(E)-5-[(1R,2S,4aR,8aR)-1,2,4a,5-tetramethyl-3-oxo-4,7,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: ecba56d1-248d-4f3a-820b-acfef79aab5b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (E)-5-[(1R,2S,4aR,8aR)-1,2,4a,5-tetramethyl-3-oxo-4,7,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid
• SMILES (Canonical): CC1C(=O)CC2(C(C1(C)CCC(=CC(=O)O)C)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1C(=O)C[C@@]2([C@@H]([C@@]1(C)CC/C(=C/C(=O)O)/C)CCC=C2C)C
• InChI: InChI=1S/C20H30O3/c1-13(11-18(22)23)9-10-19(4)15(3)16(21)12-20(5)14(2)7-6-8-17(19)20/h7,11,15,17H,6,8-10,12H2,1-5H3,(H,22,23)/b13-11+/t15-,17-,19+,20+/m1/s1
• InChI Key: HWCYFTKMERSBHI-ULXLJDAISA-N
• Popularity: 0 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: 4.60
• 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	+	0.9925	99.25%
Caco-2	+	0.7544	75.44%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8097	80.97%
OATP2B1 inhibitior	-	0.8647	86.47%
OATP1B1 inhibitior	+	0.8854	88.54%
OATP1B3 inhibitior	+	0.9295	92.95%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6001	60.01%
P-glycoprotein inhibitior	-	0.5974	59.74%
P-glycoprotein substrate	-	0.7644	76.44%
CYP3A4 substrate	+	0.5998	59.98%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.6840	68.40%
CYP2C9 inhibition	-	0.9254	92.54%
CYP2C19 inhibition	-	0.9032	90.32%
CYP2D6 inhibition	-	0.9460	94.60%
CYP1A2 inhibition	-	0.8702	87.02%
CYP2C8 inhibition	-	0.6850	68.50%
CYP inhibitory promiscuity	-	0.8927	89.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6172	61.72%
Eye corrosion	-	0.9957	99.57%
Eye irritation	-	0.9042	90.42%
Skin irritation	+	0.6660	66.60%
Skin corrosion	-	0.9625	96.25%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8231	82.31%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5071	50.71%
skin sensitisation	-	0.5360	53.60%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.8519	85.19%
Estrogen receptor binding	+	0.5989	59.89%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	+	0.7165	71.65%
Glucocorticoid receptor binding	+	0.6251	62.51%
Aromatase binding	+	0.6401	64.01%
PPAR gamma	+	0.7414	74.14%
Honey bee toxicity	-	0.9018	90.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	97.60%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.89%	83.82%
CHEMBL2581	P07339	Cathepsin D	90.12%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.34%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.93%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.18%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.79%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.25%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.19%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.53%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.16%	86.33%

Plants that contains it

• Pulicaria aucheri

Cross-Links

• PubChem: 10881695
• LOTUS: LTS0208664
• wikiData: Q105034606