6-Prenylindole

Details

• Internal ID: b9301bc3-41e9-495a-8a68-fb082d25a75a
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles
• IUPAC Name: 6-(3-methylbut-2-enyl)-1H-indole
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1)C=CN2)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1)C=CN2)C
• InChI: InChI=1S/C13H15N/c1-10(2)3-4-11-5-6-12-7-8-14-13(12)9-11/h3,5-9,14H,4H2,1-2H3
• InChI Key: TWLHPMIWLQNHPM-UHFFFAOYSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.26 g/mol
• Exact Mass: 185.120449483 g/mol
• Topological Polar Surface Area (TPSA): 15.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 0
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 6-Prenyl-1H-indole
• 23158-16-9
• 6-(3-methylbut-2-enyl)-1H-indole
• SCHEMBL11574440
• AKOS040754653
• BS-1337
• PD069373

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5462	54.62%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.6073	60.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9348	93.48%
OATP1B3 inhibitior	+	0.9520	95.20%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5511	55.11%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	-	0.7484	74.84%
CYP3A4 substrate	-	0.6634	66.34%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	+	0.3835	38.35%
CYP3A4 inhibition	-	0.7161	71.61%
CYP2C9 inhibition	+	0.5328	53.28%
CYP2C19 inhibition	+	0.6811	68.11%
CYP2D6 inhibition	+	0.6023	60.23%
CYP1A2 inhibition	+	0.8278	82.78%
CYP2C8 inhibition	-	0.8596	85.96%
CYP inhibitory promiscuity	+	0.8080	80.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.5854	58.54%
Eye corrosion	-	0.9647	96.47%
Eye irritation	+	0.9261	92.61%
Skin irritation	-	0.5390	53.90%
Skin corrosion	-	0.8077	80.77%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6751	67.51%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5410	54.10%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8863	88.63%
Acute Oral Toxicity (c)	III	0.7096	70.96%
Estrogen receptor binding	+	0.5315	53.15%
Androgen receptor binding	-	0.6864	68.64%
Thyroid receptor binding	-	0.6299	62.99%
Glucocorticoid receptor binding	-	0.5438	54.38%
Aromatase binding	+	0.7471	74.71%
PPAR gamma	-	0.5627	56.27%
Honey bee toxicity	-	0.9465	94.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9639	96.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.75%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.04%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.46%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	90.47%	90.24%
CHEMBL4208	P20618	Proteasome component C5	85.45%	90.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.42%	83.10%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	85.24%	85.49%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.24%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	80.50%	94.73%

Plants that contains it

• Monodora tenuifolia
• Riccardia multifida

Cross-Links

• PubChem: 11229197
• LOTUS: LTS0004695
• wikiData: Q104386192