(2R)-2-ammonio-3-hydroxypropanoate

Details

• Internal ID: e9394be0-3e58-4659-b79b-0e0cd6e67b3b
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Serine and derivatives
• IUPAC Name: (2R)-2-azaniumyl-3-hydroxypropanoate
• SMILES (Canonical): C(C(C(=O)[O-])[NH3+])O
• SMILES (Isomeric): C([C@H](C(=O)[O-])[NH3+])O
• InChI: InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
• InChI Key: MTCFGRXMJLQNBG-UWTATZPHSA-N
• Popularity: 109 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃H₇NO₃
• Molecular Weight: 105.09 g/mol
• Exact Mass: 105.042593085 g/mol
• Topological Polar Surface Area (TPSA): 88.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -3.66
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• (2R)-2-azaniumyl-3-hydroxypropanoate
• 2rcb
• D-serine zwitterion
• 2v3u
• CHEBI:35247

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9343	93.43%
Caco-2	-	0.9411	94.11%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5864	58.64%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.9681	96.81%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9272	92.72%
P-glycoprotein inhibitior	-	0.9871	98.71%
P-glycoprotein substrate	-	0.9841	98.41%
CYP3A4 substrate	-	0.7733	77.33%
CYP2C9 substrate	-	0.8085	80.85%
CYP2D6 substrate	-	0.8447	84.47%
CYP3A4 inhibition	-	0.9563	95.63%
CYP2C9 inhibition	-	0.9527	95.27%
CYP2C19 inhibition	-	0.9439	94.39%
CYP2D6 inhibition	-	0.9215	92.15%
CYP1A2 inhibition	-	0.8905	89.05%
CYP2C8 inhibition	-	0.9953	99.53%
CYP inhibitory promiscuity	-	0.9903	99.03%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6500	65.00%
Carcinogenicity (trinary)	Non-required	0.7425	74.25%
Eye corrosion	-	0.7737	77.37%
Eye irritation	+	0.7445	74.45%
Skin irritation	-	0.5578	55.78%
Skin corrosion	-	0.6675	66.75%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8509	85.09%
Micronuclear	+	0.5274	52.74%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9637	96.37%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	-	0.6000	60.00%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6167	61.67%
Estrogen receptor binding	-	0.9562	95.62%
Androgen receptor binding	-	0.8910	89.10%
Thyroid receptor binding	-	0.8897	88.97%
Glucocorticoid receptor binding	-	0.9282	92.82%
Aromatase binding	-	0.9033	90.33%
PPAR gamma	-	0.8563	85.63%
Honey bee toxicity	-	0.9022	90.22%
Biodegradation	+	0.8500	85.00%
Crustacea aquatic toxicity	-	0.9200	92.00%
Fish aquatic toxicity	-	0.9366	93.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.5 nM; 2.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.05%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.36%	96.09%
CHEMBL2581	P07339	Cathepsin D	81.30%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.14%	99.17%

Plants that contains it

• Allium sativum
• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Brassica juncea
• Ginkgo biloba
• Sinapis alba
• Vigna radiata

Cross-Links

• PubChem: 6857549
• NPASS: NPC226265
• ChEMBL: CHEMBL285123