3-methyl-2-[(Z)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopent-2-en-1-one

Details

• Internal ID: 1b6d1a8c-5592-48cc-9d7b-8faa0bb36d3b
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: 3-methyl-2-[(Z)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopent-2-en-1-one
• SMILES (Canonical): CC1=C(C(=O)CC1)CC=CCCOC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)CC1)C/C=C\CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C17H26O7/c1-10-6-7-12(19)11(10)5-3-2-4-8-23-17-16(22)15(21)14(20)13(9-18)24-17/h2-3,13-18,20-22H,4-9H2,1H3/b3-2-/t13-,14-,15+,16-,17-/m1/s1
• InChI Key: GQQXMGOLSQFKPZ-ODWDTFMPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₇
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.16785316 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.18
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

• 2-[(Z)-5-(beta-D-Glucopyranosyloxy)-2-pentenyl]-3-methyl-2-cyclopentene-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5706	57.06%
Caco-2	-	0.7141	71.41%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8598	85.98%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.8632	86.32%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8615	86.15%
P-glycoprotein inhibitior	-	0.8713	87.13%
P-glycoprotein substrate	-	0.9306	93.06%
CYP3A4 substrate	+	0.5931	59.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.9626	96.26%
CYP2C9 inhibition	-	0.8991	89.91%
CYP2C19 inhibition	-	0.8143	81.43%
CYP2D6 inhibition	-	0.8994	89.94%
CYP1A2 inhibition	-	0.7951	79.51%
CYP2C8 inhibition	-	0.8661	86.61%
CYP inhibitory promiscuity	-	0.8911	89.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7470	74.70%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9589	95.89%
Skin irritation	-	0.7283	72.83%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4679	46.79%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.8876	88.76%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4564	45.64%
Acute Oral Toxicity (c)	III	0.5419	54.19%
Estrogen receptor binding	-	0.7109	71.09%
Androgen receptor binding	+	0.5264	52.64%
Thyroid receptor binding	-	0.5632	56.32%
Glucocorticoid receptor binding	-	0.6178	61.78%
Aromatase binding	-	0.6800	68.00%
PPAR gamma	-	0.5369	53.69%
Honey bee toxicity	-	0.8253	82.53%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8936	89.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.00%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.24%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.64%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.58%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.10%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.28%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.41%	90.08%

Plants that contains it

• Thymus vulgaris

Cross-Links

• PubChem: 11359817
• NPASS: NPC280367