8-Prenylnaringenin C

ID: ALA4852770

PubChem CID: 14187085

Max Phase: Preclinical

Molecular Formula: C20H18O5

Molecular Weight: 338.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)C=Cc2c(cc(O)c3c2OC(c2ccc(O)cc2)CC3=O)O1

Standard InChI:  InChI=1S/C20H18O5/c1-20(2)8-7-13-17(25-20)10-15(23)18-14(22)9-16(24-19(13)18)11-3-5-12(21)6-4-11/h3-8,10,16,21,23H,9H2,1-2H3

Standard InChI Key:  JTJIFFUHXHGAOQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    5.3074  -13.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0145  -14.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7211  -13.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7202  -13.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0069  -12.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032  -13.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267  -12.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2394  -13.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0566  -13.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515  -12.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680  -15.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4761  -15.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692  -14.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734  -13.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697  -13.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633  -12.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0611  -13.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954  -16.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759  -16.4043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829  -14.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863  -15.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8947  -15.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043  -15.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6010  -14.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8880  -13.9395    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 21  2  0
 20 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
 22 18  2  0
 12 19  1  0
 20 21  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4852770

   Citflavanone

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: 338.36

Molecular Weight (Monoisotopic): 338.1154

AlogP: 3.99

#Rotatable Bonds: 1

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: 8.80

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 2.61

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