(2Z)-2-[(3S,4aR,8R,8aS)-3-hydroxy-3-methoxy-8,8a-dimethyl-7-oxo-1,4,4a,8-tetrahydronaphthalen-2-ylidene]propanoic acid

Details

• Internal ID: 6be39384-51a9-4281-9d73-5fbfe68b1273
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (2Z)-2-[(3S,4aR,8R,8aS)-3-hydroxy-3-methoxy-8,8a-dimethyl-7-oxo-1,4,4a,8-tetrahydronaphthalen-2-ylidene]propanoic acid
• SMILES (Canonical): CC1C(=O)C=CC2C1(CC(=C(C)C(=O)O)C(C2)(O)OC)C
• SMILES (Isomeric): C[C@H]1C(=O)C=C[C@@H]2[C@@]1(C/C(=C(\C)/C(=O)O)/[C@@](C2)(O)OC)C
• InChI: InChI=1S/C16H22O5/c1-9(14(18)19)12-8-15(3)10(2)13(17)6-5-11(15)7-16(12,20)21-4/h5-6,10-11,20H,7-8H2,1-4H3,(H,18,19)/b12-9-/t10-,11-,15+,16-/m0/s1
• InChI Key: UHHGRWMKYDCKAJ-IYOVNXGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.34 g/mol
• Exact Mass: 294.14672380 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.91
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.5664	56.64%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7808	78.08%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9167	91.67%
OATP1B3 inhibitior	+	0.8217	82.17%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5866	58.66%
P-glycoprotein inhibitior	-	0.9121	91.21%
P-glycoprotein substrate	-	0.7479	74.79%
CYP3A4 substrate	+	0.6190	61.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9068	90.68%
CYP3A4 inhibition	-	0.6230	62.30%
CYP2C9 inhibition	-	0.8942	89.42%
CYP2C19 inhibition	-	0.9303	93.03%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.8601	86.01%
CYP2C8 inhibition	-	0.8664	86.64%
CYP inhibitory promiscuity	-	0.9210	92.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9156	91.56%
Carcinogenicity (trinary)	Non-required	0.5983	59.83%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9353	93.53%
Skin irritation	-	0.5456	54.56%
Skin corrosion	-	0.9608	96.08%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3971	39.71%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5544	55.44%
skin sensitisation	-	0.6682	66.82%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5788	57.88%
Acute Oral Toxicity (c)	III	0.6135	61.35%
Estrogen receptor binding	-	0.6768	67.68%
Androgen receptor binding	+	0.5582	55.82%
Thyroid receptor binding	-	0.5502	55.02%
Glucocorticoid receptor binding	-	0.7419	74.19%
Aromatase binding	-	0.7248	72.48%
PPAR gamma	-	0.6593	65.93%
Honey bee toxicity	-	0.8653	86.53%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	95.87%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.66%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.82%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.77%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.08%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.01%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.94%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	83.21%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.83%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.45%	90.00%

Plants that contains it

• Senecio pseudoorientalis

Cross-Links

• PubChem: 163190558
• LOTUS: LTS0004060
• wikiData: Q105272883