3,4-Dihydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid

Details

• Internal ID: 2a9b4acd-df25-4064-a67b-96b0235e7e8e
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives
• IUPAC Name: 3,4-dihydroxy-5-(3-methylbut-2-enyl)benzoic acid
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C(=O)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)C(=O)O)O)O)C
• InChI: InChI=1S/C12H14O4/c1-7(2)3-4-8-5-9(12(15)16)6-10(13)11(8)14/h3,5-6,13-14H,4H2,1-2H3,(H,15,16)
• InChI Key: NMAKQSXJWYBYRF-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.24 g/mol
• Exact Mass: 222.08920892 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)benzoic acid
• 101330-67-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	-	0.5918	59.18%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8421	84.21%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9563	95.63%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9150	91.50%
P-glycoprotein inhibitior	-	0.9693	96.93%
P-glycoprotein substrate	-	0.9493	94.93%
CYP3A4 substrate	-	0.6993	69.93%
CYP2C9 substrate	-	0.8120	81.20%
CYP2D6 substrate	-	0.8713	87.13%
CYP3A4 inhibition	-	0.8711	87.11%
CYP2C9 inhibition	+	0.7093	70.93%
CYP2C19 inhibition	-	0.5064	50.64%
CYP2D6 inhibition	-	0.6476	64.76%
CYP1A2 inhibition	+	0.5162	51.62%
CYP2C8 inhibition	-	0.8110	81.10%
CYP inhibitory promiscuity	-	0.5906	59.06%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7230	72.30%
Carcinogenicity (trinary)	Non-required	0.7185	71.85%
Eye corrosion	-	0.9596	95.96%
Eye irritation	+	0.9772	97.72%
Skin irritation	-	0.5333	53.33%
Skin corrosion	-	0.7189	71.89%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6873	68.73%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.6597	65.97%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.6766	67.66%
Acute Oral Toxicity (c)	III	0.6544	65.44%
Estrogen receptor binding	+	0.5952	59.52%
Androgen receptor binding	-	0.5630	56.30%
Thyroid receptor binding	-	0.7088	70.88%
Glucocorticoid receptor binding	+	0.7279	72.79%
Aromatase binding	-	0.6253	62.53%
PPAR gamma	-	0.4862	48.62%
Honey bee toxicity	-	0.9724	97.24%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	97.49%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.88%	94.73%
CHEMBL3194	P02766	Transthyretin	89.96%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.90%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.56%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.28%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.74%	89.34%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.44%	94.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.70%	95.56%
CHEMBL4208	P20618	Proteasome component C5	81.86%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.15%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.13%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.91%	96.00%

Plants that contains it

• Deinandra lobbii
• Peperomia obtusifolia

Cross-Links

• PubChem: 57339269
• LOTUS: LTS0236591
• wikiData: Q103816410