(3S,3aR,4S,6E,11aR)-4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 0c6b1235-9417-44f4-afad-74da00edb7aa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aR,4S,6E,11aR)-4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2OC1=O)CO)C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](C/C(=C/CCC(=C[C@H]2OC1=O)CO)/C)O
• InChI: InChI=1S/C15H22O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h4,7,10,12-14,16-17H,3,5-6,8H2,1-2H3/b9-4+,11-7?/t10-,12-,13+,14+/m0/s1
• InChI Key: HKIIPLGMBYVADK-ODXVOOCZSA-N
• Popularity: 1 reference 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	+	0.9845	98.45%
Caco-2	+	0.6958	69.58%
Blood Brain Barrier	+	0.5784	57.84%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7077	70.77%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9171	91.71%
OATP1B3 inhibitior	+	0.9670	96.70%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6031	60.31%
BSEP inhibitior	-	0.8680	86.80%
P-glycoprotein inhibitior	-	0.9260	92.60%
P-glycoprotein substrate	-	0.8057	80.57%
CYP3A4 substrate	+	0.5389	53.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.5299	52.99%
CYP2C9 inhibition	-	0.9329	93.29%
CYP2C19 inhibition	-	0.9073	90.73%
CYP2D6 inhibition	-	0.9134	91.34%
CYP1A2 inhibition	-	0.6069	60.69%
CYP2C8 inhibition	-	0.9163	91.63%
CYP inhibitory promiscuity	-	0.9062	90.62%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6525	65.25%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9584	95.84%
Skin irritation	-	0.6077	60.77%
Skin corrosion	-	0.9529	95.29%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8592	85.92%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5949	59.49%
skin sensitisation	-	0.8910	89.10%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4621	46.21%
Acute Oral Toxicity (c)	III	0.4053	40.53%
Estrogen receptor binding	-	0.8135	81.35%
Androgen receptor binding	-	0.6683	66.83%
Thyroid receptor binding	-	0.6969	69.69%
Glucocorticoid receptor binding	-	0.5304	53.04%
Aromatase binding	-	0.8859	88.59%
PPAR gamma	-	0.7619	76.19%
Honey bee toxicity	-	0.9074	90.74%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9440	94.40%

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	94.26%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.25%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.82%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.80%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.34%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.18%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.41%	97.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.36%	86.00%
CHEMBL3401	O75469	Pregnane X receptor	80.93%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.87%	86.33%

Plants that contains it

• Anthemis pseudocotula
• Centaurea pullata

Cross-Links

• PubChem: 163004748
• LOTUS: LTS0122612
• wikiData: Q104946249