2-Azetidinecarboxylic acid, (S)-

Details

• Internal ID: 29b7d256-c047-40e7-a6d8-0240448921e7
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (2S)-azetidine-2-carboxylic acid
• SMILES (Canonical): C1CNC1C(=O)O
• SMILES (Isomeric): C1CN[C@@H]1C(=O)O
• InChI: InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
• InChI Key: IADUEWIQBXOCDZ-VKHMYHEASA-N
• Popularity: 177 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.10 g/mol
• Exact Mass: 101.047678466 g/mol
• Topological Polar Surface Area (TPSA): 49.30 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -0.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• L-Azetidine-2-carboxylic acid
• (S)-Azetidine-2-carboxylic acid
• (2S)-azetidine-2-carboxylic acid
• (S)-(-)-2-Azetidinecarboxylic acid
• (S)-2-Azetidinecarboxylic acid
• Azetidyl-2-carboxylic acid
• 2-Azetidinecarboxylic acid, (S)-
• 2-Azetidinecarboxylic acid, (2S)-
• (S)-(-)-Azetidine-2-carboxylic acid
• L-Azetidine 2-carboxylic acid
• Azetidine-2-carboxylic acid, L-
• CHEBI:6198
• (L)-AZETIDINE-2-CARBOXYLIC ACID
• Azetidinecarboxylic acid
• 2-Azetidinecarboxylic acid, L-
• (S)-L-Azetidine-2-carboxylic acid
• MFCD00005166
• (S)-(-)-2-azetidine carboxylic acid
• 5GZ3E0L9ZU
• L-2-Azetidinecarboxylic acid
• Acide L-azetidine-2-carboxylic
• CHEMBL1165239
• L-azetidine-2-carboxylate
• azetidine-2-carboxylate
• HSDB 3465
• (2S)azetidine-2-carboxylic acid
• AzeOH
• 02A
• EINECS 218-362-5
• L-AzeOH
• L-Trimethyleneimine-2-carboxylic Acid
• (S)-(-) Azetidine-2-carboxylic acid
• Acide L-azetidine-2-carboxylic [French]
• ST059592
• H-Aze(2)-OH
• UNII-5GZ3E0L9ZU
• L-azetidine-2caboxylic acid
• (S)-Azetidin-2-carbonsaure
• L-azetidine-2carboxylic acid
• Lopac0_000023
• SCHEMBL20296
• (S)-2-azetidinecarboxyic acid
• GTPL4686
• (S)-Azetidine-2-carboxylicacid
• 2-(S)-azetidinecarboxylic acid
• azetidine-2(S)-carboxylic acid
• L--Azetidine-2-carboxylic acid
• DTXSID0044020
• (S)-2-azetidine carboxylic acid
• azetidine-2-(S)-carboxylic acid
• HMS3260E07
• Tox21_500023
• (-)-AZETIDINECARBOXYLIC ACID
• BDBM50357225
• AKOS005254687
• AKOS006239010
• (S)-(-)-2-azetidine-carboxylic acid
• AC-5699
• CCG-204119
• HY-W050044
• LP00023
• SDCCGSBI-0050012.P002
• L-Azetidine-2-carboxylic acid, >=99%
• NCGC00093546-01
• NCGC00093546-02
• NCGC00093546-03
• NCGC00093546-04
• NCGC00260708-01
• DS-16309
• (S)-2-Azetidinecarboxylic acid;H-Aze-OH
• AZETIDYL-2-CARBOXYLIC ACID [HSDB]
• A1043
• A4601
• AM20090185
• CS-0031389
• EU-0100023
• EN300-85821
• A 0760
• C08267
• Q793715
• SR-01000075656
• SR-01000075656-1
• W-107562
• azetidine-2-carboxylic acid;(S)-Azetidine-2-carboxylic acid
• L-Azetidine-2-carboxylic acid is known as a proline analog.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9724	97.24%
Caco-2	-	0.8690	86.90%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Lysosomes	0.5090	50.90%
OATP2B1 inhibitior	-	0.8343	83.43%
OATP1B1 inhibitior	+	0.9800	98.00%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9735	97.35%
P-glycoprotein inhibitior	-	0.9913	99.13%
P-glycoprotein substrate	-	0.9824	98.24%
CYP3A4 substrate	-	0.7385	73.85%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.7338	73.38%
CYP3A4 inhibition	-	0.9787	97.87%
CYP2C9 inhibition	-	0.9489	94.89%
CYP2C19 inhibition	-	0.9381	93.81%
CYP2D6 inhibition	-	0.9529	95.29%
CYP1A2 inhibition	-	0.9118	91.18%
CYP2C8 inhibition	-	0.9933	99.33%
CYP inhibitory promiscuity	-	1.0000	100.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6724	67.24%
Eye corrosion	-	0.9173	91.73%
Eye irritation	+	0.9511	95.11%
Skin irritation	-	0.6383	63.83%
Skin corrosion	-	0.5925	59.25%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8340	83.40%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.9099	90.99%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4503	45.03%
Acute Oral Toxicity (c)	III	0.5099	50.99%
Estrogen receptor binding	-	0.9369	93.69%
Androgen receptor binding	-	0.7998	79.98%
Thyroid receptor binding	-	0.9069	90.69%
Glucocorticoid receptor binding	-	0.9272	92.72%
Aromatase binding	-	0.8969	89.69%
PPAR gamma	-	0.8565	85.65%
Honey bee toxicity	-	0.9563	95.63%
Biodegradation	+	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	-	0.9819	98.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.43%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.92%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.77%	96.09%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	82.14%	98.24%

Plants that contains it

• Convallaria majalis
• Delonix regia
• Polygonatum multiflorum

Cross-Links

• PubChem: 16486
• LOTUS: LTS0201230
• wikiData: Q793715