(2R,3S,4S,5S)-2-[(3E,5S)-5-hydroxy-4,8-dimethylnona-3,7-dienyl]oxane-3,4,5-triol

Details

• Internal ID: f75ef355-3034-4736-b5f9-2ebb1f4c5ec0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (2R,3S,4S,5S)-2-[(3E,5S)-5-hydroxy-4,8-dimethylnona-3,7-dienyl]oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCC(C(=CCCC1C(C(C(CO1)O)O)O)C)O)C
• SMILES (Isomeric): CC(=CC[C@@H](/C(=C/CC[C@@H]1[C@H]([C@H]([C@H](CO1)O)O)O)/C)O)C
• InChI: InChI=1S/C16H28O5/c1-10(2)7-8-12(17)11(3)5-4-6-14-16(20)15(19)13(18)9-21-14/h5,7,12-20H,4,6,8-9H2,1-3H3/b11-5+/t12-,13-,14+,15-,16+/m0/s1
• InChI Key: KVQNAYKJHQZVPK-VCYHANCMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₈O₅
• Molecular Weight: 300.39 g/mol
• Exact Mass: 300.19367399 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6744	67.44%
Caco-2	-	0.7674	76.74%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8161	81.61%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9085	90.85%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6109	61.09%
BSEP inhibitior	-	0.8722	87.22%
P-glycoprotein inhibitior	-	0.9176	91.76%
P-glycoprotein substrate	-	0.8345	83.45%
CYP3A4 substrate	-	0.5064	50.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7564	75.64%
CYP3A4 inhibition	-	0.8759	87.59%
CYP2C9 inhibition	-	0.8748	87.48%
CYP2C19 inhibition	-	0.7614	76.14%
CYP2D6 inhibition	-	0.8774	87.74%
CYP1A2 inhibition	-	0.8309	83.09%
CYP2C8 inhibition	-	0.9311	93.11%
CYP inhibitory promiscuity	-	0.9506	95.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7345	73.45%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9857	98.57%
Skin irritation	-	0.7211	72.11%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6682	66.82%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7046	70.46%
skin sensitisation	-	0.7570	75.70%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9083	90.83%
Acute Oral Toxicity (c)	III	0.6868	68.68%
Estrogen receptor binding	-	0.5555	55.55%
Androgen receptor binding	-	0.7888	78.88%
Thyroid receptor binding	+	0.5692	56.92%
Glucocorticoid receptor binding	-	0.5298	52.98%
Aromatase binding	+	0.5476	54.76%
PPAR gamma	+	0.6178	61.78%
Honey bee toxicity	-	0.8298	82.98%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.9100	91.00%
Fish aquatic toxicity	+	0.7492	74.92%

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	95.39%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.04%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.23%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.46%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.25%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	90.89%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.70%	94.45%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.56%	98.75%
CHEMBL4040	P28482	MAP kinase ERK2	84.53%	83.82%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.67%	95.58%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.43%	97.21%

Plants that contains it

• Rhodiola rosea

Cross-Links

• PubChem: 163104804
• LOTUS: LTS0262791
• wikiData: Q105146659