Macrophilone C

ID: ALA4168800

PubChem CID: 145953684

Max Phase: Preclinical

Molecular Formula: C11H11N3O2S

Molecular Weight: 249.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C1C2=C(NCCS2)C(=O)c2[nH]cc(CO)c21

Standard InChI:  InChI=1S/C11H11N3O2S/c12-7-6-5(4-15)3-14-8(6)10(16)9-11(7)17-2-1-13-9/h3,12-15H,1-2,4H2

Standard InChI Key:  OBDLRFWZOITVME-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
    9.1363   -3.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1363   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -4.3514    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -2.7008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5608   -3.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5573   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2663   -4.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2734   -2.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9868   -3.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9808   -3.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7634   -4.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2533   -3.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7732   -2.8746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2757   -1.8805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2624   -5.1815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0127   -4.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8187   -5.1736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  1  0
  8 14  2  0
  7 15  2  0
 11 16  1  0
 16 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4168800

   ---

Molecule Features

Natural Product: Yes

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: 249.29

Molecular Weight (Monoisotopic): 249.0572

AlogP: 0.62

#Rotatable Bonds: 1

Polar Surface Area: 88.97

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.89

CX Basic pKa: 9.36

CX LogP: -1.03

CX LogD: -2.98

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.59

Np Likeness Score: 0.90

References

1. Yan P, Ritt DA, Zlotkowski K, Bokesch HR, Reinhold WC, Schneekloth JS, Morrison DK, Gustafson KR..  (2018)  Macrophilones from the Marine Hydroid Macrorhynchia philippina Can Inhibit ERK Cascade Signaling.,  81  (7): [PMID:29979591] [10.1021/acs.jnatprod.8b00343]

Source

Source(1):

• Scientific Literature