4'-hydroxymonocillin IV

ID: ALA4214851

PubChem CID: 139050663

Max Phase: Preclinical

Molecular Formula: C19H24O6

Molecular Weight: 348.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1CC/C=C/C[C@@H](C)OC(=O)c2c(O)cc(O)cc2CC(=O)C1

Standard InChI:  InChI=1S/C19H24O6/c1-12-6-4-3-5-7-16(24-2)10-14(20)8-13-9-15(21)11-17(22)18(13)19(23)25-12/h3-4,9,11-12,16,21-22H,5-8,10H2,1-2H3/b4-3+/t12-,16-/m1/s1

Standard InChI Key:  JJIOMTUAXLXSBA-KWTXBODISA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    9.9411   -9.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9399  -10.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6480  -11.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6462   -9.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6396   -8.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2319  -11.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3498   -9.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3495  -10.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0577   -9.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0581  -11.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0539  -12.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7596  -12.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4668  -12.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1676  -12.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8831  -12.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8933  -11.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7699   -9.9801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1895   -9.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4776   -9.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0569   -8.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4767   -8.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724  -11.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1871  -10.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3394  -12.4269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7634  -10.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  4  5  1  0
  2  6  1  0
  7  8  1  0
  7  9  1  0
  8 10  1  0
 17  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 23  2  0
 17 19  1  0
 23 18  1  0
 18 19  1  0
  9 20  2  0
 19 21  1  6
 13 22  1  6
 11 24  2  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214851

   ---

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: 348.40

Molecular Weight (Monoisotopic): 348.1573

AlogP: 2.90

#Rotatable Bonds: 1

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: 3.67

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: 2.03

References

1. Xu L, Wu P, Xue J, Molnar I, Wei X..  (2017)  Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species.,  80  (8): [PMID:28749671] [10.1021/acs.jnatprod.7b00066]

Source

Source(1):

• Scientific Literature