(1R,4R,5R)-1,4,5-trihydroxy-3-(1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4 yl)cyclohex-2-enecarboxylic acid

ID: ALA3221805

PubChem CID: 90668072

Max Phase: Preclinical

Molecular Formula: C14H15N3O5S

Molecular Weight: 337.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@]1(O)C=C(c2cn(Cc3cccs3)nn2)[C@@H](O)[C@H](O)C1

Standard InChI:  InChI=1S/C14H15N3O5S/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:  SELLXOCFSLUGHF-BZPMIXESSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.7036  -17.6522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4931  -18.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2846  -18.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1037  -19.2177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8515  -19.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3960  -18.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9847  -18.2317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1861  -18.4047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2064  -19.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5402  -19.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3495  -19.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8309  -19.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6819  -18.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8666  -18.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4961  -17.4366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6818  -20.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0608  -20.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3975  -19.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4006  -20.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417  -20.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9972  -21.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8144  -21.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0639  -20.9291    0.0000 S   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:

   

   ALA3221805

   (1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)triazol-4-yl]cyclohex-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: 337.36

Molecular Weight (Monoisotopic): 337.0732

AlogP: -0.29

#Rotatable Bonds: 4

Polar Surface Area: 128.70

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.67

CX Basic pKa: ┄

CX LogP: -0.01

CX LogD: -3.33

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -0.66

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