Mrv1718009031813302D          

 36 39  0  0  0  0            999 V2000
    2.8456    0.7538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3338    2.2566    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456   -0.0654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1135   -0.4823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2154   -1.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -0.0654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6641   -0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309    1.0156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6641   -1.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6261    1.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135    1.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058    0.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4736   -1.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1135   -1.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -0.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135   -1.7233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0513    1.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7362    2.9740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169    2.9740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2299   -0.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659   -1.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4058   -1.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0963    0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7659   -0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456    1.5827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2854   -2.5523    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513   -1.3742    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8989   -2.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6406   -1.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5728   -2.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3387   -1.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203   -0.8943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456   -0.8604    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039    0.3563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5 13  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  9  7  2  0  0  0  0
  8 10  1  1  0  0  0
 11  1  1  0  0  0  0
 12 11  1  0  0  0  0
 13 23  1  0  0  0  0
 14  3  1  0  0  0  0
 15  4  1  0  0  0  0
 16  7  1  0  0  0  0
 17  5  1  0  0  0  0
 18  2  1  0  0  0  0
 19  2  1  0  0  0  0
 20  2  2  0  0  0  0
 21  5  2  0  0  0  0
 22  9  1  0  0  0  0
 23 26  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 26 16  2  0  0  0  0
  1 27  1  1  0  0  0
 28 32  1  0  0  0  0
 29 33  1  0  0  0  0
 30 17  1  0  0  0  0
 31 17  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
  6 34  1  6  0  0  0
  3 35  1  6  0  0  0
  4 36  1  1  0  0  0
 12  6  1  0  0  0  0
 14 25  1  0  0  0  0
 24  9  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
DB14674

> <DATABASE_NAME>
drugbank

> <SMILES>
[H][C@@]12CC[C@H](OP(O)(O)=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC(=O)N(CCCl)CCCl)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C23H32Cl2NO6P/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30)/t18-,19-,20+,21+,23+/m1/s1

> <INCHI_KEY>
ADFOJJHRTBFFOF-RBRWEJTLSA-N

> <FORMULA>
C23H32Cl2NO6P

> <MOLECULAR_WEIGHT>
520.38

> <EXACT_MASS>
519.1344302

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.819228711414794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1S,3aS,3bR,9bS,11aS)-7-{[bis(2-chloroethyl)carbamoyl]oxy}-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
4.975547878666667

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.884563323113222

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.857862348342322

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
127.08579999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.68e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,3aS,3bR,9bS,11aS)-7-{[bis(2-chloroethyl)carbamoyl]oxy}-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

> <DRUGBANK_ID>
DB14674

> <SECONDARY_ACCESSION_NUMBERS>
DBSALT002563

> <DRUG_GROUPS>
approved; investigational

> <GENERIC_NAME>
Estramustine phosphate

> <SYNONYMS>
Estramustine 17-(dihydrogen phosphate)

> <INTERNATIONAL_BRANDS>
Estracyt

$$$$