Vanillylmandelic acid

Details

• Internal ID: 36f068c6-e859-48b9-9b5c-37b13fac7eb2
• Taxonomy: Benzenoids > Phenols > Methoxyphenols
• IUPAC Name: 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C(C(=O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(C(=O)O)O)O
• InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
• InChI Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N
• Popularity: 4,168 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.17 g/mol
• Exact Mass: 198.05282342 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 55-10-7
• dl-4-Hydroxy-3-methoxymandelic acid
• 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
• 4-HYDROXY-3-METHOXYMANDELIC ACID
• 2394-20-9
• Vanilmandelic acid
• DL-vanillylmandelic acid
• (+/-)-Vanillylmandelic acid
• VMA
• DL-vanillomandelic acid
• Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
• Mandelic acid, 4-hydroxy-3-methoxy-
• Benzeneacetic acid, .alpha.,4-dihydroxy-3-methoxy-
• UNII-0DQI268449
• CHEBI:20106
• 3-methoxy-4-hydroxymandelic acid
• Benzeneacetic acid, alpha,4-dihydroxy-3-methoxy-
• Vanillomandelic acid
• 3-Methoxy-4-hydroxymandelate
• EINECS 200-224-0
• dl-3-Methoxy-4-hydroxymandelic acid
• Vanillinmandelic Acid
• 0DQI268449
• 4-Hydroxy-3-methoxy-DL-mandelic acid
• (4-Hydroxy-3-methoxyphenyl)glycolic acid
• 3-Methoxy-4-hydroxyphenylhydroxyacetic acid
• 53587-34-1
• DL-4-HYDROXY-3-METHOXYMANDELIC-2-D1 ACID
• Benzeneacetic acid, a,4-dihydroxy-3-methoxy-, (A+/-)-
• 4'-Hydroxy-3'-methoxymandelic acid
• alpha,4-Dihydroxy-3-methoxybenzeneacetic acid
• Vanillomandelc acid
• MFCD00004235
• (y)-Vanillylmandelic acid
• Benzeneacetic acid, ?,4-dihydroxy-3-methoxy-
• (?)-Vanillylmandelic acid
• D0D8XF
• Lopac0_000602
• Oprea1_553862
• MLS002153465
• 4-hydroxy-3-methoxymandelsyre
• SCHEMBL134326
• (.+/-.)-Vanilmandelic acid
• GTPL6645
• VANILMANDELIC ACID [MI]
• CHEMBL1256396
• FEMA NO. 4660
• SCHEMBL10085823
• DTXSID10861583
• HMS2235H06
• HMS3261J06
• HMS3371D20
• (+/-)-VANILMANDELIC ACID
• BCP33203
• Tox21_500602
• STL558222
• 4-hydroxy-3-methoxyphenylglycolic acid
• AKOS015851906
• CCG-204691
• LP00602
• SDCCGSBI-0050584.P002
• NCGC00015492-02
• NCGC00015492-03
• NCGC00015492-04
• NCGC00015492-05
• NCGC00015492-07
• NCGC00093978-01
• NCGC00093978-02
• NCGC00093978-03
• NCGC00261287-01
• AS-62192
• SMR001230822
• HY-113121
• Mandelic acid, 4-hydroxy-3-methoxy-, DL-
• CS-0059631
• EU-0100602
• FT-0634243
• FT-0669752
• FT-0669753
• H0268
• S6613
• ( inverted question mark)-Vanillylmandelic acid
• C05584
• D90829
• H 0131
• H-6500
• (+/-)-3-METHOXY-4-HYDROXYMANDELIC ACID
• EN300-1868166
• Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid #
• A817001
• dl-.alpha.,4-Dihydroxy-3-methoxyphenylacetic acid
• Q901369
• SR-01000075241
• 2-(4-Hydroxy-3-methoxyphenyl)-2-hydroxyacetic acid
• SR-01000075241-1
• 2-(4'-Hydroxy-3'-methoxyphenyl) 2-hydroxyethanoic acid
• DCD57880-FBEE-4ED4-A834-92387D266E8A
• DL-4-Hydroxy-3-methoxymandelic acid, analytical standard
• ( inverted question mark)-4-Hydroxy-3-methoxymandelic acid
• Benzeneacetic acid, .alpha.,4-dihydroxy-3-methoxy-, (.+.)-
• DL-4-Hydroxy-3-methoxymandelic acid, >=98% (TLC), powder
• DL-4-HYDROXY-3-METHOXYMANDELIC ACID (DL-VANILLYLMANDELIC ACID)
• 4-Hydroxy-3-methoxy-DL-mandelic acid;2-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)acetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9585	95.85%
Caco-2	-	0.7369	73.69%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8911	89.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9362	93.62%
OATP1B3 inhibitior	+	0.9757	97.57%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9589	95.89%
P-glycoprotein inhibitior	-	0.9820	98.20%
P-glycoprotein substrate	-	0.9550	95.50%
CYP3A4 substrate	-	0.7184	71.84%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	-	0.7922	79.22%
CYP3A4 inhibition	-	0.9706	97.06%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9104	91.04%
CYP2D6 inhibition	-	0.9743	97.43%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9027	90.27%
CYP inhibitory promiscuity	-	0.9357	93.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7311	73.11%
Carcinogenicity (trinary)	Non-required	0.5931	59.31%
Eye corrosion	+	0.5582	55.82%
Eye irritation	+	0.9628	96.28%
Skin irritation	+	0.7545	75.45%
Skin corrosion	-	0.7841	78.41%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8380	83.80%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.6553	65.53%
skin sensitisation	-	0.7972	79.72%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8278	82.78%
Acute Oral Toxicity (c)	III	0.5089	50.89%
Estrogen receptor binding	-	0.7379	73.79%
Androgen receptor binding	-	0.7690	76.90%
Thyroid receptor binding	-	0.5420	54.20%
Glucocorticoid receptor binding	-	0.6822	68.22%
Aromatase binding	-	0.7758	77.58%
PPAR gamma	+	0.5640	56.40%
Honey bee toxicity	-	0.9213	92.13%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.9110	91.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	3981.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.29%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.26%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	91.23%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.70%	99.17%
CHEMBL4208	P20618	Proteasome component C5	89.41%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.84%	94.45%
CHEMBL2535	P11166	Glucose transporter	85.65%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.47%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.65%	85.14%
CHEMBL3194	P02766	Transthyretin	82.30%	90.71%

Plants that contains it

• Mentha arvensis
• Mentha canadensis
• Pogostemon cablin

Cross-Links

• PubChem: 1245
• NPASS: NPC307006
• ChEMBL: CHEMBL1256396
• LOTUS: LTS0152032
• wikiData: Q901369