3-Indolepropionic acid

Details

• Internal ID: 8628d58b-1f69-48bb-8278-49062c241a9d
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: 3-(1H-indol-3-yl)propanoic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
• InChI: InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
• InChI Key: GOLXRNDWAUTYKT-UHFFFAOYSA-N
• Popularity: 739 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21 g/mol
• Exact Mass: 189.078978594 g/mol
• Topological Polar Surface Area (TPSA): 53.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 1
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 830-96-6
• Indole-3-propionic acid
• 3-(1H-Indol-3-yl)propanoic acid
• 1H-Indole-3-propanoic acid
• Indolepropionic acid
• 3-(3-Indolyl)propionic acid
• 3-(3-Indolyl)propanoic acid
• Indolylpropionic Acid
• Oxigon
• IPA (auxin)
• 1H-INDOLE-3-PROPIONIC ACID
• 3-(Indol-3-yl)propionic acid
• 3-(3-Indole)propionic acid
• 3-(2-Carboxyethyl)-1H-indole
• 3-Indolepropionicacid
• beta-Indolylpropionate
• beta-(3-Indolyl)propionic acid
• MFCD00005660
• 3-(Indol-3-yl)propanoic acid
• indole-3-propanoic acid
• 3-(1H-Indol-3-yl)propionic acid
• NSC 3252
• NSC 47831
• 3-(1H-indol-3-yl)-propionic acid
• .beta.-Indolepropionic acid
• JF49U1Q7KN
• VP-20629
• .beta.-Indole-3-propionic acid
• CHEBI:43580
• .beta.-(3-Indolyl)propionic acid
• NSC-3252
• NSC-47831
• .beta.-Indolylpropionate
• 3-(1H-Indol-3-yl)propionate
• 1H-Indole-3-proponoic acid
• CCRIS 4424
• EINECS 212-600-1
• UNII-JF49U1Q7KN
• BRN 0147733
• AI3-17433
• b-Indolepropionate
• 4ejl
• 3-Indolepropionate
• Indole-3-propionic
• beta-Indolepropionate
• 3-indolpropionic acid
• b-Indolepropionic acid
• b-Indole-3-propionate
• 3-Indolepropenoic Acid
• Acid, 7
• VP 20629
• 3-Indole propionic acid
• 1H-Indole-3-propionate
• beta-Indolepropionic acid
• indole-3-proprionic acid
• b-(3-Indolyl)propionate
• beta-Indole-3-propionate
• Maybridge1_002431
• 3-(3-Indolyl)propanoate
• 3-(3-Indolyl)propionate
• b-Indole-3-propionic acid
• beta-(3-Indolyl)propionate
• Oprea1_071255
• b-(3-Indolyl)propionic acid
• beta-Indole-3-propionic acid
• Trihy(droxymethyl)aminomethane
• 5-22-03-00114 (Beilstein Handbook Reference)
• BIDD:GT0788
• DivK1c_001183
• SCHEMBL195405
• 3-(3-indolyl)-propionic acid
• CHEMBL207225
• GTPL4709
• SCHEMBL1767754
• SHP622
• DTXSID7061192
• BDBM31879
• HMS548G11
• NSC3252
• SHP-622
• HMS3604I20
• HMS3886E03
• BCP26573
• NSC47831
• s4809
• 3-(1H-Indol-3-yl)propanoic acid #
• AKOS000120911
• CCG-115418
• CS-W015945
• DB02758
• FS-3158
• HY-W015229
• SDCCGMLS-0065895.P001
• VP20629
• CDS1_000143
• NCGC00340705-01
• AC-10570
• BP-21044
• SY015400
• Indole-3-propionic acid, >=97.0% (T)
• Indole-3-propionic acid, >=99.0% (T)
• AM20060737
• FT-0627221
• I0032
• EN300-20789
• 3-Indolepropionic acid, ReagentPlus(R), 99%
• A15833
• C22236
• I-4000
• AB01333057-02
• J-650104
• Q21098993
• 3-Indolepropionic acid, Vetec(TM) reagent grade, 99%
• F0849-0388
• Z104482518
• 10265-77-7
• InChI=1/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7706	77.06%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5216	52.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9509	95.09%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7666	76.66%
P-glycoprotein inhibitior	-	0.9933	99.33%
P-glycoprotein substrate	-	0.9552	95.52%
CYP3A4 substrate	-	0.6009	60.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7907	79.07%
CYP3A4 inhibition	-	0.9402	94.02%
CYP2C9 inhibition	-	0.8397	83.97%
CYP2C19 inhibition	-	0.8916	89.16%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.7261	72.61%
CYP2C8 inhibition	-	0.8355	83.55%
CYP inhibitory promiscuity	-	0.9181	91.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6383	63.83%
Eye corrosion	-	0.9924	99.24%
Eye irritation	+	0.9628	96.28%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.8992	89.92%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6113	61.13%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.6177	61.77%
skin sensitisation	-	0.8699	86.99%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8995	89.95%
Acute Oral Toxicity (c)	III	0.6589	65.89%
Estrogen receptor binding	-	0.7718	77.18%
Androgen receptor binding	-	0.8923	89.23%
Thyroid receptor binding	-	0.8240	82.40%
Glucocorticoid receptor binding	-	0.5733	57.33%
Aromatase binding	-	0.6073	60.73%
PPAR gamma	+	0.6969	69.69%
Honey bee toxicity	-	0.9684	96.84%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	-	0.7497	74.97%

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	98.23%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.69%	94.62%
CHEMBL2581	P07339	Cathepsin D	94.75%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.22%	96.09%
CHEMBL1781	P11387	DNA topoisomerase I	85.87%	97.00%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	84.47%	90.71%
CHEMBL1255126	O15151	Protein Mdm4	82.31%	90.20%
CHEMBL221	P23219	Cyclooxygenase-1	80.55%	90.17%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.23%	88.56%

Plants that contains it

• Cucurbita pepo

Cross-Links

• PubChem: 3744
• LOTUS: LTS0057375
• wikiData: Q21098993