Irinotecan (CPT-11) carboxylate

ID: ALA2074712

Cas Number: 142706-06-7

PubChem CID: 443147

Max Phase: Preclinical

Molecular Formula: C33H40N4O7

Molecular Weight: 604.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc([C@@](O)(CC)C(=O)O)c(CO)c(=O)n1C2

Standard InChI:  InChI=1S/C33H40N4O7/c1-3-22-23-16-21(44-32(42)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26(25(19-38)30(37)39)33(43,4-2)31(40)41/h8-9,16-17,20,38,43H,3-7,10-15,18-19H2,1-2H3,(H,40,41)/t33-/m0/s1

Standard InChI Key:  DCYPPLWVDXGNOW-XIFFEERXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2074712

   (2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid

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: 604.70

Molecular Weight (Monoisotopic): 604.2897

AlogP: 3.61

#Rotatable Bonds: 7

Polar Surface Area: 145.43

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.00

CX Basic pKa: 9.47

CX LogP: -0.62

CX LogD: -0.62

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.29

Np Likeness Score: -0.05

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]

3. Chu XY, Kato Y, Sugiyama Y..  (1999)  Possible involvement of P-glycoprotein in biliary excretion of CPT-11 in rats.,  27  (1): [PMID:10101137]

Source

Source(1):

• TP-search Transporter Database