(2S)-2-amino-5-hydroxy-5-oxopentanoate;hydron

Details

• Internal ID: 81776222-c105-48f3-9400-f757847cfa58
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Glutamic acid and derivatives
• IUPAC Name: (2S)-2-amino-5-hydroxy-5-oxopentanoate;hydron
• SMILES (Canonical): [H+].C(CC(=O)O)C(C(=O)[O-])N
• SMILES (Isomeric): [H+].C(CC(=O)O)[C@@H](C(=O)[O-])N
• InChI: InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
• InChI Key: WHUUTDBJXJRKMK-VKHMYHEASA-N
• Popularity: 195 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₉NO₄
• Molecular Weight: 147.13 g/mol
• Exact Mass: 147.05315777 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.96
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6947	69.47%
Caco-2	-	0.9559	95.59%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4336	43.36%
OATP2B1 inhibitior	-	0.8408	84.08%
OATP1B1 inhibitior	+	0.9588	95.88%
OATP1B3 inhibitior	+	0.9529	95.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9798	97.98%
P-glycoprotein inhibitior	-	0.9922	99.22%
P-glycoprotein substrate	-	0.9813	98.13%
CYP3A4 substrate	-	0.7413	74.13%
CYP2C9 substrate	-	0.6055	60.55%
CYP2D6 substrate	-	0.8246	82.46%
CYP3A4 inhibition	-	0.9594	95.94%
CYP2C9 inhibition	-	0.9718	97.18%
CYP2C19 inhibition	-	0.9706	97.06%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.9212	92.12%
CYP2C8 inhibition	-	0.9867	98.67%
CYP inhibitory promiscuity	-	0.9968	99.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.6814	68.14%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.6519	65.19%
Skin irritation	-	0.8444	84.44%
Skin corrosion	+	0.6494	64.94%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8297	82.97%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7449	74.49%
skin sensitisation	-	0.9692	96.92%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8170	81.70%
Acute Oral Toxicity (c)	III	0.5440	54.40%
Estrogen receptor binding	-	0.9521	95.21%
Androgen receptor binding	-	0.8831	88.31%
Thyroid receptor binding	-	0.9090	90.90%
Glucocorticoid receptor binding	-	0.7400	74.00%
Aromatase binding	-	0.9217	92.17%
PPAR gamma	-	0.8830	88.30%
Honey bee toxicity	-	0.9428	94.28%
Biodegradation	+	0.9500	95.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.9360	93.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	613 nM	IC50	PMID: 16250647
CHEMBL3356	P05177	Cytochrome P450 1A2	39810.72 nM	AC50	via CMAUP
CHEMBL2721	P43005	Excitatory amino acid transporter 3	51 nM	Ki	PMID: 18578477
CHEMBL1918	P39086	Glutamate receptor ionotropic kainate 1	701 nM; 701 nM	Ki; Ki	PMID: 10969973; PMID: 10821708
CHEMBL3683	Q13002	Glutamate receptor ionotropic kainate 2	1106 nM; 1106 nM	Ki; Ki	PMID: 10821708; PMID: 10969973
CHEMBL3684	Q13003	Glutamate receptor ionotropic kainate 3	789 nM; 789 nM	Ki; Ki	PMID: 10821708; PMID: 10969973
CHEMBL2675	Q16478	Glutamate receptor ionotropic kainate 5	750 nM; 750 nM	Ki; Ki	PMID: 10821708; PMID: 10969973
CHEMBL2009	P42261	Glutamate receptor ionotropic, AMPA 1	22000 nM; 2260 nM; 71000 nM	EC50; EC50; EC50	PMID: 20096591; PMID: 20096591; PMID: 17672447
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	940 nM; 940 nM; 940 nM	Ki; Ki; Ki	PMID: 10821708; PMID: 9357531; PMID: 10969973
CHEMBL3190	P48058	Glutamate receptor ionotropic, AMPA 4	868 nM; 868 nM; 868 nM	Ki; Ki; Ki	PMID: 10821708; PMID: 9357531; PMID: 10969973
CHEMBL3772	Q13255	Metabotropic glutamate receptor 1	570 nM; 1584.89 nM; 250 nM	Ki; Ki; Ki	PMID: 19042134; DOI: 10.1039/C1MD00186H; PMID: 17725337
CHEMBL5137	Q14416	Metabotropic glutamate receptor 2	4700 nM; 8500 nM; 290 nM; 7400 nM; 1800 nM; 2575 nM; 1827 nM; 2351 nM; 1767 nM	EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50; EC50	PMID: 7738999; PMID: 8759641; PMID: 9572889; PMID: 11720869; DOI: 10.1039/C1MD00186H; PMID: 26313429; PMID: 26313429; PMID: 26313429; PMID: 26313429
CHEMBL2888	Q14832	Metabotropic glutamate receptor 3	1002 nM; 2500 nM; 60 nM; 5118 nM; 1484 nM; 4182 nM	EC50; EC50; EC50; EC50; EC50; EC50	PMID: 26313429; PMID: 10397508; DOI: 10.1039/C1MD00186H; PMID: 26313429; PMID: 26313429; PMID: 26313429
CHEMBL2736	Q14833	Metabotropic glutamate receptor 4	3235.94 nM; 2400 nM; 1600 nM; 1400 nM	Ki; Ki; Ki; Ki	DOI: 10.1039/C1MD00186H; PMID: 17725337; PMID: 12109902; PMID: 19042134
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	4677.35 nM; 390 nM; 1160 nM	Ki; Ki; Ki	DOI: 10.1039/C1MD00186H; PMID: 17725337; PMID: 19042134
CHEMBL3228	O00222	Metabotropic glutamate receptor 8	5.7 nM	IC50	PMID: 15603952

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.72%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.54%	96.09%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	88.63%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.14%	99.17%
CHEMBL2581	P07339	Cathepsin D	86.42%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.78%	94.45%
CHEMBL1255126	O15151	Protein Mdm4	82.02%	90.20%
CHEMBL340	P08684	Cytochrome P450 3A4	81.37%	91.19%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	81.02%	92.26%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.75%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.53%	96.95%

Plants that contains it

• Achyranthes bidentata
• Acorus calamus var. angustatus
• Acorus gramineus
• Allium sativum
• Brassica juncea
• Cornus officinalis
• Ginkgo biloba
• Humulus scandens
• Santalum album
• Silybum marianum
• Sinapis alba
• Tussilago farfara
• Vigna radiata

Cross-Links

• PubChem: 88747398
• NPASS: NPC137958
• ChEMBL: CHEMBL575060