(3aS,4R,5E,9Z,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 18e27124-918d-44a2-904b-9dd11907e448
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,4R,5E,9Z,11aS)-4-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CC(C2C(CC(=CCC1)CO)OC(=O)C2=C)O
• SMILES (Isomeric): C/C/1=C\[C@H]([C@H]2[C@H](C/C(=C/CC1)/CO)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O4/c1-9-4-3-5-11(8-16)7-13-14(12(17)6-9)10(2)15(18)19-13/h5-6,12-14,16-17H,2-4,7-8H2,1H3/b9-6+,11-5-/t12-,13+,14+/m1/s1
• InChI Key: YNPBZSCRCPJJDJ-IKPFQDNJSA-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	+	0.9812	98.12%
Caco-2	+	0.6880	68.80%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6711	67.11%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9251	92.51%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6489	64.89%
BSEP inhibitior	-	0.9446	94.46%
P-glycoprotein inhibitior	-	0.9134	91.34%
P-glycoprotein substrate	-	0.9043	90.43%
CYP3A4 substrate	+	0.5282	52.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.8504	85.04%
CYP2C9 inhibition	-	0.9006	90.06%
CYP2C19 inhibition	-	0.8466	84.66%
CYP2D6 inhibition	-	0.9053	90.53%
CYP1A2 inhibition	-	0.5782	57.82%
CYP2C8 inhibition	-	0.7973	79.73%
CYP inhibitory promiscuity	-	0.8759	87.59%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6708	67.08%
Eye corrosion	-	0.9750	97.50%
Eye irritation	-	0.7411	74.11%
Skin irritation	-	0.6494	64.94%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5847	58.47%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8641	86.41%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7049	70.49%
Acute Oral Toxicity (c)	III	0.4848	48.48%
Estrogen receptor binding	-	0.7951	79.51%
Androgen receptor binding	-	0.5905	59.05%
Thyroid receptor binding	-	0.6946	69.46%
Glucocorticoid receptor binding	+	0.6736	67.36%
Aromatase binding	-	0.7684	76.84%
PPAR gamma	-	0.5651	56.51%
Honey bee toxicity	-	0.8179	81.79%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9761	97.61%

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	93.15%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.00%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.60%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.57%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.12%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.03%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.69%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.62%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.12%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.64%	89.00%

Plants that contains it

• Perymenium klattianum

Cross-Links

• PubChem: 162937559
• LOTUS: LTS0052349
• wikiData: Q105351055