Ismine

Details

• Internal ID: cd695432-a78b-4ab0-a922-8ac657ca421d
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids
• IUPAC Name: [6-[2-(methylamino)phenyl]-1,3-benzodioxol-5-yl]methanol
• SMILES (Canonical): CNC1=CC=CC=C1C2=CC3=C(C=C2CO)OCO3
• SMILES (Isomeric): CNC1=CC=CC=C1C2=CC3=C(C=C2CO)OCO3
• InChI: InChI=1S/C15H15NO3/c1-16-13-5-3-2-4-11(13)12-7-15-14(18-9-19-15)6-10(12)8-17/h2-7,16-17H,8-9H2,1H3
• InChI Key: GSEKYIWUAPZIEF-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₅NO₃
• Molecular Weight: 257.28 g/mol
• Exact Mass: 257.10519334 g/mol
• Topological Polar Surface Area (TPSA): 50.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.62
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 1805-78-3
• [6-[2-(methylamino)phenyl]-1,3-benzodioxol-5-yl]methanol
• C12181
• 6-[2-(Methylamino)phenyl]-1,3-benzodioxole-5-methanol
• (6-(2-(Methylamino)phenyl)benzo[d][1,3]dioxol-5-yl)methanol
• {6-[2-(methylamino)phenyl]-1,3-benzodioxol-5-yl}methanol
• 1,3-benzodioxole-5-methanol, 6-[2-(methylamino)phenyl]-
• CHEMBL4102889
• SCHEMBL17685681
• CHEBI:31723
• DTXSID90170968
• Q27114669
• InChI=1/C15H15NO3/c1-16-13-5-3-2-4-11(13)12-7-15-14(18-9-19-15)6-10(12)8-17/h2-7,16-17H,8-9H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9695	96.95%
Caco-2	+	0.8128	81.28%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5311	53.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8751	87.51%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6914	69.14%
P-glycoprotein inhibitior	-	0.8907	89.07%
P-glycoprotein substrate	-	0.8437	84.37%
CYP3A4 substrate	-	0.5601	56.01%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	+	0.3902	39.02%
CYP3A4 inhibition	+	0.5678	56.78%
CYP2C9 inhibition	+	0.5202	52.02%
CYP2C19 inhibition	+	0.8391	83.91%
CYP2D6 inhibition	+	0.6931	69.31%
CYP1A2 inhibition	+	0.7524	75.24%
CYP2C8 inhibition	-	0.7582	75.82%
CYP inhibitory promiscuity	+	0.9460	94.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.4864	48.64%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9231	92.31%
Skin irritation	-	0.7116	71.16%
Skin corrosion	-	0.9146	91.46%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4112	41.12%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6660	66.60%
Acute Oral Toxicity (c)	III	0.5993	59.93%
Estrogen receptor binding	+	0.9058	90.58%
Androgen receptor binding	+	0.6394	63.94%
Thyroid receptor binding	+	0.6679	66.79%
Glucocorticoid receptor binding	+	0.7763	77.63%
Aromatase binding	+	0.8827	88.27%
PPAR gamma	+	0.7363	73.63%
Honey bee toxicity	-	0.9136	91.36%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7962	79.62%

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	99.07%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.98%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.89%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.75%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.56%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.05%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.30%	94.80%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.87%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.42%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.72%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.81%	95.83%
CHEMBL4208	P20618	Proteasome component C5	80.65%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.19%	99.17%

Plants that contains it

• Crinum firmifolium
• Ferula persica
• Galanthus nivalis
• Hippeastrum elegans
• Hippeastrum vittatum
• Hymenocallis rotata
• Lapiedra martinezii
• Ligularia przewalskii
• Lycoris squamigera
• Narcissus cuneiflorus
• Sprekelia formosissima
• Stachys aegyptiaca

Cross-Links

• PubChem: 188957
• NPASS: NPC189121
• LOTUS: LTS0074802
• wikiData: Q27114669