Penicilone G

ID: ALA4521660

PubChem CID: 145720776

Max Phase: Preclinical

Molecular Formula: C29H35BrO7

Molecular Weight: 575.50

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(C3=C(C)C[C@@H](O)CC3=O)=CC2=C(Br)C1=O

Standard InChI:  InChI=1S/C29H35BrO7/c1-6-7-8-9-10-16(2)11-18(4)28(35)37-29(5)26(33)21-15-36-23(14-20(21)25(30)27(29)34)24-17(3)12-19(31)13-22(24)32/h11,14-16,19,31H,6-10,12-13H2,1-5H3/b18-11+/t16-,19+,29+/m0/s1

Standard InChI Key:  VJHUSRCFHWWYCT-LWGLPVJESA-N

Molfile:  

 
     RDKit          2D

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   23.3766   -9.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0860  -10.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0860   -8.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.4982  -10.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2123   -9.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   28.3474   -8.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3559   -7.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6506   -7.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9325   -7.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.0869  -10.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.9559   -8.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.8222  -10.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2470  -10.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.9790  -10.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2665   -9.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.3725  -10.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0860   -7.5693    0.0000 Br  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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  6  7  2  0
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 12 18  2  0
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  1 20  2  0
  2 21  1  0
  3 22  2  0
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 27 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
  2 36  1  6
  4 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521660

   ---

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: 575.50

Molecular Weight (Monoisotopic): 574.1566

AlogP: 5.48

#Rotatable Bonds: 9

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.86

CX LogD: 5.86

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: 2.06

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