moracin D

ID: ALA463241

Cas Number: 69120-07-6

PubChem CID: 641378

Max Phase: Preclinical

Molecular Formula: C19H16O4

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Moracin D | Moracin D|69120-07-6|7-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol|7-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol|7-(6-Hydroxybenzofuran-2-yl)-2,2-dimethyl-2H-chromen-5-ol|starbld0006163|CHEMBL463241|SCHEMBL6822795|CHEBI:174942|DTXSID301178570|BDBM50062362|AKOS032962426|FS-8967|HY-122943|CS-0090596|7-(6-hydroxy-1-benzouran-2-yl)-2,2-dimethylchromen-5-ol|2H-1-benzopyran-5-ol, 7-(6-hydroxy-2-benzofuranyl)-2,2-dimethyl-|7-(6-Hydroxy-2-benzofuranyl)-2,2-dimethyl-Show More⌵

Canonical SMILES:  CC1(C)C=Cc2c(O)cc(-c3cc4ccc(O)cc4o3)cc2O1

Standard InChI:  InChI=1S/C19H16O4/c1-19(2)6-5-14-15(21)7-12(9-18(14)23-19)16-8-11-3-4-13(20)10-17(11)22-16/h3-10,20-21H,1-2H3

Standard InChI Key:  CHAAQDMHLLQJRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    3.7519   -6.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -7.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7519   -8.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -8.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144   -8.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -8.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -8.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -7.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144   -7.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -6.5970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269   -9.4563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5265   -6.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098   -5.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -8.6942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519   -8.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -7.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175   -7.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8175   -8.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -8.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -8.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -7.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -7.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -8.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  9 10  1  0
  1 10  1  0
  5 11  1  0
  1 12  1  0
  1 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 14 18  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 18 19  2  0
 20 23  1  0
  7 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463241

   MORACIN D

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: 308.33

Molecular Weight (Monoisotopic): 308.1049

AlogP: 4.70

#Rotatable Bonds: 1

Polar Surface Area: 62.83

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.74

CX Basic pKa: ┄

CX LogP: 3.99

CX LogD: 3.97

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: 2.17

References

1. Lee D, Bhat KP, Fong HH, Farnsworth NR, Pezzuto JM, Kinghorn AD..  (2001)  Aromatase inhibitors from Broussonetia papyrifera.,  64  (10): [PMID:11678652] [10.1021/np010288l]

2. Naik R, Harmalkar DS, Xu X, Jang K, Lee K..  (2015)  Bioactive benzofuran derivatives: moracins A-Z in medicinal chemistry.,  90  [PMID:25461329] [10.1016/j.ejmech.2014.11.047]

Source

Source(1):

• Scientific Literature