2-azaniumyl-3-(1H-indol-3-yl)propanoate

Details

• Internal ID: ba27823d-0ae2-4442-83e1-091539935031
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: 2-azaniumyl-3-(1H-indol-3-yl)propanoate
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CC(C(=O)[O-])[NH3+]
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)CC(C(=O)[O-])[NH3+]
• InChI: InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)
• InChI Key: QIVBCDIJIAJPQS-UHFFFAOYSA-N
• Popularity: 34 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22 g/mol
• Exact Mass: 204.089877630 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.93
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• D-Tryptophan, 20
• (2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate
• L-Tryptophan, 5
• tryptophan zwitterion
• SCHEMBL23141136
• BDBM92685
• CHEBI:64554
• 2-ammonio-3-(1H-indol-3-yl)propanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	-	0.5406	54.06%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4372	43.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9519	95.19%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6827	68.27%
P-glycoprotein inhibitior	-	0.9918	99.18%
P-glycoprotein substrate	-	0.8994	89.94%
CYP3A4 substrate	-	0.5504	55.04%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.7979	79.79%
CYP3A4 inhibition	-	0.8843	88.43%
CYP2C9 inhibition	-	0.8997	89.97%
CYP2C19 inhibition	-	0.8805	88.05%
CYP2D6 inhibition	-	0.8289	82.89%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	-	0.8582	85.82%
CYP inhibitory promiscuity	-	0.7015	70.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.7516	75.16%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8988	89.88%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7086	70.86%
Micronuclear	+	0.7374	73.74%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9101	91.01%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7774	77.74%
Acute Oral Toxicity (c)	III	0.4560	45.60%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.7630	76.30%
Thyroid receptor binding	-	0.7898	78.98%
Glucocorticoid receptor binding	-	0.5889	58.89%
Aromatase binding	-	0.6975	69.75%
PPAR gamma	-	0.4871	48.71%
Honey bee toxicity	-	0.8948	89.48%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7049	70.49%
Fish aquatic toxicity	-	0.5545	55.45%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	7943.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.69%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.04%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.04%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.31%	98.95%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.39%	88.56%
CHEMBL2535	P11166	Glucose transporter	88.19%	98.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.86%	83.10%
CHEMBL255	P29275	Adenosine A2b receptor	84.98%	98.59%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.47%	94.62%
CHEMBL1255126	O15151	Protein Mdm4	83.17%	90.20%
CHEMBL4040	P28482	MAP kinase ERK2	80.93%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.31%	89.00%

Plants that contains it

• Glehnia littoralis

Cross-Links

• PubChem: 4099458
• NPASS: NPC110500
• ChEMBL: CHEMBL484901