Glyceollin III

ID: ALA2229450

Cas Number: 61080-23-7

PubChem CID: 11954193

Max Phase: Preclinical

Molecular Formula: C20H18O5

Molecular Weight: 338.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H18O5/c1-10(2)15-6-11-5-13-17(8-16(11)24-15)23-9-20(22)14-4-3-12(21)7-18(14)25-19(13)20/h3-5,7-8,15,19,21-22H,1,6,9H2,2H3/t15-,19-,20+/m0/s1

Standard InChI Key:  MIYTVBARXCVVHZ-RYGJVYDSSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   22.7028   -3.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9777   -4.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2653   -3.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1528   -5.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3152   -4.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2653   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9735   -5.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5528   -2.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9861   -2.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7028   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5528   -4.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4527   -5.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1277   -4.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4110   -3.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2734   -5.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6109   -5.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7526   -6.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8358   -3.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8404   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0493   -2.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5558   -3.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0418   -4.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7308   -3.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3223   -2.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3144   -4.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  2  4  1  1
  5  1  1  0
  6  9  1  0
  7  5  2  0
  8  6  2  0
  9 10  1  0
 19  8  1  0
 10  1  1  0
 11  3  2  0
 12  7  1  0
 13  5  1  0
 18 11  1  0
  1 14  1  6
 15 16  1  0
 16 13  2  0
 17 15  1  0
  4  7  1  0
  6  3  1  0
 12 15  2  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 21 23  1  1
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229450

   GLYCEOLLIN III

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: 2.99

#Rotatable Bonds: 1

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: 2.93

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: 2.44

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]

2. Selvam C, Jordan BC, Prakash S, Mutisya D, Thilagavathi R..  (2017)  Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties.,  128  [PMID:28189086] [10.1016/j.ejmech.2017.01.023]

Source

Source(1):

• Scientific Literature