[(3aR,4R,6E,10E,11aS)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S,3S)-2,3-dihydroxy-2-methylbutanoate

Details

• Internal ID: 102ca7ce-a67b-44a3-9e50-ae557bd5342a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: [(3aR,4R,6E,10E,11aS)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2S,3S)-2,3-dihydroxy-2-methylbutanoate
• SMILES (Canonical): CC1=CC2C(C(CC(=CCC1)C)OC(=O)C(C)(C(C)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\[C@H]2[C@@H]([C@@H](C/C(=C/CC1)/C)OC(=O)[C@](C)([C@H](C)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C20H28O6/c1-11-7-6-8-12(2)10-16(26-19(23)20(5,24)14(4)21)17-13(3)18(22)25-15(17)9-11/h8-9,14-17,21,24H,3,6-7,10H2,1-2,4-5H3/b11-9+,12-8+/t14-,15-,16+,17-,20-/m0/s1
• InChI Key: KVJTZBSGBYRUOR-CYBHVJCNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9532	95.32%
Caco-2	+	0.5691	56.91%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6711	67.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	+	0.8502	85.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	-	0.7749	77.49%
P-glycoprotein inhibitior	-	0.6484	64.84%
P-glycoprotein substrate	-	0.7386	73.86%
CYP3A4 substrate	+	0.6136	61.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.6628	66.28%
CYP2C9 inhibition	-	0.7827	78.27%
CYP2C19 inhibition	-	0.7637	76.37%
CYP2D6 inhibition	-	0.9499	94.99%
CYP1A2 inhibition	+	0.7033	70.33%
CYP2C8 inhibition	-	0.6296	62.96%
CYP inhibitory promiscuity	-	0.9713	97.13%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5650	56.50%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9504	95.04%
Skin irritation	+	0.5544	55.44%
Skin corrosion	-	0.8989	89.89%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4068	40.68%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8056	80.56%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6206	62.06%
Acute Oral Toxicity (c)	III	0.3695	36.95%
Estrogen receptor binding	+	0.5539	55.39%
Androgen receptor binding	-	0.5117	51.17%
Thyroid receptor binding	+	0.5836	58.36%
Glucocorticoid receptor binding	+	0.7444	74.44%
Aromatase binding	-	0.4948	49.48%
PPAR gamma	+	0.5544	55.44%
Honey bee toxicity	-	0.7382	73.82%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9904	99.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.77%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.39%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.07%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.98%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	87.40%	97.79%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.31%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	86.97%	94.73%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.65%	97.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.21%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.19%	96.47%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.99%	90.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.87%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.14%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.68%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.19%	95.89%
CHEMBL5028	O14672	ADAM10	82.04%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.31%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.31%	83.82%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.27%	94.97%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.12%	95.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.09%	94.08%

Plants that contains it

• Ursinia anthemoides
• Ursinia cakilefolia

Cross-Links

• PubChem: 163185452
• LOTUS: LTS0048294
• wikiData: Q105146560