monocillin IV

ID: ALA470883

PubChem CID: 5275906

Max Phase: Preclinical

Molecular Formula: C18H22O5

Molecular Weight: 318.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Monocillin IV | Monocillin IV|(4R,6E)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,12-dione|Microlactone, 14c|CHEMBL470883|BDBM68255|CHEBI:200268|(8E,11R)-15,17-dihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),8,15,17-tetraene-3,13-dione|1H-2-Benzoxacyclotetradecin-1,11(12H)-dione, 3,4,7,8,9,10-hexahydro-14,16-dihydroxy-3-methyl-, (3R,5E)-

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

Standard InChI:  InChI=1S/C18H22O5/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/h3,5,10-12,20-21H,2,4,6-9H2,1H3/b5-3+/t12-/m1/s1

Standard InChI Key:  WSBASKMWDAUNEI-OGOUPESXSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    9.7616  -17.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4708  -16.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4708  -15.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7616  -15.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0481  -16.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0481  -15.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3362  -15.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3362  -17.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6198  -16.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6237  -15.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9137  -15.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1953  -15.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060  -17.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1950  -16.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4794  -17.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4734  -18.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1889  -18.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9017  -18.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6162  -15.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4811  -15.5384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3374  -18.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1863  -19.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708  -16.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12 14  1  0
  5  1  1  0
  1  2  1  0
 13 14  2  0
  5  8  1  0
 14 15  1  0
  6  7  1  0
 15 16  2  0
  7 10  1  0
 16 17  1  0
  9  8  1  0
 17 18  2  0
 18 13  1  0
  2  3  1  0
 10 19  1  1
  3  4  1  0
 12 20  2  0
  8 21  2  0
  6  4  2  0
 17 22  1  0
  9 13  1  0
 15 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA470883

   MONOCILLIN IV

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: 318.37

Molecular Weight (Monoisotopic): 318.1467

AlogP: 3.28

#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: 1.97

References

1. Bryant FO, Cutler HG, Parker SR, Jacyno JM.  (1994)  Effect of Fungal Natural Products in an Agrobacterium tumefaciens Potato Disc Assay,  57  (5): [10.1021/np50107a012]

2. Gao J, Radwan MM, León F, Dale OR, Husni AS, Wu Y, Lupien S, Wang X, Manly SP, Hill RA, Dugan FM, Cutler HG, Cutler SJ..  (2013)  Neocosmospora sp.-derived resorcylic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors.,  76  (5): [PMID:23659286] [10.1021/np300653d]

3. 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