2-[(2S,4S,4aS)-4-hydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: e7bd6118-76e8-4504-8553-bbce38d5d80d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2S,4S,4aS)-4-hydroxy-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=C2CC(CC(C2(CCC1)C)O)C(=C)C(=O)O
• SMILES (Isomeric): CC1=C2C[C@@H](C[C@@H]([C@]2(CCC1)C)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-9-5-4-6-15(3)12(9)7-11(8-13(15)16)10(2)14(17)18/h11,13,16H,2,4-8H2,1,3H3,(H,17,18)/t11-,13-,15-/m0/s1
• InChI Key: KDLYDQTZNOWHRN-WHOFXGATSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 2
• 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	+	0.9961	99.61%
Caco-2	+	0.7506	75.06%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.8545	85.45%
OATP1B3 inhibitior	+	0.9306	93.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5581	55.81%
BSEP inhibitior	-	0.8874	88.74%
P-glycoprotein inhibitior	-	0.9398	93.98%
P-glycoprotein substrate	-	0.9070	90.70%
CYP3A4 substrate	+	0.5719	57.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7949	79.49%
CYP2C9 inhibition	-	0.9223	92.23%
CYP2C19 inhibition	-	0.8967	89.67%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8896	88.96%
CYP2C8 inhibition	-	0.8030	80.30%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9934	99.34%
Eye irritation	+	0.5357	53.57%
Skin irritation	+	0.5831	58.31%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5954	59.54%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5678	56.78%
skin sensitisation	-	0.5368	53.68%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5967	59.67%
Acute Oral Toxicity (c)	III	0.7004	70.04%
Estrogen receptor binding	-	0.5815	58.15%
Androgen receptor binding	-	0.4856	48.56%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5484	54.84%
Aromatase binding	+	0.6067	60.67%
PPAR gamma	+	0.5600	56.00%
Honey bee toxicity	-	0.8849	88.49%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9971	99.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.14%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.53%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	85.81%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.70%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.69%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.16%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.09%	97.09%

Plants that contains it

• Ajania fruticulosa
• Artemisia biennis
• Tessaria fastigiata

Cross-Links

• PubChem: 14527143
• LOTUS: LTS0257693
• wikiData: Q105139223