methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-{[(furan-2-ylmethyl)carbamoyl]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: ALA2314553

PubChem CID: 71719779

Max Phase: Preclinical

Molecular Formula: C52H64N6O10

Molecular Weight: 933.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(NC(=O)NCc2ccco2)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/C52H64N6O10/c1-8-48(55-47(62)53-28-33-14-12-23-67-33)26-32-27-51(45(60)65-6,41-35(17-21-57(29-32)30-48)34-15-10-11-16-38(34)54-41)37-24-36-39(25-40(37)64-5)56(4)43-50(36)19-22-58-20-13-18-49(9-2,42(50)58)44(68-31(3)59)52(43,63)46(61)66-7/h10-16,18,23-25,32,42-44,54,63H,8-9,17,19-22,26-30H2,1-7H3,(H2,53,55,62)/t32-,42+,43-,44-,48+,49-,50-,51+,52+/m1/s1

Standard InChI Key:  BQOXSORIULRVRZ-XHRCUMCMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2314553

   methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-(furan-2-ylmethylcarbamoylamino)-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-diazapenta

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: 933.12

Molecular Weight (Monoisotopic): 932.4684

AlogP: 5.09

#Rotatable Bonds: 10

Polar Surface Area: 188.14

Molecular Species: BASE

HBA: 13

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 10.87

CX Basic pKa: 8.70

CX LogP: 4.57

CX LogD: 2.61

Aromatic Rings: 4

Heavy Atoms: 68

QED Weighted: 0.09

Np Likeness Score: 1.01

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