(3aR,4R,5R,8S,8aR,9aS)-4,5,8-trihydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 8bcfbb18-14eb-4eed-8037-21b5bf22f6dc
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,4R,5R,8S,8aR,9aS)-4,5,8-trihydroxy-5,8-dimethyl-1-methylidene-3a,4,7,8a,9,9a-hexahydroazuleno[6,5-b]furan-2-one
• InChI: InChI=1S/C15H20O5/c1-7-8-6-10-9(4-5-14(10,2)18)15(3,19)12(16)11(8)20-13(7)17/h4,8,10-12,16,18-19H,1,5-6H2,2-3H3/t8-,10+,11+,12+,14-,15+/m0/s1
• InChI Key: VJXOJXBYJRLXQZ-HZYUEDJHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.6537	65.37%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9101	91.01%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9590	95.90%
P-glycoprotein inhibitior	-	0.9316	93.16%
P-glycoprotein substrate	-	0.8562	85.62%
CYP3A4 substrate	+	0.5718	57.18%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.6837	68.37%
CYP2C9 inhibition	-	0.7638	76.38%
CYP2C19 inhibition	-	0.6879	68.79%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.5173	51.73%
CYP2C8 inhibition	-	0.8394	83.94%
CYP inhibitory promiscuity	-	0.9652	96.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5156	51.56%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9490	94.90%
Skin irritation	-	0.5160	51.60%
Skin corrosion	-	0.9028	90.28%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7461	74.61%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.8324	83.24%
skin sensitisation	-	0.7861	78.61%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4920	49.20%
Acute Oral Toxicity (c)	II	0.2959	29.59%
Estrogen receptor binding	+	0.6527	65.27%
Androgen receptor binding	+	0.5630	56.30%
Thyroid receptor binding	+	0.6264	62.64%
Glucocorticoid receptor binding	+	0.6713	67.13%
Aromatase binding	-	0.5239	52.39%
PPAR gamma	-	0.5388	53.88%
Honey bee toxicity	-	0.7894	78.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	94.05%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.42%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.84%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	92.10%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.98%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.54%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.95%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.85%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.06%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.24%	100.00%

Plants that contains it

• Helenium autumnale

Cross-Links

• PubChem: 162907030
• LOTUS: LTS0224565
• wikiData: Q105287574