(2R)-2-hydroxy-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-1-enyl]cyclohex-3-en-1-one

Details

• Internal ID: 2f6fc4a5-187e-48a0-81ad-f083330f4ab9
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (2R)-2-hydroxy-3,5,5-trimethyl-4-[(E,3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-1-enyl]cyclohex-3-en-1-one
• SMILES (Canonical): CC1=C(C(CC(=O)C1O)(C)C)C=CC(C)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(CC(=O)[C@@H]1O)(C)C)/C=C/[C@@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• InChI: InChI=1S/C19H30O8/c1-9(26-18-17(25)16(24)15(23)13(8-20)27-18)5-6-11-10(2)14(22)12(21)7-19(11,3)4/h5-6,9,13-18,20,22-25H,7-8H2,1-4H3/b6-5+/t9-,13-,14-,15-,16+,17-,18-/m1/s1
• InChI Key: UGEWAWWHOAMOFI-PNEHDANUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₈
• Molecular Weight: 386.40 g/mol
• Exact Mass: 386.19406791 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5080	50.80%
Caco-2	-	0.7566	75.66%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8414	84.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8603	86.03%
OATP1B3 inhibitior	+	0.8949	89.49%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6237	62.37%
P-glycoprotein inhibitior	-	0.8161	81.61%
P-glycoprotein substrate	-	0.8707	87.07%
CYP3A4 substrate	+	0.6141	61.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.9065	90.65%
CYP2C9 inhibition	-	0.7380	73.80%
CYP2C19 inhibition	-	0.8087	80.87%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.8129	81.29%
CYP2C8 inhibition	-	0.8314	83.14%
CYP inhibitory promiscuity	-	0.7509	75.09%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6473	64.73%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9635	96.35%
Skin irritation	-	0.7989	79.89%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3704	37.04%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7723	77.23%
skin sensitisation	-	0.7758	77.58%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5367	53.67%
Acute Oral Toxicity (c)	III	0.7159	71.59%
Estrogen receptor binding	-	0.6349	63.49%
Androgen receptor binding	-	0.6566	65.66%
Thyroid receptor binding	+	0.5892	58.92%
Glucocorticoid receptor binding	-	0.6022	60.22%
Aromatase binding	-	0.4861	48.61%
PPAR gamma	-	0.6141	61.41%
Honey bee toxicity	-	0.7151	71.51%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.8263	82.63%

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	98.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.32%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	92.48%	94.75%
CHEMBL2581	P07339	Cathepsin D	90.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.39%	96.47%
CHEMBL3401	O75469	Pregnane X receptor	86.76%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.01%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.99%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.82%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.59%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.50%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.46%	89.34%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.36%	91.24%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.29%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.18%	86.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.38%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.91%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.89%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.41%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.32%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.17%	96.77%

Plants that contains it

• Amaranthus caudatus

Cross-Links

• PubChem: 162940810
• LOTUS: LTS0258222
• wikiData: Q105272294