(R)-7-hydroxy-3-(4-hydroxybenzyl)-5-methoxychroman-4-one

ID: ALA4473936

Cas Number: 27245-81-4

PubChem CID: 92446293

Max Phase: Preclinical

Molecular Formula: C17H16O5

Molecular Weight: 300.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(O)cc2c1C(=O)[C@H](Cc1ccc(O)cc1)CO2

Standard InChI:  InChI=1S/C17H16O5/c1-21-14-7-13(19)8-15-16(14)17(20)11(9-22-15)6-10-2-4-12(18)5-3-10/h2-5,7-8,11,18-19H,6,9H2,1H3/t11-/m1/s1

Standard InChI Key:  COVYMSXAVAIXCI-LLVKDONJSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   33.1499   -3.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2898   -2.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2886   -3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0034   -4.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0016   -2.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7170   -2.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7158   -3.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4288   -4.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1486   -2.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4311   -2.5016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4264   -4.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5752   -2.5084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0051   -4.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2915   -5.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8629   -4.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5788   -3.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2902   -4.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0056   -3.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0089   -2.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2909   -2.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5784   -2.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7243   -2.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  1  8  1  0
  1  9  1  0
  9 10  1  0
  8 11  2  0
  2 12  1  0
  4 13  1  0
 13 14  1  0
  1 15  1  1
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4473936

   (3R)-7-hydroxy-3-[(4-hydroxyphenyl)methyl]-5-methoxy-2,3-dihydrochromen-4-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 300.31

Molecular Weight (Monoisotopic): 300.0998

AlogP: 2.54

#Rotatable Bonds: 3

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.85

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: 1.70

References

1. Schwikkard S, Whitmore H, Sishtla K, Sulaiman RS, Shetty T, Basavarajappa HD, Waller C, Alqahtani A, Frankemoelle L, Chapman A, Crouch N, Wetschnig W, Knirsch W, Andriantiana J, Mas-Claret E, Langat MK, Mulholland D, Corson TW..  (2019)  The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae ( sensu APGII).,  82  (5): [PMID:30951308] [10.1021/acs.jnatprod.8b00989]

Source

Source(1):

• Scientific Literature