SN-38 carboxylate

ID: ALA2074578

PubChem CID: 443149

Max Phase: Preclinical

Molecular Formula: C22H22N2O6

Molecular Weight: 410.43

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCc1c2c(nc3ccc(O)cc13)-c1cc([C@@](O)(CC)C(=O)O)c(CO)c(=O)n1C2

Standard InChI:  InChI=1S/C22H22N2O6/c1-3-12-13-7-11(26)5-6-17(13)23-19-14(12)9-24-18(19)8-16(15(10-25)20(24)27)22(30,4-2)21(28)29/h5-8,25-26,30H,3-4,9-10H2,1-2H3,(H,28,29)/t22-/m0/s1

Standard InChI Key:  IRKZFHZUIBLGKU-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

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   10.7470  -22.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5317  -22.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8672  -21.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.4780  -23.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8438  -21.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5384  -20.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3588  -20.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7415  -20.6797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8138  -19.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1838  -20.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0325  -25.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181  -25.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 20 16  1  6
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 11 29  1  0
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M  END

Associated Targets(non-human)

Abcb1a P-glycoprotein 3 (492 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Abcc2 Canalicular multispecific organic anion transporter 1 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 410.43Molecular Weight (Monoisotopic): 410.1478AlogP: 1.87#Rotatable Bonds: 5
Polar Surface Area: 132.88Molecular Species: ACIDHBA: 7HBD: 4
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 3.29CX Basic pKa: 4.04CX LogP: 0.27CX LogD: -2.19
Aromatic Rings: 3Heavy Atoms: 30QED Weighted: 0.39Np Likeness Score: 0.70

References

1. Chu XY, Kato Y, Niinuma K, Sudo KI, Hakusui H, Sugiyama Y..  (1997)  Multispecific organic anion transporter is responsible for the biliary excretion of the camptothecin derivative irinotecan and its metabolites in rats.,  281  (1): [PMID:9103511]
2. Arimori K, Kuroki N, Hidaka M, Iwakiri T, Yamsaki K, Okumura M, Ono H, Takamura N, Kikuchi M, Nakano M..  (2003)  Effect of P-glycoprotein modulator, cyclosporin A, on the gastrointestinal excretion of irinotecan and its metabolite SN-38 in rats.,  20  (1): [PMID:12817897] [10.1023/a:1023847521767]