(3S,3aR,4S,9aS,9bR)-3,4-dihydroxy-3-(hydroxymethyl)-6,9-dimethyl-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 5e4b217c-057d-43de-b4cf-15867ab358a2
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aR,4S,9aS,9bR)-3,4-dihydroxy-3-(hydroxymethyl)-6,9-dimethyl-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• InChI: InChI=1S/C15H18O6/c1-6-4-9(18)12-13(21-14(19)15(12,20)5-16)11-7(2)3-8(17)10(6)11/h3,9,11-13,16,18,20H,4-5H2,1-2H3/t9-,11-,12+,13+,15+/m0/s1
• InChI Key: BJPCIEHNZYNRIY-IGMMHVEYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.11033829 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.52
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8761	87.61%
Caco-2	-	0.7659	76.59%
Blood Brain Barrier	+	0.5267	52.67%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6434	64.34%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9349	93.49%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8268	82.68%
P-glycoprotein inhibitior	-	0.9466	94.66%
P-glycoprotein substrate	-	0.6784	67.84%
CYP3A4 substrate	+	0.5652	56.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8980	89.80%
CYP3A4 inhibition	-	0.8906	89.06%
CYP2C9 inhibition	-	0.8225	82.25%
CYP2C19 inhibition	-	0.8634	86.34%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8076	80.76%
CYP2C8 inhibition	-	0.9269	92.69%
CYP inhibitory promiscuity	-	0.9465	94.65%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5542	55.42%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.8861	88.61%
Skin irritation	-	0.6260	62.60%
Skin corrosion	-	0.9251	92.51%
Ames mutagenesis	-	0.6291	62.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.7591	75.91%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6539	65.39%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7381	73.81%
Acute Oral Toxicity (c)	III	0.4514	45.14%
Estrogen receptor binding	-	0.5657	56.57%
Androgen receptor binding	+	0.6022	60.22%
Thyroid receptor binding	-	0.5318	53.18%
Glucocorticoid receptor binding	+	0.6820	68.20%
Aromatase binding	-	0.7965	79.65%
PPAR gamma	-	0.6890	68.90%
Honey bee toxicity	-	0.9151	91.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8287	82.87%

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	96.93%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.79%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.91%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.32%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.54%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	86.63%	90.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.59%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.56%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.54%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.90%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.48%	94.00%

Plants that contains it

• Taraxacum platycarpum

Cross-Links

• PubChem: 56930611
• LOTUS: LTS0118762
• wikiData: Q104937222