5-Methoxygramine

Details

• Internal ID: 6f1e17a7-f891-42d7-88c1-dcce7ad0b9a5
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine
• SMILES (Canonical): CN(C)CC1=CNC2=C1C=C(C=C2)OC
• SMILES (Isomeric): CN(C)CC1=CNC2=C1C=C(C=C2)OC
• InChI: InChI=1S/C12H16N2O/c1-14(2)8-9-7-13-12-5-4-10(15-3)6-11(9)12/h4-7,13H,8H2,1-3H3
• InChI Key: GOERTRUXQHDLHC-UHFFFAOYSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.27 g/mol
• Exact Mass: 204.126263138 g/mol
• Topological Polar Surface Area (TPSA): 28.30 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.24
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 16620-52-3
• Methoxygramine
• 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine
• 1H-Indole-3-methanamine, 5-methoxy-N,N-dimethyl-
• 3-(Dimethylaminomethyl)-5-methoxyindole
• INDOLE, 3-((DIMETHYLAMINO)METHYL)-5-METHOXY-
• J6ZN008RY8
• N-[(5-Methoxy-1H-indol-3-yl)methyl]-N,N-dimethylamine
• [(5-methoxy-1H-indol-3-yl)methyl]dimethylamine
• NSC-88885
• Indole, 3-[(dimethylamino)methyl]-5-methoxy-
• 3-Dimethylaminomethyl-5-methoxyindole
• 1-(5-Methoxy-1h-Indol-3-Yl)-N,N-Dimethyl-Methanamine
• 3-((Dimethylamino)methyl)-5-methoxyindole
• 3-[(Dimethylamino)methyl]-5-methoxyindole
• 5-Methoxy-3-((dimethylamino)methyl)indole
• 5-Methoxy-3-[(dimethylamino)methyl]indole
• EINECS 240-669-8
• NSC 88885
• 2-Dimethylaminomethyl-5-methoxyindole
• 5-Methoxy-3-(dimethylaminomethyl)indole
• BRN 0170533
• 5-methoxy gramine
• 7ZC
• 5-Methoxygramine, 99%
• UNII-J6ZN008RY8
• Oprea1_614357
• 5-22-12-00008 (Beilstein Handbook Reference)
• SCHEMBL1196012
• CHEMBL3769622
• DTXSID30168081
• HMS1661A01
• AMY25941
• NSC88885
• MFCD00005630
• AKOS005202959
• CCG-235466
• SDCCGMLS-0065813.P001
• WLN: T56 BMJ D1N1&1 GO1
• AS-76881
• CS-0214833
• FT-0620567
• E83698
• EN300-197563
• M-3400
• SR-01000003310
• SR-01000003310-1
• (5-Methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine #
• 5-METHOXY-N,N-DIMETHYL-1H-INDOLE-3-METHANAMINE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	+	0.7511	75.11%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6988	69.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9010	90.10%
OATP1B3 inhibitior	+	0.9429	94.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6652	66.52%
P-glycoprotein inhibitior	-	0.9779	97.79%
P-glycoprotein substrate	-	0.6175	61.75%
CYP3A4 substrate	+	0.5201	52.01%
CYP2C9 substrate	+	0.5862	58.62%
CYP2D6 substrate	+	0.7106	71.06%
CYP3A4 inhibition	-	0.5362	53.62%
CYP2C9 inhibition	-	0.7405	74.05%
CYP2C19 inhibition	-	0.8160	81.60%
CYP2D6 inhibition	+	0.7715	77.15%
CYP1A2 inhibition	+	0.8201	82.01%
CYP2C8 inhibition	-	0.9261	92.61%
CYP inhibitory promiscuity	+	0.7155	71.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5718	57.18%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.5277	52.77%
Skin irritation	-	0.7613	76.13%
Skin corrosion	-	0.8553	85.53%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6837	68.37%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.7350	73.50%
skin sensitisation	-	0.8726	87.26%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8333	83.33%
Acute Oral Toxicity (c)	II	0.4446	44.46%
Estrogen receptor binding	-	0.7278	72.78%
Androgen receptor binding	-	0.7811	78.11%
Thyroid receptor binding	-	0.7158	71.58%
Glucocorticoid receptor binding	-	0.6263	62.63%
Aromatase binding	-	0.5546	55.46%
PPAR gamma	-	0.7732	77.32%
Honey bee toxicity	-	0.8545	85.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.6495	64.95%

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%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.73%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.59%	96.09%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	91.18%	90.71%
CHEMBL228	P31645	Serotonin transporter	90.14%	95.51%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.14%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.05%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	87.70%	98.59%
CHEMBL4208	P20618	Proteasome component C5	87.46%	90.00%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	86.42%	95.48%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.11%	85.49%
CHEMBL1907	P15144	Aminopeptidase N	84.48%	93.31%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	84.45%	96.11%
CHEMBL2535	P11166	Glucose transporter	83.77%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.26%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.16%	90.24%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	80.95%	82.86%

Plants that contains it

• Phalaris aquatica

Cross-Links

• PubChem: 27965
• LOTUS: LTS0138927
• wikiData: Q72489934