Mrv2304 09112316582D          

 36 38  0  0  1  0            999 V2000
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   -2.6961   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671   -4.5079    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2671   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1618   -5.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763   -4.0954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8763   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908   -4.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -4.0954    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
    2.7177   -4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487   -3.6829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5349   -2.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419   -2.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7544   -3.4053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2023   -4.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5748   -3.4916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0598   -2.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8802   -2.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2158   -3.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0363   -3.7503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309   -4.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9104   -4.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4255   -4.9127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -0.5230    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
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  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 12 11  1  1  0  0  0
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 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
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 29 30  1  0  0  0  0
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 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 36  1  0  0  0  0
M  END
> <DATABASE_ID>
DB18090

> <DATABASE_NAME>
drugbank

> <SMILES>
CCC[C@H](C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1OC[C@H](O1)N1C=CC(N)=NC1=O)OC1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30BrN4O8P/c1-4-5-14(2)33-21(28)15(3)26-36(30,35-17-8-6-16(23)7-9-17)32-13-20-31-12-19(34-20)27-11-10-18(24)25-22(27)29/h6-11,14-15,19-20H,4-5,12-13H2,1-3H3,(H,26,30)(H2,24,25,29)/t14-,15-,19-,20-,36+/m0/s1

> <INCHI_KEY>
JBYKMODFCUCTGY-LLSQRQBFSA-N

> <FORMULA>
C22H30BrN4O8P

> <MOLECULAR_WEIGHT>
589.38

> <EXACT_MASS>
588.098464

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_NEUTRAL_MICROSPECIES_CHARGE>
0.9997220293674186

> <JCHEM_AVERAGE_POLARIZABILITY>
52.71153007591048

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-pentan-2-yl (2S)-2-{[(S)-{[(2S,4S)-4-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-1,3-dioxolan-2-yl]methoxy}(4-bromophenoxy)phosphoryl]amino}propanoate

> <JCHEM_LOGP>
2.9453096216666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NEUTRAL_CHARGE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.21704392185249

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.235971538377093

> <JCHEM_PKA_STRONGEST_BASIC>
3.4391112396980734

> <JCHEM_POLAR_SURFACE_AREA>
151.01

> <JCHEM_REFRACTIVITY>
131.5584

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-pentan-2-yl (2S)-2-{[(S)-[(2S,4S)-4-(4-amino-2-oxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methoxy(4-bromophenoxy)phosphoryl]amino}propanoate

> <JCHEM_VEBER_RULE>
0

> <DRUGBANK_ID>
DB18090

> <DRUG_GROUPS>
investigational

> <GENERIC_NAME>
Fostroxacitabine bralpamide

> <SYNONYMS>
Troxacitabine nucleotide prodrug miv-818

> <SALTS>
Fostroxacitabine bralpamide hydrochloride

$$$$