methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-({[2-(4-fluorophenyl)ethyl]carbamothioyl}amino)-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-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: ALA2314557

PubChem CID: 71718570

Max Phase: Preclinical

Molecular Formula: C55H67FN6O8S

Molecular Weight: 991.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(NC(=S)NCCc2ccc(F)cc2)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/C55H67FN6O8S/c1-8-51(59-50(71)57-23-19-34-15-17-36(56)18-16-34)29-35-30-54(48(64)68-6,44-38(20-25-61(31-35)32-51)37-13-10-11-14-41(37)58-44)40-27-39-42(28-43(40)67-5)60(4)46-53(39)22-26-62-24-12-21-52(9-2,45(53)62)47(70-33(3)63)55(46,66)49(65)69-7/h10-18,21,27-28,35,45-47,58,66H,8-9,19-20,22-26,29-32H2,1-7H3,(H2,57,59,71)/t35-,45+,46-,47-,51+,52-,53-,54+,55+/m1/s1

Standard InChI Key:  ZUTREUGBXJLPAB-WYLAMRMSSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2314557

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

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: 991.24

Molecular Weight (Monoisotopic): 990.4725

AlogP: 5.84

#Rotatable Bonds: 11

Polar Surface Area: 157.93

Molecular Species: BASE

HBA: 12

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.86

CX Basic pKa: 8.73

CX LogP: 6.83

CX LogD: 4.77

Aromatic Rings: 4

Heavy Atoms: 71

QED Weighted: 0.06

Np Likeness Score: 0.93

References

1. Leggans EK, Duncan KK, Barker TJ, Schleicher KD, Boger DL..  (2013)  A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20' urea derivatives.,  56  (3): [PMID:23244701] [10.1021/jm3015684]

Source

Source(1):

• Scientific Literature