4-Hydroxy-7-hydroxymethyl-1-(2-hydroxy-2-phenyl-butyryloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizinium

ID: ALA2114415

PubChem CID: 71454547

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@](O)(C(=O)O[C@H]1CC[N+]2([O-])CC=C(CO)[C@H]12)c1ccccc1

Standard InChI:  InChI=1S/C18H23NO5/c1-2-18(22,14-6-4-3-5-7-14)17(21)24-15-9-11-19(23)10-8-13(12-20)16(15)19/h3-8,15-16,20,22H,2,9-12H2,1H3/t15-,16+,18+,19?/m0/s1

Standard InChI Key:  IOJAGKJQHGKBCB-QVUZWJOHSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  1  0  0  0  0  0999 V2000
    8.1174   -4.4183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -3.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3570   -2.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3581   -3.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9401   -3.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2535   -1.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1279   -2.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4061   -4.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8941   -4.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8575   -3.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3235   -4.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1002   -5.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7012   -2.6982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9093   -0.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614   -0.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2162   -2.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4941   -1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0332   -2.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6802   -1.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8230   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8383   -1.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616    0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3418   -0.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2383    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1347   -2.7499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  2  1  0
  5  2  1  0
  6  3  1  0
  4  7  1  6
  8  9  1  0
  9  1  1  0
 10 11  1  0
 11  1  1  0
 12  1  1  0
 13  3  2  0
 14  6  1  0
  6 15  1  6
 16  5  1  0
 17  6  1  0
 18 16  1  0
 19 14  2  0
 20 14  1  0
 21 17  1  0
 22 20  2  0
 23 19  1  0
 24 22  1  0
  2 25  1  6
  4 10  1  0
  8  5  2  0
 23 24  2  0
M  CHG  2   1   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2114415

   [(1S,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-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: 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: 11.71

CX Basic pKa: 2.82

CX LogP: 0.22

CX LogD: 0.22

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.37

Np Likeness Score: 1.68

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