Gramine

Details

• Internal ID: 13c2f869-b46d-44b6-81f4-01afaee922f4
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
• SMILES (Canonical): CN(C)CC1=CNC2=CC=CC=C21
• SMILES (Isomeric): CN(C)CC1=CNC2=CC=CC=C21
• InChI: InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
• InChI Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
• Popularity: 943 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24 g/mol
• Exact Mass: 174.115698455 g/mol
• Topological Polar Surface Area (TPSA): 19.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 87-52-5
• 3-(Dimethylaminomethyl)indole
• Donaxine
• Donaxin
• Gramin
• 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
• 1H-Indole-3-methanamine, N,N-dimethyl-
• beta-Dimethylaminomethylindole
• Indol-3-ylmethyldimethylamine
• NSC 16892
• (1H-Indol-3-ylmethyl)-dimethyl-amine
• (Indol-3-ylmethyl)dimethylamine
• 3-[(Dimethylamino)methyl]indole
• Donaxine;Gramine
• 3-(N,N-Dimethylaminomethyl)indole
• (1H-indol-3-ylmethyl)dimethylamine
• MFCD00005629
• N,N-Dimethyl-1H-indole-3-methanamine
• EINECS 201-749-8
• Indole, 3-[(dimethylamino)methyl]-
• UNII-FGQ8A78L14
• AI3-52146
• FGQ8A78L14
• .beta.-Dimethylaminomethylindole
• NSC-16892
• N,N-Dimethyl-1H-indole-3-methylamine
• INDOLE, 3-((DIMETHYLAMINO)METHYL)-
• 3-[Dimethylaminomethyl]indole
• 3-((Dimethylamino)methyl)-Indole
• 3-[(Dimethylamino)methyl]-Indole
• 3-((DIMETHYLAMINO)METHYL)INDOLE
• 1-(1H-indol-3-yl)-N,N-dimethyl-methanamine
• Prestwick_245
• Gramine, 99%
• Enamine_005691
• GRAMINE [MI]
• Prestwick0_000629
• Prestwick1_000629
• Prestwick2_000629
• Prestwick3_000629
• indol-3-ylmethyldimethylamin
• Oprea1_150946
• SCHEMBL63578
• b-(Dimethylaminomethyl)indole
• BSPBio_000598
• MLS002153919
• beta -dimethylaminomethylindole
• SCHEMBL445889
• SPBio_002817
• BPBio1_000658
• CHEMBL254348
• beta-(Dimethylaminomethyl)indole
• DTXSID3058955
• CHEBI:28948
• HMS1410C15
• HMS1569N20
• HMS2096N20
• HMS2268O03
• HMS3651E18
• 3-Dimethylaminomethylindol (gramin)
• HY-N0166
• NSC16892
• TNP00029
• WLN: T56 BMJ D1N1&1
• CCG-46378
• HB0305
• s2304
• STL146344
• (1H-Indol-3-ylmethyl)-dimethylamine
• [(1H-indol-3-yl)methyl]dimethylamine
• AKOS001055234
• 1H-Indol-3-yl-N,N-dimethylmethanamine
• CAS-87-52-5
• IDI1_007926
• NCGC00016343-01
• NCGC00016343-02
• NCGC00016343-03
• NCGC00016343-04
• NCGC00016343-05
• NCGC00142364-01
• NCGC00142364-02
• NCGC00142364-03
• (1H-indol-3-yl)-N,N-dimethylmethanamine
• .BETA.-(DIMETHYLAMINOMETHYL)INDOLE
• AC-15584
• AS-11847
• LS-82953
• SMR000112262
• SY005107
• 1H-Indol-3-yl-N,N-dimethylmethanamine #
• CS-0007885
• D0653
• FT-0603302
• N,N-Dimethyl-1H-indole-3-methanamine, 9CI
• N-(1H-indol-3-ylmethyl)-N,N-dimethylamine
• SW196552-2
• EN300-05999
• C08304
• A842252
• Q420118
• SR-01000636080
• SR-01000636080-1
• SR-01000636080-4
• BRD-K26005076-001-03-7
• BRD-K26005076-001-06-0
• Z56917380
• 3-Dimethylaminomethylindole;3-(DIMETHYLAMINOMETHYL)INDOLE
• 4,5,6,7-TETRAHYDRO-THIAZOLO[5,4-C]PYRIDINEHYDROCHLORIDESALT
• InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.8713	87.13%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5124	51.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8835	88.35%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.8628	86.28%
P-glycoprotein inhibitior	-	0.9905	99.05%
P-glycoprotein substrate	-	0.8945	89.45%
CYP3A4 substrate	+	0.5153	51.53%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.6725	67.25%
CYP3A4 inhibition	+	0.6799	67.99%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8651	86.51%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9610	96.10%
CYP inhibitory promiscuity	-	0.5747	57.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9797	97.97%
Eye irritation	+	0.7337	73.37%
Skin irritation	-	0.6635	66.35%
Skin corrosion	-	0.7865	78.65%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7172	71.72%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.5802	58.02%
skin sensitisation	-	0.8363	83.63%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7538	75.38%
Acute Oral Toxicity (c)	III	0.4562	45.62%
Estrogen receptor binding	-	0.7585	75.85%
Androgen receptor binding	-	0.8875	88.75%
Thyroid receptor binding	-	0.8336	83.36%
Glucocorticoid receptor binding	-	0.7534	75.34%
Aromatase binding	-	0.5108	51.08%
PPAR gamma	-	0.8893	88.93%
Honey bee toxicity	-	0.8823	88.23%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.7590	75.90%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	31622.8 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM; 158.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3162.3 nM; 3162.3 nM; 15848.9 nM; 15848.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.33%	93.99%
CHEMBL2581	P07339	Cathepsin D	94.00%	98.95%
CHEMBL228	P31645	Serotonin transporter	93.46%	95.51%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.32%	90.08%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	93.05%	90.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.92%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.26%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.16%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	87.65%	97.79%
CHEMBL1937	Q92769	Histone deacetylase 2	83.84%	94.75%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.44%	95.48%
CHEMBL255	P29275	Adenosine A2b receptor	82.13%	98.59%
CHEMBL3401	O75469	Pregnane X receptor	81.22%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.20%	92.62%

Plants that contains it

• Acer rubrum
• Acer saccharinum
• Arundo donax
• Desmanthus illinoensis
• Hordeum lechleri
• Hordeum vulgare
• Loropetalum chinense
• Lupinus arbustus
• Magnolia coco
• Murraya paniculata
• Ocimum basilicum
• Oryza sativa
• Phalaris aquatica
• Phalaris arundinacea
• Phyllodium pulchellum
• Pinus hartwegii
• Pseudopiptadenia contorta
• Smilax china
• Stenostomum lucidum
• Triticum aestivum

Cross-Links

• PubChem: 6890
• NPASS: NPC110126
• ChEMBL: CHEMBL254348
• LOTUS: LTS0099391
• wikiData: Q420118