Penicilone D

ID: ALA4552969

PubChem CID: 155556264

Max Phase: Preclinical

Molecular Formula: C29H33ClO6

Molecular Weight: 513.03

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCC[C@H](C)/C=C(\C)C(=O)O[C@@]1(C)C(=O)C2=COC(c3c(C)cccc3O)=CC2=C(Cl)C1=O

Standard InChI:  InChI=1S/C29H33ClO6/c1-6-7-8-9-11-17(2)14-19(4)28(34)36-29(5)26(32)21-16-35-23(15-20(21)25(30)27(29)33)24-18(3)12-10-13-22(24)31/h10,12-17,31H,6-9,11H2,1-5H3/b19-14+/t17-,29-/m0/s1

Standard InChI Key:  VBEXROICVMHLSP-ZIPCLRBCSA-N

Molfile:  

 
     RDKit          2D

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   10.1984   -9.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9078  -10.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9078   -8.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3199  -10.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1692   -8.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1777   -7.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7735   -8.9416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3552   -9.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6439  -10.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9078   -7.7014    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  2  0
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  9 11  1  0
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  1 19  2  0
  2 20  1  0
  3 21  2  0
 20 22  1  0
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 23 25  2  0
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 23 27  1  0
 26 28  1  0
 26 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
  2 35  1  1
  4 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552969

   ---

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: 513.03

Molecular Weight (Monoisotopic): 512.1966

AlogP: 6.46

#Rotatable Bonds: 9

Polar Surface Area: 89.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 7.50

CX LogD: 7.41

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.18

Np Likeness Score: 1.87

References

1. Chen M, Zheng YY, Chen ZQ, Shen NX, Shen L, Zhang FM, Zhou XJ, Wang CY..  (2019)  NaBr-Induced Production of Brominated Azaphilones and Related Tricyclic Polyketides by the Marine-Derived Fungus Penicillium janthinellum HK1-6.,  82  (2): [PMID:30693772] [10.1021/acs.jnatprod.8b00930]

Source

Source(1):

• Scientific Literature