Giffonin J

ID: ALA4849304

PubChem CID: 164615524

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c2cc(c(OC)c1O)Oc1ccc(cc1)[C@@H](O)C[C@H](O)CC/C=C/2

Standard InChI:  InChI=1S/C21H24O6/c1-25-20-14-5-3-4-6-15(22)12-17(23)13-7-9-16(10-8-13)27-18(11-14)21(26-2)19(20)24/h3,5,7-11,15,17,22-24H,4,6,12H2,1-2H3/b5-3+/t15-,17+/m1/s1

Standard InChI Key:  ATGCIUOLONYVDU-LDHYMBSASA-N

Molfile:  

 
     RDKit          2D

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   40.2753  -11.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8614  -12.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2670  -13.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0821  -13.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4900  -12.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0862  -11.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8697  -11.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.2812  -10.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0483  -12.5356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8551  -13.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0420  -13.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4846  -13.9585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.2976  -13.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6995  -14.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5118  -14.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9192  -13.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5123  -13.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7014  -13.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7322  -13.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1397  -14.6718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.1419  -13.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.7344  -12.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1441  -11.8533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4487  -12.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2282  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8103  -12.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9492  -11.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  4 12  1  0
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 18 13  1  0
 16 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  1
 24 25  1  0
 25 26  1  0
 22 26  1  0
 24 27  2  0
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4849304

   ---

Molecule Features

Natural Product: No

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: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.79

#Rotatable Bonds: 2

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.92

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: 1.96

References

1. Masullo M, Lauro G, Cerulli A, Kontek B, Olas B, Bifulco G, Piacente S, Pizza C..  (2021)  Giffonins, Antioxidant Diarylheptanoids from Corylus avellana, and Their Ability to Prevent Oxidative Changes in Human Plasma Proteins.,  84  (3.0): [PMID:33616390] [10.1021/acs.jnatprod.0c01251]

Source

Source(1):

• Scientific Literature