[(4S,4aR,5R,6S)-6-hydroxy-3,4a,5-trimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 35a2d215-349f-4717-a8e3-bf8e4c7225cf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aR,5R,6S)-6-hydroxy-3,4a,5-trimethyl-9-oxo-4,5,6,7-tetrahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
• InChI: InChI=1S/C20H24O5/c1-6-10(2)19(23)25-18-15-11(3)9-24-17(15)16(22)13-7-8-14(21)12(4)20(13,18)5/h6-7,9,12,14,18,21H,8H2,1-5H3/b10-6-/t12-,14-,18+,20+/m0/s1
• InChI Key: RSSZMBALEANRPG-RHRVENRLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.8413	84.13%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6932	69.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8769	87.69%
OATP1B3 inhibitior	+	0.8811	88.11%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7739	77.39%
P-glycoprotein inhibitior	-	0.5890	58.90%
P-glycoprotein substrate	-	0.6173	61.73%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.6718	67.18%
CYP2C9 inhibition	-	0.7819	78.19%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.8992	89.92%
CYP1A2 inhibition	+	0.5200	52.00%
CYP2C8 inhibition	-	0.7611	76.11%
CYP inhibitory promiscuity	-	0.7306	73.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4481	44.81%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9740	97.40%
Skin irritation	-	0.5761	57.61%
Skin corrosion	-	0.9247	92.47%
Ames mutagenesis	-	0.5654	56.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7688	76.88%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.7174	71.74%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6658	66.58%
Acute Oral Toxicity (c)	III	0.4353	43.53%
Estrogen receptor binding	+	0.7408	74.08%
Androgen receptor binding	+	0.6358	63.58%
Thyroid receptor binding	+	0.5632	56.32%
Glucocorticoid receptor binding	+	0.6376	63.76%
Aromatase binding	+	0.6762	67.62%
PPAR gamma	+	0.7084	70.84%
Honey bee toxicity	-	0.6849	68.49%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9853	98.53%

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	98.42%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.94%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.49%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.83%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.44%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.40%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.06%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.80%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.25%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.00%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.10%	95.50%

Plants that contains it

• Euryops spathaceus

Cross-Links

• PubChem: 101596882
• LOTUS: LTS0004389
• wikiData: Q105244860