E3040 glucuronide

ID: ALA2074599

PubChem CID: 443294

Max Phase: Preclinical

Molecular Formula: C22H25N3O7S

Molecular Weight: 475.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc2c(Cc3cccnc3)c(C)c(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(C)c2s1

Standard InChI:  InChI=1S/C22H25N3O7S/c1-9-12(7-11-5-4-6-24-8-11)13-19(33-22(23-3)25-13)10(2)17(9)31-21-16(28)14(26)15(27)18(32-21)20(29)30/h4-6,8,14-16,18,21,26-28H,7H2,1-3H3,(H,23,25)(H,29,30)/t14-,15-,16+,18-,21+/m0/s1

Standard InChI Key:  RJBKVKVYNJTHJS-DQSYDGHTSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
    2.0701   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    2.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  7  9  2  0
  2  7  1  1
  3 10  1  6
  4 11  1  1
  5 12  1  6
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 22  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 24 29  1  0
 23 26  1  0
 19 23  1  0
 30 31  1  0
 16 30  1  0
 20 32  1  0
 22 33  1  0
 13 21  1  0
  6 13  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2074599

   E3040 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: 475.52

Molecular Weight (Monoisotopic): 475.1413

AlogP: 1.21

#Rotatable Bonds: 6

Polar Surface Area: 154.26

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.82

CX Basic pKa: 5.39

CX LogP: 0.56

CX LogD: -0.99

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.35

Np Likeness Score: 0.34

References

1. Akita H, Suzuki H, Hirohashi T, Takikawa H, Sugiyama Y..  (2002)  Transport activity of human MRP3 expressed in Sf9 cells: comparative studies with rat MRP3.,  19  (1): [PMID:11837698] [10.1023/a:1013699130991]

2. Hirohashi T, Suzuki H, Sugiyama Y..  (1999)  Characterization of the transport properties of cloned rat multidrug resistance-associated protein 3 (MRP3).,  274  (1): [PMID:10329726] [10.1074/jbc.274.21.15181]

3. Niinuma K, Takenaka O, Horie T, Kobayashi K, Kato Y, Suzuki H, Sugiyama Y..  (1997)  Kinetic analysis of the primary active transport of conjugated metabolites across the bile canalicular membrane: comparative study of S-(2,4-dinitrophenyl)-glutathione and 6-hydroxy-5,7-dimethyl-2-methylamino-4-(3-pyridylmethyl)benzothiazole glucuronide.,  282  (1): [PMID:9262353]

4. 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]

5. Suzuki M, Suzuki H, Sugimoto Y, Sugiyama Y..  (2003)  ABCG2 transports sulfated conjugates of steroids and xenobiotics.,  278  (1): [PMID:12682043] [10.1074/jbc.m212399200]

6. 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