20-(hex-2-enyl)-10-hydroxy-7,15-dimethylazacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

ID: ALA3780857

PubChem CID: 127029842

Max Phase: Preclinical

Molecular Formula: C27H37NO2

Molecular Weight: 407.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC/C=C/CC1C/C=C/C=C(C)/C=C/C=C\C(O)C/C=C(C)/C=C/C=C/C(=O)N1

Standard InChI:  InChI=1S/C27H37NO2/c1-4-5-6-7-17-25-18-11-8-14-23(2)15-9-12-19-26(29)22-21-24(3)16-10-13-20-27(30)28-25/h6-16,19-21,25-26,29H,4-5,17-18,22H2,1-3H3,(H,28,30)/b7-6+,11-8+,15-9+,16-10+,19-12-,20-13+,23-14+,24-21+

Standard InChI Key:  UMYFIUGQWGBKLX-MMJNJZBSSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    2.5628    3.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569    4.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586    4.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8332    5.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572    5.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802    3.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5418    2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4415    2.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    1.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9912   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1418   -4.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3205   -4.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335   -5.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -1.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -0.1753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5747   -2.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -3.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5027   -3.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -2.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859   -1.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227   -0.7184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8567    1.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3398    0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8603   -0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3395   -0.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8600   -2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3391   -2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7553   -3.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  1  8  2  0
  8  9  1  0
  9 10  2  0
 19 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 19 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 10 22  1  0
  7 24  1  0
 24 16  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3780857

   ---

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: 407.60

Molecular Weight (Monoisotopic): 407.2824

AlogP: 6.05

#Rotatable Bonds: 4

Polar Surface Area: 49.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 5.53

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: 2.43

References

1. Li L, Cai Y, Jiang Y, Liu J, Ma J, Yuan C, Mu Y, Han L, Huang X..  (2016)  A unique macrolactam derivative via a [4+6]-cycloaddition from Streptomyces niveus.,  26  (6): [PMID:26874404] [10.1016/j.bmcl.2016.02.002]

Source

Source(1):

• Scientific Literature