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

ID: ALA74406

Chembl Id: CHEMBL74406

PubChem CID: 10676714

Max Phase: Preclinical

Molecular Formula: C40H43N7O10

Molecular Weight: 781.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)Nc1cc(C(=O)Nc2cc(C(=O)NCCOc3ccc4nc5c(cc4c3)Cn3c-5cc4c(c3=O)COC(=O)C4(O)CC)n(COC)c2)n(COC)c1

Standard InChI:  InChI=1S/C40H43N7O10/c1-5-7-34(48)42-25-14-33(46(18-25)22-55-4)37(50)43-26-15-32(45(19-26)21-54-3)36(49)41-10-11-56-27-8-9-30-23(13-27)12-24-17-47-31(35(24)44-30)16-29-28(38(47)51)20-57-39(52)40(29,53)6-2/h8-9,12-16,18-19,53H,5-7,10-11,17,20-22H2,1-4H3,(H,41,49)(H,42,48)(H,43,50)

Standard InChI Key:  QVSHBSMUJLKADQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA74406

   4-(butanoylamino)-N-[5-[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)pyrrol-3-yl]-1-(methoxymethyl)pyrrole-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: 781.82

Molecular Weight (Monoisotopic): 781.3071

AlogP: 3.69

#Rotatable Bonds: 15

Polar Surface Area: 206.27

Molecular Species: NEUTRAL

HBA: 14

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.71

CX Basic pKa: 3.15

CX LogP: 1.99

CX LogD: 1.99

Aromatic Rings: 5

Heavy Atoms: 57

QED Weighted: 0.09

Np Likeness Score: -0.09

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