[6-(1-Methyl-1H-indol-7-yl)-2H-1,3-benzodioxol-5-yl]methanol

Details

• Internal ID: 569d1df9-6ccb-4fee-bb2b-ad5b64fef22d
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Galanthindole-type amaryllidaceae alkaloids
• IUPAC Name: [6-(1-methylindol-7-yl)-1,3-benzodioxol-5-yl]methanol
• SMILES (Canonical): CN1C=CC2=C1C(=CC=C2)C3=CC4=C(C=C3CO)OCO4
• SMILES (Isomeric): CN1C=CC2=C1C(=CC=C2)C3=CC4=C(C=C3CO)OCO4
• InChI: InChI=1S/C17H15NO3/c1-18-6-5-11-3-2-4-13(17(11)18)14-8-16-15(20-10-21-16)7-12(14)9-19/h2-8,19H,9-10H2,1H3
• InChI Key: YMAGZXPVILPRAP-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.30 g/mol
• Exact Mass: 281.10519334 g/mol
• Topological Polar Surface Area (TPSA): 43.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• [6-(1-Methyl-1H-indol-7-yl)-2H-1,3-benzodioxol-5-yl]methanol
• DTXSID90792260

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9716	97.16%
Caco-2	+	0.8647	86.47%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5836	58.36%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.9294	92.94%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7388	73.88%
P-glycoprotein inhibitior	-	0.8135	81.35%
P-glycoprotein substrate	-	0.8143	81.43%
CYP3A4 substrate	-	0.5282	52.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7797	77.97%
CYP3A4 inhibition	+	0.7231	72.31%
CYP2C9 inhibition	-	0.5966	59.66%
CYP2C19 inhibition	+	0.7917	79.17%
CYP2D6 inhibition	+	0.7036	70.36%
CYP1A2 inhibition	+	0.8690	86.90%
CYP2C8 inhibition	-	0.8411	84.11%
CYP inhibitory promiscuity	+	0.9257	92.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4073	40.73%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8264	82.64%
Skin irritation	-	0.7447	74.47%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4527	45.27%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8446	84.46%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4585	45.85%
Acute Oral Toxicity (c)	III	0.6082	60.82%
Estrogen receptor binding	+	0.8581	85.81%
Androgen receptor binding	+	0.7591	75.91%
Thyroid receptor binding	+	0.7372	73.72%
Glucocorticoid receptor binding	+	0.8251	82.51%
Aromatase binding	+	0.8073	80.73%
PPAR gamma	+	0.7872	78.72%
Honey bee toxicity	-	0.9539	95.39%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4261	42.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.90%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.06%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.32%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.63%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	87.54%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.60%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.56%	94.00%
CHEMBL4208	P20618	Proteasome component C5	82.82%	90.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.53%	95.83%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.56%	93.10%

Plants that contains it

• Galanthus plicatus
• Narcissus tazetta

Cross-Links

• PubChem: 71369229
• LOTUS: LTS0271900
• wikiData: Q82761041