panepophenanthrin

ID: ALA519800

PubChem CID: 44575998

Max Phase: Preclinical

Molecular Formula: C22H28O8

Molecular Weight: 420.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Panepophenanthrin | CHEMBL519800|BDBM50478558

Canonical SMILES:  CC(C)(O)/C=C/[C@@]12[C@H]3[C@@H](O)[C@@H]4O[C@@H]4[C@]1(O)OC(C)(C)[C@@H]2C=C1C(=O)[C@H]2O[C@H]2[C@H](O)[C@H]13

Standard InChI:  InChI=1S/C22H28O8/c1-19(2,26)5-6-21-9-7-8-10(13(24)16-15(28-16)12(8)23)11(21)14(25)17-18(29-17)22(21,27)30-20(9,3)4/h5-7,9-11,13-18,24-27H,1-4H3/b6-5+/t9-,10+,11+,13+,14+,15+,16-,17-,18-,21+,22-/m0/s1

Standard InChI Key:  WQBRQZUREPTGLI-MMNRQHNKSA-N

Molfile:  

     RDKit          2D

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  6 21  1  0
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  7 10  1  0
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  7  4  1  0
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  4  5  1  0
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  3 31  1  6
  7 16  1  1
  2 37  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA519800

   PANEPOPHENANTHRIN

Molecule Features

Natural Product: No

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: 420.46

Molecular Weight (Monoisotopic): 420.1784

AlogP: -0.56

#Rotatable Bonds: 2

Polar Surface Area: 132.28

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.60

CX Basic pKa: ┄

CX LogP: -0.56

CX LogD: -0.56

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.35

Np Likeness Score: 3.24

References

1. Sekizawa R, Ikeno S, Nakamura H, Naganawa H, Matsui S, Iinuma H, Takeuchi T..  (2002)  Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin-activating enzyme.,  65  (10): [PMID:12398550] [10.1021/np020098q]

2. da Silva SR, Paiva SL, Lukkarila JL, Gunning PT..  (2013)  Exploring a new frontier in cancer treatment: targeting the ubiquitin and ubiquitin-like activating enzymes.,  56  (6): [PMID:23360215] [10.1021/jm301420b]

Source

Source(1):

• Scientific Literature