[(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-3a,4,5,9b-tetrahydro-3H-azuleno[4,5-b]furan-4-yl] acetate

Details

• Internal ID: c28a4fa6-685e-4ab3-b234-566552abd703
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: [(3S,3aR,4S,9aR,9bS)-9a-hydroxy-3,6,9-trimethyl-2,7-dioxo-3a,4,5,9b-tetrahydro-3H-azuleno[4,5-b]furan-4-yl] acetate
• SMILES (Canonical): CC1C2C(CC(=C3C(=O)C=C(C3(C2OC1=O)O)C)C)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2[C@H](CC(=C3C(=O)C=C([C@@]3([C@H]2OC1=O)O)C)C)OC(=O)C
• InChI: InChI=1S/C17H20O6/c1-7-5-12(22-10(4)18)13-9(3)16(20)23-15(13)17(21)8(2)6-11(19)14(7)17/h6,9,12-13,15,21H,5H2,1-4H3/t9-,12-,13+,15-,17+/m0/s1
• InChI Key: QFIKHFIONONHSR-OTHHFONVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.30 g/mol
• Exact Mass: 320.12598835 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9699	96.99%
Caco-2	+	0.5796	57.96%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6184	61.84%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9052	90.52%
OATP1B3 inhibitior	+	0.9012	90.12%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8243	82.43%
P-glycoprotein inhibitior	-	0.7460	74.60%
P-glycoprotein substrate	-	0.6398	63.98%
CYP3A4 substrate	+	0.6216	62.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9119	91.19%
CYP3A4 inhibition	-	0.7146	71.46%
CYP2C9 inhibition	-	0.8116	81.16%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.5425	54.25%
CYP2C8 inhibition	-	0.8933	89.33%
CYP inhibitory promiscuity	-	0.8809	88.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Danger	0.4070	40.70%
Eye corrosion	-	0.9728	97.28%
Eye irritation	-	0.8507	85.07%
Skin irritation	-	0.5891	58.91%
Skin corrosion	-	0.9015	90.15%
Ames mutagenesis	-	0.5619	56.19%
Human Ether-a-go-go-Related Gene inhibition	-	0.4935	49.35%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6995	69.95%
skin sensitisation	-	0.7444	74.44%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.7164	71.64%
Acute Oral Toxicity (c)	II	0.3611	36.11%
Estrogen receptor binding	+	0.6410	64.10%
Androgen receptor binding	+	0.5356	53.56%
Thyroid receptor binding	-	0.5685	56.85%
Glucocorticoid receptor binding	-	0.5161	51.61%
Aromatase binding	-	0.7037	70.37%
PPAR gamma	+	0.5423	54.23%
Honey bee toxicity	-	0.8143	81.43%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
Fish aquatic toxicity	+	0.9091	90.91%

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	95.51%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.20%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.42%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.19%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.64%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.88%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.53%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.01%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.69%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.02%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.95%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.36%	94.00%

Plants that contains it

• Achillea collina
• Annona rensoniana
• Archidendron clypearia
• Aristolochia maxima
• Bergenia purpurascens
• Betula pendula subsp. mandshurica
• Bischofia javanica
• Caragana tibetica
• Crataegus sinaica
• Discaria chacaye
• Euphorbia ferganensis
• Gardenia jasminoides
• Isodon rubescens
• Jasminum officinale
• Lasiocephalus ovatus
• Ligularia platyglossa
• Macrotyloma axillare
• Malus asiatica
• Mikania obtusata
• Montrouziera sphaeroidea
• Pimpinella saxifraga
• Polygala myrtifolia
• Polystichum deltodon
• Rhodiola stephani
• Sarcomelicope argyrophylla
• Scrophularia wattii
• Seriphidium vachanicum
• Solanum bahamense
• Tinospora smilacina
• Trigonostemon reidioides
• Tropaeolum speciosum
• Vatica diospyroides

Cross-Links

• PubChem: 76764466
• NPASS: NPC169232
• LOTUS: LTS0106239
• wikiData: Q105219557