(Z)-(16-Hydroxyhexadec-9-enoyl)-L-alanine Methyl Ester

ID: ALA4168698

PubChem CID: 139589881

Max Phase: Preclinical

Molecular Formula: C20H37NO4

Molecular Weight: 355.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](C)NC(=O)CCCCCCC/C=C\CCCCCCO

Standard InChI:  InChI=1S/C20H37NO4/c1-18(20(24)25-2)21-19(23)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-22/h3,5,18,22H,4,6-17H2,1-2H3,(H,21,23)/b5-3-/t18-/m0/s1

Standard InChI Key:  XWFACHYZFVZDPE-AJNOYIKESA-N

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
    4.6606   -4.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6798   -3.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3969   -3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0948   -3.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8119   -3.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5098   -3.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2269   -3.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9249   -3.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420   -3.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399   -4.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0570   -3.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7549   -4.0353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0761   -2.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4720   -3.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1700   -4.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4912   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1508   -4.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8870   -3.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5850   -4.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9435   -5.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9244   -5.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2073   -6.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1881   -7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -7.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519   -8.3130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  1
 15 17  2  0
 15 18  1  0
 18 19  1  0
  1 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168698

   ---

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: 355.52

Molecular Weight (Monoisotopic): 355.2723

AlogP: 3.89

#Rotatable Bonds: 16

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.85

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.25

Np Likeness Score: 0.46

References

1. Bruns H, Herrmann J, Müller R, Wang H, Wagner Döbler I, Schulz S..  (2018)  Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164.,  81  (1): [PMID:29261310] [10.1021/acs.jnatprod.7b00757]

Source

Source(1):

• Scientific Literature