L-Saccharopine

Details

• Internal ID: b906c2b0-fe34-49df-857a-393dd06e09ea
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Glutamic acid and derivatives
• IUPAC Name: (2S)-2-[[(5S)-5-amino-5-carboxypentyl]amino]pentanedioic acid
• SMILES (Canonical): C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N
• SMILES (Isomeric): C(CCN[C@@H](CCC(=O)O)C(=O)O)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1
• InChI Key: ZDGJAHTZVHVLOT-YUMQZZPRSA-N
• Popularity: 405 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₂₀N₂O₆
• Molecular Weight: 276.29 g/mol
• Exact Mass: 276.13213636 g/mol
• Topological Polar Surface Area (TPSA): 150.00 Ų
• XlogP: -5.50
• Atomic LogP (AlogP): -0.52
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• saccharopine
• 997-68-2
• accharopin
• epsilon-N-(L-glutar-2-yl)-L-lysine
• Saccharopin
• N6-(L-1,3-dicarboxypropyl)-L-lysine
• WBQ73O8W32
• N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID
• N-[(5S)-5-amino-5-carboxypentyl]-L-glutamic acid
• N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid
• ((S)-5-amino-5-carboxypentyl)-L-glutamic acid
• L-Glutamic acid, N-[(5S)-5-amino-5-carboxypentyl]-
• N-((5S)-5-AMINO-5-CARBOXYPENTYL)-L-GLUTAMIC ACID
• UNII-WBQ73O8W32
• L-GLUTAMIC ACID, N-((5S)-5-AMINO-5-CARBOXYPENTYL)-
• (2S)-2-[[(5S)-5-amino-5-carboxypentyl]amino]pentanedioic acid
• (2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
• L-Saccharopin
• SACCHAROPINE, L-
• N-(5-amino-5-carboxypentyl)-L-glutamic acid
• L-SACCHAROPINE [MI]
• SCHEMBL187831
• L-Glutamic acid, N-(5-amino-5-carboxypentyl)-, (S)-
• CHEBI:16927
• DTXSID80862507
• AKOS030623049
• CS-W021047
• DB04207
• HY-W040307
• N(6)-(L-1,3-dicarboxypropyl)-L-lysine
• N-(5-amino-5-carboxypentyl)-glutamic acid
• L-N-(5-amino-5-carboxypentyl)-Glutamic acid
• .EPSILON.-N-(L-GLUTAR-2-YL)-L-LYSINE
• C00449
• (S)-N-(5-amino-5-carboxypentyl)-L-Glutamic acid
• A937066
• Q3132238
• 2-[(5-Amino-5-carboxy-pentyl)amino]pentanedioic acid
• (S)-2-((S)-5-amino-5-carboxypentylamino)pentanedioic acid
• BE230516-20C4-4441-BF27-4117776E281D

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4678	46.78%
Caco-2	-	0.8444	84.44%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6413	64.13%
OATP2B1 inhibitior	-	0.8477	84.77%
OATP1B1 inhibitior	+	0.9511	95.11%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9448	94.48%
P-glycoprotein inhibitior	-	0.9557	95.57%
P-glycoprotein substrate	-	0.8533	85.33%
CYP3A4 substrate	-	0.6280	62.80%
CYP2C9 substrate	-	0.5957	59.57%
CYP2D6 substrate	-	0.7409	74.09%
CYP3A4 inhibition	-	0.9169	91.69%
CYP2C9 inhibition	-	0.9603	96.03%
CYP2C19 inhibition	-	0.9649	96.49%
CYP2D6 inhibition	-	0.9586	95.86%
CYP1A2 inhibition	-	0.9200	92.00%
CYP2C8 inhibition	-	0.9754	97.54%
CYP inhibitory promiscuity	-	0.9974	99.74%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.7215	72.15%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9396	93.96%
Skin irritation	-	0.8560	85.60%
Skin corrosion	-	0.8345	83.45%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6443	64.43%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.7573	75.73%
skin sensitisation	-	0.9450	94.50%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	-	0.7627	76.27%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8687	86.87%
Acute Oral Toxicity (c)	IV	0.5871	58.71%
Estrogen receptor binding	-	0.4899	48.99%
Androgen receptor binding	-	0.6395	63.95%
Thyroid receptor binding	-	0.5609	56.09%
Glucocorticoid receptor binding	+	0.6809	68.09%
Aromatase binding	-	0.7123	71.23%
PPAR gamma	+	0.6562	65.62%
Honey bee toxicity	-	0.9598	95.98%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.7891	78.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.29%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.53%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.06%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.62%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.09%	98.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.89%	92.29%
CHEMBL236	P41143	Delta opioid receptor	91.62%	99.35%
CHEMBL1255126	O15151	Protein Mdm4	88.56%	90.20%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.77%	100.00%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	87.48%	94.01%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.31%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.10%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.80%	90.71%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	84.48%	96.00%
CHEMBL2514	O95665	Neurotensin receptor 2	83.89%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.75%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.05%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.67%	93.56%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	82.05%	92.26%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.95%	97.29%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.27%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.96%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.70%	94.33%

Plants that contains it

• Arabidopsis thaliana
• Caylusea abyssinica
• Psophocarpus tetragonolobus
• Vigna radiata

Cross-Links

• PubChem: 160556
• LOTUS: LTS0243357
• wikiData: Q3132238