Isoxanthohumol C

ID: ALA4861182

PubChem CID: 71135523

Max Phase: Preclinical

Molecular Formula: C21H20O5

Molecular Weight: 352.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c3c1C(=O)CC(c1ccc(O)cc1)O3)C=CC(C)(C)O2

Standard InChI:  InChI=1S/C21H20O5/c1-21(2)9-8-14-17(26-21)11-18(24-3)19-15(23)10-16(25-20(14)19)12-4-6-13(22)7-5-12/h4-9,11,16,22H,10H2,1-3H3

Standard InChI Key:  FMFCFFOLQZZBDX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.7078   -8.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4148   -8.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1214   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1206   -7.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4072   -7.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7036   -7.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8271   -7.1130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6397   -7.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569   -7.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519   -6.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684   -9.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8764   -9.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1695   -8.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -8.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8700   -7.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636   -7.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -8.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2957  -10.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8762  -10.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1684  -11.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832   -8.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866   -9.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -9.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047   -9.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883   -8.3430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  9  8  1  0
 10  9  1  0
 13 11  2  0
 11 12  1  0
 12 22  2  0
 21 14  2  0
 13 14  1  0
 13 17  1  0
 14 15  1  0
 15 16  2  0
 16  9  1  0
  9 17  1  0
 23 18  2  0
 12 19  1  0
 19 20  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4861182

   2-(4-Hydroxyphenyl)-5-methoxy-8,8-dimethyl-2,3-dihydropyrano[2,3-h]chromen-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: 352.39

Molecular Weight (Monoisotopic): 352.1311

AlogP: 4.29

#Rotatable Bonds: 2

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.47

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 3.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: 2.47

References

1. Urmann C, Bieler L, Priglinger E, Aigner L, Couillard-Despres S, Riepl HM..  (2021)  Neuroregenerative Potential of Prenyl- and Pyranochalcones: A Structure-Activity Study.,  84  (10.0): [PMID:34542287] [10.1021/acs.jnatprod.1c00505]

Source

Source(1):

• Scientific Literature