4-hydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid

Details

• Internal ID: 8683e266-b5f8-4313-9186-28503d3c9f50
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 4-hydroxy-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid
• SMILES (Canonical): CC(=CCCC(=CCCC(=CCC1=C(C=CC(=C1)C(=O)O)O)C)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC/C(=C/CC1=C(C=CC(=C1)C(=O)O)O)/C)/C)C
• InChI: InChI=1S/C22H30O3/c1-16(2)7-5-8-17(3)9-6-10-18(4)11-12-19-15-20(22(24)25)13-14-21(19)23/h7,9,11,13-15,23H,5-6,8,10,12H2,1-4H3,(H,24,25)/b17-9+,18-11+
• InChI Key: QUYGEGSOVYMIEU-XURGJTJWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.50 g/mol
• Exact Mass: 342.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 6.05
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• SCHEMBL8009478

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.4910	49.10%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8972	89.72%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9127	91.27%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7836	78.36%
P-glycoprotein inhibitior	-	0.5136	51.36%
P-glycoprotein substrate	-	0.9234	92.34%
CYP3A4 substrate	-	0.6322	63.22%
CYP2C9 substrate	-	0.8151	81.51%
CYP2D6 substrate	-	0.8712	87.12%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.5292	52.92%
CYP2C19 inhibition	+	0.5515	55.15%
CYP2D6 inhibition	-	0.8063	80.63%
CYP1A2 inhibition	+	0.6967	69.67%
CYP2C8 inhibition	-	0.6716	67.16%
CYP inhibitory promiscuity	-	0.5563	55.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7477	74.77%
Carcinogenicity (trinary)	Non-required	0.6891	68.91%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.6270	62.70%
Skin irritation	-	0.6992	69.92%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6473	64.73%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	+	0.6662	66.62%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5555	55.55%
Acute Oral Toxicity (c)	III	0.5998	59.98%
Estrogen receptor binding	+	0.7794	77.94%
Androgen receptor binding	+	0.5246	52.46%
Thyroid receptor binding	+	0.7039	70.39%
Glucocorticoid receptor binding	+	0.6978	69.78%
Aromatase binding	+	0.5694	56.94%
PPAR gamma	+	0.8768	87.68%
Honey bee toxicity	-	0.9447	94.47%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7700	77.00%
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
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	96.66%	92.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.66%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.60%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.21%	94.73%
CHEMBL2581	P07339	Cathepsin D	90.48%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.07%	86.33%
CHEMBL3194	P02766	Transthyretin	88.17%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.79%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.49%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.06%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.74%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.21%	96.09%

Plants that contains it

• Ferula kuhistanica
• Phacelia pedicellata
• Piper auritum
• Piper marginatum
• Piper obliquum

Cross-Links

• PubChem: 10914851
• LOTUS: LTS0007089
• wikiData: Q105228499