5-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylidene-4-oxopentanoic acid

Details

• Internal ID: de9d5484-950a-4418-8948-cf3ea6889156
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylidene-4-oxopentanoic acid
• SMILES (Canonical): CC1=C(C2(CCCC(C2CC1)(C)C)C)CC(=O)C(=C)CC(=O)O
• SMILES (Isomeric): CC1=C([C@@]2(CCCC([C@H]2CC1)(C)C)C)CC(=O)C(=C)CC(=O)O
• InChI: InChI=1S/C20H30O3/c1-13-7-8-17-19(3,4)9-6-10-20(17,5)15(13)12-16(21)14(2)11-18(22)23/h17H,2,6-12H2,1,3-5H3,(H,22,23)/t17-,20+/m1/s1
• InChI Key: MQAVQJCOJUUCSP-XLIONFOSSA-N
• Popularity: 1 reference 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: 4.30
• Atomic LogP (AlogP): 4.92
• H-Bond Acceptor: 2
• 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	+	0.9943	99.43%
Caco-2	+	0.5768	57.68%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7026	70.26%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.8675	86.75%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5351	53.51%
P-glycoprotein inhibitior	-	0.6907	69.07%
P-glycoprotein substrate	-	0.8434	84.34%
CYP3A4 substrate	+	0.5777	57.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.5688	56.88%
CYP2C9 inhibition	-	0.8651	86.51%
CYP2C19 inhibition	-	0.8684	86.84%
CYP2D6 inhibition	-	0.9472	94.72%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	-	0.6904	69.04%
CYP inhibitory promiscuity	-	0.8860	88.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.6906	69.06%
Eye corrosion	-	0.9907	99.07%
Eye irritation	+	0.6501	65.01%
Skin irritation	+	0.5357	53.57%
Skin corrosion	-	0.9670	96.70%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.5577	55.77%
skin sensitisation	+	0.6902	69.02%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6947	69.47%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7504	75.04%
Acute Oral Toxicity (c)	III	0.7671	76.71%
Estrogen receptor binding	-	0.5733	57.33%
Androgen receptor binding	-	0.5085	50.85%
Thyroid receptor binding	-	0.5900	59.00%
Glucocorticoid receptor binding	-	0.5450	54.50%
Aromatase binding	+	0.5658	56.58%
PPAR gamma	+	0.8338	83.38%
Honey bee toxicity	-	0.9607	96.07%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
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	92.94%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.62%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.53%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.50%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.85%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.21%	96.38%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.57%	94.33%
CHEMBL5028	O14672	ADAM10	83.37%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.22%	95.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.45%	93.03%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.50%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.01%	100.00%

Plants that contains it

• Premna oligotricha

Cross-Links

• PubChem: 14847504
• LOTUS: LTS0275473
• wikiData: Q105169856