(2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid

Details

• Internal ID: daaa1f9f-be8a-4987-8988-1fb5e451c776
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Tyrosine and derivatives
• IUPAC Name: 3-[[(2S)-1-[4-(3-aminopropylamino)butylamino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl]oxirane-2-carboxylic acid
• SMILES (Canonical): C1=CC(=CC=C1CC(C(=O)NCCCCNCCCN)NC(=O)C2C(O2)C(=O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@@H](C(=O)NCCCCNCCCN)NC(=O)C2C(O2)C(=O)O)O
• InChI: InChI=1S/C20H30N4O6/c21-8-3-10-22-9-1-2-11-23-18(26)15(12-13-4-6-14(25)7-5-13)24-19(27)16-17(30-16)20(28)29/h4-7,15-17,22,25H,1-3,8-12,21H2,(H,23,26)(H,24,27)(H,28,29)/t15-,16?,17?/m0/s1
• InChI Key: MQQOZPYNKMAOLT-GTPINHCMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀N₄O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.21653469 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 14

Synonyms

• CHEBI:66239
• (2R*,3R*)-3-{[(2S)-1-({4-[(3-aminopropyl)amino]butyl}amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamoyl}oxirane-2-carboxylic acid
• (2R*,3R*)-3-(((2S)-1-((4-((3-aminopropyl)amino)butyl)amino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamoyl)oxirane-2-carboxylic acid
• RefChem:190226
• TMC 52B
• Q27134781

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6235	62.35%
Caco-2	-	0.9021	90.21%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Nucleus	0.4681	46.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6832	68.32%
P-glycoprotein inhibitior	-	0.5227	52.27%
P-glycoprotein substrate	+	0.7552	75.52%
CYP3A4 substrate	+	0.5533	55.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7407	74.07%
CYP3A4 inhibition	-	0.8645	86.45%
CYP2C9 inhibition	-	0.9151	91.51%
CYP2C19 inhibition	-	0.8574	85.74%
CYP2D6 inhibition	-	0.9149	91.49%
CYP1A2 inhibition	-	0.7912	79.12%
CYP2C8 inhibition	+	0.4717	47.17%
CYP inhibitory promiscuity	-	0.9842	98.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6466	64.66%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9656	96.56%
Skin irritation	-	0.7425	74.25%
Skin corrosion	-	0.9303	93.03%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4080	40.80%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.7598	75.98%
skin sensitisation	-	0.8553	85.53%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8484	84.84%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8615	86.15%
Acute Oral Toxicity (c)	III	0.6184	61.84%
Estrogen receptor binding	+	0.5282	52.82%
Androgen receptor binding	+	0.7725	77.25%
Thyroid receptor binding	-	0.5309	53.09%
Glucocorticoid receptor binding	-	0.5301	53.01%
Aromatase binding	-	0.5164	51.64%
PPAR gamma	+	0.7660	76.60%
Honey bee toxicity	-	0.8767	87.67%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.6805	68.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.78%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.78%	91.11%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	96.42%	97.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.25%	99.17%
CHEMBL3891	P07384	Calpain 1	96.16%	93.04%
CHEMBL1255126	O15151	Protein Mdm4	96.06%	90.20%
CHEMBL3492	P49721	Proteasome Macropain subunit	94.48%	90.24%
CHEMBL2514	O95665	Neurotensin receptor 2	94.05%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.53%	96.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.15%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.82%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.75%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.59%	91.71%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.98%	89.67%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	89.59%	95.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.60%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	86.37%	91.19%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	86.25%	89.33%
CHEMBL5701	Q9H2K8	Serine/threonine-protein kinase TAO3	85.59%	96.67%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	85.48%	92.29%
CHEMBL4777	P25929	Neuropeptide Y receptor type 1	83.84%	96.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.81%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.93%	97.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.85%	90.71%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.55%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.14%	85.00%
CHEMBL3401	O75469	Pregnane X receptor	81.41%	94.73%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	80.45%	82.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.16%	97.29%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 70678751
• LOTUS: LTS0108843
• wikiData: Q27134781