2-Hydroxy-2-phenyl-butyric acid 7-hydroxy-4-oxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

ID: ALA2115358

PubChem CID: 71456306

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@](O)(C(=O)OCC1=CC[N+]2([O-])CC[C@@H](O)[C@@H]12)c1ccccc1

Standard InChI:  InChI=1S/C18H23NO5/c1-2-18(22,14-6-4-3-5-7-14)17(21)24-12-13-8-10-19(23)11-9-15(20)16(13)19/h3-8,15-16,20,22H,2,9-12H2,1H3/t15-,16-,18+,19?/m1/s1

Standard InChI Key:  SJOLWQZOAAVHCY-DXHOFVPLSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
    6.1941  -11.4541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227  -10.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134  -10.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3340   -8.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5089   -8.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4775  -11.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9676  -11.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227  -12.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4034  -11.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1021   -9.4773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4377  -10.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392  -11.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2884   -9.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0850   -8.0448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7524   -9.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1477   -8.7496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085   -9.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7352   -8.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5603   -9.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3398  -10.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3168   -7.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7524  -10.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9900  -10.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5889  -10.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2113   -9.8039    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5 10  1  0
  6  7  1  0
  7  1  1  0
  8  1  1  0
  9  1  1  0
 10 13  1  0
 11  2  1  0
 12  9  1  0
 13  3  1  0
 14  5  2  0
 15  4  1  0
  4 16  1  1
 11 17  1  1
 18  4  1  0
 19 15  1  0
 20 15  2  0
 21 18  1  0
 22 20  1  0
 23 19  2  0
 24 22  2  0
  2 25  1  6
 11 12  1  0
  6  3  2  0
 23 24  1  0
M  CHG  2   1   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2115358

   [(7R,8R)-7-hydroxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-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: 333.38

Molecular Weight (Monoisotopic): 333.1576

AlogP: 1.22

#Rotatable Bonds: 5

Polar Surface Area: 89.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.69

CX Basic pKa: 2.83

CX LogP: 0.22

CX LogD: 0.22

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: 1.63

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