[(5R,6S)-6-hydroxy-9-methoxy-3,5-dimethyl-5,6-dihydrobenzo[f][1]benzofuran-4-yl]methyl (Z)-2-methylbut-2-enoate

Details

• Internal ID: 9f14f705-02f9-44bf-a1ec-d89a56fe2d71
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(5R,6S)-6-hydroxy-9-methoxy-3,5-dimethyl-5,6-dihydrobenzo[f][1]benzofuran-4-yl]methyl (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C21H24O5/c1-6-11(2)21(23)26-10-15-17-12(3)9-25-20(17)19(24-5)14-7-8-16(22)13(4)18(14)15/h6-9,13,16,22H,10H2,1-5H3/b11-6-/t13-,16-/m0/s1
• InChI Key: HZKKUYMQQTYDGZ-HMEXKSLASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.40 g/mol
• Exact Mass: 356.16237386 g/mol
• Topological Polar Surface Area (TPSA): 68.90 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.25
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.7585	75.85%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7718	77.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8212	82.12%
OATP1B3 inhibitior	+	0.9000	90.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8786	87.86%
P-glycoprotein inhibitior	-	0.4894	48.94%
P-glycoprotein substrate	-	0.7168	71.68%
CYP3A4 substrate	+	0.6151	61.51%
CYP2C9 substrate	-	0.8035	80.35%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	+	0.7265	72.65%
CYP2C9 inhibition	+	0.8816	88.16%
CYP2C19 inhibition	+	0.8857	88.57%
CYP2D6 inhibition	-	0.8052	80.52%
CYP1A2 inhibition	+	0.8865	88.65%
CYP2C8 inhibition	+	0.5548	55.48%
CYP inhibitory promiscuity	+	0.9305	93.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9410	94.10%
Carcinogenicity (trinary)	Non-required	0.4892	48.92%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8859	88.59%
Skin irritation	-	0.7870	78.70%
Skin corrosion	-	0.9747	97.47%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5234	52.34%
Micronuclear	+	0.6218	62.18%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7044	70.44%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8765	87.65%
Acute Oral Toxicity (c)	III	0.5119	51.19%
Estrogen receptor binding	+	0.7079	70.79%
Androgen receptor binding	+	0.5976	59.76%
Thyroid receptor binding	+	0.5645	56.45%
Glucocorticoid receptor binding	+	0.6700	67.00%
Aromatase binding	+	0.5485	54.85%
PPAR gamma	+	0.6463	64.63%
Honey bee toxicity	-	0.6933	69.33%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	95.27%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.57%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.10%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.05%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.51%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.57%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.51%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.37%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	83.28%	94.73%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.37%	85.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	81.86%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.54%	93.00%

Plants that contains it

• Senecio macrospermus

Cross-Links

• PubChem: 101596867
• LOTUS: LTS0023906
• wikiData: Q105035723