Monocillin II

ID: ALA562520

PubChem CID: 11461229

Max Phase: Preclinical

Molecular Formula: C18H20O5

Molecular Weight: 316.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1C/C=C/CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1

Standard InChI:  InChI=1S/C18H20O5/c1-12-7-5-3-2-4-6-8-14(19)9-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,5-6,8,10-12,20-21H,2,4,7,9H2,1H3/b5-3+,8-6+/t12-/m1/s1

Standard InChI Key:  AGKSYPMAQRUJJY-RNLVMQRLSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -3.1889   -8.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901   -9.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4753   -9.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7588   -9.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617   -8.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4771   -7.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488   -7.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3328   -8.2034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519   -6.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3802   -7.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -8.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0993   -9.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153   -9.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184  -10.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055  -10.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0437   -9.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0424  -10.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273  -10.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865  -10.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7562  -10.6893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9049   -9.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -6.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770   -6.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 14 15  1  0
 15 19  1  0
  3  4  2  0
  4 16  1  0
  7  8  1  0
 16 17  1  0
 17 18  1  0
  7  9  2  0
 18 19  2  0
  4  5  1  0
 17 20  2  0
  8 10  1  0
  2 21  1  0
  2  3  1  0
  6 22  1  0
 10 11  1  0
 10 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA562520

   (4R,6E,10E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,10,15,17-pentaene-2,12-dione

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: 316.35

Molecular Weight (Monoisotopic): 316.1311

AlogP: 3.05

#Rotatable Bonds: ┄

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.26

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: 2.30

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