2-(5,8-Dihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid

Details

• Internal ID: 7a889ae9-c303-4e90-8651-8cc0fbeccc22
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-(5,8-dihydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl)prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1C(CCC2O)(C)O)C(=C)C(=O)O
• SMILES (Isomeric): CC12CCC(CC1C(CCC2O)(C)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H24O4/c1-9(13(17)18)10-4-6-14(2)11(8-10)15(3,19)7-5-12(14)16/h10-12,16,19H,1,4-8H2,2-3H3,(H,17,18)
• InChI Key: PZBDZGWRGBSTOL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₄
• Molecular Weight: 268.35 g/mol
• Exact Mass: 268.16745924 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.5618	56.18%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8142	81.42%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.9330	93.30%
OATP1B3 inhibitior	-	0.2129	21.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6490	64.90%
BSEP inhibitior	-	0.8804	88.04%
P-glycoprotein inhibitior	-	0.9481	94.81%
P-glycoprotein substrate	-	0.8740	87.40%
CYP3A4 substrate	+	0.6250	62.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8918	89.18%
CYP3A4 inhibition	-	0.7296	72.96%
CYP2C9 inhibition	-	0.9496	94.96%
CYP2C19 inhibition	-	0.9397	93.97%
CYP2D6 inhibition	-	0.9411	94.11%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	-	0.8774	87.74%
CYP inhibitory promiscuity	-	0.9515	95.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6209	62.09%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.6597	65.97%
Skin irritation	+	0.6260	62.60%
Skin corrosion	-	0.9484	94.84%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5934	59.34%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5069	50.69%
skin sensitisation	+	0.4761	47.61%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6930	69.30%
Acute Oral Toxicity (c)	III	0.7352	73.52%
Estrogen receptor binding	+	0.8227	82.27%
Androgen receptor binding	-	0.5749	57.49%
Thyroid receptor binding	-	0.4940	49.40%
Glucocorticoid receptor binding	+	0.7112	71.12%
Aromatase binding	+	0.6205	62.05%
PPAR gamma	+	0.5648	56.48%
Honey bee toxicity	-	0.8947	89.47%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.78%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	95.21%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.90%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.07%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	87.28%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.85%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.70%	96.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.41%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.49%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.94%	91.11%

Plants that contains it

• Laggera alata

Cross-Links

• PubChem: 85100553
• LOTUS: LTS0045137
• wikiData: Q105216899