rac-acremine G

ID: ALA274744

PubChem CID: 44448248

Max Phase: Preclinical

Molecular Formula: C24H26O5

Molecular Weight: 394.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rac-Acremine G | rac-acremine G|CHEMBL274744

Canonical SMILES:  CC1=CC2c3cc(O)c(C)cc3OC3(C1)C(=O)C(C)=CC(=O)C23/C=C/C(C)(C)O

Standard InChI:  InChI=1S/C24H26O5/c1-13-8-17-16-11-18(25)14(2)9-19(16)29-24(12-13)21(27)15(3)10-20(26)23(17,24)7-6-22(4,5)28/h6-11,17,25,28H,12H2,1-5H3/b7-6+

Standard InChI Key:  ZJBCEAAFFNQWIJ-VOTSOKGWSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    2.1481  -15.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468  -16.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598  -17.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5758  -15.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749  -16.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924  -17.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941  -15.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0162  -15.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139  -16.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333  -17.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596  -16.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4618  -15.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7378  -15.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7389  -14.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1777  -15.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047  -17.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4607  -18.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0950  -18.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313  -19.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3555  -18.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332  -19.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893  -17.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735  -18.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5704  -19.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605  -17.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319  -17.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4333  -15.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7299  -17.8955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  8  1  0
 13 16  1  0
  6  7  1  0
 10 17  1  0
  7 10  1  0
  9  8  1  0
 17 18  2  0
  9 10  1  0
 18 19  1  0
  5  4  2  0
 19 20  1  0
  4  1  1  0
 19 21  1  0
  5  6  1  0
 19 22  1  0
  7 23  1  0
  2  3  1  0
 23 24  2  0
  3  6  2  0
 24 25  1  0
  9 14  1  0
 24 26  1  0
 26  9  1  0
 10 11  1  0
  2 27  1  0
 11 12  1  0
  1 28  1  0
 11 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA274744

   rac-acremine G

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: 394.47

Molecular Weight (Monoisotopic): 394.1780

AlogP: 3.68

#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: 10.15

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: 2.69

References

1. Arnone A, Nasini G, Panzeri W, de Pava OV, Malpezzi L..  (2008)  Acremine G, dimeric metabolite from cultures of Acremonium byssoides A20.,  71  (1): [PMID:18154270] [10.1021/np070413e]

Source

Source(1):

• Scientific Literature