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

ID: ALA2115356

PubChem CID: 21771304

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+/m1/s1

Standard InChI Key:  ZGWFGHLFROCFLB-NUJGCVRESA-N

Molfile:  

     RDKit          2D

 24 26  0  0  1  0  0  0  0  0999 V2000
    6.3624   -4.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377   -5.9271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6817   -3.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -5.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8571   -3.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8263   -5.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4447   -3.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3108   -6.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475   -6.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2836   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6373   -4.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7818   -4.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4276   -2.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0940   -3.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4892   -3.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -4.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0768   -2.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6817   -4.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9015   -3.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6645   -1.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0940   -5.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3310   -4.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9358   -5.3488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5549   -4.2778    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  1
 17  3  1  0
 18 14  2  0
 19 14  1  0
 20 17  1  0
 21 18  1  0
 22 19  2  0
 23 22  1  0
  4 24  1  6
  8  2  1  0
  9 10  1  0
 23 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115356

   [(7R,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