methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(13S,15S,17S)-17-{[(2,3-dihydro-1H-isoindol-2-yl)carbonyl]amino}-17-ethyl-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate

ID: ALA2441610

PubChem CID: 73351141

Max Phase: Preclinical

Molecular Formula: C55H66N6O9

Molecular Weight: 955.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(NC(=O)N2Cc3ccccc3C2)C[C@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1

Standard InChI:  InChI=1S/C55H66N6O9/c1-8-51(57-50(65)61-30-35-15-10-11-16-36(35)31-61)27-34-28-54(48(63)68-6,44-38(19-23-59(29-34)32-51)37-17-12-13-18-41(37)56-44)40-25-39-42(26-43(40)67-5)58(4)46-53(39)21-24-60-22-14-20-52(9-2,45(53)60)47(70-33(3)62)55(46,66)49(64)69-7/h10-18,20,25-26,34,45-47,56,66H,8-9,19,21-24,27-32H2,1-7H3,(H,57,65)/t34-,45+,46-,47-,51+,52-,53-,54+,55+/m1/s1

Standard InChI Key:  LZGJXJDYJABMAW-ZEANNSDJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2441610

   methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(13S,15S,17S)-17-(1,3-dihydroisoindole-2-carbonylamino)-17-ethyl-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diaz

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: 955.17

Molecular Weight (Monoisotopic): 954.4891

AlogP: 5.72

#Rotatable Bonds: 8

Polar Surface Area: 166.21

Molecular Species: BASE

HBA: 12

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.87

CX Basic pKa: 8.70

CX LogP: 5.48

CX LogD: 3.54

Aromatic Rings: 4

Heavy Atoms: 70

QED Weighted: 0.11

Np Likeness Score: 1.11

References

1. Barker TJ, Duncan KK, Otrubova K, Boger DL..  (2013)  Potent Vinblastine C20' Ureas Displaying Additionally Improved Activity Against a Vinblastine-Resistant Cancer Cell Line.,  4  (10): [PMID:24223237] [10.1021/ml400281w]

2. Radakovic A, Boger DL..  (2019)  Ultra-potent vinblastine analogues improve on-target activity of the parent microtubulin-targeting compound.,  29  (11): [PMID:30952593] [10.1016/j.bmcl.2019.03.036]

Source

Source(1):

• Scientific Literature