(2E,4E)-3-methyl-5-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoic acid

Details

• Internal ID: 33624018-ccf3-4e34-9af7-f05dee377751
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2E,4E)-3-methyl-5-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]penta-2,4-dienoic acid
• SMILES (Canonical): CC(=CC(=O)O)C=CC1(C(C(CCC1(C)O)O)(C)C)O
• SMILES (Isomeric): C/C(=C\C(=O)O)/C=C/[C@@]1([C@](CC[C@@H](C1(C)C)O)(C)O)O
• InChI: InChI=1S/C15H24O5/c1-10(9-12(17)18)5-8-15(20)13(2,3)11(16)6-7-14(15,4)19/h5,8-9,11,16,19-20H,6-7H2,1-4H3,(H,17,18)/b8-5+,10-9+/t11-,14+,15+/m0/s1
• InChI Key: REBVVIXEBBWIHO-DNWRCJROSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₅
• Molecular Weight: 284.35 g/mol
• Exact Mass: 284.16237386 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.24
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9232	92.32%
Caco-2	-	0.5661	56.61%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7535	75.35%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9316	93.16%
OATP1B3 inhibitior	+	0.8784	87.84%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6329	63.29%
P-glycoprotein inhibitior	-	0.9728	97.28%
P-glycoprotein substrate	-	0.8632	86.32%
CYP3A4 substrate	+	0.6129	61.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9009	90.09%
CYP3A4 inhibition	-	0.9042	90.42%
CYP2C9 inhibition	-	0.7374	73.74%
CYP2C19 inhibition	-	0.8132	81.32%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	-	0.8780	87.80%
CYP2C8 inhibition	-	0.9029	90.29%
CYP inhibitory promiscuity	-	0.9602	96.02%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6470	64.70%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8043	80.43%
Skin irritation	+	0.5724	57.24%
Skin corrosion	-	0.8975	89.75%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7444	74.44%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	+	0.4757	47.57%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7025	70.25%
Acute Oral Toxicity (c)	III	0.5604	56.04%
Estrogen receptor binding	+	0.7395	73.95%
Androgen receptor binding	-	0.5357	53.57%
Thyroid receptor binding	+	0.6363	63.63%
Glucocorticoid receptor binding	+	0.6306	63.06%
Aromatase binding	+	0.6609	66.09%
PPAR gamma	+	0.7195	71.95%
Honey bee toxicity	-	0.8312	83.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9339	93.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2061	P19793	Retinoid X receptor alpha	96.19%	91.67%
CHEMBL221	P23219	Cyclooxygenase-1	94.52%	90.17%
CHEMBL1870	P28702	Retinoid X receptor beta	93.15%	95.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	92.43%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.01%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.12%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.64%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.10%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	85.08%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.25%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.00%	89.00%

Plants that contains it

• Rehmannia glutinosa

Cross-Links

• PubChem: 15693862
• NPASS: NPC176523
• LOTUS: LTS0069383
• wikiData: Q104398683