5-Hydroxylysine

Details

• Internal ID: 3fd964c0-cb8a-45f1-bd98-abbf64f8f382
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid
• SMILES (Canonical): C(CC(C(=O)O)N)C(CN)O
• SMILES (Isomeric): C(C[C@@H](C(=O)O)N)[C@H](CN)O
• InChI: InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1
• InChI Key: YSMODUONRAFBET-UHNVWZDZSA-N
• Popularity: 2,268 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₄N₂O₃
• Molecular Weight: 162.19 g/mol
• Exact Mass: 162.10044231 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: -4.20
• Atomic LogP (AlogP): -1.50
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• HYDROXYLYSINE
• erythro-5-Hydroxy-L-lysine
• 1190-94-9
• (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid
• L-Hydroxylysine
• 5-hydroxy-L-lysine
• (2S,5R)-5-hydroxylysine
• (5R)-5-hydroxy-L-lysine
• delta-Hydroxylysine
• L-delta-Hydroxylysine
• L-normal-5-hydroxylysine
• L-Lysine, 5-hydroxy-, (5R)-
• L-erythro-5-hydroxylysine
• 2GQB349IUB
• CHEMBL457104
• CHEBI:18040
• alpha,epsilon-diamino-delta-hydroxycaproic acid
• d-Hydroxylysine
• 5R-Hydroxy-L-lysine
• delta-hydroxy-L-lysine
• (2S,5R)-2,6-diamino-5-hydroxyhexanoate
• Alpha,epsilon-diamino-delta-hydroxycaproate
• UNII-2GQB349IUB
• L-d-Hydroxylysine
• d-Hydroxy-L-lysine
• EINECS 214-726-2
• delta-dl-hydroxylysine
• 5-HYDROXY-LYSINE
• SCHEMBL48408
• .DELTA.-HYDROXYLYSINE
• HYDROXYLYSINE [WHO-DD]
• procollagen 5-hydroxy-L-lysine
• L-Lysine, 5-hydroxy-, erythro-
• YSMODUONRAFBET-UHNVWZDZSA-N
• DTXSID701317083
• BDBM50260535
• AKOS006272677
• procollagen L-erythro-5-hydroxy-L-lysine
• EN300-6496987
• Q419226
• LYZ

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8727	87.27%
Caco-2	-	0.9757	97.57%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6870	68.70%
OATP2B1 inhibitior	-	0.8404	84.04%
OATP1B1 inhibitior	+	0.9703	97.03%
OATP1B3 inhibitior	+	0.9526	95.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9729	97.29%
P-glycoprotein inhibitior	-	0.9906	99.06%
P-glycoprotein substrate	-	0.9679	96.79%
CYP3A4 substrate	-	0.7492	74.92%
CYP2C9 substrate	+	0.5872	58.72%
CYP2D6 substrate	-	0.7330	73.30%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.9689	96.89%
CYP2C19 inhibition	-	0.9586	95.86%
CYP2D6 inhibition	-	0.9524	95.24%
CYP1A2 inhibition	-	0.9241	92.41%
CYP2C8 inhibition	-	0.9873	98.73%
CYP inhibitory promiscuity	-	0.9872	98.72%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.6972	69.72%
Eye corrosion	-	0.9701	97.01%
Eye irritation	-	0.7968	79.68%
Skin irritation	-	0.7984	79.84%
Skin corrosion	-	0.6457	64.57%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8000	80.00%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9330	93.30%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.7263	72.63%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8592	85.92%
Acute Oral Toxicity (c)	IV	0.6077	60.77%
Estrogen receptor binding	-	0.8538	85.38%
Androgen receptor binding	-	0.8756	87.56%
Thyroid receptor binding	-	0.8315	83.15%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.9104	91.04%
PPAR gamma	-	0.8353	83.53%
Honey bee toxicity	-	0.9712	97.12%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	-	0.9694	96.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.25%	96.09%
CHEMBL233	P35372	Mu opioid receptor	90.11%	97.93%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	89.07%	92.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.47%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.15%	96.95%
CHEMBL236	P41143	Delta opioid receptor	84.91%	99.35%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.22%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.57%	97.29%
CHEMBL2581	P07339	Cathepsin D	80.96%	98.95%

Plants that contains it

• Medicago sativa

Cross-Links

• PubChem: 3032849
• LOTUS: LTS0237970
• wikiData: Q419226