methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(13S,15S,17S)-17-[(diethylcarbamoyl)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: ALA2314559

PubChem CID: 71716755

Max Phase: Preclinical

Molecular Formula: C51H68N6O9

Molecular Weight: 909.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)N[C@@]1(CC)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/C51H68N6O9/c1-10-47(53-46(61)56(12-3)13-4)27-32-28-50(44(59)64-8,40-34(19-23-55(29-32)30-47)33-17-14-15-18-37(33)52-40)36-25-35-38(26-39(36)63-7)54(6)42-49(35)21-24-57-22-16-20-48(11-2,41(49)57)43(66-31(5)58)51(42,62)45(60)65-9/h14-18,20,25-26,32,41-43,52,62H,10-13,19,21-24,27-30H2,1-9H3,(H,53,61)/t32-,41+,42-,43-,47+,48-,49-,50+,51+/m1/s1

Standard InChI Key:  VCFUEIZROYENMP-RYFFIQGFSA-N

Molfile:  

     RDKit          2D

 69 77  0  0  0  0  0  0  0  0999 V2000
    6.9247  -27.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3370  -26.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404  -28.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4234  -24.5176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362  -26.9787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2158  -26.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133  -26.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1616  -29.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5267  -26.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4364  -28.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901  -25.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362  -26.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7256  -26.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404  -26.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5846  -28.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2757  -29.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0348  -25.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5485  -27.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006  -24.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8739  -25.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8234  -26.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9226  -29.0424    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3731  -27.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134  -25.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0871  -30.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1635  -25.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362  -25.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6968  -28.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9478  -26.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3133  -27.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2249  -27.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2970  -30.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5267  -27.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9881  -29.2115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6261  -29.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764  -25.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7256  -28.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147  -28.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8902  -26.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7256  -27.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0603  -28.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0618  -29.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000  -27.6807    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3879  -29.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4868  -29.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510  -29.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0369  -26.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110  -27.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000  -27.6173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239  -28.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8849  -28.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7256  -24.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8254  -25.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7619  -29.7275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110  -26.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7132  -26.4544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1757  -25.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1507  -28.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110  -25.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2015  -28.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2483  -28.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4107  -27.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1352  -24.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596  -24.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1224  -23.2627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8340  -22.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3979  -22.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3851  -22.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8212  -22.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 34  1  0
 31  1  1  0
 42 46  1  0
 39  6  1  0
  2 47  1  0
 47 31  1  0
 52 59  1  0
 50 38  1  0
 31 43  1  6
 61 41  1  1
 51 23  1  0
  6 14  2  0
 30 48  1  0
 32  8  1  0
 44 61  1  0
 19 11  1  0
 28 51  1  0
 13  5  1  1
 59 55  1  0
 39 36  2  0
 20 26  1  0
 27 12  1  0
 10 22  1  1
 10  1  1  0
 48 38  1  1
 52 27  1  0
 56 31  1  0
 19 59  1  0
 37 48  1  0
 55 13  1  0
 46 37  2  0
 18 23  1  1
 53  2  2  0
 16 34  1  0
 57  9  2  0
 24 56  1  0
 13 40  1  0
 36 57  1  0
 35 38  2  0
  3 50  1  0
 14  9  1  0
 54 44  2  0
 34 60  1  0
  9  7  1  0
 18 61  1  0
 53 24  1  0
 60 45  2  0
 11  7  1  0
 14 33  1  0
 45 46  1  0
 18 47  1  0
 62 37  1  0
  8 44  1  0
 29 56  1  0
 40 48  1  0
 33 30  1  0
 25 42  1  0
 12 13  1  0
 29 49  1  0
 27 26  1  6
 17 21  1  0
  7 30  2  0
 58 62  2  0
 47 21  1  6
 15 51  2  0
 61 10  1  0
  1 58  1  0
  4 27  1  0
  1 49  1  1
 60 58  1  0
  4 63  1  0
 63 64  2  0
 63 65  1  0
 65 66  1  0
 65 67  1  0
 67 68  1  0
 66 69  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2314559

   methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(13S,15S,17S)-17-(diethylcarbamoylamino)-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-diazapentacyclo[10.

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: 909.14

Molecular Weight (Monoisotopic): 908.5048

AlogP: 5.05

#Rotatable Bonds: 10

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: 4.72

CX LogD: 2.78

Aromatic Rings: 3

Heavy Atoms: 66

QED Weighted: 0.14

Np Likeness Score: 1.15

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