(3R)-12-[(2R,5R,6S)-5-hydroxy-6-methylpiperidin-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydodecanoic acid

Details

• Internal ID: 168262c3-d0e2-4b05-ac20-fb8670eb6a5c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Rhamnolipids
• IUPAC Name: (3R)-12-[(2R,5R,6S)-5-hydroxy-6-methylpiperidin-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydodecanoic acid
• SMILES (Canonical): CC1C(CCC(N1)CCCCCCCCCC(CC(=O)O)OC2C(C(C(C(O2)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H](CC[C@H](N1)CCCCCCCCC[C@H](CC(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• InChI: InChI=1S/C24H45NO9/c1-15-18(27)12-11-16(25-15)9-7-5-3-2-4-6-8-10-17(13-20(28)29)33-24-23(32)22(31)21(30)19(14-26)34-24/h15-19,21-27,30-32H,2-14H2,1H3,(H,28,29)/t15-,16+,17+,18+,19+,21+,22-,23+,24+/m0/s1
• InChI Key: TYCHJCWFXCTGEJ-JVDSRXGHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₅NO₉
• Molecular Weight: 491.60 g/mol
• Exact Mass: 491.30943201 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7541	75.41%
Caco-2	-	0.8603	86.03%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6428	64.28%
OATP2B1 inhibitior	-	0.5652	56.52%
OATP1B1 inhibitior	+	0.8885	88.85%
OATP1B3 inhibitior	+	0.9250	92.50%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8863	88.63%
P-glycoprotein inhibitior	-	0.5888	58.88%
P-glycoprotein substrate	-	0.6069	60.69%
CYP3A4 substrate	+	0.6477	64.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8384	83.84%
CYP3A4 inhibition	-	0.9370	93.70%
CYP2C9 inhibition	-	0.9436	94.36%
CYP2C19 inhibition	-	0.9369	93.69%
CYP2D6 inhibition	-	0.8576	85.76%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	-	0.7162	71.62%
CYP inhibitory promiscuity	-	0.9591	95.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7324	73.24%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.7739	77.39%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7901	79.01%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.7620	76.20%
skin sensitisation	-	0.8869	88.69%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6809	68.09%
Acute Oral Toxicity (c)	III	0.6059	60.59%
Estrogen receptor binding	+	0.5692	56.92%
Androgen receptor binding	-	0.5775	57.75%
Thyroid receptor binding	-	0.6300	63.00%
Glucocorticoid receptor binding	-	0.6166	61.66%
Aromatase binding	+	0.6450	64.50%
PPAR gamma	+	0.5360	53.60%
Honey bee toxicity	-	0.8573	85.73%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7269	72.69%
Fish aquatic toxicity	-	0.8121	81.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.80%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.21%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.80%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	95.44%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	93.56%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.46%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.80%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	91.19%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.28%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.43%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.79%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.88%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.34%	93.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.29%	97.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.57%	93.56%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.42%	97.86%
CHEMBL2514	O95665	Neurotensin receptor 2	81.19%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.15%	95.93%
CHEMBL3776	Q14790	Caspase-8	81.08%	97.06%
CHEMBL237	P41145	Kappa opioid receptor	81.08%	98.10%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.51%	96.47%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.15%	96.00%

Plants that contains it

• Morus alba

Cross-Links

• PubChem: 11812977
• LOTUS: LTS0141920
• wikiData: Q105267232