(2Z)-2-[(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]propanoic acid

Details

• Internal ID: 2e1dfad0-e71a-4ac8-ab2c-3741c2761e36
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids
• IUPAC Name: (2Z)-2-[(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]propanoic acid
• SMILES (Canonical): CC(=C1C(=O)CC2C1(CCC3C2(CCC(=O)C3(C)C)C)C)C(=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(=O)O
• InChI: InChI=1S/C20H28O4/c1-11(17(23)24)16-12(21)10-14-19(4)9-7-15(22)18(2,3)13(19)6-8-20(14,16)5/h13-14H,6-10H2,1-5H3,(H,23,24)/b16-11+/t13-,14-,19-,20-/m0/s1
• InChI Key: XGGSQRQFHZEBIY-ZRBMVCIFSA-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: 3.30
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

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	+	0.7343	73.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8290	82.90%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8870	88.70%
OATP1B3 inhibitior	+	0.8552	85.52%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8289	82.89%
P-glycoprotein inhibitior	-	0.6498	64.98%
P-glycoprotein substrate	-	0.9030	90.30%
CYP3A4 substrate	+	0.5590	55.90%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
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	-	0.8094	80.94%
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	-	0.6834	68.34%
Skin irritation	+	0.7048	70.48%
Skin corrosion	-	0.9572	95.72%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3928	39.28%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6426	64.26%
skin sensitisation	+	0.5167	51.67%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5756	57.56%
Acute Oral Toxicity (c)	III	0.6811	68.11%
Estrogen receptor binding	+	0.7195	71.95%
Androgen receptor binding	-	0.5053	50.53%
Thyroid receptor binding	+	0.6939	69.39%
Glucocorticoid receptor binding	+	0.7745	77.45%
Aromatase binding	+	0.6660	66.60%
PPAR gamma	+	0.6823	68.23%
Honey bee toxicity	-	0.8842	88.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
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	93.99%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.40%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.26%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.02%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.89%	93.04%
CHEMBL340	P08684	Cytochrome P450 3A4	84.29%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.61%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	82.57%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.26%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162947068
• LOTUS: LTS0273344
• wikiData: Q105327594