2-[(2S,4aS)-4a,8-dimethyl-4-oxo-1,2,3,5,6,7-hexahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 9eb6d467-6add-4098-9b91-5984c8ab2967
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2S,4aS)-4a,8-dimethyl-4-oxo-1,2,3,5,6,7-hexahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=C2CC(CC(=O)C2(CCC1)C)C(=C)C(=O)O
• SMILES (Isomeric): CC1=C2C[C@@H](CC(=O)[C@]2(CCC1)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H20O3/c1-9-5-4-6-15(3)12(9)7-11(8-13(15)16)10(2)14(17)18/h11H,2,4-8H2,1,3H3,(H,17,18)/t11-,15-/m0/s1
• InChI Key: NDUKUJGEYDDPGK-NHYWBVRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 2
• 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	+	0.9929	99.29%
Caco-2	+	0.7661	76.61%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8352	83.52%
OATP2B1 inhibitior	-	0.8507	85.07%
OATP1B1 inhibitior	+	0.8423	84.23%
OATP1B3 inhibitior	+	0.9109	91.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.7919	79.19%
P-glycoprotein inhibitior	-	0.9066	90.66%
P-glycoprotein substrate	-	0.9351	93.51%
CYP3A4 substrate	+	0.5307	53.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.7249	72.49%
CYP2C9 inhibition	-	0.9167	91.67%
CYP2C19 inhibition	-	0.9066	90.66%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.7173	71.73%
CYP2C8 inhibition	-	0.8852	88.52%
CYP inhibitory promiscuity	-	0.9467	94.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5509	55.09%
Eye corrosion	-	0.9931	99.31%
Eye irritation	+	0.5527	55.27%
Skin irritation	+	0.6281	62.81%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6265	62.65%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.6676	66.76%
skin sensitisation	-	0.5547	55.47%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6691	66.91%
Acute Oral Toxicity (c)	III	0.8152	81.52%
Estrogen receptor binding	-	0.6617	66.17%
Androgen receptor binding	-	0.5176	51.76%
Thyroid receptor binding	-	0.6153	61.53%
Glucocorticoid receptor binding	-	0.6036	60.36%
Aromatase binding	-	0.4915	49.15%
PPAR gamma	+	0.5554	55.54%
Honey bee toxicity	-	0.9392	93.92%
Biodegradation	-	0.7000	70.00%
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
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.93%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.56%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.46%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.49%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.39%	97.25%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.14%	93.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.13%	95.50%
CHEMBL1902	P62942	FK506-binding protein 1A	81.94%	97.05%

Plants that contains it

• Artemisia biennis
• Tessaria fastigiata

Cross-Links

• PubChem: 13855808
• LOTUS: LTS0058001
• wikiData: Q105177721