(1R,4R,5R)-1,5-Dihydroxy-4-(4-hydroxymethyl-benzyloxy)-cyclohex-2-enecarboxylic acid

ID: ALA347210

PubChem CID: 11289383

Max Phase: Preclinical

Molecular Formula: C15H18O6

Molecular Weight: 294.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C[C@@H](OCc2ccc(CO)cc2)[C@H](O)C1

Standard InChI:  InChI=1S/C15H18O6/c16-8-10-1-3-11(4-2-10)9-21-13-5-6-15(20,14(18)19)7-12(13)17/h1-6,12-13,16-17,20H,7-9H2,(H,18,19)/t12-,13-,15+/m1/s1

Standard InChI Key:  NYRGKZZCDVIYRL-NFAWXSAZSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  1  0  0  0  0  0999 V2000
    1.5000   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -2.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    1.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    0.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  1  4  1  1
  5  3  2  0
  6  2  1  0
  7  5  1  0
  7  8  1  6
  9  4  2  0
  1 10  1  6
 11  4  1  0
 12  8  1  0
 13 12  1  0
  6 14  1  1
 15 19  1  0
 16 13  2  0
 17 13  1  0
 18 16  1  0
 19 17  2  0
 20 21  1  0
 21 15  1  0
  6  7  1  0
 15 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA347210

   (1R,4R,5R)-1,5-Dihydroxy-4-(4-hydroxymethyl-benzyloxy)-cyclohex-2-enecarboxylic acid

Molecule Features

Natural Product: No

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: 294.30

Molecular Weight (Monoisotopic): 294.1103

AlogP: 0.20

#Rotatable Bonds: 5

Polar Surface Area: 107.22

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.52

CX Basic pKa: ┄

CX LogP: 0.00

CX LogD: -3.37

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 1.19

References

1. González-Bello C, Lence E, Toscano MD, Castedo L, Coggins JR, Abell C..  (2003)  Parallel solid-phase synthesis and evaluation of inhibitors of Streptomyces coelicolor type II dehydroquinase.,  46  (26): [PMID:14667226] [10.1021/jm030987q]

Source

Source(1):

• Scientific Literature