Allicin

Details

• Internal ID: eb45888c-7158-47c7-9079-0a7ee743c0f2
• Taxonomy: Organic acids and derivatives > Thiosulfinic acid esters
• IUPAC Name: 3-prop-2-enylsulfinylsulfanylprop-1-ene
• SMILES (Canonical): C=CCSS(=O)CC=C
• SMILES (Isomeric): C=CCSS(=O)CC=C
• InChI: InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
• InChI Key: JDLKFOPOAOFWQN-UHFFFAOYSA-N
• Popularity: 2,214 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₀OS₂
• Molecular Weight: 162.30 g/mol
• Exact Mass: 162.01730729 g/mol
• Topological Polar Surface Area (TPSA): 61.60 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 539-86-6
• Diallyl thiosulfinate
• S-allyl prop-2-ene-1-sulfinothioate
• Diallyldisulfid-S-oxid
• Thio-2-propene-1-sulfinic acid S-allyl ester
• Allylthiosulphinic acid allyl ester
• DADSO
• S-Allyl acrylo-1-sulphinothioate
• 2-Propene-1-sulfinothioic acid, S-2-propenyl ester
• diallyl disulfide-oxide
• C6H10OS2
• CCRIS 9053
• S-allyl 2-propene-1-sulfinothioate
• EINECS 208-727-7
• UNII-3C39BY17Y6
• BRN 1752823
• 3-prop-2-enylsulfinylsulfanylprop-1-ene
• 2-Propene-1-sulfinothioic acid S-2-propenyl ester
• CHEBI:28411
• 3C39BY17Y6
• 2-Propene-1-sulfinic acid, thio-, S-allyl ester
• CHEMBL359965
• DTXSID6043707
• 3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
• 4-04-00-00007 (Beilstein Handbook Reference)
• S-prop-2-en-1-yl prop-2-ene-1-sulfinothioate
• S-2-PROPEN-1-YL 2-PROPENE-1-SULFINOTHIOATE
• allimin
• allylthiosulfinate
• Allicin kit
• 3-allylsulfinylsulfanylprop-1-ene
• ALLTRIDE
• Allicin, tech. grade
• Diallyldisulfid-S-oxide
• Allicin (not validated)
• Dianyctrsnlgide;Allisatin
• ALLICIN [MI]
• ALLICIN [WHO-DD]
• D0X9YD
• ALLICIN(TECH GRADE)
• SCHEMBL2920
• Allicin (Allyl-S(O)S-Allyl)
• GTPL2419
• 2-Propene-1-sulfinothioic Acid S-2-Propen-1-yl Ester
• DTXCID4023707
• JDLKFOPOAOFWQN-UHFFFAOYSA-N
• 3-allylsulfinylsulfanyl-prop-1-ene
• BCP08391
• HY-N0315
• BDBM50240948
• MFCD00468100
• NSC707388
• s3860
• 4,5-Dithia-1,7-octadiene 4-oxide
• AKOS006282482
• ALLICIN (CONSTITUENT OF GARLIC)
• CCG-266298
• DB11780
• FD10435
• NSC-707388
• 3-(prop-2-enylsulfinylthio)-1-propene
• AC-34150
• XA162045
• XA176305
• LS-123525
• CS-0008813
• FT-0621982
• ALLICIN (CONSTITUENT OF GARLIC) [DSC]
• C07600
• EN300-217463
• S-2-Propenyl 2-propene-1-sulfinothioate, 9CI
• A829889
• Q409641
• Q-200609
• 2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9CI)
• Diallyl thiosulfinate and Allylthiosulphinic acid allyl ester
• Diallyldisulfid-S-oxid, 3-prop-2-enylsulfinylsulfanylprop-1-ene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9573	95.73%
Caco-2	+	0.5861	58.61%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Lysosomes	0.3646	36.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9604	96.04%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9473	94.73%
P-glycoprotein inhibitior	-	0.9831	98.31%
P-glycoprotein substrate	-	0.9847	98.47%
CYP3A4 substrate	-	0.6513	65.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8022	80.22%
CYP3A4 inhibition	-	0.9277	92.77%
CYP2C9 inhibition	-	0.6919	69.19%
CYP2C19 inhibition	-	0.6455	64.55%
CYP2D6 inhibition	-	0.8802	88.02%
CYP1A2 inhibition	-	0.6793	67.93%
CYP2C8 inhibition	-	0.9176	91.76%
CYP inhibitory promiscuity	-	0.5988	59.88%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.6410	64.10%
Carcinogenicity (trinary)	Non-required	0.5621	56.21%
Eye corrosion	+	0.6290	62.90%
Eye irritation	+	0.9468	94.68%
Skin irritation	-	0.5469	54.69%
Skin corrosion	+	0.5432	54.32%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7482	74.82%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.5884	58.84%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	-	0.8667	86.67%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.7620	76.20%
Acute Oral Toxicity (c)	III	0.4334	43.34%
Estrogen receptor binding	-	0.9015	90.15%
Androgen receptor binding	-	0.8536	85.36%
Thyroid receptor binding	-	0.6776	67.76%
Glucocorticoid receptor binding	-	0.8037	80.37%
Aromatase binding	-	0.7545	75.45%
PPAR gamma	-	0.7802	78.02%
Honey bee toxicity	+	0.5621	56.21%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9166	91.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4072	P07858	Cathepsin B	8600 nM	Ki	PMID: 20692829
CHEMBL3837	P07711	Cathepsin L	9300 nM	Ki	PMID: 20692829
CHEMBL2916	O14746	Telomerase reverse transcriptase	500 nM	IC50	DOI: 10.1039/C0MD00241K
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	1910 nM	EC50	PMID: 20356305

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.08%	89.34%

Plants that contains it

• Allium cepa
• Allium chinense
• Allium fistulosum
• Allium macrostemon
• Allium sativum
• Allium ursinum

Cross-Links

• PubChem: 65036
• NPASS: NPC2088
• ChEMBL: CHEMBL359965
• LOTUS: LTS0248420
• wikiData: Q409641