1,4,9-trihydroxy-10-oxo-2,10-dihydro-1H-phenaleno[1,2,3-de]chromene-2-carboxylic acid

ID: ALA1082048

PubChem CID: 137629518

Max Phase: Preclinical

Molecular Formula: C20H12O7

Molecular Weight: 364.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: xanalteric acid I

Canonical SMILES:  O=C1C=Cc2c3c4c(c(O)ccc4c4ccc(O)c1c24)OC(C(=O)O)C3O

Standard InChI:  InChI=1S/C20H12O7/c21-10-4-1-7-8-2-6-12(23)18-15(8)14(17(24)19(27-18)20(25)26)9-3-5-11(22)16(10)13(7)9/h1-6,17,19,21,23-24H,(H,25,26)

Standard InChI Key:  SRAOLIZIJYDHTE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.0910    0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754    1.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599    0.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2261    0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2272    0.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9464    1.4144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588    0.1675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -0.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -0.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824   -1.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951   -2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3804   -2.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508   -1.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647   -2.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538   -2.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2407   -2.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2383   -1.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9557   -3.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3781   -3.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754    2.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5093    1.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    0.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    2.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -0.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  4  7  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 17  2  0
 15 16  1  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  4  3  2  0
  4  8  1  0
  8  9  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
  9 11  1  0
 18 21  2  0
  1  2  2  0
 14 22  1  0
 15 10  2  0
  3 23  1  0
 10  8  1  0
  6 24  1  0
 16 11  2  0
 24 25  1  0
 24 26  2  0
  1  3  1  0
  5 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1082048

   XANALTERIC ACID I

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: 364.31

Molecular Weight (Monoisotopic): 364.0583

AlogP: 2.49

#Rotatable Bonds: 1

Polar Surface Area: 124.29

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: -0.88

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 1.93

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