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

Details

• Internal ID: 2e1d6f13-9613-43cc-9245-f029c4d45267
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Rhamnolipids
• IUPAC Name: (3R)-12-[(2R,5R,6S)-5-hydroxy-6-(hydroxymethyl)piperidin-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydodecanoic acid
• SMILES (Canonical): C1CC(C(NC1CCCCCCCCCC(CC(=O)O)OC2C(C(C(C(O2)CO)O)O)O)CO)O
• SMILES (Isomeric): C1C[C@H]([C@@H](N[C@@H]1CCCCCCCCC[C@H](CC(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)CO)O
• InChI: InChI=1S/C24H45NO10/c26-13-17-18(28)11-10-15(25-17)8-6-4-2-1-3-5-7-9-16(12-20(29)30)34-24-23(33)22(32)21(31)19(14-27)35-24/h15-19,21-28,31-33H,1-14H2,(H,29,30)/t15-,16-,17+,18-,19-,21-,22+,23-,24-/m1/s1
• InChI Key: OAVANBAUUXSKIH-LGKKHPCTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₅NO₁₀
• Molecular Weight: 507.60 g/mol
• Exact Mass: 507.30434663 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8606	86.06%
Caco-2	-	0.8857	88.57%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6178	61.78%
OATP2B1 inhibitior	+	0.5717	57.17%
OATP1B1 inhibitior	+	0.9111	91.11%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8766	87.66%
P-glycoprotein inhibitior	-	0.5560	55.60%
P-glycoprotein substrate	-	0.6543	65.43%
CYP3A4 substrate	+	0.6411	64.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8260	82.60%
CYP3A4 inhibition	-	0.9573	95.73%
CYP2C9 inhibition	-	0.9310	93.10%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.8474	84.74%
CYP1A2 inhibition	-	0.9044	90.44%
CYP2C8 inhibition	-	0.6671	66.71%
CYP inhibitory promiscuity	-	0.9705	97.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7304	73.04%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8846	88.46%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8751	87.51%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.7745	77.45%
skin sensitisation	-	0.9059	90.59%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6240	62.40%
Acute Oral Toxicity (c)	III	0.5062	50.62%
Estrogen receptor binding	+	0.5899	58.99%
Androgen receptor binding	-	0.5124	51.24%
Thyroid receptor binding	-	0.6254	62.54%
Glucocorticoid receptor binding	-	0.6289	62.89%
Aromatase binding	+	0.6718	67.18%
PPAR gamma	+	0.6084	60.84%
Honey bee toxicity	-	0.8169	81.69%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7469	74.69%
Fish aquatic toxicity	-	0.9384	93.84%

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	97.94%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.35%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.80%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	93.93%	94.45%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.16%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.55%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.45%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	90.30%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.58%	95.50%
CHEMBL3776	Q14790	Caspase-8	85.63%	97.06%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.31%	97.86%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.28%	93.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.79%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	83.58%	98.10%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	82.54%	95.00%
CHEMBL274	P51681	C-C chemokine receptor type 5	82.39%	98.77%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.31%	93.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.14%	94.23%
CHEMBL2514	O95665	Neurotensin receptor 2	82.09%	100.00%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.86%	97.29%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.77%	100.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.19%	90.08%

Plants that contains it

• Morus alba

Cross-Links

• PubChem: 10885684
• NPASS: NPC302555
• LOTUS: LTS0118133
• wikiData: Q105188827