(3S,3aR,5Z,11R,11aR)-11-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: f8764dec-342b-48d7-9106-8203ecc55748
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,5Z,11R,11aR)-11-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2CC=C(CCC=C(C(C2OC1=O)O)C)CO
• SMILES (Isomeric): C[C@H]1[C@H]2C/C=C(/CCC=C([C@H]([C@@H]2OC1=O)O)C)\CO
• InChI: InChI=1S/C15H22O4/c1-9-4-3-5-11(8-16)6-7-12-10(2)15(18)19-14(12)13(9)17/h4,6,10,12-14,16-17H,3,5,7-8H2,1-2H3/b9-4?,11-6-/t10-,12+,13+,14+/m0/s1
• InChI Key: YXXIBSGMPXSYQJ-XHAQVNOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9718	97.18%
Caco-2	+	0.7109	71.09%
Blood Brain Barrier	+	0.5605	56.05%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7768	77.68%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6320	63.20%
BSEP inhibitior	-	0.8984	89.84%
P-glycoprotein inhibitior	-	0.9569	95.69%
P-glycoprotein substrate	-	0.7845	78.45%
CYP3A4 substrate	+	0.5227	52.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.6905	69.05%
CYP2C9 inhibition	-	0.8075	80.75%
CYP2C19 inhibition	-	0.8062	80.62%
CYP2D6 inhibition	-	0.8388	83.88%
CYP1A2 inhibition	+	0.5351	53.51%
CYP2C8 inhibition	-	0.9202	92.02%
CYP inhibitory promiscuity	-	0.7601	76.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6646	66.46%
Eye corrosion	-	0.9781	97.81%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.6586	65.86%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6074	60.74%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4925	49.25%
Acute Oral Toxicity (c)	III	0.5164	51.64%
Estrogen receptor binding	-	0.6186	61.86%
Androgen receptor binding	-	0.6202	62.02%
Thyroid receptor binding	-	0.5638	56.38%
Glucocorticoid receptor binding	+	0.6328	63.28%
Aromatase binding	-	0.8091	80.91%
PPAR gamma	-	0.6374	63.74%
Honey bee toxicity	-	0.8914	89.14%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9536	95.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.97%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.12%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.87%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.39%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.48%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.22%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.01%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.68%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.48%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.07%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.81%	96.77%

Plants that contains it

• Avena sativa
• Hordeum vulgare

Cross-Links

• PubChem: 5321427
• NPASS: NPC210267