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

ID: ALA1079563

PubChem CID: 137629886

Max Phase: Preclinical

Molecular Formula: C20H12O7

Molecular Weight: 364.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: xanalteric acid II

Canonical SMILES:  O=C1C=Cc2c3c4c(c(O)ccc4c4ccc(O)c1c24)OC(O)(C(=O)O)C3

Standard InChI:  InChI=1S/C20H12O7/c21-12-4-1-8-9-3-6-14(23)18-16(9)11(7-20(26,27-18)19(24)25)10-2-5-13(22)17(12)15(8)10/h1-6,21,23,26H,7H2,(H,24,25)

Standard InChI Key:  XVJPOZBUOYPLTL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    2.3742    0.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3742    0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897    1.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8053    0.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2390    0.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379    0.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5188    1.3557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064    0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -0.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829   -1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722   -1.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -2.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144   -1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012   -1.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8005   -2.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113   -2.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2246   -2.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2269   -1.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5094   -3.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0871   -3.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0897    2.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9559    1.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9557    2.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8204    0.3560    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
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079563

   XANALTERIC ACID II

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: 2.32

#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: 2.80

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: -0.28

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: 2.00

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