Geranyl gallate

Details

• Internal ID: 136e524f-eb3c-4abc-b5e4-5d87fc376c9b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives > Galloyl esters
• IUPAC Name: [(2E)-3,7-dimethylocta-2,6-dienyl] 3,4,5-trihydroxybenzoate
• SMILES (Canonical): CC(=CCCC(=CCOC(=O)C1=CC(=C(C(=C1)O)O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/COC(=O)C1=CC(=C(C(=C1)O)O)O)/C)C
• InChI: InChI=1S/C17H22O5/c1-11(2)5-4-6-12(3)7-8-22-17(21)13-9-14(18)16(20)15(19)10-13/h5,7,9-10,18-20H,4,6,8H2,1-3H3/b12-7+
• InChI Key: MSJJHLNDRMIKET-KPKJPENVSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• CHEMBL85907
• SCHEMBL4742151
• SCHEMBL4742152
• BDBM50093878
• 3,4,5-Trihydroxy-benzoic acid (E)-3,7-dimethyl-octa-2,6-dienyl ester
• 3,4,5-Trihydroxybenzoic acid (E)-3,7-dimethyl-2,6-octadienyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	+	0.5636	56.36%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.9058	90.58%
OATP2B1 inhibitior	-	0.7180	71.80%
OATP1B1 inhibitior	+	0.8027	80.27%
OATP1B3 inhibitior	+	0.8959	89.59%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5128	51.28%
P-glycoprotein inhibitior	-	0.8231	82.31%
P-glycoprotein substrate	-	0.9374	93.74%
CYP3A4 substrate	-	0.5346	53.46%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8185	81.85%
CYP3A4 inhibition	-	0.6648	66.48%
CYP2C9 inhibition	+	0.5589	55.89%
CYP2C19 inhibition	+	0.5909	59.09%
CYP2D6 inhibition	-	0.7883	78.83%
CYP1A2 inhibition	+	0.7906	79.06%
CYP2C8 inhibition	-	0.6535	65.35%
CYP inhibitory promiscuity	-	0.7360	73.60%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8023	80.23%
Carcinogenicity (trinary)	Non-required	0.7102	71.02%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.5299	52.99%
Skin irritation	-	0.7809	78.09%
Skin corrosion	-	0.9683	96.83%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4035	40.35%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5715	57.15%
skin sensitisation	+	0.6461	64.61%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.7573	75.73%
Acute Oral Toxicity (c)	III	0.6597	65.97%
Estrogen receptor binding	+	0.8581	85.81%
Androgen receptor binding	+	0.7270	72.70%
Thyroid receptor binding	+	0.5411	54.11%
Glucocorticoid receptor binding	+	0.7917	79.17%
Aromatase binding	+	0.7401	74.01%
PPAR gamma	+	0.8262	82.62%
Honey bee toxicity	-	0.9344	93.44%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.16%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.78%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	91.99%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.78%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.96%	98.95%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.92%	92.08%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.04%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.59%	94.45%
CHEMBL4208	P20618	Proteasome component C5	81.29%	90.00%
CHEMBL3194	P02766	Transthyretin	81.10%	90.71%

Plants that contains it

• Sargentodoxa cuneata

Cross-Links

• PubChem: 10946694
• NPASS: NPC18646
• ChEMBL: CHEMBL85907