3-(Acetyloxymethyl)-5-(5,5,8a-trimethyl-2-methylidene-7-oxo-1,3,4,4a,6,8-hexahydronaphthalen-1-yl)pent-2-enoic acid

Details

• Internal ID: 71c95843-690d-4ff2-a62b-3a400695e781
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 3-(acetyloxymethyl)-5-(5,5,8a-trimethyl-2-methylidene-7-oxo-1,3,4,4a,6,8-hexahydronaphthalen-1-yl)pent-2-enoic acid
• InChI: InChI=1S/C22H32O5/c1-14-6-9-19-21(3,4)11-17(24)12-22(19,5)18(14)8-7-16(10-20(25)26)13-27-15(2)23/h10,18-19H,1,6-9,11-13H2,2-5H3,(H,25,26)
• InChI Key: WREBBAFENCAPFB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.50 g/mol
• Exact Mass: 376.22497412 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9842	98.42%
Caco-2	-	0.5872	58.72%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8974	89.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8555	85.55%
OATP1B3 inhibitior	-	0.2180	21.80%
MATE1 inhibitior	-	0.5200	52.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8379	83.79%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7734	77.34%
CYP3A4 substrate	+	0.6530	65.30%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9141	91.41%
CYP3A4 inhibition	-	0.6600	66.00%
CYP2C9 inhibition	-	0.7861	78.61%
CYP2C19 inhibition	-	0.8440	84.40%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.7368	73.68%
CYP2C8 inhibition	+	0.5239	52.39%
CYP inhibitory promiscuity	-	0.8395	83.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6703	67.03%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8312	83.12%
Skin irritation	+	0.5155	51.55%
Skin corrosion	-	0.9749	97.49%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7804	78.04%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5824	58.24%
skin sensitisation	-	0.7019	70.19%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5224	52.24%
Acute Oral Toxicity (c)	III	0.8841	88.41%
Estrogen receptor binding	+	0.6931	69.31%
Androgen receptor binding	+	0.5738	57.38%
Thyroid receptor binding	-	0.5434	54.34%
Glucocorticoid receptor binding	+	0.7436	74.36%
Aromatase binding	+	0.6880	68.80%
PPAR gamma	-	0.5384	53.84%
Honey bee toxicity	-	0.7900	79.00%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.42%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.21%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.01%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.16%	94.45%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.22%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.94%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	84.21%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.90%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	82.78%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.87%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.71%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.37%	92.50%

Plants that contains it

• Leiocarpa semicalva

Cross-Links

• PubChem: 162885986
• LOTUS: LTS0194069
• wikiData: Q105311190