[(9R,10Z,11aR)-3-(hydroxymethyl)-10-methyl-6-methylidene-2,7-dioxo-5,8,9,11a-tetrahydro-4H-cyclodeca[b]furan-9-yl] acetate

Details

• Internal ID: cbfe18d5-1900-4f09-a8f7-abda6b5f2fe9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(9R,10Z,11aR)-3-(hydroxymethyl)-10-methyl-6-methylidene-2,7-dioxo-5,8,9,11a-tetrahydro-4H-cyclodeca[b]furan-9-yl] acetate
• SMILES (Canonical): CC1=CC2C(=C(C(=O)O2)CO)CCC(=C)C(=O)CC1OC(=O)C
• SMILES (Isomeric): C/C/1=C/[C@@H]2C(=C(C(=O)O2)CO)CCC(=C)C(=O)C[C@H]1OC(=O)C
• InChI: InChI=1S/C17H20O6/c1-9-4-5-12-13(8-18)17(21)23-16(12)6-10(2)15(7-14(9)20)22-11(3)19/h6,15-16,18H,1,4-5,7-8H2,2-3H3/b10-6-/t15-,16-/m1/s1
• InChI Key: BPBLQZHCVCIWBH-KETLTQCKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9722	97.22%
Caco-2	-	0.5176	51.76%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7848	78.48%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8713	87.13%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6284	62.84%
P-glycoprotein inhibitior	-	0.7306	73.06%
P-glycoprotein substrate	-	0.7605	76.05%
CYP3A4 substrate	+	0.5815	58.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8992	89.92%
CYP3A4 inhibition	-	0.5406	54.06%
CYP2C9 inhibition	-	0.8405	84.05%
CYP2C19 inhibition	-	0.8517	85.17%
CYP2D6 inhibition	-	0.9043	90.43%
CYP1A2 inhibition	+	0.6060	60.60%
CYP2C8 inhibition	-	0.6778	67.78%
CYP inhibitory promiscuity	-	0.8594	85.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6965	69.65%
Eye corrosion	-	0.9680	96.80%
Eye irritation	-	0.8572	85.72%
Skin irritation	-	0.5565	55.65%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6230	62.30%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.6244	62.44%
skin sensitisation	-	0.8504	85.04%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5953	59.53%
Acute Oral Toxicity (c)	III	0.5564	55.64%
Estrogen receptor binding	+	0.5838	58.38%
Androgen receptor binding	-	0.5625	56.25%
Thyroid receptor binding	-	0.5805	58.05%
Glucocorticoid receptor binding	-	0.4764	47.64%
Aromatase binding	-	0.6573	65.73%
PPAR gamma	-	0.5664	56.64%
Honey bee toxicity	-	0.7367	73.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9750	97.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.70%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.74%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.75%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.37%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.83%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.49%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.65%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.42%	99.17%

Plants that contains it

• Achillea fragrantissima
• Catharanthus roseus

Cross-Links

• PubChem: 162951084
• LOTUS: LTS0051803
• wikiData: Q105121096