erythroglaucin

ID: ALA463597

Cas Number: 476-57-3

PubChem CID: 10152

Max Phase: Preclinical

Molecular Formula: C16H12O6

Molecular Weight: 300.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Erythroglaucin | Parietin | Erythroglaucin|Erythroglaucine|476-57-3|1,4,5-trihydroxy-7-methoxy-2-methylanthracene-9,10-dione|CHEBI:68790|ANTHRAQUINONE, 7-METHOXY-2-METHYL-1,4,5-TRIHYDROXY-|9,10-Anthracenedione, 1,4,5-trihydroxy-7-methoxy-2-methyl-|CCRIS 6424|BRN 1890890|CHEMBL463597|SCHEMBL16226462|DTXSID30197215|VUUONEBXXLQCQX-UHFFFAOYSA-N|Q27137181|1,4,5-Trihydroxy-7-methoxy-2-methylanthra-9,10-quinone #

Canonical SMILES:  COc1cc(O)c2c(c1)C(=O)c1c(O)c(C)cc(O)c1C2=O

Standard InChI:  InChI=1S/C16H12O6/c1-6-3-9(17)12-13(14(6)19)15(20)8-4-7(22-2)5-10(18)11(8)16(12)21/h3-5,17-19H,1-2H3

Standard InChI Key:  VUUONEBXXLQCQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.6488   -5.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -4.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -4.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -4.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -4.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -5.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -5.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9340   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -6.3484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233   -3.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0786   -5.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6320   -5.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -5.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -3.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -3.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -6.3484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
  5 14  1  0
  1 14  2  0
 13 15  2  0
  6 16  2  0
  2 17  1  0
 18 19  1  0
 10 18  1  0
  8 20  1  0
  4 21  1  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA463597

   PARIETIN

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: 300.27

Molecular Weight (Monoisotopic): 300.0634

AlogP: 1.90

#Rotatable Bonds: 1

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.00

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 4.21

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: 1.35

References

1. Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG..  (2006)  Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata.,  69  (11): [PMID:17125234] [10.1021/np060248n]

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

3. Yoon MY, Choi NH, Min BS, Choi GJ, Choi YH, Jang KS, Han SS, Cha B, Kim JC..  (2011)  Potent in vivo antifungal activity against powdery mildews of pregnane glycosides from the roots of Cynanchum wilfordii.,  59  (22): [PMID:21992072] [10.1021/jf2039185]

4. Giez I, Lange OL, Proksch P.  (1994)  Growth retarding activity of lichen substances against the polyphagous herbivorous insect Spodoptera littoralis,  22  (2): [10.1016/0305-1978(94)90001-9]

Source

Source(1):

• Scientific Literature