(1R,3aR,5S,5aR,9aR)-5a-hydroxy-1,5,8-trimethyl-3a,4,5,6,9,9a-hexahydro-1H-azuleno[6,5-b]furan-2,7-dione

Details

• Internal ID: 7553088a-7fdd-48d8-98b5-ad7db0b520de
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1R,3aR,5S,5aR,9aR)-5a-hydroxy-1,5,8-trimethyl-3a,4,5,6,9,9a-hexahydro-1H-azuleno[6,5-b]furan-2,7-dione
• SMILES (Canonical): CC1CC2C(CC3=C(C(=O)CC13O)C)C(C(=O)O2)C
• SMILES (Isomeric): C[C@H]1C[C@@H]2[C@H](CC3=C(C(=O)C[C@@]13O)C)[C@H](C(=O)O2)C
• InChI: InChI=1S/C15H20O4/c1-7-4-13-10(8(2)14(17)19-13)5-11-9(3)12(16)6-15(7,11)18/h7-8,10,13,18H,4-6H2,1-3H3/t7-,8+,10+,13+,15+/m0/s1
• InChI Key: GLHITFKRBRXLBN-BZBOMAMASA-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): 63.60 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 4
• 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	+	0.9939	99.39%
Caco-2	+	0.7821	78.21%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6434	64.34%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9295	92.95%
OATP1B3 inhibitior	+	0.9379	93.79%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9052	90.52%
P-glycoprotein inhibitior	-	0.8879	88.79%
P-glycoprotein substrate	-	0.7761	77.61%
CYP3A4 substrate	+	0.5450	54.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9043	90.43%
CYP3A4 inhibition	-	0.7642	76.42%
CYP2C9 inhibition	-	0.8395	83.95%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9704	97.04%
CYP1A2 inhibition	-	0.6560	65.60%
CYP2C8 inhibition	-	0.9345	93.45%
CYP inhibitory promiscuity	-	0.9804	98.04%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5135	51.35%
Eye corrosion	-	0.9804	98.04%
Eye irritation	-	0.8533	85.33%
Skin irritation	+	0.5369	53.69%
Skin corrosion	-	0.9020	90.20%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4931	49.31%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5709	57.09%
skin sensitisation	-	0.7662	76.62%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6640	66.40%
Acute Oral Toxicity (c)	II	0.4324	43.24%
Estrogen receptor binding	-	0.6537	65.37%
Androgen receptor binding	-	0.4900	49.00%
Thyroid receptor binding	-	0.5570	55.70%
Glucocorticoid receptor binding	-	0.6609	66.09%
Aromatase binding	-	0.8444	84.44%
PPAR gamma	-	0.5406	54.06%
Honey bee toxicity	-	0.8273	82.73%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9857	98.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.61%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.50%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.78%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	86.94%	97.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.40%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.65%	93.04%
CHEMBL1902	P62942	FK506-binding protein 1A	83.25%	97.05%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.14%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.12%	89.00%

Plants that contains it

• Stevia achalensis

Cross-Links

• PubChem: 162886184
• LOTUS: LTS0113455
• wikiData: Q105010927