Rhizopycnin C

ID: ALA3926145

PubChem CID: 134141491

Max Phase: Preclinical

Molecular Formula: C15H11ClO7

Molecular Weight: 338.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(=O)oc3c(c2c1)[C@@](C)(O)C(Cl)=C(O)C3=O

Standard InChI:  InChI=1S/C15H11ClO7/c1-15(21)9-6-3-5(22-2)4-7(17)8(6)14(20)23-12(9)10(18)11(19)13(15)16/h3-4,17,19,21H,1-2H3/t15-/m1/s1

Standard InChI Key:  ATVFPTGTIZZMLF-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   10.8578  -10.8591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2685  -11.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6768  -10.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2691  -13.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5686  -11.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5686  -12.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9795  -11.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9742  -12.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6747  -13.2090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3873  -12.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6853  -11.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3885  -11.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0998  -11.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1132  -10.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4058  -10.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6892  -10.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8588  -13.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0929  -13.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8051  -12.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4169   -9.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1294   -9.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2679  -14.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8586  -11.5776    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  5  6  2  0
  5  2  1  0
  6  4  1  0
  4  8  1  0
  7  2  1  0
  7  8  2  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  1  0
 11 16  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  6 17  1  0
 10 18  2  0
 13 19  1  0
 15 20  1  0
 20 21  1  0
  4 22  2  0
  5 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3926145

   ---

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: 338.70

Molecular Weight (Monoisotopic): 338.0193

AlogP: 1.92

#Rotatable Bonds: 1

Polar Surface Area: 117.20

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.26

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.73

Np Likeness Score: 0.97

References

1. Lai D, Wang A, Cao Y, Zhou K, Mao Z, Dong X, Tian J, Xu D, Dai J, Peng Y, Zhou L, Liu Y..  (2016)  Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22.,  79  (8): [PMID:27441892] [10.1021/acs.jnatprod.6b00327]

Source

Source(1):

• Scientific Literature