(3aR,5S,8R,8aR,9aR)-8-hydroxy-5,8-dimethyl-1-methylidene-4,5,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one

Details

• Internal ID: 5c2e4a8d-6340-4320-9ca2-82c5601ccb83
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,5S,8R,8aR,9aR)-8-hydroxy-5,8-dimethyl-1-methylidene-4,5,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CC2C(CC3C1=CCC3(C)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H](C[C@@H]3C1=CC[C@@]3(C)O)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h4,8,11-13,17H,2,5-7H2,1,3H3/t8-,11+,12+,13+,15+/m0/s1
• InChI Key: XRMJVTYQUFNCJQ-RPMKOLLGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.21
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.7450	74.50%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6121	61.21%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.8965	89.65%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9450	94.50%
P-glycoprotein inhibitior	-	0.9227	92.27%
P-glycoprotein substrate	-	0.8809	88.09%
CYP3A4 substrate	+	0.5677	56.77%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.7165	71.65%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.8494	84.94%
CYP2D6 inhibition	-	0.9506	95.06%
CYP1A2 inhibition	-	0.6158	61.58%
CYP2C8 inhibition	-	0.8588	85.88%
CYP inhibitory promiscuity	-	0.9565	95.65%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5306	53.06%
Eye corrosion	-	0.9775	97.75%
Eye irritation	-	0.7168	71.68%
Skin irritation	-	0.5243	52.43%
Skin corrosion	-	0.9024	90.24%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7574	75.74%
skin sensitisation	-	0.5901	59.01%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4872	48.72%
Acute Oral Toxicity (c)	III	0.4601	46.01%
Estrogen receptor binding	+	0.6467	64.67%
Androgen receptor binding	-	0.5376	53.76%
Thyroid receptor binding	+	0.5920	59.20%
Glucocorticoid receptor binding	+	0.6781	67.81%
Aromatase binding	-	0.6866	68.66%
PPAR gamma	+	0.5468	54.68%
Honey bee toxicity	-	0.8726	87.26%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9896	98.96%

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	96.37%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.37%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.31%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.73%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.28%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.33%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	84.62%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.72%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.02%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.59%	99.23%

Plants that contains it

• Pulicaria sicula
• Pulicaria undulata subsp. undulata

Cross-Links

• PubChem: 14021502
• LOTUS: LTS0154814
• wikiData: Q105340599