(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(2S,5R)-5-[(4S)-4-hydroxy-4-methylhexa-1,5-dienyl]-5-methyloxolan-2-yl]propan-2-yloxy]oxane-3,4,5-triol

Details

• Internal ID: 6bc8fcb0-0d49-4eb8-bffa-cb27876633b7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-[(2S,5R)-5-[(4S)-4-hydroxy-4-methylhexa-1,5-dienyl]-5-methyloxolan-2-yl]propan-2-yloxy]oxane-3,4,5-triol
• SMILES (Canonical): CC1(CCC(O1)C(C)(C)OC2C(C(C(C(O2)CO)O)O)O)C=CCC(C)(C=C)O
• SMILES (Isomeric): C[C@@]1(CC[C@H](O1)C(C)(C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C=CC[C@@](C)(C=C)O
• InChI: InChI=1S/C21H36O8/c1-6-20(4,26)9-7-10-21(5)11-8-14(28-21)19(2,3)29-18-17(25)16(24)15(23)13(12-22)27-18/h6-7,10,13-18,22-26H,1,8-9,11-12H2,2-5H3/t13-,14+,15-,16+,17-,18+,20-,21+/m1/s1
• InChI Key: UBWUZHMCADSLDT-OVRLBIBNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₈
• Molecular Weight: 416.50 g/mol
• Exact Mass: 416.24101810 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.40
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5763	57.63%
Caco-2	-	0.7560	75.60%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7298	72.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8748	87.48%
OATP1B3 inhibitior	+	0.8945	89.45%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8724	87.24%
P-glycoprotein inhibitior	-	0.6354	63.54%
P-glycoprotein substrate	-	0.8667	86.67%
CYP3A4 substrate	+	0.6788	67.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
CYP3A4 inhibition	-	0.7773	77.73%
CYP2C9 inhibition	-	0.8379	83.79%
CYP2C19 inhibition	-	0.8906	89.06%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8862	88.62%
CYP2C8 inhibition	+	0.5097	50.97%
CYP inhibitory promiscuity	-	0.9338	93.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9755	97.55%
Skin irritation	-	0.6806	68.06%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4830	48.30%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5101	51.01%
skin sensitisation	-	0.8539	85.39%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.4529	45.29%
Estrogen receptor binding	+	0.5357	53.57%
Androgen receptor binding	+	0.5207	52.07%
Thyroid receptor binding	+	0.6740	67.40%
Glucocorticoid receptor binding	+	0.7013	70.13%
Aromatase binding	+	0.6956	69.56%
PPAR gamma	+	0.5874	58.74%
Honey bee toxicity	-	0.7127	71.27%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8193	81.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.74%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.36%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.01%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.05%	97.09%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	89.62%	97.47%
CHEMBL1977	P11473	Vitamin D receptor	88.07%	99.43%
CHEMBL259	P32245	Melanocortin receptor 4	87.70%	95.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.45%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.97%	96.21%
CHEMBL2996	Q05655	Protein kinase C delta	84.95%	97.79%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.70%	90.93%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.60%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	83.59%	94.73%
CHEMBL233	P35372	Mu opioid receptor	82.81%	97.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.73%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.52%	91.03%
CHEMBL3589	P55263	Adenosine kinase	82.46%	98.05%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.45%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	82.43%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.20%	97.36%
CHEMBL237	P41145	Kappa opioid receptor	81.94%	98.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.86%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.62%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.44%	91.07%

Plants that contains it

• Crataegus pinnatifida

Cross-Links

• PubChem: 162923112
• LOTUS: LTS0121604
• wikiData: Q105269706