2-{2-[Bis-(2-chloro-ethyl)-amino]-3-methyl-2-oxo-2lambda*5*-[1,3,2]oxazaphosphinan-4-ylsulfanyl}-ethanesulfonic acid anion

ID: ALA1160092

PubChem CID: 10001873

Max Phase: Preclinical

Molecular Formula: C10H21Cl2N2O5PS2

Molecular Weight: 415.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(SCCS(=O)(=O)O)CCOP1(=O)N(CCCl)CCCl

Standard InChI:  InChI=1S/C10H21Cl2N2O5PS2/c1-13-10(21-8-9-22(16,17)18)2-7-19-20(13,15)14(5-3-11)6-4-12/h10H,2-9H2,1H3,(H,16,17,18)

Standard InChI Key:  KHCFJAOIAZNBJC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    6.1292   -2.8292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -2.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.3667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -3.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -3.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -2.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4792   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3042   -1.5167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -2.2792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -5.1917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  2  1  0
  5  1  1  0
  6  1  1  0
  7  1  2  0
  8 18  1  0
  9  3  1  0
 10  3  2  0
 11  3  2  0
 12 15  1  0
 13  4  1  0
 14  2  1  0
 15  6  1  0
 16  5  1  0
 17  5  1  0
 18 13  1  0
 19 22  1  0
 20 21  1  0
 21 17  1  0
 22 16  1  0
 12  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160092

   2-[[2-[Bis(2-chloroethyl)amino]-3-methyl-2-oxo-1,3,2lambda5-oxazaphosphinan-4-yl]sulfanyl]ethanesulfonic acid

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: 415.30

Molecular Weight (Monoisotopic): 414.0007

AlogP: 2.17

#Rotatable Bonds: 9

Polar Surface Area: 87.15

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.83

CX Basic pKa: 0.16

CX LogP: -0.59

CX LogD: -2.10

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.35

Np Likeness Score: -0.13

References

1. Moon KY, Kwon CH..  (1998)  N3-methyl-mafosfamide as a chemically stable, alternative prodrug of mafosfamide.,  8  (13): [PMID:9873412] [10.1016/s0960-894x(98)00287-x]

Source

Source(1):

• Scientific Literature