(R)-4-(4-Amino-4-carboxybutyl)thiophene-3-carboxylic acid

ID: ALA3235239

PubChem CID: 77461163

Max Phase: Preclinical

Molecular Formula: C10H13NO4S

Molecular Weight: 243.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](CCCc1cscc1C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C10H13NO4S/c11-8(10(14)15)3-1-2-6-4-16-5-7(6)9(12)13/h4-5,8H,1-3,11H2,(H,12,13)(H,14,15)/t8-/m1/s1

Standard InChI Key:  SYTYECVGVGQBED-MRVPVSSYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   12.6169  -10.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1245   -9.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8885   -9.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8580  -10.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0743  -10.8352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.9015   -8.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4716   -8.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1093   -8.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5684   -9.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2844   -9.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9830   -9.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6980   -9.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4006   -9.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1116   -9.7023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3873   -8.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7073  -10.5357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  1  0
  6  7  2  0
  6  8  1  0
  2  6  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 14  2  0
 13 15  1  0
 12 13  1  0
 12 16  1  6
  3  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3235239

   4-[(4R)-4-amino-4-carboxybutyl]thiophene-3-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: 243.28

Molecular Weight (Monoisotopic): 243.0565

AlogP: 1.18

#Rotatable Bonds: 6

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.08

CX Basic pKa: 9.53

CX LogP: -0.94

CX LogD: -4.04

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.70

Np Likeness Score: 0.52

References

1. Pinto A, Tamborini L, Mastronardi F, Ettari R, Romano D, Nielsen B, De Micheli C, Conti P..  (2014)  Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors.,  24  (8): [PMID:24630559] [10.1016/j.bmcl.2014.02.058]

Source

Source(1):

• Scientific Literature