2-Hydroxy-2-phenyl-butyric acid 7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

ID: ALA2115354

PubChem CID: 71456305

Max Phase: Preclinical

Molecular Formula: C18H23NO4

Molecular Weight: 317.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@](O)(C(=O)OCC1=CCN2CC[C@H](O)[C@@H]12)c1ccccc1

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

Standard InChI Key:  ZGWFGHLFROCFLB-JZXOWHBKSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
   13.3254   -6.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5059   -7.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6466   -4.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5345   -6.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8099   -4.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7782   -6.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4144   -5.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2796   -7.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7150   -7.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2507   -6.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6005   -5.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7493   -6.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3972   -3.7025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0651   -5.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4605   -4.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5200   -5.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0479   -3.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6524   -5.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8732   -5.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6294   -2.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3030   -5.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0651   -6.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9018   -6.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5231   -5.4677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  1  1  0
  5  7  1  0
  6  1  2  0
  7 11  1  0
  8  6  1  0
  9  2  1  0
 10 12  1  0
 11  1  1  0
 12  4  1  0
 13  5  2  0
 14  3  1  0
  3 15  1  1
 12 16  1  6
 17  3  1  0
 18 14  2  0
 19 14  1  0
 20 17  1  0
 21 19  2  0
 22 18  1  0
 23 21  1  0
  4 24  1  6
  2  8  1  0
 10  9  1  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115354

   [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-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: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: 8.82

CX LogP: 1.34

CX LogD: -0.09

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 1.20

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