(3aS,5aS,7S,8aR,9aR)-7,8a-dihydroxy-1,5,8-trimethylidene-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one

Details

• Internal ID: dda135f6-7ca7-414a-b9d4-72b1aa1cfcba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5aS,7S,8aR,9aR)-7,8a-dihydroxy-1,5,8-trimethylidene-4,5a,6,7,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one
• InChI: InChI=1S/C15H18O4/c1-7-4-13-10(8(2)14(17)19-13)6-15(18)9(3)12(16)5-11(7)15/h10-13,16,18H,1-6H2/t10-,11+,12+,13+,15+/m1/s1
• InChI Key: SBAZJIWQCOBVQK-MCZMQQNQSA-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): 66.80 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9522	95.22%
Caco-2	-	0.7903	79.03%
Blood Brain Barrier	-	0.5973	59.73%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5205	52.05%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9022	90.22%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9642	96.42%
P-glycoprotein inhibitior	-	0.9237	92.37%
P-glycoprotein substrate	-	0.8273	82.73%
CYP3A4 substrate	+	0.5531	55.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8173	81.73%
CYP3A4 inhibition	-	0.9056	90.56%
CYP2C9 inhibition	-	0.8908	89.08%
CYP2C19 inhibition	-	0.8276	82.76%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	-	0.8325	83.25%
CYP2C8 inhibition	-	0.8882	88.82%
CYP inhibitory promiscuity	-	0.9353	93.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Non-required	0.5416	54.16%
Eye corrosion	-	0.9638	96.38%
Eye irritation	-	0.5370	53.70%
Skin irritation	-	0.6278	62.78%
Skin corrosion	-	0.9078	90.78%
Ames mutagenesis	-	0.5070	50.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6805	68.05%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	+	0.8199	81.99%
skin sensitisation	-	0.7658	76.58%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.7618	76.18%
Acute Oral Toxicity (c)	III	0.3829	38.29%
Estrogen receptor binding	+	0.7581	75.81%
Androgen receptor binding	+	0.5741	57.41%
Thyroid receptor binding	-	0.5149	51.49%
Glucocorticoid receptor binding	+	0.7333	73.33%
Aromatase binding	-	0.5481	54.81%
PPAR gamma	-	0.5112	51.12%
Honey bee toxicity	-	0.7097	70.97%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9321	93.21%

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	96.50%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.07%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	89.28%	98.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.96%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.51%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.35%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.76%	99.23%
CHEMBL217	P14416	Dopamine D2 receptor	81.10%	95.62%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 162937900
• LOTUS: LTS0105443
• wikiData: Q105249294