4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one

ID: ALA3109310

PubChem CID: 76310262

Max Phase: Preclinical

Molecular Formula: C17H28O6

Molecular Weight: 328.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(O)cc(C[C@@H](O)C[C@H](O)CCCCCCCO)oc1=O

Standard InChI:  InChI=1S/C17H28O6/c1-12-16(21)11-15(23-17(12)22)10-14(20)9-13(19)7-5-3-2-4-6-8-18/h11,13-14,18-21H,2-10H2,1H3/t13-,14+/m1/s1

Standard InChI Key:  NAFBSCAXPHZFLQ-KGLIPLIRSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    8.5747  -17.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2866  -17.3461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2866  -16.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5747  -16.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8626  -17.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8652  -16.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0023  -16.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7157  -16.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4314  -16.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1446  -16.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8603  -16.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5736  -16.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2893  -16.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1481  -17.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5747  -18.5794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1494  -16.1126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7133  -17.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1422  -17.3544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0025  -16.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7182  -16.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4315  -16.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1472  -16.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8604  -16.5462    0.0000 O   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
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3109310

   6-((2S,4R)-2,4,11-trihydroxyundecyl)-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: 328.41

Molecular Weight (Monoisotopic): 328.1886

AlogP: 1.64

#Rotatable Bonds: 11

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.55

CX Basic pKa: ┄

CX LogP: 1.11

CX LogD: 0.88

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.46

Np Likeness Score: 1.80

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