(1R,4R,5R)-3-(1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid

ID: ALA3221804

PubChem CID: 90668071

Max Phase: Preclinical

Molecular Formula: C14H15N3O6

Molecular Weight: 321.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(Cc3ccco3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C14H15N3O6/c18-11-5-14(22,13(20)21)4-9(12(11)19)10-7-17(16-15-10)6-8-2-1-3-23-8/h1-4,7,11-12,18-19,22H,5-6H2,(H,20,21)/t11-,12-,14+/m1/s1

Standard InChI Key:  NYWTZVOKGDKDQA-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.3365  -17.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260  -18.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175  -18.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366  -19.4323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844  -19.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289  -19.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176  -18.4463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8190  -18.6193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393  -19.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731  -19.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9824  -20.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4638  -19.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148  -18.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4995  -19.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1290  -17.6512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147  -20.8161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937  -20.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0304  -19.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335  -20.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746  -21.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301  -21.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473  -21.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968  -21.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  9 10  1  0
  9 13  2  0
 10 11  1  0
 11 12  1  0
 12  2  1  0
  2 13  1  0
  6  9  1  0
  3 14  1  0
  3 15  2  0
 11 16  1  1
 10 17  1  6
  4 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221804

   (1R,4R,5R)-3-[1-(furan-2-ylmethyl)triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic 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: 321.29

Molecular Weight (Monoisotopic): 321.0961

AlogP: -0.76

#Rotatable Bonds: 4

Polar Surface Area: 141.84

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: -0.86

CX LogD: -4.25

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.33

References

1. Tran AT, Cergol KM, Britton WJ, Imran Bokhari SA, Ibrahim M, Lapthorn AJ, Payne RJ.  (2010)  Rapid assembly of potent type II dehydroquinase inhibitors viaClick chemistry,  1  (4): [10.1039/C0MD00097C]

Source

Source(1):

• Scientific Literature