[(3aR,4S,6E,10Z,11aR)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 253d58e9-cd57-400f-8f6b-0eb836044557
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(3aR,4S,6E,10Z,11aR)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): CC1=CCCC=CC2C(C(C1)OC(=O)C(=C)CO)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\CC/C=C\[C@@H]2[C@@H]([C@H](C1)OC(=O)C(=C)CO)C(=C)C(=O)O2
• InChI: InChI=1S/C18H22O5/c1-11-7-5-4-6-8-14-16(13(3)18(21)22-14)15(9-11)23-17(20)12(2)10-19/h6-8,14-16,19H,2-5,9-10H2,1H3/b8-6-,11-7+/t14-,15+,16+/m1/s1
• InChI Key: ZYEUWDVPMGDEQL-DIPLVCCSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.14672380 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	+	0.5301	53.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6796	67.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9199	91.99%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.8100	81.00%
P-glycoprotein inhibitior	-	0.7497	74.97%
P-glycoprotein substrate	-	0.7197	71.97%
CYP3A4 substrate	+	0.6013	60.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8597	85.97%
CYP3A4 inhibition	-	0.6711	67.11%
CYP2C9 inhibition	-	0.8707	87.07%
CYP2C19 inhibition	-	0.8453	84.53%
CYP2D6 inhibition	-	0.9258	92.58%
CYP1A2 inhibition	+	0.5651	56.51%
CYP2C8 inhibition	-	0.7221	72.21%
CYP inhibitory promiscuity	-	0.9051	90.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6825	68.25%
Eye corrosion	-	0.9657	96.57%
Eye irritation	-	0.6648	66.48%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5180	51.80%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6464	64.64%
skin sensitisation	-	0.8482	84.82%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.8715	87.15%
Acute Oral Toxicity (c)	III	0.6544	65.44%
Estrogen receptor binding	-	0.6342	63.42%
Androgen receptor binding	-	0.5842	58.42%
Thyroid receptor binding	-	0.5603	56.03%
Glucocorticoid receptor binding	+	0.5666	56.66%
Aromatase binding	-	0.5226	52.26%
PPAR gamma	+	0.6967	69.67%
Honey bee toxicity	-	0.8172	81.72%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9825	98.25%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.95%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.72%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.05%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.98%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.70%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	85.50%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.34%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.13%	97.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.06%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.66%	99.23%

Plants that contains it

• Onopordum illyricum

Cross-Links

• PubChem: 163066566
• LOTUS: LTS0264129
• wikiData: Q105386083