Mrv1902 02051922482D          

 30 31  0  0  0  0            999 V2000
   -3.7540    1.6276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2389    0.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7540    0.2927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9694    0.5477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9694    1.3726    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0089    2.4122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0089   -0.4918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3019    0.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0480    1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3809    1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8099    1.8575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5244    1.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2389    1.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    0.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1585    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5559    0.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5559   -0.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1585   -1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1585   -1.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5559   -2.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -1.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -1.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0953    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730   -0.7622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  6  0  0  0
  3  7  1  6  0  0  0
  5  8  1  6  0  0  0
  4  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 29  2  0  0  0  0
 20 30  1  6  0  0  0
M  END
> <DATABASE_ID>
DB00905

> <DATABASE_NAME>
drugbank

> <SMILES>
CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1

> <INCHI_KEY>
AQOKCDNYWBIDND-FTOWTWDKSA-N

> <FORMULA>
C25H37NO4

> <MOLECULAR_WEIGHT>
415.5656

> <EXACT_MASS>
415.272258677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.240213082151996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.629262466666666

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.850948591893511

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.34702039391217

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2597020031487451

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
122.8312

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({3-[(isopropyl-C-hydroxycarbonimidoyl)aminosulfonyl]-1H-pyridin-4-ylidene}amino)benzoic acid

> <JCHEM_VEBER_RULE>
0

> <DRUGBANK_ID>
DB00905

> <SECONDARY_ACCESSION_NUMBERS>
APRD00826; DB06863

> <DRUG_GROUPS>
approved; investigational

> <GENERIC_NAME>
Bimatoprost

> <SYNONYMS>
(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide; Bimatoprost; Bimatoprostum

> <PRODUCTS>
Apo-bimatoprost; Bimatoprost; Durysta; Ganfort; Latisse; Lumigan; Lumigan PF; Lumigan Rc; Vistitan; Zimed PF

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