(9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 3f7c7e30-8fc0-459f-a1d3-b4eed8bf624e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (9-methyl-3,6-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl) 4-hydroxy-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC1=CCC2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)CO3
• SMILES (Isomeric): CC1=CCC2C1C3C(C(CC2=C)OC(=O)C(=CCO)CO)C(=C)CO3
• InChI: InChI=1S/C20H26O5/c1-11-4-5-15-12(2)8-16(25-20(23)14(9-22)6-7-21)18-13(3)10-24-19(18)17(11)15/h4,6,15-19,21-22H,2-3,5,7-10H2,1H3
• InChI Key: UQQBRVPVFILOGY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.40 g/mol
• Exact Mass: 346.17802393 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.92
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9599	95.99%
Caco-2	+	0.4905	49.05%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5357	53.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8941	89.41%
OATP1B3 inhibitior	+	0.9543	95.43%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5312	53.12%
P-glycoprotein inhibitior	-	0.6009	60.09%
P-glycoprotein substrate	-	0.6705	67.05%
CYP3A4 substrate	+	0.6258	62.58%
CYP2C9 substrate	-	0.6085	60.85%
CYP2D6 substrate	-	0.8797	87.97%
CYP3A4 inhibition	-	0.8057	80.57%
CYP2C9 inhibition	-	0.8428	84.28%
CYP2C19 inhibition	-	0.7377	73.77%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	-	0.6455	64.55%
CYP2C8 inhibition	-	0.7264	72.64%
CYP inhibitory promiscuity	-	0.7614	76.14%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6691	66.91%
Eye corrosion	-	0.9673	96.73%
Eye irritation	-	0.8258	82.58%
Skin irritation	-	0.7156	71.56%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6589	65.89%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.7915	79.15%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6298	62.98%
Acute Oral Toxicity (c)	III	0.4673	46.73%
Estrogen receptor binding	+	0.6973	69.73%
Androgen receptor binding	+	0.6177	61.77%
Thyroid receptor binding	+	0.5471	54.71%
Glucocorticoid receptor binding	+	0.5389	53.89%
Aromatase binding	+	0.6438	64.38%
PPAR gamma	+	0.5476	54.76%
Honey bee toxicity	-	0.7151	71.51%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9441	94.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.76%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.21%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.33%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.85%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.67%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.33%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.16%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.80%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.60%	95.56%

Plants that contains it

• Stevia alpina

Cross-Links

• PubChem: 162962483
• LOTUS: LTS0102758
• wikiData: Q105277393