(E)-5-[(1S,4aS,7R,8aS)-7-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 6b6f4c4e-c225-44b2-b287-c13f3c3d3475
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1S,4aS,7R,8aS)-7-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• InChI: InChI=1S/C22H34O4/c1-14(11-20(24)25)7-9-18-15(2)8-10-19-21(4,5)12-17(26-16(3)23)13-22(18,19)6/h11,17-19H,2,7-10,12-13H2,1,3-6H3,(H,24,25)/b14-11+/t17-,18+,19+,22-/m1/s1
• InChI Key: VMWOMELLRUSCGH-HMPFRBTMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.24570956 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.14
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	+	0.5305	53.05%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8449	84.49%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.8630	86.30%
OATP1B3 inhibitior	-	0.4497	44.97%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.4648	46.48%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.7777	77.77%
CYP3A4 substrate	+	0.6334	63.34%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.9167	91.67%
CYP3A4 inhibition	-	0.5337	53.37%
CYP2C9 inhibition	-	0.8720	87.20%
CYP2C19 inhibition	-	0.8717	87.17%
CYP2D6 inhibition	-	0.9445	94.45%
CYP1A2 inhibition	-	0.7987	79.87%
CYP2C8 inhibition	+	0.5274	52.74%
CYP inhibitory promiscuity	-	0.8642	86.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.7100	71.00%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.8448	84.48%
Skin irritation	+	0.5884	58.84%
Skin corrosion	-	0.9707	97.07%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3612	36.12%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6976	69.76%
skin sensitisation	-	0.5650	56.50%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.5605	56.05%
Acute Oral Toxicity (c)	III	0.8832	88.32%
Estrogen receptor binding	+	0.8099	80.99%
Androgen receptor binding	+	0.6571	65.71%
Thyroid receptor binding	+	0.6437	64.37%
Glucocorticoid receptor binding	+	0.6941	69.41%
Aromatase binding	+	0.6825	68.25%
PPAR gamma	+	0.6697	66.97%
Honey bee toxicity	-	0.7958	79.58%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5855	58.55%
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	96.84%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.71%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.07%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.88%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	86.90%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.97%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.74%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.32%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.87%	94.33%
CHEMBL2061	P19793	Retinoid X receptor alpha	80.73%	91.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.43%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.31%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	80.17%	83.82%

Plants that contains it

• Nolana filifolia

Cross-Links

• PubChem: 14108837
• LOTUS: LTS0261532
• wikiData: Q105289347