[(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-4-hydroxypent-3-enoate

Details

• Internal ID: d1666b45-93cc-4909-ac5a-b06dc6ff6f58
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: [(4S,4aR,5S,8aR)-3,4a,5-trimethyl-9-oxo-4,5,6,7,8,8a-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-4-hydroxypent-3-enoate
• InChI: InChI=1S/C20H26O5/c1-11-10-24-18-16(11)19(25-15(22)9-8-13(3)21)20(4)12(2)6-5-7-14(20)17(18)23/h8,10,12,14,19,21H,5-7,9H2,1-4H3/b13-8-/t12-,14-,19+,20+/m0/s1
• InChI Key: GTBPCZMOJPRRIW-HBYOXYBFSA-N
• Popularity: 2 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): 76.70 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.8404	84.04%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7487	74.87%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8321	83.21%
OATP1B3 inhibitior	-	0.5805	58.05%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.4494	44.94%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8026	80.26%
CYP3A4 substrate	+	0.6352	63.52%
CYP2C9 substrate	+	0.6173	61.73%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	-	0.7464	74.64%
CYP2C9 inhibition	-	0.7683	76.83%
CYP2C19 inhibition	-	0.7822	78.22%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	+	0.5266	52.66%
CYP2C8 inhibition	+	0.4608	46.08%
CYP inhibitory promiscuity	-	0.7848	78.48%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5784	57.84%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9490	94.90%
Skin irritation	-	0.5988	59.88%
Skin corrosion	-	0.9108	91.08%
Ames mutagenesis	-	0.5318	53.18%
Human Ether-a-go-go-Related Gene inhibition	+	0.6821	68.21%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5589	55.89%
skin sensitisation	-	0.8310	83.10%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8329	83.29%
Acute Oral Toxicity (c)	IV	0.3526	35.26%
Estrogen receptor binding	+	0.6908	69.08%
Androgen receptor binding	+	0.6887	68.87%
Thyroid receptor binding	-	0.5522	55.22%
Glucocorticoid receptor binding	+	0.7980	79.80%
Aromatase binding	+	0.6493	64.93%
PPAR gamma	+	0.6484	64.84%
Honey bee toxicity	-	0.8429	84.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	97.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.00%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.72%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.10%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.78%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.22%	90.17%
CHEMBL5255	O00206	Toll-like receptor 4	86.94%	92.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.90%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.36%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.69%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.56%	99.23%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.92%	90.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.45%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.18%	89.00%

Plants that contains it

• Senecio rosmarinifolius

Cross-Links

• PubChem: 163188850
• LOTUS: LTS0205363
• wikiData: Q105018408