3-hydroxy-3-(hydroxymethyl)-6-methyl-9-methylidene-4,6a,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: a44fe437-cbbd-40fc-941f-18c6c3c6c7d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 3-hydroxy-3-(hydroxymethyl)-6-methyl-9-methylidene-4,6a,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2C(C3C1CCC3=C)OC(=O)C2(CO)O
• SMILES (Isomeric): CC1=CCC2C(C3C1CCC3=C)OC(=O)C2(CO)O
• InChI: InChI=1S/C15H20O4/c1-8-4-6-11-13(12-9(2)3-5-10(8)12)19-14(17)15(11,18)7-16/h4,10-13,16,18H,2-3,5-7H2,1H3
• InChI Key: ZLYAGNQILGTOEV-UHFFFAOYSA-N
• Popularity: 0 references 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: 1.20
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9448	94.48%
Caco-2	-	0.6579	65.79%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6851	68.51%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8982	89.82%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6792	67.92%
BSEP inhibitior	-	0.9345	93.45%
P-glycoprotein inhibitior	-	0.9534	95.34%
P-glycoprotein substrate	-	0.8372	83.72%
CYP3A4 substrate	+	0.5813	58.13%
CYP2C9 substrate	-	0.7799	77.99%
CYP2D6 substrate	-	0.8399	83.99%
CYP3A4 inhibition	-	0.9011	90.11%
CYP2C9 inhibition	-	0.8103	81.03%
CYP2C19 inhibition	-	0.7907	79.07%
CYP2D6 inhibition	-	0.9297	92.97%
CYP1A2 inhibition	-	0.7065	70.65%
CYP2C8 inhibition	-	0.8372	83.72%
CYP inhibitory promiscuity	-	0.9662	96.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6085	60.85%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.8004	80.04%
Skin irritation	-	0.5550	55.50%
Skin corrosion	-	0.9232	92.32%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7581	75.81%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6804	68.04%
skin sensitisation	-	0.8658	86.58%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4673	46.73%
Acute Oral Toxicity (c)	III	0.4520	45.20%
Estrogen receptor binding	-	0.6144	61.44%
Androgen receptor binding	+	0.5626	56.26%
Thyroid receptor binding	-	0.4940	49.40%
Glucocorticoid receptor binding	+	0.6260	62.60%
Aromatase binding	-	0.7656	76.56%
PPAR gamma	-	0.7290	72.90%
Honey bee toxicity	-	0.9123	91.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9252	92.52%

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	91.21%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.52%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.13%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.87%	100.00%
CHEMBL1871	P10275	Androgen Receptor	85.04%	96.43%
CHEMBL4581	P52732	Kinesin-like protein 1	83.05%	93.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.10%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.97%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.44%	99.23%

Plants that contains it

• Chresta sphaerocephala

Cross-Links

• PubChem: 162974247
• LOTUS: LTS0100640
• wikiData: Q105379280