L-cystathionine

Details

• Internal ID: 336769f0-bb48-4d69-9395-9670b3d0fae6
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Cysteine and derivatives > L-cysteine-S-conjugates
• IUPAC Name: (2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
• SMILES (Canonical): C(CSCC(C(=O)O)N)C(C(=O)O)N
• SMILES (Isomeric): C(CSC[C@@H](C(=O)O)N)[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
• InChI Key: ILRYLPWNYFXEMH-WHFBIAKZSA-N
• Popularity: 3,447 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₄N₂O₄S
• Molecular Weight: 222.26 g/mol
• Exact Mass: 222.06742811 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -6.00
• Atomic LogP (AlogP): -1.07
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 56-88-2
• cystathionine
• L-(+)-Cystathionine
• Cystathionine, L-
• (R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine
• L-Homocysteine, S-(2-amino-2-carboxyethyl)-, (R)-
• (2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid
• 375YFJ481O
• (2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid
• (2S)-2-amino-4-[(2R)-2-amino-2-carboxyethyl]sulfanylbutanoic acid
• L-Homocysteine, S-((2R)-2-amino-2-carboxyethyl)-
• Butanoic acid, 2-amino-4-((2-amino-2-carboxyethyl)thio)-, (R-(R*,S*))-
• L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]-
• UNII-375YFJ481O
• Butanoic acid, 2-amino-4-[(2-amino-2-carboxyethyl)thio]-, [R-(R*,S*)]-
• EINECS 200-295-8
• Cystathionine (6CI,7CI)
• Cystathionine, L- (8CI)
• S-[(2R)-2-amino-2-carboxyethyl]-L-Homocysteine
• SCHEMBL81862
• L-CYSTATHIONINE [MI]
• GTPL5173
• CHEBI:17482
• DTXSID20971384
• L-Cystathionine, >=98% (TLC)
• MFCD00036685
• AKOS030240717
• CS-W010465
• HY-W009749
• AS-56691
• S-(beta-amino-beta-carboxyethyl)homocysteine
• C02291
• E79085
• L-Cystathionine, technical, >=90.0% (TLC)
• Q28529685
• FD1436D6-F116-4693-B9DB-B8A83420BD09
• L-Homocysteine, S-[(2R)-2-amino-2-carboxyethyl]- (9CI)
• (S)-2-amino-4-((R)-2-amino-2-carboxyethylthio)butanoic acid
• [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoate
• [R-(R*,S*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-Butanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6155	61.55%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5346	53.46%
OATP2B1 inhibitior	-	0.8456	84.56%
OATP1B1 inhibitior	+	0.9594	95.94%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9381	93.81%
P-glycoprotein inhibitior	-	0.9669	96.69%
P-glycoprotein substrate	-	0.9654	96.54%
CYP3A4 substrate	-	0.7179	71.79%
CYP2C9 substrate	+	0.5929	59.29%
CYP2D6 substrate	-	0.7911	79.11%
CYP3A4 inhibition	-	0.8331	83.31%
CYP2C9 inhibition	-	0.9407	94.07%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9597	95.97%
CYP1A2 inhibition	-	0.7979	79.79%
CYP2C8 inhibition	-	0.9794	97.94%
CYP inhibitory promiscuity	-	0.9972	99.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5331	53.31%
Eye corrosion	-	0.9587	95.87%
Eye irritation	-	0.8929	89.29%
Skin irritation	-	0.7875	78.75%
Skin corrosion	-	0.7351	73.51%
Ames mutagenesis	-	0.6478	64.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6000	60.00%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9173	91.73%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7915	79.15%
Acute Oral Toxicity (c)	III	0.5900	59.00%
Estrogen receptor binding	-	0.8227	82.27%
Androgen receptor binding	-	0.6970	69.70%
Thyroid receptor binding	-	0.7854	78.54%
Glucocorticoid receptor binding	-	0.5513	55.13%
Aromatase binding	-	0.8743	87.43%
PPAR gamma	-	0.5314	53.14%
Honey bee toxicity	-	0.9450	94.50%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.8300	83.00%
Fish aquatic toxicity	-	0.6565	65.65%

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	95.31%	96.09%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	92.66%	92.29%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	89.99%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.61%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.05%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.17%	96.95%
CHEMBL236	P41143	Delta opioid receptor	81.58%	99.35%
CHEMBL2581	P07339	Cathepsin D	80.25%	98.95%

Plants that contains it

• Arabidopsis thaliana
• Astragalus pectinatus
• Ginkgo biloba
• Neptunia amplexicaulis

Cross-Links

• PubChem: 439258
• LOTUS: LTS0062382
• wikiData: Q28529685