2-Hydroxy-2-phenyl-butyric acid 7-hydroxymethyl-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester

ID: ALA2114411

PubChem CID: 71461699

Max Phase: Preclinical

Molecular Formula: C18H23NO4

Molecular Weight: 317.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@](O)(C(=O)O[C@H]1CCN2CC=C(CO)[C@H]12)c1ccccc1

Standard InChI:  InChI=1S/C18H23NO4/c1-2-18(22,14-6-4-3-5-7-14)17(21)23-15-9-11-19-10-8-13(12-20)16(15)19/h3-8,15-16,20,22H,2,9-12H2,1H3/t15-,16+,18+/m0/s1

Standard InChI Key:  OPPDIFZZBCFSSI-LZLYRXPVSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
    8.8942   -2.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -3.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6479   -5.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6651   -4.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4559   -3.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7911   -2.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6507   -3.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9201   -4.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3870   -4.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4215   -5.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8512   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2352   -3.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4444   -1.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6879   -1.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7310   -3.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0346   -1.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5504   -3.0488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3527   -0.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2009   -1.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3755   -2.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8656   -1.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9946   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7624   -0.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6593   -3.3755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  6
  3  4  1  0
  4  2  1  0
  5  4  1  0
  6  1  1  0
  7  1  1  0
  8  5  2  0
  9  2  1  0
 10  3  1  0
 11  9  1  0
 12  1  2  0
 13  6  1  0
  6 14  1  6
 15  5  1  0
 16  6  1  0
 17 15  1  0
 18 13  1  0
 19 13  2  0
 20 16  1  0
 21 19  1  0
 22 18  2  0
 23 21  2  0
  4 24  1  6
 11  3  1  0
 10  8  1  0
 23 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114411

   [(1S,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (2R)-2-hydroxy-2-phenylbutanoate

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: 317.38

Molecular Weight (Monoisotopic): 317.1627

AlogP: 1.20

#Rotatable Bonds: 5

Polar Surface Area: 70.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: 6.80

CX LogP: 1.34

CX LogD: 1.24

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 1.33

References

1. Zalkow LH, Glinski JA, Gelbaum LT, Moore D, Melder D, Powis G..  (1988)  Semisynthetic pyrrolizidine alkaloid N-oxide antitumor agents. Esters of heliotridine.,  31  (8): [PMID:3397989] [10.1021/jm00403a008]

Source

Source(1):

• Scientific Literature