(E,4E)-4-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]pent-2-enoic acid

Details

• Internal ID: 4a6cf9d4-780b-4a75-a9c0-68a8a37d0e0b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids
• IUPAC Name: (E,4E)-4-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]pent-2-enoic acid
• SMILES (Canonical): CC(=C1C(=O)CC2C1(CCC3C2(CCC(=O)C3(C)C)C)C)C=CC(=O)O
• SMILES (Isomeric): C/C(=C/1\C(=O)C[C@@H]2[C@@]1(CC[C@@H]3[C@@]2(CCC(=O)C3(C)C)C)C)/C=C/C(=O)O
• InChI: InChI=1S/C22H30O4/c1-13(6-7-18(25)26)19-14(23)12-16-21(4)11-9-17(24)20(2,3)15(21)8-10-22(16,19)5/h6-7,15-16H,8-12H2,1-5H3,(H,25,26)/b7-6+,19-13-/t15-,16-,21-,22-/m0/s1
• InChI Key: WDZPJYXYXAWZDI-AYQQWVINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.50 g/mol
• Exact Mass: 358.21440943 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9933	99.33%
Caco-2	+	0.6943	69.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8290	82.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.8552	85.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.5919	59.19%
P-glycoprotein inhibitior	-	0.5757	57.57%
P-glycoprotein substrate	-	0.8323	83.23%
CYP3A4 substrate	+	0.5896	58.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9133	91.33%
CYP3A4 inhibition	-	0.8134	81.34%
CYP2C9 inhibition	-	0.9334	93.34%
CYP2C19 inhibition	-	0.9673	96.73%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	-	0.9071	90.71%
CYP2C8 inhibition	-	0.7365	73.65%
CYP inhibitory promiscuity	-	0.9573	95.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6480	64.80%
Eye corrosion	-	0.9960	99.60%
Eye irritation	-	0.9304	93.04%
Skin irritation	+	0.7048	70.48%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7641	76.41%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6959	69.59%
skin sensitisation	+	0.5167	51.67%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6798	67.98%
Acute Oral Toxicity (c)	III	0.6811	68.11%
Estrogen receptor binding	+	0.7343	73.43%
Androgen receptor binding	+	0.5351	53.51%
Thyroid receptor binding	+	0.7306	73.06%
Glucocorticoid receptor binding	+	0.7398	73.98%
Aromatase binding	+	0.6928	69.28%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.8526	85.26%
Biodegradation	-	0.7500	75.00%
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	94.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.34%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.90%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	85.69%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.94%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.41%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.14%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.33%	82.69%
CHEMBL5028	O14672	ADAM10	81.84%	97.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.53%	93.04%

Plants that contains it

• Scilla luciliae

Cross-Links

• PubChem: 46898025
• LOTUS: LTS0233825
• wikiData: Q105324162