10-[2-[1-(Methoxymethyl)-4-[1-(methoxymethyl)-4-butyramidoimidazole-2-carboxamido]imidazole-2-carboxamido]ethoxy]-20(R,S)-camptothecin

ID: ALA311855

Chembl Id: CHEMBL311855

PubChem CID: 10795337

Max Phase: Preclinical

Molecular Formula: C38H41N9O10

Molecular Weight: 783.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)Nc1cn(COC)c(C(=O)Nc2cn(COC)c(C(=O)NCCOc3ccc4nc5c(cc4c3)Cn3c-5cc4c(c3=O)COC(=O)C4(O)CC)n2)n1

Standard InChI:  InChI=1S/C38H41N9O10/c1-5-7-30(48)41-28-16-46(20-55-4)33(42-28)35(50)44-29-17-45(19-54-3)32(43-29)34(49)39-10-11-56-23-8-9-26-21(13-23)12-22-15-47-27(31(22)40-26)14-25-24(36(47)51)18-57-37(52)38(25,53)6-2/h8-9,12-14,16-17,53H,5-7,10-11,15,18-20H2,1-4H3,(H,39,49)(H,41,48)(H,44,50)

Standard InChI Key:  UXJWWYWMMPKWNK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA311855

   4-(butanoylamino)-N-[2-[2-[(19-ethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl)oxy]ethylcarbamoyl]-1-(methoxymethyl)imidazol-4-yl]-1-(methoxymethyl)imidazole-2-carboxamide

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: 783.80

Molecular Weight (Monoisotopic): 783.2976

AlogP: 2.48

#Rotatable Bonds: 15

Polar Surface Area: 232.05

Molecular Species: NEUTRAL

HBA: 16

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.21

CX Basic pKa: 3.15

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: 5

Heavy Atoms: 57

QED Weighted: 0.09

Np Likeness Score: 0.00

References

1. Zhao R, al-Said NH, Sternbach DL, Lown JW..  (1997)  Camptothecin and minor-groove binder hybrid molecules: synthesis, inhibition of topoisomerase I, and anticancer cytotoxicity in vitro.,  40  (2): [PMID:9003520] [10.1021/jm9605804]

Source

Source(1):

• Scientific Literature