isoalvaxanthone

ID: ALA517059

Cas Number: 199851-56-4

PubChem CID: 10596886

Max Phase: Preclinical

Molecular Formula: C23H24O6

Molecular Weight: 396.44

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Isoalvaxanthone | isoalvaxanthone|1,3,5,6-Tetrahydroxy-7-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one|199851-56-4|CHEMBL517059|1,3,5,6-tetrahydroxy-2-(2-methylbut-3-en-2-yl)-7-(3-methylbut-2-enyl)xanthen-9-one|InChI=1/C23H24O6/c1-6-23(4,5)17-14(24)10-15-16(20(17)27)19(26)13-9-12(8-7-11(2)3)18(25)21(28)22(13)29-15/h6-7,9-10,24-25,27-28H,1,8H2,2-5H

Canonical SMILES:  C=CC(C)(C)c1c(O)cc2oc3c(O)c(O)c(CC=C(C)C)cc3c(=O)c2c1O

Standard InChI:  InChI=1S/C23H24O6/c1-6-23(4,5)17-14(24)10-15-16(20(17)27)19(26)13-9-12(8-7-11(2)3)18(25)21(28)22(13)29-15/h6-7,9-10,24-25,27-28H,1,8H2,2-5H3

Standard InChI Key:  HSGGSJBRVQFVGH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.6797  -24.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6815  -22.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661  -23.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9672  -23.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2542  -24.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518  -22.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343  -23.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5360  -23.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764  -24.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1757  -22.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518  -21.7996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738  -21.8061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931  -23.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873  -23.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3946  -23.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3904  -23.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0972  -22.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125  -23.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054  -24.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6781  -25.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5238  -22.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430  -23.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5174  -21.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076  -22.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3169  -22.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238  -23.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1922  -21.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356  -22.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013  -24.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  6  1  0
  4  5  1  0
 15 16  2  0
  5  8  1  0
  7  6  1  0
  2 16  1  0
  3  4  1  0
  7  8  2  0
 15 19  1  0
 16 17  1  0
 17 18  1  0
 15  1  1  0
  1 20  1  0
  8  9  1  0
 18 21  2  0
  9 14  2  0
 21 22  1  0
  1  4  2  0
 21 23  1  0
 13 10  2  0
 13 24  1  0
 10  7  1  0
 24 25  1  0
 24 26  1  0
  6 11  2  0
 24 27  1  0
  3  2  2  0
 25 28  2  0
 10 12  1  0
 14 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517059

   ISOALVAXANTHONE

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: 396.44

Molecular Weight (Monoisotopic): 396.1573

AlogP: 4.74

#Rotatable Bonds: 4

Polar Surface Area: 111.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.05

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 5.16

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: 2.26

References

1. Hou A, Fukai T, Shimazaki M, Sakagami H, Sun H, Nomura T..  (2001)  Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis.,  64  (1): [PMID:11170668] [10.1021/np000406p]

Source

Source(1):

• Scientific Literature