dihydrorobinetin

ID: ALA1163000

PubChem CID: 17751005

Max Phase: Preclinical

Molecular Formula: C15H12O7

Molecular Weight: 304.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 3,7,3',4',5'-Pentahydroxyflavanone | Dihydrorobinetin | Dihydrorobinetin|3,7,3',4',5'-Pentahydroxyflavanone|SCHEMBL432879|CHEMBL1163000

Canonical SMILES:  O=C1c2ccc(O)cc2O[C@@H](c2cc(O)c(O)c(O)c2)[C@@H]1O

Standard InChI:  InChI=1S/C15H12O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,14-18,20-21H/t14-,15+/m1/s1

Standard InChI Key:  VSJCDPYIMBSOKN-CABCVRRESA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883    3.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885    3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5309    0.9045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5268    3.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1865    4.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  7  6  1  0
  5  6  2  0
  5  8  1  0
  7 10  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  9 12  1  6
  8 13  2  0
  2 14  1  0
 16 11  2  0
 11 17  1  0
 15 16  1  0
 15 19  2  0
 17 18  2  0
 18 19  1  0
 15 20  1  0
 19 21  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1163000

   DIHYDROROBINETIN

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: 304.25

Molecular Weight (Monoisotopic): 304.0583

AlogP: 1.19

#Rotatable Bonds: 1

Polar Surface Area: 127.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: ┄

CX LogP: 1.17

CX LogD: 0.97

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.50

Np Likeness Score: 2.07

References

1. Lale A, Herbert JM, Augereau JM, Billon M, Leconte M, Gleye J..  (1996)  Ability of different flavonoids to inhibit the procoagulant activity of adherent human monocytes.,  59  (3): [PMID:8882428] [10.1021/np960057s]

2. Lee S, Woo Y, Shin SY, Lee YH, Lim Y..  (2009)  Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.,  19  (8): [PMID:19307119] [10.1016/j.bmcl.2009.03.017]

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

Source

Source(1):

• Scientific Literature