Violacin A

ID: ALA4214012

PubChem CID: 145964226

Max Phase: Preclinical

Molecular Formula: C13H14O5

Molecular Weight: 250.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)CC1(O)CC(=O)c2c(C)cc(O)cc2O1

Standard InChI:  InChI=1S/C13H14O5/c1-7-3-9(15)4-11-12(7)10(16)6-13(17,18-11)5-8(2)14/h3-4,15,17H,5-6H2,1-2H3

Standard InChI Key:  RMPWJHGWNLSRQT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.6029   -5.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017   -5.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098   -6.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080   -4.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0166   -5.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154   -5.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216   -6.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335   -5.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347   -5.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7239   -4.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8951   -4.6061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3114   -7.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194   -7.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1434   -4.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8501   -5.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5588   -4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8481   -5.8336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273   -4.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  3 12  1  0
  7 13  2  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214012

   ---

Molecule Features

Natural Product: Yes

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: 250.25

Molecular Weight (Monoisotopic): 250.0841

AlogP: 1.33

#Rotatable Bonds: 2

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: 7.88

CX Basic pKa: ┄

CX LogP: 1.44

CX LogD: 1.31

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: 1.36

References

1. Ma J, Cao B, Chen X, Xu M, Bi X, Guan P, Jiang Y, Xu J, Han L, Huang X..  (2018)  Violacin A, a new chromanone produced by Streptomyces violaceoruber and its anti-inflammatory activity.,  28  (5): [PMID:29426772] [10.1016/j.bmcl.2018.01.051]

Source

Source(1):

• Scientific Literature