(3R)-3-hydroxy-L-aspartic acid

Details

• Internal ID: 832d1f90-8fa3-4de5-a0cb-73e73037e6a3
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Aspartic acid and derivatives
• IUPAC Name: (2S,3R)-2-amino-3-hydroxybutanedioic acid
• SMILES (Canonical): C(C(C(=O)O)O)(C(=O)O)N
• SMILES (Isomeric): [C@H]([C@H](C(=O)O)O)(C(=O)O)N
• InChI: InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2+/m0/s1
• InChI Key: YYLQUHNPNCGKJQ-NHYDCYSISA-N
• Popularity: 158 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₇NO₅
• Molecular Weight: 149.10 g/mol
• Exact Mass: 149.03242232 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: -4.40
• Atomic LogP (AlogP): -2.16
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 7298-98-8
• (2S,3R)-2-amino-3-hydroxybutanedioic acid
• erythro-beta-Hydroxyaspartic acid
• Erythro-beta-hydroxy-L-aspartic acid
• (2S,3R)-2-amino-3-hydroxysuccinic acid
• (3R)-3-Hydroxyaspartate
• 1186-90-9
• CHEBI:17576
• 6532-76-9
• erythro-3-Hydroxy-L-aspartic acid
• GDV0MSK2SG
• UNII-GDV0MSK2SG
• erythro-3-Hydroxy-DL-aspartic acid
• L-Aspartic acid, 3-hydroxy-, (3R)-
• beta-Hydroxyaspartic acid
• CHEMBL3317781
• erythro-3-Hydroxy-Ls-aspartic acid
• EINECS 229-431-4
• erythro-3-Hydroxy-L-aspartate
• Aspartic acid, L-threo-beta-hydroxy-
• beta-Hydroxy-L-aspartic acid, erythro-
• ASPARTIC ACID, 3-HYDROXY-, (erythro)-
• (2S,3R)-2-AMINO-3-HYDROXY-BUTANEDIOIC ACID
• erythro-3-hydroxy-Ls-aspartate
• C4-H7-N-O5
• NSC-158205
• (2S,3R)-2-Amino-3-hydroxysuccinicacid
• C4H7NO5
• (3R)-3-Hydroxyaspartic acid
• SCHEMBL336362
• (2s,3r)-3-hydroxyaspartic acid
• Erythro-b-hydroxy-l-aspartic acid
• YYLQUHNPNCGKJQ-NHYDCYSISA-N
• DTXSID201295781
• 3-HYDROXYASPARTATE, (3R)-
• BDBM50055467
• 3-HYDROXY ASPARTATE, (3R)-
• AKOS006274477
• DB03640
• NSC 119129
• NSC 158205
• Aspartic acid, 3-hydroxy-, DL-erythro-
• DL-Aspartic acid, 3-hydroxy-, erythro-
• LS-22114
• CS-0438358
• C03961
• ERYTHRO-.BETA.-HYDROXY-L-ASPARTIC ACID
• EN300-1721166
• .BETA.-HYDROXY-L-ASPARTIC ACID, ERYTHRO-
• Q27094559

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6232	62.32%
Caco-2	-	0.9889	98.89%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4398	43.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9799	97.99%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9799	97.99%
P-glycoprotein inhibitior	-	0.9810	98.10%
P-glycoprotein substrate	-	0.9927	99.27%
CYP3A4 substrate	-	0.7991	79.91%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.7769	77.69%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9886	98.86%
CYP inhibitory promiscuity	-	0.9946	99.46%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7276	72.76%
Carcinogenicity (trinary)	Non-required	0.7193	71.93%
Eye corrosion	-	0.9963	99.63%
Eye irritation	+	0.5928	59.28%
Skin irritation	-	0.7488	74.88%
Skin corrosion	-	0.9878	98.78%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8523	85.23%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6925	69.25%
skin sensitisation	-	0.9569	95.69%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6865	68.65%
Acute Oral Toxicity (c)	III	0.5597	55.97%
Estrogen receptor binding	-	0.8920	89.20%
Androgen receptor binding	-	0.8753	87.53%
Thyroid receptor binding	-	0.8011	80.11%
Glucocorticoid receptor binding	-	0.7771	77.71%
Aromatase binding	-	0.8709	87.09%
PPAR gamma	-	0.7747	77.47%
Honey bee toxicity	-	0.9336	93.36%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.9400	94.00%
Fish aquatic toxicity	-	0.9060	90.60%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	28.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	94.52%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.90%	96.09%

Plants that contains it

• Eucommia ulmoides

Cross-Links

• PubChem: 14463
• NPASS: NPC43169
• ChEMBL: CHEMBL3317781