(1S,3aS,8R,9aS)-8-hydroxy-1,5,8-trimethyl-1,3a,4,6,7,9a-hexahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: f6b459b0-bb1e-4482-b509-bfc7b08fdf97
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1S,3aS,8R,9aS)-8-hydroxy-1,5,8-trimethyl-1,3a,4,6,7,9a-hexahydroazuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1C2C=C3C(=C(CC2OC1=O)C)CCC3(C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C=C3C(=C(C[C@@H]2OC1=O)C)CC[C@@]3(C)O
• 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/h7,9,11,13,17H,4-6H2,1-3H3/t9-,11-,13-,15+/m0/s1
• InChI Key: CGDGYZBZFFIIQO-YARBFKLUSA-N
• Popularity: 0 references 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: 0.90
• Atomic LogP (AlogP): 2.36
• 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	+	0.9950	99.50%
Caco-2	+	0.9045	90.45%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6750	67.50%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8812	88.12%
OATP1B3 inhibitior	+	0.9725	97.25%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.8979	89.79%
P-glycoprotein inhibitior	-	0.9010	90.10%
P-glycoprotein substrate	-	0.7665	76.65%
CYP3A4 substrate	+	0.5680	56.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.7366	73.66%
CYP2C9 inhibition	-	0.7870	78.70%
CYP2C19 inhibition	-	0.7217	72.17%
CYP2D6 inhibition	-	0.9443	94.43%
CYP1A2 inhibition	+	0.6421	64.21%
CYP2C8 inhibition	-	0.9110	91.10%
CYP inhibitory promiscuity	-	0.9356	93.56%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5381	53.81%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.6765	67.65%
Skin irritation	+	0.6053	60.53%
Skin corrosion	-	0.9149	91.49%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5862	58.62%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.7409	74.09%
skin sensitisation	-	0.7146	71.46%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5985	59.85%
Acute Oral Toxicity (c)	III	0.4494	44.94%
Estrogen receptor binding	-	0.6985	69.85%
Androgen receptor binding	-	0.5980	59.80%
Thyroid receptor binding	+	0.6119	61.19%
Glucocorticoid receptor binding	+	0.5972	59.72%
Aromatase binding	-	0.8377	83.77%
PPAR gamma	-	0.5692	56.92%
Honey bee toxicity	-	0.8627	86.27%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9702	97.02%

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	93.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.72%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.60%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.86%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.79%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.11%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.07%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.93%	99.23%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.93%	86.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.96%	97.25%
CHEMBL2581	P07339	Cathepsin D	82.04%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.22%	94.80%

Plants that contains it

• Artemisia absinthium

Cross-Links

• PubChem: 163044014
• LOTUS: LTS0239300
• wikiData: Q104957514