[(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-4,9-dihydroxy-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-6-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 5c01140b-aad2-41f1-b5d6-2d417240a49a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(3aR,4R,5S,5aS,6S,8R,8aR,9R,9aS)-4,9-dihydroxy-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-6-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(C2(C1C(C(C3C(C2O)C(=C)C(=O)O3)O)C)C)OC(=O)CC(C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@H]([C@@]2([C@@H]1[C@@H]([C@H]([C@H]3[C@H]([C@H]2O)C(=C)C(=O)O3)O)C)C)OC(=O)CC(C)C
• InChI: InChI=1S/C25H36O8/c1-8-12(4)23(29)31-15-10-16(32-17(26)9-11(2)3)25(7)19(15)14(6)20(27)21-18(22(25)28)13(5)24(30)33-21/h8,11,14-16,18-22,27-28H,5,9-10H2,1-4,6-7H3/b12-8-/t14-,15-,16+,18+,19+,20+,21+,22+,25+/m0/s1
• InChI Key: IQWHMZWVTALWMV-PMZTZJADSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₈
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.24101810 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9632	96.32%
Caco-2	-	0.7267	72.67%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5921	59.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8381	83.81%
OATP1B3 inhibitior	-	0.2498	24.98%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5932	59.32%
P-glycoprotein inhibitior	+	0.5749	57.49%
P-glycoprotein substrate	+	0.5757	57.57%
CYP3A4 substrate	+	0.6843	68.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9055	90.55%
CYP3A4 inhibition	-	0.6648	66.48%
CYP2C9 inhibition	-	0.6940	69.40%
CYP2C19 inhibition	-	0.6789	67.89%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.5934	59.34%
CYP2C8 inhibition	-	0.6603	66.03%
CYP inhibitory promiscuity	-	0.8499	84.99%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5558	55.58%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9132	91.32%
Skin irritation	-	0.5695	56.95%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5648	56.48%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.6946	69.46%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5822	58.22%
Acute Oral Toxicity (c)	II	0.3342	33.42%
Estrogen receptor binding	+	0.7075	70.75%
Androgen receptor binding	+	0.5723	57.23%
Thyroid receptor binding	+	0.5899	58.99%
Glucocorticoid receptor binding	+	0.6376	63.76%
Aromatase binding	+	0.5869	58.69%
PPAR gamma	+	0.6053	60.53%
Honey bee toxicity	-	0.5562	55.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	98.84%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	98.79%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.28%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.84%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.93%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	90.72%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.31%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.05%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.56%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.67%	99.23%
CHEMBL299	P17252	Protein kinase C alpha	84.19%	98.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.17%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.74%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.72%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.78%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.34%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.83%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.59%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.09%	99.17%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.73%	90.08%

Plants that contains it

• Helenium donianum

Cross-Links

• PubChem: 162984109
• LOTUS: LTS0263779
• wikiData: Q105118651