6,6a,7,8,9-pentahydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 83a8f722-b6e7-47cc-974f-64f4908677c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 6,6a,7,8,9-pentahydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1(CCC2C(C3C1(C(C(C3(C)O)O)O)O)OC(=O)C2=C)O
• SMILES (Isomeric): CC1(CCC2C(C3C1(C(C(C3(C)O)O)O)O)OC(=O)C2=C)O
• InChI: InChI=1S/C15H22O7/c1-6-7-4-5-13(2,19)15(21)9(8(7)22-12(6)18)14(3,20)10(16)11(15)17/h7-11,16-17,19-21H,1,4-5H2,2-3H3
• InChI Key: FTHQHWNKKLTVLA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₇
• Molecular Weight: 314.33 g/mol
• Exact Mass: 314.13655304 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.54
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9221	92.21%
Caco-2	-	0.7539	75.39%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.4936	49.36%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.8769	87.69%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9828	98.28%
P-glycoprotein inhibitior	-	0.8849	88.49%
P-glycoprotein substrate	-	0.8507	85.07%
CYP3A4 substrate	+	0.6095	60.95%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.7807	78.07%
CYP2C9 inhibition	-	0.8057	80.57%
CYP2C19 inhibition	-	0.7563	75.63%
CYP2D6 inhibition	-	0.9047	90.47%
CYP1A2 inhibition	-	0.6142	61.42%
CYP2C8 inhibition	-	0.7882	78.82%
CYP inhibitory promiscuity	-	0.9403	94.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5629	56.29%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9454	94.54%
Skin irritation	-	0.5439	54.39%
Skin corrosion	-	0.8348	83.48%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5283	52.83%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.8627	86.27%
skin sensitisation	-	0.7714	77.14%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5929	59.29%
Acute Oral Toxicity (c)	III	0.3352	33.52%
Estrogen receptor binding	+	0.6497	64.97%
Androgen receptor binding	+	0.6465	64.65%
Thyroid receptor binding	+	0.5431	54.31%
Glucocorticoid receptor binding	+	0.5603	56.03%
Aromatase binding	-	0.5340	53.40%
PPAR gamma	-	0.5805	58.05%
Honey bee toxicity	-	0.7978	79.78%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9056	90.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.87%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.68%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.34%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.78%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.69%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	81.22%	95.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.73%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.45%	93.03%

Plants that contains it

• Artemisia rutifolia
• Artemisia xerophytica

Cross-Links

• PubChem: 162972507
• LOTUS: LTS0056786
• wikiData: Q105001045