(E)-2-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-oxobut-2-enoic acid

Details

• Internal ID: 8abcc949-c0a0-445d-9f2c-28ae39ff3fa6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (E)-2-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-4-oxobut-2-enoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CC=O)C(=O)O)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC/C(=C\C=O)/C(=O)O)CCC=C2C)C
• InChI: InChI=1S/C20H30O3/c1-14-6-5-7-17-19(14,3)11-8-15(2)20(17,4)12-9-16(10-13-21)18(22)23/h6,10,13,15,17H,5,7-9,11-12H2,1-4H3,(H,22,23)/b16-10+/t15-,17+,19+,20+/m1/s1
• InChI Key: VDJGJNIZFLWFMY-MTNWJFRSSA-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: 4.80
• Atomic LogP (AlogP): 4.78
• 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	+	0.9934	99.34%
Caco-2	+	0.8551	85.51%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7068	70.68%
OATP2B1 inhibitior	-	0.8646	86.46%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	-	0.2588	25.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6111	61.11%
P-glycoprotein inhibitior	-	0.5674	56.74%
P-glycoprotein substrate	-	0.8737	87.37%
CYP3A4 substrate	+	0.5725	57.25%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.9118	91.18%
CYP3A4 inhibition	-	0.7823	78.23%
CYP2C9 inhibition	-	0.7325	73.25%
CYP2C19 inhibition	-	0.7709	77.09%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.8590	85.90%
CYP2C8 inhibition	-	0.6520	65.20%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6267	62.67%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9507	95.07%
Skin irritation	-	0.6040	60.40%
Skin corrosion	-	0.9771	97.71%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8401	84.01%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5209	52.09%
skin sensitisation	+	0.7761	77.61%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8523	85.23%
Acute Oral Toxicity (c)	III	0.6652	66.52%
Estrogen receptor binding	+	0.7640	76.40%
Androgen receptor binding	+	0.5811	58.11%
Thyroid receptor binding	+	0.7056	70.56%
Glucocorticoid receptor binding	+	0.5707	57.07%
Aromatase binding	+	0.6513	65.13%
PPAR gamma	+	0.5524	55.24%
Honey bee toxicity	-	0.9331	93.31%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.69%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.84%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.97%	97.09%
CHEMBL2581	P07339	Cathepsin D	82.72%	98.95%
CHEMBL5028	O14672	ADAM10	82.30%	97.50%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.67%	90.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.64%	100.00%

Plants that contains it

• Piscidia piscipula
• Symphyopappus reticulatus

Cross-Links

• PubChem: 162981920
• LOTUS: LTS0109741
• wikiData: Q105326573