3,4-Dihydroxymandelic acid

ID: ALA2074780

Cas Number: 64998-15-8

PubChem CID: 6950181

Max Phase: Preclinical

Molecular Formula: C8H8O5

Molecular Weight: 184.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](O)c1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)/t7-/m1/s1

Standard InChI Key:  RGHMISIYKIHAJW-SSDOTTSWSA-N

Molfile:  

     RDKit          2D

 13 13  0  0  1  0  0  0  0  0999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   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
    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
    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
    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
  2  1  1  6
  2  3  1  0
  3  4  1  0
  3  5  2  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074780

   3,4-Dihydroxymandelic acid, (R)-

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: 184.15

Molecular Weight (Monoisotopic): 184.0372

AlogP: 0.22

#Rotatable Bonds: 2

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.98

CX Basic pKa: ┄

CX LogP: 0.29

CX LogD: -3.20

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.49

Np Likeness Score: 1.13

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