Glyceollin II

ID: ALA2229451

Cas Number: 67314-98-1

PubChem CID: 181883

Max Phase: Preclinical

Molecular Formula: C20H18O5

Molecular Weight: 338.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C=Cc2cc3c(cc2O1)OC[C@@]1(O)c2ccc(O)cc2O[C@@H]31

Standard InChI:  InChI=1S/C20H18O5/c1-19(2)6-5-11-7-13-16(9-15(11)25-19)23-10-20(22)14-4-3-12(21)8-17(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1

Standard InChI Key:  DDJVLBCETGUEBO-AZUAARDMSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    8.9824   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8073   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3949   -2.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1110   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3861   -4.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6737   -4.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5611   -5.3037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7235   -4.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6737   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3819   -5.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9613   -2.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3944   -2.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1110   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9613   -4.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8610   -6.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5359   -4.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8194   -3.6663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6817   -5.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0192   -5.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1608   -6.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2488   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2488   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5312   -2.8395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8090   -4.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5312   -4.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  5  7  1  1
  8  4  1  0
  9 12  1  0
 10  8  2  0
 11  9  2  0
 12 13  1  0
 22 11  1  0
 13  4  1  0
 14  6  2  0
 15 10  1  0
 16  8  1  0
 21 14  1  0
  4 17  1  6
 18 19  1  0
 19 16  2  0
 20 18  1  0
  7 10  1  0
  9  6  1  0
 15 18  2  0
 21 22  2  0
 21 25  1  0
 22 23  1  0
 23  2  1  0
  2 24  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229451

   GLYCEOLLIN II

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: 338.36

Molecular Weight (Monoisotopic): 338.1154

AlogP: 3.29

#Rotatable Bonds: ┄

Polar Surface Area: 68.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: 2.91

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: 2.92

References

1. Kim HJ, Suh HJ, Lee CH, Kim JH, Kang SC, Park S, Kim JS..  (2010)  Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae.,  58  (17): [PMID:20666365] [10.1021/jf101694t]

Source

Source(1):

• Scientific Literature