monocillin III

ID: ALA404204

PubChem CID: 23305941

Max Phase: Preclinical

Molecular Formula: C18H20O6

Molecular Weight: 332.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Monocillin III | Monocillin III|(4R,6R,8R,11E)-17,19-Dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraene-2,13-dione|CHEMBL404204|CHEBI:221018

Canonical SMILES:  C[C@@H]1C[C@H]2O[C@@H]2CC/C=C/C(=O)Cc2cc(O)cc(O)c2C(=O)O1

Standard InChI:  InChI=1S/C18H20O6/c1-10-6-16-15(24-16)5-3-2-4-12(19)7-11-8-13(20)9-14(21)17(11)18(22)23-10/h2,4,8-10,15-16,20-21H,3,5-7H2,1H3/b4-2+/t10-,15-,16-/m1/s1

Standard InChI Key:  XFALPAMSDFFXGY-XLFSOCHTSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  1  0  0  0  0  0999 V2000
   -0.2108   -4.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124   -5.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056   -6.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262   -5.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029   -4.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2206   -4.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146   -3.3338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975   -3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9320   -3.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302   -4.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6337   -4.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -3.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512   -4.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0581   -4.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -4.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764   -3.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -3.3357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -4.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3551   -3.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -3.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -2.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304   -5.8064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4772   -2.6175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -4.3799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5053   -7.0635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -4.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  2  0
  3  4  2  0
  5  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 20  1  0
  6 10  1  0
  8 17  2  0
  9  7  1  0
  9 18  1  1
 20 19  1  0
 21 20  1  0
 19 21  1  0
  7  8  1  0
  4  6  1  0
  5  1  1  0
  5  6  2  0
 11 22  2  0
 20 23  1  1
  9 12  1  0
 10 11  1  0
 11 13  1  0
 19 24  1  6
 19 12  1  0
  3 25  1  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA404204

   MONOCILLIN III

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: 332.35

Molecular Weight (Monoisotopic): 332.1260

AlogP: 2.26

#Rotatable Bonds: ┄

Polar Surface Area: 96.36

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: 3.28

CX LogD: 3.25

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: 2.53

References

1. Paranagama PA, Wijeratne EM, Gunatilaka AA..  (2007)  Uncovering biosynthetic potential of plant-associated fungi: effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii.,  70  (12): [PMID:18052326] [10.1021/np070504b]

2. Hellwig V, Mayer-Bartschmid A, Müller H, Greif G, Kleymann G, Zitzmann W, Tichy HV, Stadler M..  (2003)  Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata.,  66  (6): [PMID:12828470] [10.1021/np020556v]

3. Shinonaga H, Noguchi T, Ikeda A, Aoki M, Fujimoto N, Kawashima A..  (2009)  Synthesis and structure-activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity.,  17  (13): [PMID:19447629] [10.1016/j.bmc.2009.04.060]

4. 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