[(3aS,5R,5aS,6S,8R,8aS,9R,9aR)-6-hydroxy-5,8a-dimethyl-8-(3-methylbutanoyloxy)-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 5d6019af-eb13-461a-8c02-3e2d6825c466
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aS,5R,5aS,6S,8R,8aS,9R,9aR)-6-hydroxy-5,8a-dimethyl-8-(3-methylbutanoyloxy)-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C(CC(C3C1(C(CC3O)OC(=O)CC(C)C)C)C)OC(=O)C2=C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@H]2[C@H](C[C@H]([C@H]3[C@]1([C@@H](C[C@@H]3O)OC(=O)CC(C)C)C)C)OC(=O)C2=C
• InChI: InChI=1S/C25H36O7/c1-8-13(4)23(28)32-22-20-15(6)24(29)30-17(20)10-14(5)21-16(26)11-18(25(21,22)7)31-19(27)9-12(2)3/h8,12,14,16-18,20-22,26H,6,9-11H2,1-5,7H3/b13-8-/t14-,16+,17+,18-,20-,21-,22-,25-/m1/s1
• InChI Key: MLTRRVPOGLBRTK-WZCJNOIXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₇
• Molecular Weight: 448.50 g/mol
• Exact Mass: 448.24610348 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9817	98.17%
Caco-2	-	0.5888	58.88%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5360	53.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	-	0.2168	21.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7527	75.27%
P-glycoprotein inhibitior	+	0.6769	67.69%
P-glycoprotein substrate	-	0.5161	51.61%
CYP3A4 substrate	+	0.6699	66.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	-	0.5862	58.62%
CYP2C9 inhibition	-	0.7429	74.29%
CYP2C19 inhibition	-	0.7640	76.40%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.6687	66.87%
CYP2C8 inhibition	-	0.6506	65.06%
CYP inhibitory promiscuity	-	0.8940	89.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9032	90.32%
Skin irritation	-	0.5261	52.61%
Skin corrosion	-	0.9066	90.66%
Ames mutagenesis	+	0.5168	51.68%
Human Ether-a-go-go-Related Gene inhibition	-	0.4937	49.37%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.7764	77.64%
skin sensitisation	-	0.6579	65.79%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6998	69.98%
Acute Oral Toxicity (c)	II	0.4374	43.74%
Estrogen receptor binding	+	0.7948	79.48%
Androgen receptor binding	+	0.6176	61.76%
Thyroid receptor binding	+	0.5881	58.81%
Glucocorticoid receptor binding	+	0.7312	73.12%
Aromatase binding	+	0.6094	60.94%
PPAR gamma	+	0.6616	66.16%
Honey bee toxicity	-	0.5844	58.44%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9886	98.86%

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	98.30%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.01%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.76%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.15%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.94%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	95.23%	97.79%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.19%	95.50%
CHEMBL299	P17252	Protein kinase C alpha	91.19%	98.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.17%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.86%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.37%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.06%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.92%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.14%	96.47%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.14%	89.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.95%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.84%	85.14%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.23%	90.08%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.30%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.27%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.78%	93.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.37%	89.34%

Plants that contains it

• Gaillardia coahuilensis
• Gaillardia pulchella

Cross-Links

• PubChem: 163017543
• LOTUS: LTS0061660
• wikiData: Q105167126