(3R,3aR,4S,5E,9E,11aS)-4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: 877d9cf2-3fa9-4e2a-a10f-c7b07f162779
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3R,3aR,4S,5E,9E,11aS)-4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3a,4,7,8,11,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• SMILES (Canonical): CC1C2C(CC(=CCCC(=CC2O)C)CO)OC1=O
• SMILES (Isomeric): C[C@@H]1[C@H]2[C@H](C/C(=C\CC/C(=C/[C@@H]2O)/C)/CO)OC1=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/h5-6,10,12-14,16-17H,3-4,7-8H2,1-2H3/b9-6+,11-5+/t10-,12+,13+,14-/m1/s1
• InChI Key: UHJKINURUMDUOJ-RNVSPCOHSA-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	+	0.9798	97.98%
Caco-2	+	0.7037	70.37%
Blood Brain Barrier	+	0.6034	60.34%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7336	73.36%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9340	93.40%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6239	62.39%
BSEP inhibitior	-	0.9114	91.14%
P-glycoprotein inhibitior	-	0.9497	94.97%
P-glycoprotein substrate	-	0.8558	85.58%
CYP3A4 substrate	+	0.5297	52.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.5911	59.11%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.8910	89.10%
CYP2D6 inhibition	-	0.9053	90.53%
CYP1A2 inhibition	-	0.5116	51.16%
CYP2C8 inhibition	-	0.8919	89.19%
CYP inhibitory promiscuity	-	0.8618	86.18%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6529	65.29%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9418	94.18%
Skin irritation	-	0.6396	63.96%
Skin corrosion	-	0.9527	95.27%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6970	69.70%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8831	88.31%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7136	71.36%
Acute Oral Toxicity (c)	III	0.4219	42.19%
Estrogen receptor binding	-	0.7174	71.74%
Androgen receptor binding	-	0.6356	63.56%
Thyroid receptor binding	-	0.7027	70.27%
Glucocorticoid receptor binding	+	0.5955	59.55%
Aromatase binding	-	0.8458	84.58%
PPAR gamma	-	0.6440	64.40%
Honey bee toxicity	-	0.8726	87.26%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9625	96.25%

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	93.02%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.83%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.15%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.30%	96.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	88.50%	86.00%
CHEMBL2581	P07339	Cathepsin D	88.03%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.33%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.99%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.22%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.69%	94.80%

Plants that contains it

• Schkuhria pinnata

Cross-Links

• PubChem: 162890756
• LOTUS: LTS0174353
• wikiData: Q105272918