3-Methoxy-4-hydroxymandelic acid

ID: ALA2074737

Cas Number: 41093-71-4

PubChem CID: 736173

Max Phase: Preclinical

Molecular Formula: C9H10O5

Molecular Weight: 198.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H](O)C(=O)O)ccc1O

Standard 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)/t8-/m1/s1

Standard InChI Key:  CGQCWMIAEPEHNQ-MRVPVSSYSA-N

Molfile:  

     RDKit          2D

 14 14  0  0  1  0  0  0  0  0999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  3  9  1  0
  8 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 12 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074737

   (-)-Vanilmandelic acid

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 198.17

Molecular Weight (Monoisotopic): 198.0528

AlogP: 0.52

#Rotatable Bonds: 3

Polar Surface Area: 86.99

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.11

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: -3.03

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.66

Np Likeness Score: 0.94

References

1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T..  (2002)  Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain.,  83  (1): [PMID:12358729] [10.1046/j.1471-4159.2002.01108.x]

Source

Source(1):

• TP-search Transporter Database