5-[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 50958fc7-fdbf-458d-b293-2d438af3d6d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCC(=O)C2(C)C)C
• SMILES (Isomeric): CC(=CC(=O)O)CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC(=O)C2(C)C)C
• InChI: InChI=1S/C20H30O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h12,15-16H,2,6-11H2,1,3-5H3,(H,22,23)/t15-,16-,20+/m0/s1
• InChI Key: HZIPQMQRBXJVNO-TWOQFEAHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.7824	78.24%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8238	82.38%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.8471	84.71%
OATP1B3 inhibitior	-	0.2473	24.73%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.5578	55.78%
P-glycoprotein inhibitior	-	0.6016	60.16%
P-glycoprotein substrate	-	0.8171	81.71%
CYP3A4 substrate	+	0.5962	59.62%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.6381	63.81%
CYP2C9 inhibition	-	0.8798	87.98%
CYP2C19 inhibition	-	0.8362	83.62%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.8771	87.71%
CYP2C8 inhibition	-	0.6630	66.30%
CYP inhibitory promiscuity	-	0.8803	88.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6678	66.78%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.6694	66.94%
Skin irritation	+	0.6021	60.21%
Skin corrosion	-	0.9593	95.93%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8306	83.06%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	+	0.5700	57.00%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6033	60.33%
Acute Oral Toxicity (c)	III	0.8632	86.32%
Estrogen receptor binding	+	0.6468	64.68%
Androgen receptor binding	+	0.6474	64.74%
Thyroid receptor binding	+	0.6186	61.86%
Glucocorticoid receptor binding	+	0.6699	66.99%
Aromatase binding	+	0.6024	60.24%
PPAR gamma	+	0.6728	67.28%
Honey bee toxicity	-	0.8674	86.74%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	98.31%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.19%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	84.80%	90.17%
CHEMBL2581	P07339	Cathepsin D	83.99%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.40%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.81%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.58%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	81.50%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.31%	82.69%
CHEMBL2061	P19793	Retinoid X receptor alpha	81.12%	91.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.87%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.33%	100.00%

Plants that contains it

• Callicarpa macrophylla

Cross-Links

• PubChem: 163006207
• LOTUS: LTS0254531
• wikiData: Q105216617