(S)-Mandelic acid

Details

• Internal ID: cbb8743b-9326-4f50-a1ec-93fc8af7fea4
• Taxonomy: Benzenoids > Benzene and substituted derivatives
• IUPAC Name: (2S)-2-hydroxy-2-phenylacetic acid
• SMILES (Canonical): C1=CC=C(C=C1)C(C(=O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)[C@@H](C(=O)O)O
• InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
• InChI Key: IWYDHOAUDWTVEP-ZETCQYMHSA-N
• Popularity: 224 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15 g/mol
• Exact Mass: 152.047344113 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• (S)-(+)-Mandelic acid
• (S)-Mandelic acid
• L-mandelic acid
• (S)-2-Hydroxy-2-phenylacetic acid
• (2S)-2-hydroxy-2-phenylacetic acid
• S-(+)-Mandelic acid
• L-(+)-MANDELIC ACID
• Mandelic acid, (S)-
• Mandelic acid, L-
• l(+)-mandelic acid
• D-2-Hydroxy-2-phenylacetic acid
• UNII-L0UMW58G3T
• L0UMW58G3T
• (S)-(+)-Mandelic acid, 98% e.e.
• CHEMBL58910
• MLS000069517
• CHEBI:32800
• (S)-alpha-Hydroxyphenylacetic acid
• (S)-alpha-hydroxybenzeneacetic acid
• EINECS 241-240-8
• Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-
• (S)-A-HYDROXYPHENYLACETIC ACID
• alpha-Hydroxybenzeneacetic acid, (S)-
• SMR000058582
• MFCD00004495
• Benzeneacetic acid, alpha-hydroxy-, (alphaS)-
• EC 241-240-8
• (2S)-2-Hydroxy-2-phenylacetic Acid (L-Mandelic Acid)
• DL-Amygdalic Acid
• SMN
• (S)-(+)-Mandelic acid, ReagentPlus(R), >=99%
• alpha-hydroxybenzeneacetate
• Amygdalate
• Paramandelate
• Phenylglycolate
• s-mandelic acid
• DL-Amygdalate
• (S)-Hydroxy-phenyl-acetic acid
• DL-Mandelate
• 2-Phenylglycolate
• (RS)-Mandelate
• (S)-Mandelsaeure
• Phenylhydroxyacetate
• a-Hydroxy-a-toluate
• a-Hydroxyphenylacetate
• L-(+)mandelic acid
• a-Hydroxybenzeneacetate
• Benzeneacetic acid, .alpha.-hydroxy-, (S)-
• (S)-L-Mandelic acid
• Opera_ID_622
• a-Hydroxy-a-toluic acid
• (s)(+)-mandelic acid
• alpha-Hydroxyphenylacetate
• a-Hydroxyphenylacetic acid
• Mandelic acid, L-()-
• DL-Hydroxy(phenyl)acetate
• (+)-(s)-mandelic acid
• a-Hydroxybenzeneacetic acid
• 2-Phenyl-2-hydroxyacetate
• (S)-hydroxyphenylaceticacid
• alpha-Hydroxy-alpha-toluate
• cid_1292
• (S)-(+)-Amygdalic Acid
• 2-Hydroxy-2-phenylethanoate
• (S)--(+)--mandelic acid
• SCHEMBL255601
• cid_439616
• BDBM16420
• IWYDHOAUDWTVEP-ZETCQYMHSA-N
• (2s)-hydroxy(phenyl)ethanoic acid
• DTXSID301014792
• HMS2233J03
• CS-D1423
• STR07719
• AKOS006343440
• AKOS007930623
• AC-2496
• DB03357
• Benzeneacetic acid, ?-hydroxy-, (S)-
• Benzeneacetic acid, alpha-hydroxy-, (S)-
• AM20050159
• M0661
• (+)-.ALPHA.-HYDROXYPHENYLACETIC ACID
• EN300-97210
• C01984
• MLS-0090889.0001
• L-(+)-Mandelic acid, purum, >=98.0% (T)
• J-520416
• Q-201693
• Q27096314
• (S)-(+)-Mandelic acid, Vetec(TM) reagent grade, 99%
• Z1201618616
• ATOMOXETINE HYDROCHLORIDE IMPURITY E [ EP IMPURITY]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9689	96.89%
Caco-2	+	0.6197	61.97%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8285	82.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9750	97.50%
OATP1B3 inhibitior	+	0.9587	95.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9524	95.24%
P-glycoprotein inhibitior	-	0.9895	98.95%
P-glycoprotein substrate	-	0.9934	99.34%
CYP3A4 substrate	-	0.8211	82.11%
CYP2C9 substrate	+	0.8062	80.62%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	-	0.9729	97.29%
CYP2C9 inhibition	-	0.8957	89.57%
CYP2C19 inhibition	-	0.9812	98.12%
CYP2D6 inhibition	-	0.9730	97.30%
CYP1A2 inhibition	-	0.9456	94.56%
CYP2C8 inhibition	-	0.9932	99.32%
CYP inhibitory promiscuity	-	0.9714	97.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6078	60.78%
Carcinogenicity (trinary)	Non-required	0.6808	68.08%
Eye corrosion	+	0.4750	47.50%
Eye irritation	+	0.9931	99.31%
Skin irritation	+	0.9066	90.66%
Skin corrosion	-	0.6069	60.69%
Ames mutagenesis	-	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9492	94.92%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	+	0.7563	75.63%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.7778	77.78%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.7731	77.31%
Acute Oral Toxicity (c)	III	0.6497	64.97%
Estrogen receptor binding	-	0.9488	94.88%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.7662	76.62%
Glucocorticoid receptor binding	-	0.8275	82.75%
Aromatase binding	-	0.8826	88.26%
PPAR gamma	-	0.5279	52.79%
Honey bee toxicity	-	0.9242	92.42%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.7703	77.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	90.92%	90.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.59%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.53%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.97%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.56%	96.09%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.03%	93.81%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.97%	94.23%

Plants that contains it

• Aloe africana
• Aloe ferox
• Aloe spicata
• Aloe vera
• Pogostemon cablin
• Prunus zippeliana

Cross-Links

• PubChem: 439616
• NPASS: NPC175852
• ChEMBL: CHEMBL58910
• LOTUS: LTS0141331
• wikiData: Q27096314