2-[(1S,2S)-3-oxo-2-[(Z)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid

Details

• Internal ID: 6512a455-fcbc-446a-82fc-396c320509c3
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: 2-[(1S,2S)-3-oxo-2-[(Z)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid
• SMILES (Canonical): C1CC(=O)C(C1CC(=O)O)CC=CCCOC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): C1CC(=O)[C@H]([C@@H]1CC(=O)O)C/C=C\CCOC2C(C(C(C(O2)CO)O)O)O
• InChI: InChI=1S/C18H28O9/c19-9-13-15(23)16(24)17(25)18(27-13)26-7-3-1-2-4-11-10(8-14(21)22)5-6-12(11)20/h1-2,10-11,13,15-19,23-25H,3-9H2,(H,21,22)/b2-1-/t10-,11-,13?,15?,16?,17?,18?/m0/s1
• InChI Key: JFDNMLUPLXZXGV-DKCJQCKPSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₈O₉
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.17333247 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.79
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• 124649-25-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8542	85.42%
Caco-2	-	0.8968	89.68%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8473	84.73%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8722	87.22%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9294	92.94%
P-glycoprotein inhibitior	-	0.8588	85.88%
P-glycoprotein substrate	-	0.8913	89.13%
CYP3A4 substrate	+	0.5739	57.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8768	87.68%
CYP3A4 inhibition	-	0.9431	94.31%
CYP2C9 inhibition	-	0.9370	93.70%
CYP2C19 inhibition	-	0.8778	87.78%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.9213	92.13%
CYP2C8 inhibition	-	0.7585	75.85%
CYP inhibitory promiscuity	-	0.9805	98.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7855	78.55%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9428	94.28%
Skin irritation	-	0.8286	82.86%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4092	40.92%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6694	66.94%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6053	60.53%
Acute Oral Toxicity (c)	III	0.5477	54.77%
Estrogen receptor binding	-	0.6130	61.30%
Androgen receptor binding	+	0.6259	62.59%
Thyroid receptor binding	-	0.7069	70.69%
Glucocorticoid receptor binding	-	0.6040	60.40%
Aromatase binding	-	0.6824	68.24%
PPAR gamma	-	0.5443	54.43%
Honey bee toxicity	-	0.8613	86.13%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	-	0.5000	50.00%

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	98.10%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.68%	99.17%
CHEMBL2581	P07339	Cathepsin D	90.88%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.17%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.14%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.08%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.52%	92.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.74%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.48%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.46%	89.00%
CHEMBL1881	P43116	Prostanoid EP2 receptor	80.06%	93.00%

Plants that contains it

• Phyllanthus emblica
• Solanum tuberosum

Cross-Links

• PubChem: 133554324
• LOTUS: LTS0139714
• wikiData: Q104375880