(2S,3R,4S,5S,6R)-2-[2-[(2R,4aR,6R,7R,8aR)-6,7-dihydroxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 5105d98e-0a87-4233-9a9a-f5f7bde94b51
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-[(2R,4aR,6R,7R,8aR)-6,7-dihydroxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC12CCC(CC1C(=C)C(C(C2)O)O)C(C)(C)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@H](C[C@H]1C(=C)[C@H]([C@@H](C2)O)O)C(C)(C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C21H36O8/c1-10-12-7-11(5-6-21(12,4)8-13(23)15(10)24)20(2,3)29-19-18(27)17(26)16(25)14(9-22)28-19/h11-19,22-27H,1,5-9H2,2-4H3/t11-,12+,13-,14-,15-,16-,17+,18-,19+,21-/m1/s1
• InChI Key: LDPAVRBHBSJMIE-JBZYYGELSA-N
• Popularity: 1 reference 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): 140.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.31
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7610	76.10%
Caco-2	-	0.8040	80.40%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	-	0.7213	72.13%
OATP1B1 inhibitior	+	0.8786	87.86%
OATP1B3 inhibitior	+	0.7928	79.28%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6542	65.42%
BSEP inhibitior	-	0.8927	89.27%
P-glycoprotein inhibitior	-	0.8058	80.58%
P-glycoprotein substrate	-	0.8075	80.75%
CYP3A4 substrate	+	0.6611	66.11%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.7528	75.28%
CYP2C9 inhibition	-	0.7639	76.39%
CYP2C19 inhibition	-	0.7864	78.64%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.7660	76.60%
CYP2C8 inhibition	+	0.4534	45.34%
CYP inhibitory promiscuity	-	0.9235	92.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7434	74.34%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.7554	75.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3763	37.63%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5274	52.74%
skin sensitisation	-	0.8688	86.88%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6817	68.17%
Acute Oral Toxicity (c)	III	0.6629	66.29%
Estrogen receptor binding	+	0.5643	56.43%
Androgen receptor binding	+	0.5789	57.89%
Thyroid receptor binding	+	0.6465	64.65%
Glucocorticoid receptor binding	-	0.4750	47.50%
Aromatase binding	+	0.6611	66.11%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7261	72.61%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9682	96.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.76%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.66%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.45%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.79%	96.09%
CHEMBL1871	P10275	Androgen Receptor	92.67%	96.43%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.68%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.41%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.05%	94.45%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.86%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.81%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	86.53%	95.38%
CHEMBL1937	Q92769	Histone deacetylase 2	86.31%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	85.63%	98.10%
CHEMBL2996	Q05655	Protein kinase C delta	85.47%	97.79%
CHEMBL1977	P11473	Vitamin D receptor	84.80%	99.43%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.55%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.34%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.51%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.19%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.13%	95.83%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.13%	92.94%
CHEMBL2581	P07339	Cathepsin D	81.12%	98.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.46%	97.28%

Plants that contains it

• Atractylodes lancea

Cross-Links

• PubChem: 101831405
• NPASS: NPC209527
• LOTUS: LTS0131925
• wikiData: Q105150303