Tryptamine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	09553a9a-854e-409a-b89a-cdfb3d258510
Taxonomy	Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives
IUPAC Name	2-(1H-indol-3-yl)ethanamine
SMILES (Canonical)	C1=CC=C2C(=C1)C(=CN2)CCN
SMILES (Isomeric)	C1=CC=C2C(=C1)C(=CN2)CCN
InChI	InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChI Key	APJYDQYYACXCRM-UHFFFAOYSA-N
Popularity	6,655 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₀H₁₂N₂
Molecular Weight	160.22 g/mol
Exact Mass	160.100048391 g/mol
Topological Polar Surface Area (TPSA)	41.80 Å²
XlogP	1.60
Atomic LogP (AlogP)	1.67
H-Bond Acceptor	1
H-Bond Donor	2
Rotatable Bonds	2

Synonyms

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61-54-1

2-(1H-Indol-3-yl)ethanamine

3-(2-aminoethyl)indole

1H-Indole-3-ethanamine

2-(3-Indolyl)ethylamine

Indol-3-ethylamine

Tryptamin

Indole, 3-(2-aminoethyl)-

2-(1H-Indol-3-Yl)Ethan-1-Amine

2-(Indol-3-yl)ethylamine

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.8781	87.81%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Lysosomes	0.5261	52.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.8857	88.57%
P-glycoprotein inhibitior	-	0.9928	99.28%
P-glycoprotein substrate	-	0.9003	90.03%
CYP3A4 substrate	-	0.6478	64.78%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.6306	63.06%
CYP3A4 inhibition	-	0.8346	83.46%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.5648	56.48%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7469	74.69%
CYP inhibitory promiscuity	-	0.6446	64.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6924	69.24%
Eye corrosion	-	0.9712	97.12%
Eye irritation	-	0.5889	58.89%
Skin irritation	-	0.6377	63.77%
Skin corrosion	-	0.6310	63.10%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4436	44.36%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7073	70.73%
skin sensitisation	-	0.8331	83.31%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8491	84.91%
Acute Oral Toxicity (c)	III	0.4823	48.23%
Estrogen receptor binding	-	0.7271	72.71%
Androgen receptor binding	-	0.8933	89.33%
Thyroid receptor binding	-	0.7178	71.78%
Glucocorticoid receptor binding	-	0.7359	73.59%
Aromatase binding	-	0.6256	62.56%
PPAR gamma	-	0.5911	59.11%
Honey bee toxicity	-	0.9386	93.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.8573	85.73%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL268	P43235	Cathepsin K	15000 nM	IC50	PMID: 11975521
CHEMBL3356	P05177	Cytochrome P450 1A2	3162.28 nM	AC50	via CMAUP
CHEMBL3542436	Q16696	Cytochrome P450 2A13	16000 nM	Ki	PMID: 22696418
CHEMBL5282	P11509	Cytochrome P450 2A6	1700 nM	Ki	PMID: 22696418
CHEMBL289	P10635	Cytochrome P450 2D6	31622.78 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM 39810.7 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2439	P05164	Myeloperoxidase	770 nM 770 nM	IC50 IC50	via Super-PRED PMID: 23581551
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	12589.3 nM 12589.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1898	P28222	Serotonin 1b (5-HT1b) receptor	36 nM	Ki	PMID: 8568822
CHEMBL1983	P28221	Serotonin 1d (5-HT1d) receptor	23 nM 61 nM	Ki Ki	PMID: 8568822 PMID: 8568822
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	7.36 nM 7.36 nM	EC50 EC50	via Super-PRED PMID: 25193229
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	50 nM	Ki	PMID: 3543362
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	70 nM 70 nM 180 nM	Ki Ki Ki	via Super-PRED DOI: 10.1007/s00044-004-0121-8 PMID: 10715164
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	158.49 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.55%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.01%	96.09%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.72%	88.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.71%	89.62%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.70%	94.62%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.95%	83.10%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.94%	95.48%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.95%	97.09%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	82.37%	82.86%
CHEMBL2996	Q05655	Protein kinase C delta	81.82%	97.79%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.02%	96.25%
CHEMBL2885	P07451	Carbonic anhydrase III	80.29%	87.45%
CHEMBL255	P29275	Adenosine A2b receptor	80.00%	98.59%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Dysoxylum lenticellatum

Hesperocyparis macrocarpa

Hordeum vulgare

Isocoma veneta

Kochia trichophylla