3,4-Dihydroxy-5-[(S)-1,2,2-trimethylcyclopentyl]benzoic acid methyl ester

Details

• Internal ID: 945148fd-c663-406f-a51c-32c41dc7fa0d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl 3,4-dihydroxy-5-[(1S)-1,2,2-trimethylcyclopentyl]benzoate
• SMILES (Canonical): CC1(CCCC1(C)C2=C(C(=CC(=C2)C(=O)OC)O)O)C
• SMILES (Isomeric): C[C@@]1(CCCC1(C)C)C2=C(C(=CC(=C2)C(=O)OC)O)O
• InChI: InChI=1S/C16H22O4/c1-15(2)6-5-7-16(15,3)11-8-10(14(19)20-4)9-12(17)13(11)18/h8-9,17-18H,5-7H2,1-4H3/t16-/m1/s1
• InChI Key: GBHHPTZARQQNFO-MRXNPFEDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.34 g/mol
• Exact Mass: 278.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 4
• 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	+	0.9637	96.37%
Caco-2	+	0.8397	83.97%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.9108	91.08%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.7470	74.70%
OATP1B3 inhibitior	+	0.9284	92.84%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8570	85.70%
P-glycoprotein inhibitior	-	0.9103	91.03%
P-glycoprotein substrate	-	0.8311	83.11%
CYP3A4 substrate	+	0.5679	56.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8246	82.46%
CYP3A4 inhibition	-	0.6352	63.52%
CYP2C9 inhibition	+	0.5793	57.93%
CYP2C19 inhibition	-	0.6995	69.95%
CYP2D6 inhibition	-	0.8958	89.58%
CYP1A2 inhibition	-	0.6008	60.08%
CYP2C8 inhibition	-	0.7089	70.89%
CYP inhibitory promiscuity	-	0.8546	85.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7054	70.54%
Carcinogenicity (trinary)	Non-required	0.5810	58.10%
Eye corrosion	-	0.9826	98.26%
Eye irritation	+	0.7086	70.86%
Skin irritation	-	0.6449	64.49%
Skin corrosion	-	0.9408	94.08%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4894	48.94%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.5198	51.98%
skin sensitisation	-	0.8200	82.00%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8455	84.55%
Acute Oral Toxicity (c)	III	0.5461	54.61%
Estrogen receptor binding	+	0.6937	69.37%
Androgen receptor binding	+	0.5824	58.24%
Thyroid receptor binding	+	0.5154	51.54%
Glucocorticoid receptor binding	-	0.4654	46.54%
Aromatase binding	+	0.6139	61.39%
PPAR gamma	+	0.6645	66.45%
Honey bee toxicity	-	0.9519	95.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9949	99.49%

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	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.08%	96.09%
CHEMBL4208	P20618	Proteasome component C5	92.90%	90.00%
CHEMBL233	P35372	Mu opioid receptor	89.14%	97.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.05%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.52%	94.42%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.16%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.36%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.60%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.56%	90.71%
CHEMBL2535	P11166	Glucose transporter	80.60%	98.75%

Plants that contains it

• Herbertus aduncus

Cross-Links

• PubChem: 102445399
• LOTUS: LTS0227663
• wikiData: Q105005851