(+-)-4-Hydroxymandelic acid

Details

• Internal ID: ffef8b04-f5f7-4c66-96dd-6bde5184c508
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: 2-hydroxy-2-(4-hydroxyphenyl)acetic acid
• InChI: InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)
• InChI Key: YHXHKYRQLYQUIH-UHFFFAOYSA-N
• Popularity: 139 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15 g/mol
• Exact Mass: 168.04225873 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 2-hydroxy-2-(4-hydroxyphenyl)acetic acid
• 4-Hydroxymandelic acid
• 4-Hydroxy-DL-mandelic acid
• (RS)-p-Hydroxymandelic acid
• HV52GS53BA
• CHEBI:16388
• 2-(4-Hydroxyphenyl)-2-hydroxyacetic acid
• alpha,4-Dihydroxybenzeneacetic acid
• (+-)-4-Hydroxymandelic acid
• 4-HMA
• para-hydroxymandelic acid
• RefChem:905499
• 214-839-7
• 230-569-2
• pisolithin B
• 4-Hydroxyphenylglycolic acid
• p-Hydroxymandelic acid
• DL-4-Hydroxymandelic acid
• Hydroxy(4-hydroxyphenyl)acetic acid
• Benzeneacetic acid, alpha,4-dihydroxy-
• Mandelic acid, p-hydroxy-
• MFCD00004234
• DL-p-Hydroxymandelic acid
• p-Hydroxyphenylglycolic acid
• DL-p-Hydroxyphenylglycolic acid
• 4-Hydroxymandelic Acid Hydrate
• p-Hydroxymandelate
• p-hydroxy-Mandelate
• EINECS 214-839-7
• DL-p-Hydroxymandelate
• DL-4-Hydroxymandelate
• parahydroxymandelic acid
• p-Hydroxyphenylglycolate
• delta-p-hydroxymandelate
• p-hydroxy-Mandelic acid
• 4-Hydroxyphenylglycolate
• 4-Hydroxy-DL-mandelate
• 4-hydroxy-mandelic acid
• Benzeneacetic acid, .alpha.,4-dihydroxy-
• delta-4-hydroxymandelate
• 4'-Hydroxymandelic acid
• (RS)-p-Hydroxymandelate
• 2-(4'-hydroxyphenyl)-2-hydroxyethanoic acid
• DL-p-Hydroxyphenylglycolate
• UNII-HV52GS53BA
• (+-)-p-Hydroxymandelic acid
• SCHEMBL352555
• alpha,4-Dihydroxybenzeneacetate
• racemic parahydroxymandelic acid
• AC1Q76K5
• AC1Q76K6
• orb1301943
• p-Hydroxymandelic acid (PHMA)
• (+/-)-4-hydroxymandelic acid
• alpha,4-dihydroxy-Benzeneacetate
• CHEMBL2087618
• DTXSID70862596
• alpha,4-dihydroxy-Benzeneacetic acid
• Benzeneacetic acid, ?,4-dihydroxy-
• EINECS 230-569-2
• SBB065018
• .alpha.,4-Dihydroxybenzeneacetic acid
• Benzeneacetic acid, |A,4-dihydroxy-
• 2-(4-Hydroxyphenyl)-2-hydroxyacetate
• AKOS009156762
• DL-alpha,4-Dihydroxyphenylacetic Acid
• (+/-)-P-HYDROXYMANDELIC ACID
• FH66217
• (+/-)-alpha,4-dihydroxy-Benzeneacetate
• 2-hydroxy-2-(4-hydroxyphenyl)aceticacid
• (+-)-alpha,4-Dihydroxybenzeneacetic acid
• AC-19775
• AK-88708
• DS-18506
• SY113769
• HY-113027
• (+/-)-alpha,4-dihydroxy-Benzeneacetic acid
• CS-0059383
• H0660
• NS00014743
• ST50406742
• 2-(4-hydroxyphenyl)-2-oxidanyl-ethanoic acid
• D95528
• EN300-204954
• A837374
• AE-562/40848536
• F209478
• I01-6699
• I01-9207
• (+/-)-.ALPHA.,4-DIHYDROXYBENZENEACETIC ACID
• Q10395570

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9595	95.95%
Caco-2	-	0.5291	52.91%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8562	85.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9234	92.34%
OATP1B3 inhibitior	+	0.9542	95.42%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9647	96.47%
P-glycoprotein inhibitior	-	0.9897	98.97%
P-glycoprotein substrate	-	0.9748	97.48%
CYP3A4 substrate	-	0.7870	78.70%
CYP2C9 substrate	+	0.6027	60.27%
CYP2D6 substrate	-	0.8212	82.12%
CYP3A4 inhibition	-	0.9263	92.63%
CYP2C9 inhibition	-	0.9672	96.72%
CYP2C19 inhibition	-	0.9837	98.37%
CYP2D6 inhibition	-	0.9762	97.62%
CYP1A2 inhibition	-	0.9564	95.64%
CYP2C8 inhibition	-	0.9552	95.52%
CYP inhibitory promiscuity	-	0.9742	97.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7078	70.78%
Carcinogenicity (trinary)	Non-required	0.5992	59.92%
Eye corrosion	-	0.6388	63.88%
Eye irritation	+	0.9964	99.64%
Skin irritation	+	0.8575	85.75%
Skin corrosion	-	0.7220	72.20%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9245	92.45%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	+	0.6451	64.51%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	-	0.6771	67.71%
Acute Oral Toxicity (c)	III	0.5152	51.52%
Estrogen receptor binding	-	0.8780	87.80%
Androgen receptor binding	-	0.5584	55.84%
Thyroid receptor binding	-	0.6425	64.25%
Glucocorticoid receptor binding	-	0.8365	83.65%
Aromatase binding	-	0.8792	87.92%
PPAR gamma	-	0.5380	53.80%
Honey bee toxicity	-	0.9130	91.30%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	+	0.8784	87.84%

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	89.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.60%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.36%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.22%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.60%	94.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.82%	94.45%
CHEMBL4208	P20618	Proteasome component C5	81.50%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.10%	99.17%

Plants that contains it

• Citrus × aurantium
• Citrus × aurantium nothof. deliciosa

Cross-Links

• PubChem: 328
• NPASS: NPC137123