monocillin I

ID: ALA215853

PubChem CID: 6440561

Max Phase: Preclinical

Molecular Formula: C18H18O6

Molecular Weight: 330.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Monocillin I | Monocillin I|MLS004257395|CHEMBL215853|SMR003082525|6H-Oxireno(e)(2)benzoxacyclotetradecin-6,12(7H)-dione,1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,2Z,4E,14R,15aR)-

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

Standard InChI:  InChI=1S/C18H18O6/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/h2-5,8-10,15-16,20-21H,6-7H2,1H3/b4-2+,5-3-/t10-,15-,16-/m1/s1

Standard InChI Key:  XTUZVEOWUSGCSV-HLZLSLRQSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    7.2880    0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2925   -0.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0044    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4296   -0.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437    0.3664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623   -0.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -0.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5779   -1.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5758    0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2925   -0.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0069   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7284   -0.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7308   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5779   -2.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7145    0.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437   -1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4325   -0.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -1.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -2.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4350   -2.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438   -2.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368   -3.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -0.8736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1442   -0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5779   -0.4489    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5843    0.9620    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
  2  1  1  0
  8 14  2  0
  3  2  1  0
  4 15  2  0
  4 17  1  0
  1  3  1  0
 16 17  2  0
  6  9  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
  8 10  1  0
 19 20  1  0
  2  9  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
  4  5  1  0
 18 23  1  0
 16  7  1  0
  6 24  1  1
  6  5  1  0
  2 25  1  6
 10 11  2  0
  3 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA215853

   MONOCILLIN I

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: 330.34

Molecular Weight (Monoisotopic): 330.1103

AlogP: 2.04

#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: 3.07

CX LogD: 3.04

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: 2.61

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. Turbyville TJ, Wijeratne EM, Liu MX, Burns AM, Seliga CJ, Luevano LA, David CL, Faeth SH, Whitesell L, Gunatilaka AA..  (2006)  Search for Hsp90 inhibitors with potential anticancer activity: isolation and SAR studies of radicicol and monocillin I from two plant-associated fungi of the Sonoran desert.,  69  (2): [PMID:16499313] [10.1021/np058095b]

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