(5S,5aS,8R,8aS)-5,8a-dihydroxy-1,5,8-trimethyl-6,7,8,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one

Details

• Internal ID: bcb27635-c82a-4190-8fe4-4e1f56ea7278
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (5S,5aS,8R,8aS)-5,8a-dihydroxy-1,5,8-trimethyl-6,7,8,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one
• SMILES (Canonical): CC1CCC2C1(CC3=C(C(=O)OC3=CC2(C)O)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@H]2[C@@]1(CC3=C(C(=O)OC3=C[C@]2(C)O)C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-12-14(3,17)7-11-10(6-15(8,12)18)9(2)13(16)19-11/h7-8,12,17-18H,4-6H2,1-3H3/t8-,12+,14+,15+/m1/s1
• InChI Key: GWHGITGZQCFTQM-QATIJOQPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.68
• 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	+	0.9783	97.83%
Caco-2	+	0.7419	74.19%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5830	58.30%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9201	92.01%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	-	0.9049	90.49%
P-glycoprotein inhibitior	-	0.9265	92.65%
P-glycoprotein substrate	-	0.8923	89.23%
CYP3A4 substrate	+	0.5620	56.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	-	0.7511	75.11%
CYP2C9 inhibition	-	0.7349	73.49%
CYP2C19 inhibition	-	0.7777	77.77%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	+	0.6519	65.19%
CYP2C8 inhibition	-	0.8533	85.33%
CYP inhibitory promiscuity	-	0.9253	92.53%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5273	52.73%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8833	88.33%
Skin irritation	+	0.5728	57.28%
Skin corrosion	-	0.9118	91.18%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4271	42.71%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5333	53.33%
skin sensitisation	-	0.8102	81.02%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6914	69.14%
Acute Oral Toxicity (c)	II	0.3558	35.58%
Estrogen receptor binding	+	0.5636	56.36%
Androgen receptor binding	-	0.5475	54.75%
Thyroid receptor binding	+	0.6958	69.58%
Glucocorticoid receptor binding	-	0.4647	46.47%
Aromatase binding	-	0.7189	71.89%
PPAR gamma	+	0.5876	58.76%
Honey bee toxicity	-	0.9286	92.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9686	96.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.56%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.20%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.12%	97.25%
CHEMBL240	Q12809	HERG	86.93%	89.76%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.14%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	85.16%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.33%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.10%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.56%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.40%	82.69%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.90%	86.00%

Plants that contains it

• Curcuma phaeocaulis

Cross-Links

• PubChem: 71725780
• NPASS: NPC471185
• ChEMBL: CHEMBL2386507
• LOTUS: LTS0047348
• wikiData: Q105022370