4-Hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 79c3d235-9c79-46d8-993c-7548647591af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: 4-hydroxy-6-(hydroxymethyl)-10-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=CC(C2C(C1)OC(=O)C2=C)O)CO
• SMILES (Isomeric): CC1=CCCC(=CC(C2C(C1)OC(=O)C2=C)O)CO
• InChI: InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-12(17)14-10(2)15(18)19-13(14)6-9/h4,7,12-14,16-17H,2-3,5-6,8H2,1H3
• InChI Key: WMFCEEAYDCXJCA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.49
• 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	+	0.9778	97.78%
Caco-2	+	0.5701	57.01%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6649	66.49%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6239	62.39%
BSEP inhibitior	-	0.9320	93.20%
P-glycoprotein inhibitior	-	0.9147	91.47%
P-glycoprotein substrate	-	0.8878	88.78%
CYP3A4 substrate	+	0.5170	51.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.7476	74.76%
CYP2C9 inhibition	-	0.8967	89.67%
CYP2C19 inhibition	-	0.8442	84.42%
CYP2D6 inhibition	-	0.9138	91.38%
CYP1A2 inhibition	-	0.5204	52.04%
CYP2C8 inhibition	-	0.8117	81.17%
CYP inhibitory promiscuity	-	0.8769	87.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6540	65.40%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.6782	67.82%
Skin irritation	-	0.6004	60.04%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6415	64.15%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8676	86.76%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7113	71.13%
Acute Oral Toxicity (c)	III	0.5101	51.01%
Estrogen receptor binding	-	0.7063	70.63%
Androgen receptor binding	-	0.5852	58.52%
Thyroid receptor binding	-	0.6889	68.89%
Glucocorticoid receptor binding	+	0.6275	62.75%
Aromatase binding	-	0.7739	77.39%
PPAR gamma	-	0.5569	55.69%
Honey bee toxicity	-	0.8696	86.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9790	97.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.77%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.76%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.75%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.78%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	83.31%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.75%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.75%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.98%	100.00%

Plants that contains it

• Ambrosia artemisiifolia
• Centaurea seridis
• Richterago discoidea

Cross-Links

• PubChem: 4663677
• LOTUS: LTS0161190
• wikiData: Q105308510