alternarian acid

ID: ALA1081907

Cas Number: 91868-93-8

PubChem CID: 23928054

Max Phase: Preclinical

Molecular Formula: C15H12O8

Molecular Weight: 320.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alternarian Acid | alternarian acid|91868-93-8|Alternarian-acid|3-(2-Carboxy-3-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-2H-pyran-6-carboxylic acid|SM5RXD78FE|2H-Pyran-6-carboxylic acid, 3-(2-carboxy-3-hydroxy-5-methoxyphenyl)-4-methyl-2-oxo-|5-(2-Carboxy-3-hydroxy-5-methoxy-phenyl)-4-methyl-6-oxo-pyran-2-carboxylic acid|UNII-SM5RXD78FE|MEGxm0_000135|CHEMBL1081907|SCHEMBL16224899|ACon0_001033|ACon1_000958|DTXSID30635940|CHEBI:214769|5-(2-carboxy-3-hydroxy-5-methoxyphenyl)-4-methyl-6-oxopyran-2-carShow More⌵

Canonical SMILES:  COc1cc(O)c(C(=O)O)c(-c2c(C)cc(C(=O)O)oc2=O)c1

Standard InChI:  InChI=1S/C15H12O8/c1-6-3-10(13(17)18)23-15(21)11(6)8-4-7(22-2)5-9(16)12(8)14(19)20/h3-5,16H,1-2H3,(H,17,18)(H,19,20)

Standard InChI Key:  DTWGKAWUEOJXKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    8.5645  -21.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5760  -20.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2728  -19.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9580  -20.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448  -21.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2480  -21.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6321  -21.5723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289  -21.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2859  -19.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650  -19.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8773  -19.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1428  -20.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8416  -21.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1381  -21.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4175  -21.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3996  -22.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1085  -22.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8354  -22.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5455  -22.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6739  -22.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664  -22.3111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571  -23.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188  -20.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  2  0
  2 10  1  0
  3  4  1  0
  1 13  1  0
 13 14  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  5  7  1  0
 13 18  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  3  9  1  0
 18 19  1  0
  1  2  1  0
  2  3  2  0
 20 21  1  0
 20 22  2  0
 16 20  1  0
 10 11  1  0
 14 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1081907

   ALTERNARIAN ACID

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: 320.25

Molecular Weight (Monoisotopic): 320.0532

AlogP: 1.73

#Rotatable Bonds: 4

Polar Surface Area: 134.27

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.16

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: -4.89

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: 0.89

References

1. Kjer J, Wray V, Edrada-Ebel R, Ebel R, Pretsch A, Lin W, Proksch P..  (2009)  Xanalteric acids I and II and related phenolic compounds from an endophytic Alternaria sp. isolated from the mangrove plant Sonneratia alba.,  72  (11): [PMID:19835393] [10.1021/np900417g]

Source

Source(1):

• Scientific Literature