7,8a-dihydroxy-1,8-dimethylidenespiro[4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-5,2'-oxirane]-2-one

Details

• Internal ID: c704a0e0-cad6-4639-a47d-7e4c9d82f071
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 7,8a-dihydroxy-1,8-dimethylidenespiro[4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-5,2'-oxirane]-2-one
• SMILES (Canonical): C=C1C(CC2C1(CC3C(CC24CO4)OC(=O)C3=C)O)O
• SMILES (Isomeric): C=C1C(CC2C1(CC3C(CC24CO4)OC(=O)C3=C)O)O
• InChI: InChI=1S/C15H18O5/c1-7-9-4-15(18)8(2)10(16)3-12(15)14(6-19-14)5-11(9)20-13(7)17/h9-12,16,18H,1-6H2
• InChI Key: NRQMQZXLJOVXEZ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.32
• H-Bond Acceptor: 5
• 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	+	0.9509	95.09%
Caco-2	-	0.7262	72.62%
Blood Brain Barrier	-	0.5473	54.73%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5876	58.76%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9119	91.19%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9393	93.93%
P-glycoprotein inhibitior	-	0.9401	94.01%
P-glycoprotein substrate	-	0.8160	81.60%
CYP3A4 substrate	+	0.5570	55.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8238	82.38%
CYP3A4 inhibition	-	0.9415	94.15%
CYP2C9 inhibition	-	0.8627	86.27%
CYP2C19 inhibition	-	0.8348	83.48%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	-	0.8151	81.51%
CYP2C8 inhibition	-	0.8163	81.63%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6225	62.25%
Eye corrosion	-	0.9747	97.47%
Eye irritation	-	0.7412	74.12%
Skin irritation	-	0.7007	70.07%
Skin corrosion	-	0.9177	91.77%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7085	70.85%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.7972	79.72%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.8178	81.78%
Acute Oral Toxicity (c)	III	0.3910	39.10%
Estrogen receptor binding	+	0.8369	83.69%
Androgen receptor binding	+	0.5604	56.04%
Thyroid receptor binding	-	0.5616	56.16%
Glucocorticoid receptor binding	+	0.8200	82.00%
Aromatase binding	+	0.5860	58.60%
PPAR gamma	+	0.5715	57.15%
Honey bee toxicity	-	0.6845	68.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9129	91.29%

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	95.54%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.40%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.58%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.55%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.05%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.18%	93.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.96%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.84%	89.34%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.76%	91.24%
CHEMBL221	P23219	Cyclooxygenase-1	83.28%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.14%	95.50%

Plants that contains it

• Arctotis stoechadifolia

Cross-Links

• PubChem: 14285667
• LOTUS: LTS0220684
• wikiData: Q105184767