(8-Hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl) 2-(hydroxymethyl)prop-2-enoate

Details

• Internal ID: 321caa89-80d6-41ff-a4ab-d475823bb62b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl) 2-(hydroxymethyl)prop-2-enoate
• SMILES (Canonical): C=C1CC(C2C(C3C1CC(C34CO4)O)OC(=O)C2=C)OC(=O)C(=C)CO
• SMILES (Isomeric): C=C1CC(C2C(C3C1CC(C34CO4)O)OC(=O)C2=C)OC(=O)C(=C)CO
• InChI: InChI=1S/C19H22O7/c1-8-4-12(25-17(22)9(2)6-20)14-10(3)18(23)26-16(14)15-11(8)5-13(21)19(15)7-24-19/h11-16,20-21H,1-7H2
• InChI Key: HEJVISJCOQSDIH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₇
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.13655304 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.27
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (8-hydroxy-3,6-dimethylidene-2-oxospiro[3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-9,2'-oxirane]-4-yl) 2-(hydroxymethyl)prop-2-enoate
• 2-(Hydroxymethyl)propenoic acid (3aR,9R)-3,3abeta,4,5,6,6abeta,7,8,9abeta,9balpha-decahydro-8alpha-hydroxy-3,6-bis(methylene)-2-oxospiro[azuleno[4,5-b]furan-9(2H),2'-oxirane]-4beta-yl ester
• DTXSID00982751
• 2-Propenoic acid, 2-(hydroxymethyl)-, decahydro-8-hydroxy-3,6-bis(methylene)-2-oxospiro(azuleno(4,5-b)furan-9(2H),2'-oxiran)-4-yl ester, (3aR- (3aalpha,4alpha,6aalpha,8beta,9alpha,9aalpha,9bbeta))-
• 8-hydroxy-3,6-dimethylidene-2-oxodecahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl 2-(hydroxymethyl)prop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8945	89.45%
Caco-2	-	0.7133	71.33%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6565	65.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8997	89.97%
OATP1B3 inhibitior	+	0.9595	95.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8682	86.82%
P-glycoprotein inhibitior	-	0.7678	76.78%
P-glycoprotein substrate	-	0.5197	51.97%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8287	82.87%
CYP3A4 inhibition	-	0.8038	80.38%
CYP2C9 inhibition	-	0.8376	83.76%
CYP2C19 inhibition	-	0.8133	81.33%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	-	0.8545	85.45%
CYP2C8 inhibition	-	0.6766	67.66%
CYP inhibitory promiscuity	-	0.9454	94.54%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9773	97.73%
Eye irritation	-	0.7870	78.70%
Skin irritation	-	0.7239	72.39%
Skin corrosion	-	0.9195	91.95%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5847	58.47%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8052	80.52%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8419	84.19%
Acute Oral Toxicity (c)	III	0.3963	39.63%
Estrogen receptor binding	+	0.7655	76.55%
Androgen receptor binding	+	0.6505	65.05%
Thyroid receptor binding	+	0.5610	56.10%
Glucocorticoid receptor binding	+	0.7388	73.88%
Aromatase binding	+	0.6480	64.80%
PPAR gamma	+	0.7077	70.77%
Honey bee toxicity	-	0.6125	61.25%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.8925	89.25%

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	98.45%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.33%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.69%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.35%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	85.27%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	84.46%	90.17%
CHEMBL2581	P07339	Cathepsin D	83.27%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.22%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.84%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.76%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.54%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.20%	96.37%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.10%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.43%	89.00%

Plants that contains it

• Centaurea hermannii
• Centaurea scoparia
• Centaurea solstitialis
• Centaurea uniflora
• Cousinia piptocephala
• Jurinea carduiformis
• Pleiotaxis rugosa

Cross-Links

• PubChem: 182407
• LOTUS: LTS0020087
• wikiData: Q82969570