4'-methoxymonocillin IV

ID: ALA4206598

PubChem CID: 139589761

Max Phase: Preclinical

Molecular Formula: C18H22O6

Molecular Weight: 334.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H22O6/c1-11-5-3-2-4-6-13(19)9-14(20)7-12-8-15(21)10-16(22)17(12)18(23)24-11/h2-3,8,10-11,13,19,21-22H,4-7,9H2,1H3/b3-2+/t11-,13-/m1/s1

Standard InChI Key:  BOOGYPBXHOLWJD-FTYDKLPRSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   17.4856  -10.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4845  -10.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1925  -11.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1908   -9.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1842   -8.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7765  -11.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8944  -10.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8941  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6023   -9.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6027  -11.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5985  -12.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3041  -12.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0114  -12.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7122  -12.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4277  -12.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4379  -11.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3145  -10.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7341  -10.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0222   -9.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6015   -8.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0213   -8.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0170  -11.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7316  -10.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8840  -12.4682    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA4206598

   ---

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: 334.37

Molecular Weight (Monoisotopic): 334.1416

AlogP: 2.25

#Rotatable Bonds: ┄

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.50

CX Basic pKa: ┄

CX LogP: 3.06

CX LogD: 3.03

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.50

Np Likeness Score: 2.26

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