4-hydroxy-3,5-bis[(2R)-2-hydroxy-3-methylbut-3-enyl]benzoic acid

Details

• Internal ID: 5ef0bc1a-801d-41f3-b5b3-1f8859e8cfd9
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives
• IUPAC Name: 4-hydroxy-3,5-bis[(2R)-2-hydroxy-3-methylbut-3-enyl]benzoic acid
• SMILES (Canonical): CC(=C)C(CC1=CC(=CC(=C1O)CC(C(=C)C)O)C(=O)O)O
• SMILES (Isomeric): CC(=C)[C@@H](CC1=CC(=CC(=C1O)C[C@H](C(=C)C)O)C(=O)O)O
• InChI: InChI=1S/C17H22O5/c1-9(2)14(18)7-11-5-13(17(21)22)6-12(16(11)20)8-15(19)10(3)4/h5-6,14-15,18-20H,1,3,7-8H2,2,4H3,(H,21,22)/t14-,15-/m1/s1
• InChI Key: IDEXXWNBJNRLNY-HUUCEWRRSA-N
• Popularity: 0 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): 98.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.5063	50.63%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8813	88.13%
OATP2B1 inhibitior	-	0.5712	57.12%
OATP1B1 inhibitior	+	0.8946	89.46%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8297	82.97%
P-glycoprotein inhibitior	-	0.8495	84.95%
P-glycoprotein substrate	-	0.9351	93.51%
CYP3A4 substrate	-	0.6674	66.74%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	-	0.8448	84.48%
CYP3A4 inhibition	-	0.7624	76.24%
CYP2C9 inhibition	-	0.7632	76.32%
CYP2C19 inhibition	-	0.6182	61.82%
CYP2D6 inhibition	-	0.8119	81.19%
CYP1A2 inhibition	-	0.7833	78.33%
CYP2C8 inhibition	-	0.8756	87.56%
CYP inhibitory promiscuity	-	0.8083	80.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7228	72.28%
Carcinogenicity (trinary)	Non-required	0.7812	78.12%
Eye corrosion	-	0.9712	97.12%
Eye irritation	+	0.8556	85.56%
Skin irritation	-	0.6105	61.05%
Skin corrosion	-	0.9164	91.64%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	+	0.5711	57.11%
skin sensitisation	+	0.7601	76.01%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6339	63.39%
Acute Oral Toxicity (c)	III	0.7028	70.28%
Estrogen receptor binding	-	0.5256	52.56%
Androgen receptor binding	-	0.5671	56.71%
Thyroid receptor binding	+	0.5276	52.76%
Glucocorticoid receptor binding	+	0.5879	58.79%
Aromatase binding	-	0.6262	62.62%
PPAR gamma	-	0.5217	52.17%
Honey bee toxicity	-	0.9431	94.31%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.64%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.60%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.55%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.84%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.10%	94.73%
CHEMBL1811	P34995	Prostanoid EP1 receptor	84.51%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.64%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.87%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.54%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.13%	97.21%

Plants that contains it

• Piper acutifolium

Cross-Links

• PubChem: 162908643
• LOTUS: LTS0034666
• wikiData: Q105111308