10-[[[1-(Methoxymethyl)-2-[[1-(methoxymethyl)-2-carbethoxypyrrol-4-yl]carbamoyl]pyrrol-4-yl]carbamoyl]methoxy]-2(R,S)-camptothecin

ID: ALA72353

Chembl Id: CHEMBL72353

PubChem CID: 44311921

Max Phase: Preclinical

Molecular Formula: C38H38N6O12

Molecular Weight: 770.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc(NC(=O)c2cc(NOC(=O)COc3ccc4nc5c(cc4c3)Cn3c-5cc4c(c3=O)COC(=O)C4(O)CC)cn2COC)cn1COC

Standard InChI:  InChI=1S/C38H38N6O12/c1-5-38(50)27-13-29-33-22(14-44(29)35(47)26(27)17-55-37(38)49)9-21-10-25(7-8-28(21)40-33)54-18-32(45)56-41-24-12-30(42(16-24)19-51-3)34(46)39-23-11-31(36(48)53-6-2)43(15-23)20-52-4/h7-13,15-16,41,50H,5-6,14,17-20H2,1-4H3,(H,39,46)

Standard InChI Key:  YUZGQRHETITHDY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA72353

   Ethyl 4-[[4-[[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]acetyl]oxyamino]-1-(methoxymethyl)pyrrole-2-carbonyl]amino]-1-(methoxymethyl)pyrrole-2-carboxylate

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: 770.75

Molecular Weight (Monoisotopic): 770.2548

AlogP: 3.27

#Rotatable Bonds: 14

Polar Surface Area: 212.70

Molecular Species: NEUTRAL

HBA: 17

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.71

CX Basic pKa: 3.14

CX LogP: 2.41

CX LogD: 2.41

Aromatic Rings: 5

Heavy Atoms: 56

QED Weighted: 0.08

Np Likeness Score: 0.03

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