[(2R,3S,3aR,4S,6E,10E,11aR)-2-hydroxy-3,6,10-trimethyl-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: bea3ef71-1b25-4c45-83b7-c9b7eced94c1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Germacrane sesquiterpenoids
• IUPAC Name: [(2R,3S,3aR,4S,6E,10E,11aR)-2-hydroxy-3,6,10-trimethyl-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(=CCCC(=CC2C1C(C(O2)O)C)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]2[C@@H]1[C@@H]([C@@H](O2)O)C)/C)/C
• InChI: InChI=1S/C20H30O4/c1-6-14(4)19(21)23-16-10-12(2)8-7-9-13(3)11-17-18(16)15(5)20(22)24-17/h6,8,11,15-18,20,22H,7,9-10H2,1-5H3/b12-8+,13-11+,14-6-/t15-,16-,17+,18+,20+/m0/s1
• InChI Key: STIMKRWEFJAFHV-GEBZYVOSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 4
• 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	+	0.9901	99.01%
Caco-2	+	0.8921	89.21%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5337	53.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8868	88.68%
OATP1B3 inhibitior	+	0.9132	91.32%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8078	80.78%
P-glycoprotein inhibitior	-	0.5600	56.00%
P-glycoprotein substrate	-	0.8111	81.11%
CYP3A4 substrate	+	0.5954	59.54%
CYP2C9 substrate	-	0.5895	58.95%
CYP2D6 substrate	-	0.8800	88.00%
CYP3A4 inhibition	-	0.6266	62.66%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.8073	80.73%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	+	0.7275	72.75%
CYP2C8 inhibition	-	0.7342	73.42%
CYP inhibitory promiscuity	-	0.9145	91.45%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6201	62.01%
Eye corrosion	-	0.9655	96.55%
Eye irritation	-	0.9786	97.86%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.5282	52.82%
Human Ether-a-go-go-Related Gene inhibition	+	0.7425	74.25%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5699	56.99%
skin sensitisation	-	0.7886	78.86%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7146	71.46%
Acute Oral Toxicity (c)	III	0.3550	35.50%
Estrogen receptor binding	-	0.6363	63.63%
Androgen receptor binding	-	0.6318	63.18%
Thyroid receptor binding	+	0.5833	58.33%
Glucocorticoid receptor binding	+	0.5388	53.88%
Aromatase binding	-	0.6054	60.54%
PPAR gamma	-	0.5780	57.80%
Honey bee toxicity	-	0.7285	72.85%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9752	97.52%

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	96.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.92%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.06%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.73%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.43%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.05%	94.73%
CHEMBL2581	P07339	Cathepsin D	84.16%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.22%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.74%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.66%	100.00%

Plants that contains it

• Laserpitium halleri

Cross-Links

• PubChem: 162867264
• LOTUS: LTS0037978
• wikiData: Q105260272