methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-13-(methoxycarbonyl)-17-{[(4-phenylpiperidin-1-yl)carbonyl]amino}-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: ALA2441608

PubChem CID: 73349586

Max Phase: Preclinical

Molecular Formula: C58H72N6O9

Molecular Weight: 997.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(NC(=O)N2CCC(c3ccccc3)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/C58H72N6O9/c1-8-54(60-53(68)64-27-20-39(21-28-64)38-16-11-10-12-17-38)32-37-33-57(51(66)71-6,47-41(22-26-62(34-37)35-54)40-18-13-14-19-44(40)59-47)43-30-42-45(31-46(43)70-5)61(4)49-56(42)24-29-63-25-15-23-55(9-2,48(56)63)50(73-36(3)65)58(49,69)52(67)72-7/h10-19,23,30-31,37,39,48-50,59,69H,8-9,20-22,24-29,32-35H2,1-7H3,(H,60,68)/t37-,48+,49-,50-,54+,55-,56-,57+,58+/m1/s1

Standard InChI Key:  LEMSDPPPEBJQHO-WSSSWPIGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2441608

   methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-13-methoxycarbonyl-17-[(4-phenylpiperidine-1-carbonyl)amino]-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-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: 997.25

Molecular Weight (Monoisotopic): 996.5361

AlogP: 6.59

#Rotatable Bonds: 9

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: 6.28

CX LogD: 4.34

Aromatic Rings: 4

Heavy Atoms: 73

QED Weighted: 0.09

Np Likeness Score: 1.02

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]

Source

Source(1):

• Scientific Literature