS: NPC4668
• ChEMBL: CHEMBL76768
• LOTUS: LTS0119984
• wikiData: Q15322708