Piperazinium Pancratistatin 4-O-Phosphate

ID: ALA472228

PubChem CID: 49797532

Max Phase: Preclinical

Molecular Formula: C18H26N3O11P

Molecular Weight: 405.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Piperazinium Pancratistatin 4-O-Phosphate | CHEMBL472228|Piperazinium Pancratistatin 4-O-Phosphate

Canonical SMILES:  C1CNCCN1.O=C1N[C@H]2[C@H](OP(=O)(O)O)[C@H](O)[C@@H](O)[C@H](O)[C@@H]2c2cc3c(c(O)c21)OCO3

Standard InChI:  InChI=1S/C14H16NO11P.C4H10N2/c16-8-5-3-1-4-12(25-2-24-4)9(17)6(3)14(20)15-7(5)13(11(19)10(8)18)26-27(21,22)23;1-2-6-4-3-5-1/h1,5,7-8,10-11,13,16-19H,2H2,(H,15,20)(H2,21,22,23);5-6H,1-4H2/t5-,7-,8-,10+,11-,13+;/m1./s1

Standard InChI Key:  DVEFZGLWCBLVHL-FKJAIBLQSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
    2.8648  -15.3428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792  -16.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8737  -16.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4556  -15.7599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375  -14.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375  -14.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2707  -17.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725  -15.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9854  -16.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9888  -15.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7737  -15.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2554  -16.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7683  -16.9997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5572  -15.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584  -16.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455  -17.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270  -16.7414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8432  -15.4956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300  -15.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142  -15.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055  -14.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189  -14.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8408  -14.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126  -14.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963  -15.9278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5525  -14.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1116  -13.4382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1374  -15.0898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479  -17.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690  -17.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622  -15.0814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144  -15.5220    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.5956  -14.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5162  -16.1767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087  -14.8702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 13  9  1  0
 21 24  1  1
 14 15  1  0
 20 25  1  1
  8 10  1  0
 23 26  1  1
  9 10  2  0
 22 27  1  6
 19 28  1  1
  9  7  1  0
 16 29  2  0
 14 18  1  0
  7 30  1  0
 15 16  1  0
 18 31  1  6
 16 17  1  0
 25 32  1  0
 17 19  1  0
 32 33  1  0
 18 19  1  0
 32 34  1  0
  7 15  2  0
 32 35  2  0
 14  8  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 18 23  1  0
M  END

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: 405.25

Molecular Weight (Monoisotopic): 405.0461

AlogP: -2.11

#Rotatable Bonds: 2

Polar Surface Area: 195.24

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.24

CX Basic pKa: ┄

CX LogP: -2.04

CX LogD: -5.58

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.27

Np Likeness Score: 2.15

References

1. Pettit GR, Melody N, Herald DL..  (2004)  Antineoplastic agents. 511. Direct phosphorylation of phenpanstatin and pancratistatin.,  67  (3): [PMID:15043403] [10.1021/np030299+]

Source

Source(1):

• Scientific Literature