5-Methoxyindole-3-acetic acid

Details

• Internal ID: 5232604b-b60d-4f4a-a943-9ed5cce160e1
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives > Indole-3-acetic acid derivatives
• IUPAC Name: 2-(5-methoxy-1H-indol-3-yl)acetic acid
• SMILES (Canonical): COC1=CC2=C(C=C1)NC=C2CC(=O)O
• SMILES (Isomeric): COC1=CC2=C(C=C1)NC=C2CC(=O)O
• InChI: InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)
• InChI Key: COCNDHOPIHDTHK-UHFFFAOYSA-N
• Popularity: 137 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21 g/mol
• Exact Mass: 205.07389321 g/mol
• Topological Polar Surface Area (TPSA): 62.30 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 3471-31-6
• 2-(5-methoxy-1H-indol-3-yl)acetic acid
• 5-Methoxyindoleacetic acid
• 5-Methoxy-3-indoleacetic acid
• Methoxyindoleacetic acid
• 5-Methoxyindoleacetate
• 5-Methoxyindol-3-ylacetic acid
• 1H-Indole-3-acetic acid, 5-methoxy-
• (5-Methoxy-1H-indol-3-yl)acetic acid
• 5-Methoxyindole-3-aceticacid
• INDOLE-3-ACETIC ACID, 5-METHOXY-
• MSN7CK6ETH
• MFCD00005638
• 2-(5-Methoxy-3-indolyl)acetic Acid
• 142396-09-6
• (5-Methoxy-1H-indol-3-yl)-acetic acid
• 1H-Indole-3-aceticacid,5-methoxy-,radicalion(1+)(9CI)
• EINECS 222-438-3
• Methoxyindoleacetate
• (5-methoxy-3-indolyl)-acetic acid
• MYI
• 5-Methoxy-1H-indole-3-acetic acid
• UNII-MSN7CK6ETH
• 5-METHOXY-IAA
• 5-methoxy-indole acetate
• 5-Methoxyindole-3-acetate
• bmse000694
• 5-Methoxyindol-3-ylacetate
• Oprea1_126132
• MLS000515791
• CHEMBL85433
• SCHEMBL674415
• 5-Methoxy-3-indolylacetic acid
• 5-Methyloxyindole-3-acetic acid
• CHEBI:28281
• COCNDHOPIHDTHK-UHFFFAOYSA-
• DTXSID70188268
• (5-methoxy-3-indolyl)acetic acid
• (5-methoxyindol-3-yl)acetic acid
• HMS2267B20
• BCP27387
• Indole-3-acetic acid, 5- methoxy-
• (5-Methoxy-indol-3-yl)-acetic acid
• 2-(5-methoxyindole-3-yl)acetic acid
• 5-Methoxy-3-indoleacetic acid, 98%
• AKOS005207167
• CS-W007566
• FS-3050
• HY-W007566
• NCGC00247046-01
• AC-22684
• PD126571
• SMR000112265
• SY030412
• 2-(5-methoxy-1H-indol-3-yl)ethanoic acid
• A6095
• AM20060864
• FT-0620571
• M1303
• EN300-39512
• C05660
• M-3474
• Q6172526
• 5-Methoxy-3-indoleacetic acid, purum, >=99.0% (T)
• 50907E1A-6AC8-4D4D-8DE7-DD464A7A08C2
• Z385472506
• InChI=1/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.5829	58.29%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6971	69.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9359	93.59%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6306	63.06%
P-glycoprotein inhibitior	-	0.9851	98.51%
P-glycoprotein substrate	-	0.8469	84.69%
CYP3A4 substrate	-	0.5920	59.20%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.7479	74.79%
CYP3A4 inhibition	-	0.9426	94.26%
CYP2C9 inhibition	-	0.8940	89.40%
CYP2C19 inhibition	-	0.8894	88.94%
CYP2D6 inhibition	-	0.9375	93.75%
CYP1A2 inhibition	-	0.7346	73.46%
CYP2C8 inhibition	-	0.8261	82.61%
CYP inhibitory promiscuity	-	0.7330	73.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9023	90.23%
Carcinogenicity (trinary)	Non-required	0.5179	51.79%
Eye corrosion	-	0.9921	99.21%
Eye irritation	+	0.8931	89.31%
Skin irritation	-	0.8142	81.42%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7066	70.66%
Micronuclear	+	0.7433	74.33%
Hepatotoxicity	-	0.6560	65.60%
skin sensitisation	-	0.9043	90.43%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.8929	89.29%
Acute Oral Toxicity (c)	III	0.6223	62.23%
Estrogen receptor binding	-	0.7543	75.43%
Androgen receptor binding	-	0.8018	80.18%
Thyroid receptor binding	-	0.7820	78.20%
Glucocorticoid receptor binding	-	0.5053	50.53%
Aromatase binding	-	0.7540	75.40%
PPAR gamma	+	0.5832	58.32%
Honey bee toxicity	-	0.9540	95.40%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	-	0.6911	69.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.76%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.57%	98.95%
CHEMBL4208	P20618	Proteasome component C5	90.00%	90.00%
CHEMBL2535	P11166	Glucose transporter	87.67%	98.75%
CHEMBL2216739	Q92523	Carnitine O-palmitoyltransferase 1, muscle isoform	87.43%	88.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.38%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.24%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.21%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.13%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.99%	92.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.35%	91.71%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.06%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 18986
• LOTUS: LTS0267749
• wikiData: Q6172526