(r)-Mandelic acid

Details

• Internal ID: 2ef5cd29-5073-4499-a64d-6f3257348f77
• Taxonomy: Benzenoids > Benzene and substituted derivatives
• IUPAC Name: (2R)-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-/m1/s1
• InChI Key: IWYDHOAUDWTVEP-SSDOTTSWSA-N
• Popularity: 314 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

• (r)-mandelic acid
• (R)-2-Hydroxy-2-phenylacetic acid
• D-Mandelic acid
• (-)-Mandelic acid
• D(-)-Mandelic acid
• Mandelic acid, (R)-
• D-2-Phenylglycolic acid
• (-)-(R)-Mandelic acid
• (R)-alpha-Hydroxyphenylacetic acid
• (R)-alpha-Hydroxybenzeneacetic acid
• Mandelic acid, D-
• (-)-alpha-Hydroxyphenylacetic acid
• PPL7YW1M9W
• CHEBI:17656
• RefChem:905564
• 210-276-6
• (R)-(-)-Mandelic acid
• D-(-)-MANDELIC ACID
• (2R)-2-hydroxy-2-phenylacetic acid
• MFCD00064251
• R-(-)-Mandelic acid
• (R)-Mandelsaeure
• (R)-A-Hydroxyphenylacetic acid
• CHEMBL292411
• DTXSID4046523
• (2R)-hydroxy(phenyl)acetic acid
• (2R)-hydroxy(phenyl)ethanoic acid
• mandelic_acid
• (2R)-2-hydroxy-2-phenyl-acetic acid
• R(-)-Mandelic Acid
• mandelic-acid
• RMN
• (2R)-Hydroxyphenylacetic Acid ((R)-Mandelic Acid)
• DTXCID2026523
• (R)-Hydroxy(phenyl)acetic acid
• Sertraline EP Impurity E
• (R)-(-)-Amygdalic Acid
• CAS-611-71-2
• (-)-D-MANDELIC ACID
• Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-
• UNII-PPL7YW1M9W
• (L)-(+)-Mandelic acid
• 1mcz
• 1mdl
• L-2-Hydroxy-2-phenylacetic acid
• (-)-mandelate
• NCGC00166022-01
• d - mandelic acid
• EINECS 210-276-6
• D-2-Phenylglycolate
• Sertraline impurity E
• (-)-(R)-Mandelate
• (r)(-)-mandelic acid
• Benzeneacetic acid, alpha-hydroxy-, (-)-
• Maybridge1_004148
• (r)-(-) mandelic acid
• (R)-(+)-mandelic acid
• (R)-a-Hydroxyphenylacetate
• (R)-Hydroxyphenylaceticacid
• Benzeneacetic acid, alpha-hydroxy-, (alphaR)-
• (-)-a-Hydroxyphenylacetate
• (R)-a-Hydroxybenzeneacetate
• Hydroxy-phenyl-acetate anion
• (R)-(-)- mandelic acid
• (r)-(-)-d-mandelic acid
• Oprea1_502663
• cid_11914
• SCHEMBL165161
• (-)-alpha-Hydroxyphenylacetate
• (R)-alpha-Hydroxyphenylacetate
• orb1304715
• (-)-a-Hydroxyphenylacetic acid
• (R)-alpha-Hydroxybenzeneacetate
• (R)-a-Hydroxybenzeneacetic acid
• SCHEMBL29777368
• BDBM16421
• HMS553E14
• HY-Y0585R
• D,L-mandelic acid redetermination
• Hydroxy-Phenyl-Acetic Acid Anion
• D-(-)-Mandelic acid (Standard)
• HMS3650C13
• (R)-(-)-Mandelic acid, 98%
• HY-Y0585
• STR08136
• Tox21_112292
• s9003
• (2R)-HYDROXYPHENYLACETIC ACID
• AKOS005256699
• Tox21_112292_1
• AC-2490
• CCG-266220
• CS-W020074
• DB02280
• FM25007
• (-)-(R)alpha-hydroxybenzeneacetic acid
• (-)-(R) alpha-hydroxybenzeneacetic acid
• MSK163406-1000M
• NCGC00166022-02
• SY001645
• Benzeneacetic acid, alpha-hydroxy-, (R)-
• M0662
• NS00098847
• (R)-.ALPHA.-HYDROXYBENZENEACETIC ACID
• 11M712
• C01983
• D70151
• EN300-100159
• MLS-0090888.0001
• D-(-)-Mandelic acid, purum, >=98.0% (T)
• D-(-)-Mandelic acid, puriss., >=99.0% (T)
• F093732
• SR-01000946767
• (R)-(-)-Mandelic acid, ReagentPlus(R), >=99%
• (R)-Mandelic acid Solution in Methanol, 1000ug/mL
• SR-01000946767-1
• Q63390533
• (R)-(-)-Mandelic acid, Vetec(TM) reagent grade, 98%
• F1905-7046
• SERTRALINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
• Z1255390767
• 08C65DF7-6DDF-44B3-9490-02A43D9D33C1
• (R)-(-)-Mandelic acid, ChiPros(R), produced by BASF, 99%
• Sertraline impurity E, European Pharmacopoeia (EP) Reference Standard
• (R)-a-Hydroxy-benzeneacetic acid;(R)-2-Hydroxy-2-phenylacetic acid;(R)-2-Phenylglycolic acid

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 maximowiczii
• Prunus myrtifolia

Cross-Links

• PubChem: 11914
• NPASS: NPC210529
• LOTUS: LTS0016833
• wikiData: Q63390533