N-(4-amino-6-(methylamino)pyrimidin-5-yl)-N-(3,7-dimethyl-9-((1R,6S)-1,2,6-trimethylcyclohex-2-enyl)nona-2,6-dienyl)formamide

ID: ALA2337297

PubChem CID: 21679120

Max Phase: Preclinical

Molecular Formula: C26H41N5O

Molecular Weight: 439.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ncnc(N)c1N(C=O)C/C=C(\C)CC/C=C(\C)CC[C@@]1(C)C(C)=CCC[C@@H]1C

Standard InChI:  InChI=1S/C26H41N5O/c1-19(13-15-26(5)21(3)11-8-12-22(26)4)9-7-10-20(2)14-16-31(18-32)23-24(27)29-17-30-25(23)28-6/h9,11,14,17-18,22H,7-8,10,12-13,15-16H2,1-6H3,(H3,27,28,29,30)/b19-9+,20-14+/t22-,26-/m0/s1

Standard InChI Key:  NFOOQBRCQVDNGM-BEHXQNNVSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   11.2860  -14.3108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2933  -13.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -13.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8673  -13.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1645  -13.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1870  -12.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4841  -11.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5066  -10.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8036  -10.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2320  -10.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0782  -10.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0557  -11.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282  -12.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3039  -12.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048  -13.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7321  -12.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7583  -12.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7541  -11.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4666  -11.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6268  -11.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8448  -14.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5679  -14.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5606  -15.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9968  -14.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9856  -15.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6955  -15.9736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4146  -15.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4193  -14.7383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7087  -14.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7128  -13.4982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2664  -15.9592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2569  -16.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
  9 11  1  0
 12 11  1  1
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 12 19  1  0
 13 20  1  6
  4 21  1  0
  1 22  1  0
 22 23  2  0
  1 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 29 30  1  0
 25 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2337297

   N-[4-amino-6-(methylamino)pyrimidin-5-yl]-N-[(2E,6E)-3,7-dimethyl-9-[(1R,6S)-1,2,6-trimethylcyclohex-2-en-1-yl]nona-2,6-dienyl]formamide

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: 439.65

Molecular Weight (Monoisotopic): 439.3311

AlogP: 5.90

#Rotatable Bonds: 11

Polar Surface Area: 84.14

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.74

CX LogP: 4.92

CX LogD: 4.83

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: 2.14

References

1. Pettit GR, Tang Y, Zhang Q, Bourne GT, Arm CA, Leet JE, Knight JC, Pettit RK, Chapuis JC, Doubek DL, Ward FJ, Weber C, Hooper JN..  (2013)  Isolation and structures of axistatins 1-3 from the Republic of Palau marine sponge Agelas axifera Hentschel .,  76  (3): [PMID:23410078] [10.1021/np300828y]

Source

Source(1):

• Scientific Literature