(2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate

Details

• Internal ID: 8ff62f54-890b-472b-bbba-2068f6c9490e
• 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)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate
• SMILES (Canonical): C[NH2+]C(CC1=CNC2=CC=CC=C21)C(=O)[O-]
• SMILES (Isomeric): C[NH2+][C@@H](CC1=CNC2=CC=CC=C21)C(=O)[O-]
• InChI: InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1
• InChI Key: CZCIKBSVHDNIDH-NSHDSACASA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25 g/mol
• Exact Mass: 218.105527694 g/mol
• Topological Polar Surface Area (TPSA): 72.50 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.98
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEBI:57283
• N(alpha)-methyl-L-tryptophan zwitterion

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Lysosomes	0.5099	50.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5610	56.10%
P-glycoprotein inhibitior	-	0.9888	98.88%
P-glycoprotein substrate	-	0.8648	86.48%
CYP3A4 substrate	-	0.5260	52.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7882	78.82%
CYP3A4 inhibition	-	0.8803	88.03%
CYP2C9 inhibition	-	0.9382	93.82%
CYP2C19 inhibition	-	0.8666	86.66%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.7582	75.82%
CYP2C8 inhibition	-	0.7986	79.86%
CYP inhibitory promiscuity	-	0.8767	87.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8510	85.10%
Carcinogenicity (trinary)	Non-required	0.7049	70.49%
Eye corrosion	-	0.9942	99.42%
Eye irritation	-	0.7973	79.73%
Skin irritation	-	0.7939	79.39%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5683	56.83%
Micronuclear	+	0.7174	71.74%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9035	90.35%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7645	76.45%
Acute Oral Toxicity (c)	III	0.4340	43.40%
Estrogen receptor binding	-	0.6957	69.57%
Androgen receptor binding	-	0.7352	73.52%
Thyroid receptor binding	-	0.8539	85.39%
Glucocorticoid receptor binding	-	0.6620	66.20%
Aromatase binding	-	0.5878	58.78%
PPAR gamma	-	0.5692	56.92%
Honey bee toxicity	-	0.9204	92.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7349	73.49%
Fish aquatic toxicity	-	0.6302	63.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.19%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.41%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.90%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	91.10%	83.82%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.00%	88.56%
CHEMBL2535	P11166	Glucose transporter	85.84%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	83.23%	98.59%
CHEMBL3401	O75469	Pregnane X receptor	82.19%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.70%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.64%	83.10%

Plants that contains it

• Abrus precatorius

Cross-Links

• PubChem: 6921653
• NPASS: NPC248041
• ChEMBL: CHEMBL552941