(3aR,7aalpha,9aalpha)-Dodecahydro-5beta,6beta-dihydroxy-4abeta,8beta-dimethyl-3-methyleneazuleno[6,5-b]furan-2-one

Details

• Internal ID: 3ec803d8-02b7-43f0-b889-3c8ab898d657
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: 7,8-dihydroxy-5,8a-dimethyl-1-methylidene-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC3(C1CC(C3O)O)C)C(=C)C(=O)O2
• SMILES (Isomeric): CC1CC2C(CC3(C1CC(C3O)O)C)C(=C)C(=O)O2
• InChI: InChI=1S/C15H22O4/c1-7-4-12-9(8(2)14(18)19-12)6-15(3)10(7)5-11(16)13(15)17/h7,9-13,16-17H,2,4-6H2,1,3H3
• InChI Key: ZFCRHGITKWEXDY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 6605-88-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9714	97.14%
Caco-2	+	0.5333	53.33%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5985	59.85%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9048	90.48%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9487	94.87%
P-glycoprotein inhibitior	-	0.9220	92.20%
P-glycoprotein substrate	-	0.8039	80.39%
CYP3A4 substrate	+	0.6185	61.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.6904	69.04%
CYP2C9 inhibition	-	0.8294	82.94%
CYP2C19 inhibition	-	0.7330	73.30%
CYP2D6 inhibition	-	0.9327	93.27%
CYP1A2 inhibition	-	0.6051	60.51%
CYP2C8 inhibition	-	0.8635	86.35%
CYP inhibitory promiscuity	-	0.9613	96.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5690	56.90%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9196	91.96%
Skin irritation	-	0.5251	52.51%
Skin corrosion	-	0.9010	90.10%
Ames mutagenesis	+	0.6146	61.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6566	65.66%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.9337	93.37%
skin sensitisation	-	0.7356	73.56%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5970	59.70%
Acute Oral Toxicity (c)	III	0.3990	39.90%
Estrogen receptor binding	+	0.7540	75.40%
Androgen receptor binding	+	0.5345	53.45%
Thyroid receptor binding	-	0.5763	57.63%
Glucocorticoid receptor binding	+	0.6568	65.68%
Aromatase binding	-	0.5970	59.70%
PPAR gamma	-	0.6525	65.25%
Honey bee toxicity	-	0.7625	76.25%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9905	99.05%

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	98.70%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.05%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.67%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.08%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.01%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.17%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.62%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.12%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.89%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.25%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	80.30%	97.79%

Plants that contains it

• Ambrosia psilostachya
• Helenium aromaticum
• Hymenoxys hoopesii
• Hymenoxys lemmonii
• Hymenoxys odorata
• Hymenoxys richardsonii

Cross-Links

• PubChem: 4617986
• LOTUS: LTS0009388
• wikiData: Q104396552