2-(4-Hydroxybenzyl)-2-butenedioic acid

Details

• Internal ID: e12afc8c-1d91-4dbb-862d-c4693a018280
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: (Z)-2-[(4-hydroxyphenyl)methyl]but-2-enedioic acid
• SMILES (Canonical): C1=CC(=CC=C1CC(=CC(=O)O)C(=O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C/C(=C/C(=O)O)/C(=O)O)O
• InChI: InChI=1S/C11H10O5/c12-9-3-1-7(2-4-9)5-8(11(15)16)6-10(13)14/h1-4,6,12H,5H2,(H,13,14)(H,15,16)/b8-6-
• InChI Key: MJCJTSKXDTXRHF-VURMDHGXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀O₅
• Molecular Weight: 222.19 g/mol
• Exact Mass: 222.05282342 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9645	96.45%
Caco-2	-	0.6208	62.08%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8972	89.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8858	88.58%
OATP1B3 inhibitior	+	0.9118	91.18%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9380	93.80%
P-glycoprotein inhibitior	-	0.9899	98.99%
P-glycoprotein substrate	-	0.9606	96.06%
CYP3A4 substrate	-	0.6715	67.15%
CYP2C9 substrate	-	0.7632	76.32%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.8634	86.34%
CYP2C9 inhibition	-	0.7465	74.65%
CYP2C19 inhibition	-	0.8234	82.34%
CYP2D6 inhibition	-	0.8997	89.97%
CYP1A2 inhibition	-	0.9138	91.38%
CYP2C8 inhibition	+	0.4622	46.22%
CYP inhibitory promiscuity	-	0.8265	82.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6357	63.57%
Carcinogenicity (trinary)	Non-required	0.6049	60.49%
Eye corrosion	-	0.9237	92.37%
Eye irritation	+	0.9845	98.45%
Skin irritation	+	0.5702	57.02%
Skin corrosion	-	0.8685	86.85%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8192	81.92%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.5678	56.78%
skin sensitisation	+	0.7151	71.51%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7130	71.30%
Acute Oral Toxicity (c)	III	0.5713	57.13%
Estrogen receptor binding	-	0.8331	83.31%
Androgen receptor binding	+	0.7695	76.95%
Thyroid receptor binding	-	0.7511	75.11%
Glucocorticoid receptor binding	+	0.6075	60.75%
Aromatase binding	-	0.6231	62.31%
PPAR gamma	+	0.6799	67.99%
Honey bee toxicity	-	0.9466	94.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9837	98.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	90.23%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.41%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.89%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.95%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.50%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.66%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.39%	94.62%

Plants that contains it

• Eschscholzia californica
• Inulanthera nuda

Cross-Links

• PubChem: 15834321
• NPASS: NPC166981
• LOTUS: LTS0227184
• wikiData: Q104667911