(R)-5,7-dihydroxy-3-(4-hydroxybenzyl)chroman-4-one

ID: ALA1080799

Cas Number: 849727-88-4

PubChem CID: 638291

Max Phase: Preclinical

Molecular Formula: C16H14O5

Molecular Weight: 286.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2c(O)cc(O)cc2OC[C@H]1Cc1ccc(O)cc1

Standard InChI:  InChI=1S/C16H14O5/c17-11-3-1-9(2-4-11)5-10-8-21-14-7-12(18)6-13(19)15(14)16(10)20/h1-4,6-7,10,17-19H,5,8H2/t10-/m1/s1

Standard InChI Key:  FIASLUPJXGTCKM-SNVBAGLBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   12.4608   -4.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4596   -5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1740   -5.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1722   -4.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8870   -4.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8905   -5.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6091   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3290   -5.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3256   -4.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6023   -4.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0441   -5.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7570   -5.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4681   -5.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1805   -5.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1787   -4.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4586   -4.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7491   -4.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8910   -4.0046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7467   -4.0140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6114   -6.4904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1725   -6.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  5  6  1  0
  8 11  1  1
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
 17 12  1  0
  5 10  1  0
 15 18  1  0
  6  7  1  0
  1 19  1  0
  7  8  1  0
  7 20  2  0
  8  9  1  0
  3 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1080799

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

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: 286.28

Molecular Weight (Monoisotopic): 286.0841

AlogP: 2.24

#Rotatable Bonds: 2

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.86

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: 3.04

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: 1.76

References

1. Awale S, Miyamoto T, Linn TZ, Li F, Win NN, Tezuka Y, Esumi H, Kadota S..  (2009)  Cytotoxic constituents of Soymida febrifuga from Myanmar.,  72  (9): [PMID:19689125] [10.1021/np9003323]

2. Alali F, El-Elimat T, Albataineh H, Al-Balas Q, Al-Gharaibeh M, Falkinham JO, Chen WL, Swanson SM, Oberlies NH..  (2015)  Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii.,  78  (7): [PMID:26147490] [10.1021/acs.jnatprod.5b00357]

3. 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