NNAL-O-glucuronide

ID: ALA2074826

PubChem CID: 70695235

Max Phase: Preclinical

Molecular Formula: C17H25N3O7

Molecular Weight: 383.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCCC(C[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)c1cccnc1)N=O

Standard InChI:  InChI=1S/C17H25N3O7/c1-20(19-26)7-3-5-10(11-4-2-6-18-9-11)8-12-13(21)14(22)15(23)16(27-12)17(24)25/h2,4,6,9-10,12-16,21-23H,3,5,7-8H2,1H3,(H,24,25)/t10?,12-,13-,14+,15-,16-/m0/s1

Standard InChI Key:  RCWBDVYZRIRIGI-WGQZAXTISA-N

Molfile:  

     RDKit          2D

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   -3.4179   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324   -0.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1324   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4179   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5599   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690   -0.2651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    0.5599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835    0.9724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328    2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4473    2.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4473    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4473    3.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1618    4.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7329    4.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8763    2.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8763    1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5003    0.2122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 16  9  1  1
 16 17  1  0
 21 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  1
 22 23  1  0
 22 24  2  0
 19 25  1  6
 20 26  1  1
 21 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2074826

   (2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[5-[methyl(nitroso)amino]-2-pyridin-3-ylpentyl]oxane-2-carboxylic 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: 383.40

Molecular Weight (Monoisotopic): 383.1693

AlogP: -0.12

#Rotatable Bonds: 9

Polar Surface Area: 152.78

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.51

CX Basic pKa: 5.48

CX LogP: -1.91

CX LogD: -3.59

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.34

Np Likeness Score: 0.94

References

1. Leslie EM, Ito K, Upadhyaya P, Hecht SS, Deeley RG, Cole SP..  (2001)  Transport of the beta -O-glucuronide conjugate of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by the multidrug resistance protein 1 (MRP1). Requirement for glutathione or a non-sulfur-containing analog.,  276  (1): [PMID:11375986] [10.1074/jbc.m102453200]

2. 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