6-((2S,4R)-2,4-dihydroxyundecyl)-4-hydroxy-3-methyl-2H-pyran-2-one

ID: ALA3109311

PubChem CID: 76324839

Max Phase: Preclinical

Molecular Formula: C17H28O5

Molecular Weight: 312.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC[C@@H](O)C[C@H](O)Cc1cc(O)c(C)c(=O)o1

Standard InChI:  InChI=1S/C17H28O5/c1-3-4-5-6-7-8-13(18)9-14(19)10-15-11-16(20)12(2)17(21)22-15/h11,13-14,18-20H,3-10H2,1-2H3/t13-,14+/m1/s1

Standard InChI Key:  JGWPHSGDXRADJG-KGLIPLIRSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   15.9118  -12.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6239  -12.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6239  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9118  -11.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1998  -12.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2024  -11.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3395  -11.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0528  -11.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7684  -11.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4817  -11.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1974  -11.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9106  -11.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6263  -11.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4854  -12.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9118  -13.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4867  -11.1790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0504  -12.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4793  -12.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3395  -11.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0552  -11.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7684  -11.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4841  -11.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  1  0
  1 15  2  0
  6 16  1  0
  8 17  1  6
 10 18  1  1
 13 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3109311

   6-((2S,4R)-2,4-dihydroxyundec-1-yl)-4-hydroxy-3-methyl-2H-pyran-2-one

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: 312.41

Molecular Weight (Monoisotopic): 312.1937

AlogP: 2.67

#Rotatable Bonds: 10

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.32

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.58

Np Likeness Score: 1.75

References

1. McMullin DR, Nsiama TK, Miller JD..  (2014)  Isochromans and α-pyrones from Penicillium corylophilum.,  77  (2): [PMID:24456578] [10.1021/np4005486]

Source

Source(1):

• Scientific Literature