(E)-5-[(1R,4aR,7R,8aR)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid

Details

• Internal ID: d6c5bcde-ec5c-40c5-be53-7c28b6c0ce42
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1R,4aR,7R,8aR)-7-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
• InChI: InChI=1S/C22H34O5/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/h10,17-19,24H,1,6-9,11-13H2,2-5H3,(H,25,26)/b16-10+/t17-,18-,19-,22+/m1/s1
• InChI Key: PBSVBSJTGGGHRK-IGVCDNBMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.24062418 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.11
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	-	0.5596	55.96%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8825	88.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8395	83.95%
OATP1B3 inhibitior	+	0.8257	82.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6135	61.35%
BSEP inhibitior	+	0.7624	76.24%
P-glycoprotein inhibitior	-	0.6116	61.16%
P-glycoprotein substrate	-	0.7084	70.84%
CYP3A4 substrate	+	0.6496	64.96%
CYP2C9 substrate	-	0.7828	78.28%
CYP2D6 substrate	-	0.9079	90.79%
CYP3A4 inhibition	-	0.6345	63.45%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.8994	89.94%
CYP2D6 inhibition	-	0.9205	92.05%
CYP1A2 inhibition	-	0.8399	83.99%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.8549	85.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7109	71.09%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8485	84.85%
Skin irritation	+	0.5440	54.40%
Skin corrosion	-	0.9702	97.02%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4397	43.97%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.7043	70.43%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6047	60.47%
Acute Oral Toxicity (c)	III	0.8435	84.35%
Estrogen receptor binding	+	0.7076	70.76%
Androgen receptor binding	+	0.6462	64.62%
Thyroid receptor binding	-	0.5097	50.97%
Glucocorticoid receptor binding	+	0.8004	80.04%
Aromatase binding	+	0.7258	72.58%
PPAR gamma	+	0.5818	58.18%
Honey bee toxicity	-	0.7645	76.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6755	67.55%
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	95.44%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.42%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	92.27%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.70%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.38%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	87.35%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.24%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.11%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.60%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.03%	86.33%
CHEMBL5028	O14672	ADAM10	80.88%	97.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.75%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.56%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.55%	97.09%

Plants that contains it

• Leiocarpa semicalva

Cross-Links

• PubChem: 163016536
• LOTUS: LTS0246112
• wikiData: Q105205412