methyl (1S,5R,8S,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-2-ene-9-carboxylate

Details

• Internal ID: a55b5a84-c42c-49d7-83d4-18769a3aa944
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: methyl (1S,5R,8S,9S,10R,11R)-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-2-ene-9-carboxylate
• SMILES (Canonical): CC12CCCC3(C1C(C45C3=CCC(C4)C(=C)C5)C(=O)OC)OC2=O
• SMILES (Isomeric): C[C@@]12CCC[C@@]3([C@@H]1[C@@H]([C@]45C3=CC[C@H](C4)C(=C)C5)C(=O)OC)OC2=O
• InChI: InChI=1S/C20H24O4/c1-11-9-19-10-12(11)5-6-13(19)20-8-4-7-18(2,17(22)24-20)15(20)14(19)16(21)23-3/h6,12,14-15H,1,4-5,7-10H2,2-3H3/t12-,14-,15-,18-,19+,20-/m1/s1
• InChI Key: HQSDLFRIZKDOEE-VLDRLYBHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.5832	58.32%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7107	71.07%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.8736	87.36%
OATP1B3 inhibitior	+	0.9262	92.62%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7386	73.86%
P-glycoprotein inhibitior	-	0.6722	67.22%
P-glycoprotein substrate	-	0.6418	64.18%
CYP3A4 substrate	+	0.6841	68.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8554	85.54%
CYP3A4 inhibition	-	0.6461	64.61%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.8150	81.50%
CYP2D6 inhibition	-	0.9401	94.01%
CYP1A2 inhibition	+	0.5163	51.63%
CYP2C8 inhibition	+	0.4701	47.01%
CYP inhibitory promiscuity	-	0.8559	85.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8438	84.38%
Skin irritation	-	0.5897	58.97%
Skin corrosion	-	0.9137	91.37%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7408	74.08%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5727	57.27%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7992	79.92%
Acute Oral Toxicity (c)	III	0.6414	64.14%
Estrogen receptor binding	+	0.7746	77.46%
Androgen receptor binding	+	0.7062	70.62%
Thyroid receptor binding	+	0.5909	59.09%
Glucocorticoid receptor binding	+	0.7532	75.32%
Aromatase binding	-	0.5052	50.52%
PPAR gamma	-	0.5646	56.46%
Honey bee toxicity	-	0.7389	73.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	95.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.85%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.15%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.76%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.56%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.99%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.99%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.99%	97.14%
CHEMBL2581	P07339	Cathepsin D	82.63%	98.95%

Plants that contains it

• Lygodium microphyllum

Cross-Links

• PubChem: 11131270
• LOTUS: LTS0270007
• wikiData: Q105032410