2-Amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid

Details

• Internal ID: 239bdcb5-ed81-452e-851b-1bdba0b64000
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids
• IUPAC Name: 2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
• SMILES (Canonical): C1=CN(C=C(C1=O)O)CC(C(=O)O)N
• SMILES (Isomeric): C1=CN(C=C(C1=O)O)CC(C(=O)O)N
• InChI: InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)
• InChI Key: WZNJWVWKTVETCG-UHFFFAOYSA-N
• Popularity: 332 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₀N₂O₄
• Molecular Weight: 198.18 g/mol
• Exact Mass: 198.06405680 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -1.03
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• RefChem:1076441
• alpha-Amino-3-hydroxy-4-oxo-1(4H)-pyridinepropanoic acid
• DL-Mimosine
• 2-amino-3-(3-hydroxy-4-oxopyridin-1(4H)-yl)propanoic acid
• 10182-82-8
• Mimosine, (+/-)-
• NSC159548
• 1(4H)-Pyridinealanine, 3-hydroxy-4-oxo-
• 2-amino-3-(3-hydroxy-4-oxo-1,4-dihydropyridin-1-yl)propanoic acid
• X9W047UL80
• NSC69188
• NSC-159548
• 1(4H)-Pyridinepropionic acid, .alpha.-amino-3-hydroxy-4-oxo-
• 2-AMINO-3-(3-HYDROXY-4-OXO-PYRIDIN-1-YL)PROPANOIC ACID
• 3-(3-Hydroxy-4-oxopyridin-1(4H)-yl)alanine
• .beta.-[N-(3-Hydroxy-4-pyridone)]-.alpha.-aminopropionic acid
• Prestwick_830
• (+/-)-mimosine
• Spectrum_000287
• starbld0038733
• MIMOSINE, DL-
• Prestwick0_000379
• Prestwick1_000379
• Prestwick2_000379
• Spectrum2_000656
• Spectrum3_000722
• Spectrum4_000110
• Spectrum5_001484
• SCHEMBL41924
• BSPBio_002244
• KBioGR_000440
• KBioSS_000767
• DivK1c_001000
• SPECTRUM1500869
• UNII-X9W047UL80
• SPBio_000691
• SPBio_002458
• MIMOSINE DL-FORM [MI]
• CHEMBL251433
• CHEBI:95190
• HMS503G21
• KBio1_001000
• KBio2_000767
• KBio2_003335
• KBio2_005903
• KBio3_001464
• DTXSID80950337
• WLN: T6N DVJ A1YZVQ CQ
• 1(4H)-Pyridinepropanoic acid, .alpha.-amino-3-hydroxy-4-oxo-, (.alpha.S)-
• NINDS_001000
• HMS1569K19
• HMS1921M08
• HMS3744K15
• Leucena glauca .alpha.-amino acid
• CCG-38561
• SBB000370
• STL564778
• 1(4H)-Pyridinepropanoic acid, (S)-
• AKOS006228368
• NSC 159548
• SDCCGMLS-0066728.P001
• IDI1_001000
• NCGC00094870-01
• NCGC00094870-02
• NCGC00094870-03
• NCGC00178740-01
• NCI60_032990
• ST056312
• DB-134434
• CS-0119397
• NS00043037
• 2-amino-3-(3-hydroxy-4-oxo-1-pyridyl)propanoic acid
• Q27166999
• 2-amino-3-(3-hydroxy-4-oxohydropyridyl)propanoic acid
• (2S)-2-amino-3-(3-hydroxy-4-oxohydropyridyl)propanoic acid
• 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-
• 1-L-alpha-Aminopropionil, 3-hydroxi, 4-oxopiridina [Spanish]
• 2-amino-3-(3-hydroxy-4-oxo-1H-pyridin-1-yl)-propanoic acid
• (S)-alpha-Amino-beta-[1-(3-hydroxy-4-oxopyridine)]propionic acid
• 1(4H)-Pyridinepropanoicacid, a-amino-3-hydroxy-4-oxo-, (aS)-
• 1(4H)-PYRIDINEPROPANOIC ACID, .ALPHA.-AMINO-3-HYDROXY-4-OXO-
• 1(4H)-Pyridinepropanoic acid, alpha-amino-3-hydroxy-4-oxo-, (+-)-
• propanoic acid, 2-amino-3-(1,4-dihydro-3-hydroxy-4-oxo-1-pyridyl)-
• 27678-82-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6313	63.13%
Caco-2	-	0.8804	88.04%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Nucleus	0.6048	60.48%
OATP2B1 inhibitior	-	0.8640	86.40%
OATP1B1 inhibitior	+	0.9693	96.93%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9634	96.34%
BSEP inhibitior	-	0.9167	91.67%
P-glycoprotein inhibitior	-	0.9946	99.46%
P-glycoprotein substrate	-	0.9445	94.45%
CYP3A4 substrate	-	0.7502	75.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8604	86.04%
CYP3A4 inhibition	-	0.9881	98.81%
CYP2C9 inhibition	-	0.9388	93.88%
CYP2C19 inhibition	-	0.9530	95.30%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9115	91.15%
CYP2C8 inhibition	-	0.9560	95.60%
CYP inhibitory promiscuity	-	0.9919	99.19%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.6493	64.93%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.7216	72.16%
Skin irritation	-	0.7310	73.10%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8790	87.90%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	+	0.6701	67.01%
skin sensitisation	-	0.8501	85.01%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8314	83.14%
Acute Oral Toxicity (c)	III	0.6543	65.43%
Estrogen receptor binding	-	0.9327	93.27%
Androgen receptor binding	-	0.7252	72.52%
Thyroid receptor binding	-	0.8657	86.57%
Glucocorticoid receptor binding	-	0.7345	73.45%
Aromatase binding	-	0.9128	91.28%
PPAR gamma	-	0.7415	74.15%
Honey bee toxicity	-	0.9763	97.63%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	-	0.7712	77.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.95%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.75%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.43%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.50%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.08%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.79%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.62%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.92%	97.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.97%	86.33%

Plants that contains it

• Leucaena leucocephala subsp. leucocephala

Cross-Links

• PubChem: 3862
• LOTUS: LTS0006549
• wikiData: Q27166999