s-Allylmercaptocysteine

Details

• Internal ID: f8811ec9-b228-4468-a7d3-81708dd4bf5a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Cysteine and derivatives > L-cysteine-S-conjugates
• IUPAC Name: (2R)-2-amino-3-(prop-2-enyldisulfanyl)propanoic acid
• SMILES (Canonical): C=CCSSCC(C(=O)O)N
• SMILES (Isomeric): C=CCSSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H11NO2S2/c1-2-3-10-11-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
• InChI Key: WYQZZUUUOXNSCS-YFKPBYRVSA-N
• Popularity: 188 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₁NO₂S₂
• Molecular Weight: 193.30 g/mol
• Exact Mass: 193.02312094 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 2281-22-3
• S-allylmercapto-L-cysteine
• (2R)-2-amino-3-(prop-2-en-1-yldisulfanyl)propanoic acid
• 3-(prop-2-en-1-yldisulfanyl)-L-alanine
• (R)-3-(Allyldisulfanyl)-2-aminopropanoic acid
• SCHEMBL1158206
• WYQZZUUUOXNSCS-YFKPBYRVSA-N
• DTXSID401311848
• MS-23044
• HY-145532
• CS-0375776
• EN300-1716070
• Q27458612
• (2R)-2-amino-3-(prop-2-enyldisulfanyl)propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.9227	92.27%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5357	53.57%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9494	94.94%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9044	90.44%
P-glycoprotein inhibitior	-	0.9793	97.93%
P-glycoprotein substrate	-	0.9842	98.42%
CYP3A4 substrate	-	0.7111	71.11%
CYP2C9 substrate	-	0.6007	60.07%
CYP2D6 substrate	-	0.8193	81.93%
CYP3A4 inhibition	-	0.6930	69.30%
CYP2C9 inhibition	-	0.8813	88.13%
CYP2C19 inhibition	-	0.8786	87.86%
CYP2D6 inhibition	-	0.9107	91.07%
CYP1A2 inhibition	-	0.8624	86.24%
CYP2C8 inhibition	-	0.9531	95.31%
CYP inhibitory promiscuity	-	0.9744	97.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5500	55.00%
Carcinogenicity (trinary)	Non-required	0.5540	55.40%
Eye corrosion	-	0.9394	93.94%
Eye irritation	-	0.8663	86.63%
Skin irritation	-	0.7085	70.85%
Skin corrosion	-	0.8721	87.21%
Ames mutagenesis	+	0.6722	67.22%
Human Ether-a-go-go-Related Gene inhibition	-	0.7109	71.09%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8674	86.74%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.6802	68.02%
Acute Oral Toxicity (c)	III	0.6895	68.95%
Estrogen receptor binding	-	0.8621	86.21%
Androgen receptor binding	-	0.8192	81.92%
Thyroid receptor binding	-	0.7413	74.13%
Glucocorticoid receptor binding	-	0.6937	69.37%
Aromatase binding	-	0.8858	88.58%
PPAR gamma	-	0.5971	59.71%
Honey bee toxicity	-	0.8381	83.81%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8600	86.00%
Fish aquatic toxicity	+	0.7618	76.18%

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	96.19%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.25%	96.09%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.24%	92.29%
CHEMBL221	P23219	Cyclooxygenase-1	87.27%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.77%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.18%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	81.20%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.19%	94.45%

Plants that contains it

• Allium sativum
• Aniba megaphylla
• Berberis integerrima
• Calocedrus decurrens
• Digitalis sceptrum
• Herbertus sakuraii
• Nauclea latifolia
• Orthopappus angustifolius
• Scurrula parasitica

Cross-Links

• PubChem: 9794159
• NPASS: NPC298509