Islandicin

ID: ALA477724

Cas Number: 476-56-2

PubChem CID: 10151

Max Phase: Preclinical

Molecular Formula: C15H10O5

Molecular Weight: 270.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Islandicin | Islandicin|476-56-2|Rhodomycelin|Rhodomycin|FUNICULOSIN|ISLANDIN|1,4,5-Trihydroxy-2-methylanthracene-9,10-dione|Funiculosin (anthraquinone)|1,4,5-Trihydroxy-2-methylanthraquinone|NSC 264955|NSC264955|VVJ2ULR2M5|1,4,5-Trihydroxy-2-methyl-9,10-anthracenedione|ANTHRAQUINONE, 1,4,5-TRIHYDROXY-2-METHYL-|9,10-Anthracenedione, 1,4,5-trihydroxy-2-methyl-|CHEBI:80733|NSC-264955|Funiculosin (VAN)|CCRIS 3476|EINECS 207-506-2|1,4,5-Trihydroxy-2-methylanthra-9,10-quinone|BRN 2059061|UNII-VVJ2ULRShow More⌵

Canonical SMILES:  Cc1cc(O)c2c(c1O)C(=O)c1cccc(O)c1C2=O

Standard InChI:  InChI=1S/C15H10O5/c1-6-5-9(17)11-12(13(6)18)14(19)7-3-2-4-8(16)10(7)15(11)20/h2-5,16-18H,1H3

Standard InChI Key:  FHFHNVHRVKQQHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    8.9169  -13.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9169  -11.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6306  -11.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6290  -12.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3416  -13.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0564  -12.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0540  -11.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3407  -11.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2031  -12.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2057  -11.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4934  -11.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7782  -11.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7796  -12.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924  -13.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9154  -10.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9181  -14.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3387  -10.7239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4952  -10.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7730  -13.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3409  -14.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  9 10  2  0
  9  1  1  0
 10 11  1  0
  4  5  1  0
 11 12  2  0
  1  4  1  0
 12 13  1  0
  5  6  2  0
 13 14  2  0
 14  9  1  0
  3  2  1  0
  2 15  2  0
  6  7  1  0
  1 16  2  0
  8 17  1  0
  7  8  2  0
 11 18  1  0
  8  3  1  0
  6 19  1  0
 10  2  1  0
  5 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA477724

   ISLANDICIN

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: 270.24

Molecular Weight (Monoisotopic): 270.0528

AlogP: 1.89

#Rotatable Bonds: ┄

Polar Surface Area: 94.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.06

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.38

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.54

Np Likeness Score: 1.38

References

1. Lin LC, Chou CJ, Kuo YC..  (2001)  Cytotoxic principles from Ventilago leiocarpa.,  64  (5): [PMID:11374975] [10.1021/np000569d]

2. PubChem BioAssay data set, 

3. Hu Y, Martinez ED, MacMillan JB..  (2012)  Anthraquinones from a marine-derived Streptomyces spinoverrucosus.,  75  (10): [PMID:23057874] [10.1021/np3004326]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays