6-Prenylnaringenin C

ID: ALA4868903

Cas Number: 170900-13-7

PubChem CID: 14187087

Max Phase: Preclinical

Molecular Formula: C20H18O5

Molecular Weight: 338.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)C=Cc2c(cc3c(c2O)C(=O)CC(c2ccc(O)cc2)O3)O1

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

Standard InChI Key:  JSAQPDCTCSLTHA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    7.5239  -14.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3164  -14.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379  -13.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2771  -13.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9842  -14.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6907  -13.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6899  -13.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9766  -12.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2729  -13.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3964  -12.6682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4457  -15.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8650  -16.3611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4455  -16.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1526  -14.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1559  -15.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8644  -15.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5740  -15.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5707  -14.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8577  -13.8982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4277  -13.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7377  -15.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7352  -14.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0288  -13.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3227  -15.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0337  -15.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  7 10  1  0
 21 11  1  0
 11 15  2  0
 14 20  2  0
 16 12  2  0
 11 13  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18  4  1  0
 22 20  1  0
 21 22  2  0
 21 25  1  0
 22 23  1  0
 23  2  1  0
  2 24  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4868903

   Paratocarpin K

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: 8.53

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.01

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 2.55

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