(Z)-5-[(1R,4aR,8aS)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-3-formylpent-2-enoic acid

Details

• Internal ID: f4aae2d6-be94-42af-9f29-34099fe92047
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-5-[(1R,4aR,8aS)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-3-formylpent-2-enoic acid
• SMILES (Canonical): CC1=CC(=O)C2C(CCCC2(C1CCC(=CC(=O)O)C=O)C)(C)C
• SMILES (Isomeric): CC1=CC(=O)[C@H]2[C@]([C@@H]1CC/C(=C/C(=O)O)/C=O)(CCCC2(C)C)C
• InChI: InChI=1S/C20H28O4/c1-13-10-16(22)18-19(2,3)8-5-9-20(18,4)15(13)7-6-14(12-21)11-17(23)24/h10-12,15,18H,5-9H2,1-4H3,(H,23,24)/b14-11-/t15-,18-,20+/m1/s1
• InChI Key: VKEKGTDLIXNKKE-HVYDEHICSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.95
• 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	+	0.9873	98.73%
Caco-2	+	0.5436	54.36%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8400	84.00%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.7036	70.36%
OATP1B3 inhibitior	-	0.2727	27.27%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7204	72.04%
P-glycoprotein inhibitior	-	0.6060	60.60%
P-glycoprotein substrate	-	0.7691	76.91%
CYP3A4 substrate	+	0.6020	60.20%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9056	90.56%
CYP3A4 inhibition	-	0.7646	76.46%
CYP2C9 inhibition	-	0.8518	85.18%
CYP2C19 inhibition	-	0.9160	91.60%
CYP2D6 inhibition	-	0.9275	92.75%
CYP1A2 inhibition	-	0.8385	83.85%
CYP2C8 inhibition	-	0.6531	65.31%
CYP inhibitory promiscuity	-	0.8480	84.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7103	71.03%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.8933	89.33%
Skin irritation	+	0.6049	60.49%
Skin corrosion	-	0.9687	96.87%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6858	68.58%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5235	52.35%
skin sensitisation	+	0.5927	59.27%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8339	83.39%
Acute Oral Toxicity (c)	III	0.8771	87.71%
Estrogen receptor binding	+	0.6997	69.97%
Androgen receptor binding	+	0.5521	55.21%
Thyroid receptor binding	+	0.5451	54.51%
Glucocorticoid receptor binding	+	0.5760	57.60%
Aromatase binding	+	0.5329	53.29%
PPAR gamma	+	0.5861	58.61%
Honey bee toxicity	-	0.9382	93.82%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
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	95.70%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.97%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.05%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.12%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.73%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.17%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.42%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.11%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.02%	86.33%

Plants that contains it

• Acritopappus confertus

Cross-Links

• PubChem: 162982156
• LOTUS: LTS0168369
• wikiData: Q105287707