Grepafloxacin glucuronide

ID: ALA2074711

PubChem CID: 443296

Max Phase: Preclinical

Molecular Formula: C25H30FN3O9

Molecular Weight: 535.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Grepafloxacin glucuronide | Grepafloxacin glucuronide|CHEMBL2074711|Grepafloxacin 3-glucuronide|CHEBI:5544|C11597|AC1L9EE2|BDBM50391008|(2S,3S,4S,5R,6S)-6-[1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid|Q27106803|(2S,3S,4S,5R,6S)-6-[1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carbonyl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

Canonical SMILES:  Cc1c(F)c(N2CCNC(C)C2)cc2c1c(=O)c(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)cn2C1CC1

Standard InChI:  InChI=1S/C25H30FN3O9/c1-10-8-28(6-5-27-10)15-7-14-16(11(2)17(15)26)18(30)13(9-29(14)12-3-4-12)24(36)38-25-21(33)19(31)20(32)22(37-25)23(34)35/h7,9-10,12,19-22,25,27,31-33H,3-6,8H2,1-2H3,(H,34,35)/t10?,19-,20-,21+,22-,25-/m0/s1

Standard InChI Key:  XFRNDEMKHRYQIZ-NWHISXNDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2074711

   GREPAFLOXACIN GLUCURONIDE

Molecule Features

Natural Product: Yes

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: 535.53

Molecular Weight (Monoisotopic): 535.1966

AlogP: -0.37

#Rotatable Bonds: 5

Polar Surface Area: 170.79

Molecular Species: ZWITTERION

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.95

CX Basic pKa: 8.77

CX LogP: -1.70

CX LogD: -1.72

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.32

Np Likeness Score: 0.45

References

1. Sasabe H, Tsuji A, Sugiyama Y..  (1998)  Carrier-mediated mechanism for the biliary excretion of the quinolone antibiotic grepafloxacin and its glucuronide in rats.,  284  (1): [PMID:9495864]

2. Niinuma K, Kato Y, Suzuki H, Tyson CA, Weizer V, Dabbs JE, Froehlich R, Green CE, Sugiyama Y..  (1999)  Primary active transport of organic anions on bile canalicular membrane in humans.,  276  (1): [PMID:10330006] [10.1152/ajpgi.1999.276.5.g1153]

3. Jedlitschky, G G and 5 more authors.  1997-10-01  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.  [PMID:9355767]

Source

Source(1):

• TP-search Transporter Database