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

Details

• Internal ID: edf0b7db-f77d-4e7b-a593-a0af43a5360a
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,5R,8aS,9R,9aR)-9-hydroxy-5,6-dimethyl-1-methylidene-4,5,8,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2,7-dione
• InChI: InChI=1S/C15H18O4/c1-6-4-11-13(8(3)15(18)19-11)14(17)9-5-10(16)7(2)12(6)9/h6,9,11,13-14,17H,3-5H2,1-2H3/t6-,9+,11-,13+,14-/m1/s1
• InChI Key: GGHIIBMYRQUBKR-ZGQVTLAZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.39
• 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	+	0.9865	98.65%
Caco-2	+	0.4913	49.13%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6274	62.74%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.8820	88.20%
OATP1B3 inhibitior	+	0.8950	89.50%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9379	93.79%
P-glycoprotein inhibitior	-	0.9067	90.67%
P-glycoprotein substrate	-	0.8504	85.04%
CYP3A4 substrate	+	0.5381	53.81%
CYP2C9 substrate	-	0.7791	77.91%
CYP2D6 substrate	-	0.8897	88.97%
CYP3A4 inhibition	-	0.7924	79.24%
CYP2C9 inhibition	-	0.8188	81.88%
CYP2C19 inhibition	-	0.8264	82.64%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.5296	52.96%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	-	0.9493	94.93%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5864	58.64%
Eye corrosion	-	0.9640	96.40%
Eye irritation	-	0.8137	81.37%
Skin irritation	-	0.5656	56.56%
Skin corrosion	-	0.8811	88.11%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6045	60.45%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7471	74.71%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7036	70.36%
Acute Oral Toxicity (c)	II	0.5744	57.44%
Estrogen receptor binding	-	0.5797	57.97%
Androgen receptor binding	+	0.5587	55.87%
Thyroid receptor binding	-	0.6680	66.80%
Glucocorticoid receptor binding	-	0.5611	56.11%
Aromatase binding	-	0.8270	82.70%
PPAR gamma	-	0.6462	64.62%
Honey bee toxicity	-	0.8138	81.38%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9909	99.09%

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	96.05%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.38%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.56%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.63%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.46%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.36%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.62%	86.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.08%	93.03%

Plants that contains it

• Helenium mexicanum

Cross-Links

• PubChem: 163084526
• LOTUS: LTS0243197
• wikiData: Q105008092