7,8a-Dihydroxy-1-methyl-5,8-dimethylidene-1,3a,4,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 9d9e7fbf-e6fe-4f62-a166-cd9f80fe558c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 7,8a-dihydroxy-1-methyl-5,8-dimethylidene-1,3a,4,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1C2CC3(C(CC(C3=C)O)C(=C)CC2OC1=O)O
• SMILES (Isomeric): CC1C2CC3(C(CC(C3=C)O)C(=C)CC2OC1=O)O
• InChI: InChI=1S/C15H20O4/c1-7-4-13-10(8(2)14(17)19-13)6-15(18)9(3)12(16)5-11(7)15/h8,10-13,16,18H,1,3-6H2,2H3
• InChI Key: QGBCGBJTCUCSJX-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9695	96.95%
Caco-2	-	0.7529	75.29%
Blood Brain Barrier	-	0.5473	54.73%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4970	49.70%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9469	94.69%
P-glycoprotein inhibitior	-	0.9243	92.43%
P-glycoprotein substrate	-	0.6844	68.44%
CYP3A4 substrate	+	0.6003	60.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8482	84.82%
CYP3A4 inhibition	-	0.8950	89.50%
CYP2C9 inhibition	-	0.8653	86.53%
CYP2C19 inhibition	-	0.8108	81.08%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.6480	64.80%
CYP2C8 inhibition	-	0.9523	95.23%
CYP inhibitory promiscuity	-	0.9346	93.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9625	96.25%
Carcinogenicity (trinary)	Non-required	0.5382	53.82%
Eye corrosion	-	0.9792	97.92%
Eye irritation	-	0.8395	83.95%
Skin irritation	-	0.5662	56.62%
Skin corrosion	-	0.8886	88.86%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6500	65.00%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.7889	78.89%
skin sensitisation	-	0.7586	75.86%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7594	75.94%
Acute Oral Toxicity (c)	III	0.3539	35.39%
Estrogen receptor binding	+	0.6976	69.76%
Androgen receptor binding	+	0.5632	56.32%
Thyroid receptor binding	-	0.4927	49.27%
Glucocorticoid receptor binding	+	0.6655	66.55%
Aromatase binding	-	0.6203	62.03%
PPAR gamma	-	0.5854	58.54%
Honey bee toxicity	-	0.7274	72.74%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9714	97.14%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.52%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.33%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.83%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	87.66%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.78%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.33%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.03%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.48%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.63%	89.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.62%	85.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.01%	94.80%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 162917637
• LOTUS: LTS0017318
• wikiData: Q105219891