(2S)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid

Details

• Internal ID: c535f287-413c-4796-9fc6-cd0f3ecff17d
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: (2S)-2-hydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid
• SMILES (Canonical): C1=CC(=CC=C1CC(CC(=O)O)(C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C[C@](CC(=O)O)(C(=O)O)O)O
• InChI: InChI=1S/C11H12O6/c12-8-3-1-7(2-4-8)5-11(17,10(15)16)6-9(13)14/h1-4,12,17H,5-6H2,(H,13,14)(H,15,16)/t11-/m0/s1
• InChI Key: XLGKDRSWPCQYAB-NSHDSACASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₂O₆
• Molecular Weight: 240.21 g/mol
• Exact Mass: 240.06338810 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.23
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6694	66.94%
Caco-2	-	0.7224	72.24%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7105	71.05%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.8970	89.70%
OATP1B3 inhibitior	+	0.9569	95.69%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9242	92.42%
P-glycoprotein inhibitior	-	0.9887	98.87%
P-glycoprotein substrate	-	0.9541	95.41%
CYP3A4 substrate	-	0.6703	67.03%
CYP2C9 substrate	+	0.8006	80.06%
CYP2D6 substrate	-	0.8226	82.26%
CYP3A4 inhibition	-	0.8364	83.64%
CYP2C9 inhibition	-	0.9734	97.34%
CYP2C19 inhibition	-	0.9655	96.55%
CYP2D6 inhibition	-	0.9496	94.96%
CYP1A2 inhibition	-	0.9738	97.38%
CYP2C8 inhibition	-	0.7947	79.47%
CYP inhibitory promiscuity	-	0.9909	99.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8270	82.70%
Carcinogenicity (trinary)	Non-required	0.6564	65.64%
Eye corrosion	-	0.9799	97.99%
Eye irritation	+	0.8902	89.02%
Skin irritation	+	0.5250	52.50%
Skin corrosion	-	0.8498	84.98%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8836	88.36%
Micronuclear	+	0.6477	64.77%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.5969	59.69%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7681	76.81%
Acute Oral Toxicity (c)	III	0.8097	80.97%
Estrogen receptor binding	-	0.7797	77.97%
Androgen receptor binding	+	0.5238	52.38%
Thyroid receptor binding	-	0.8033	80.33%
Glucocorticoid receptor binding	-	0.5736	57.36%
Aromatase binding	-	0.6705	67.05%
PPAR gamma	+	0.6627	66.27%
Honey bee toxicity	-	0.9235	92.35%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.7226	72.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.06%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.97%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.26%	91.11%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.56%	90.93%
CHEMBL2535	P11166	Glucose transporter	82.17%	98.75%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.84%	85.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.66%	83.82%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.58%	95.50%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.77%	94.97%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.38%	95.56%

Plants that contains it

• Prosthechea michuacana

Cross-Links

• PubChem: 25243507
• LOTUS: LTS0086370
• wikiData: Q76534017