macluraxanthone

ID: ALA478960

Cas Number: 5848-14-6

PubChem CID: 5281646

Product Number: M709557, Order Now?

Max Phase: Preclinical

Molecular Formula: C23H22O6

Molecular Weight: 394.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Macluraxanthone | Macluraxanthone|5848-14-6|NSC107228|3-Hydroxyblancoxanthone|Spectrum_000523|SpecPlus_000294|5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6-one|CHEBI:6623|12-(1,1-dimethylallyl)-5,9,10-trihydroxy-2,2-dimethyl-pyrano[3,2-b]xanthen-6-one|MACLUROXANTHONE|NSC 107228|Spectrum2_000431|Spectrum3_000165|Spectrum4_001486|Spectrum5_000191|BSPBio_001629|KBioGR_002091|KBioSS_001003|DivK1c_006390|SPBio_000442|CHEMBL478960|SCHEMBL2546452|KBio1_001334|KBio2_001Show More⌵

Canonical SMILES:  C=CC(C)(C)c1c2c(c(O)c3c(=O)c4ccc(O)c(O)c4oc13)C=CC(C)(C)O2

Standard InChI:  InChI=1S/C23H22O6/c1-6-22(2,3)15-19-12(9-10-23(4,5)29-19)17(26)14-16(25)11-7-8-13(24)18(27)20(11)28-21(14)15/h6-10,24,26-27H,1H2,2-5H3

Standard InChI Key:  XRVLGJCHUWXTDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -3.2128  -23.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146  -22.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992  -22.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004  -23.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874  -23.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851  -22.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676  -22.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692  -23.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3569  -23.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576  -22.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851  -21.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596  -21.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9276  -23.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235  -22.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6383  -23.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111  -24.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3582  -22.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538  -23.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658  -23.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867  -23.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910  -22.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745  -22.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917  -24.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792  -23.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554  -24.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625  -25.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696  -24.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804  -24.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805  -25.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
  3  6  1  0
  4  5  1  0
  5  8  1  0
 13 15  1  0
  7  6  1  0
  1 16  1  0
 17 18  1  0
  2 14  1  0
  3  4  1  0
  7  8  2  0
 13  1  1  0
  8  9  1  0
  9 18  2  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  1  4  2  0
 20 23  1  0
 17 10  2  0
 20 24  1  0
 10  7  1  0
  9 25  1  0
 25 26  1  0
  6 11  2  0
 25 27  1  0
  3  2  2  0
 25 28  1  0
 10 12  1  0
 26 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA478960

   Macluraxanthone

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: 394.42

Molecular Weight (Monoisotopic): 394.1416

AlogP: 4.71

#Rotatable Bonds: 2

Polar Surface Area: 100.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.46

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 4.99

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 2.75

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]

2. Ryu YB, Curtis-Long MJ, Lee JW, Kim JH, Kim JY, Kang KY, Lee WS, Park KH..  (2009)  Characteristic of neuraminidase inhibitory xanthones from Cudrania tricuspidata.,  17  (7): [PMID:19285413] [10.1016/j.bmc.2009.02.042]

3. PubChem BioAssay data set, 

4. Tantapakul C, Phakhodee W, Ritthiwigrom T, Cheenpracha S, Prawat U, Deachathai S, Laphookhieo S..  (2012)  Rearranged benzophenones and prenylated xanthones from Garcinia propinqua twigs.,  75  (9): [PMID:22963193] [10.1021/np300487w]

5. Sukandar ER, Kaennakam S, Rassamee K, Ersam T, Siripong P, Tip-Pyang S..  (2019)  Tetrandraxanthones A-I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra.,  82  (5): [PMID:30978023] [10.1021/acs.jnatprod.9b00046]

6. Luthra T,Banothu V,Adepally U,Kumar K,M S,Chakrabarti S,Maddi SR,Sen S.  (2020)  Discovery of novel pyrido-pyrrolidine hybrid compounds as alpha-glucosidase inhibitors and alternative agent for control of type 1 diabetes.,  188  [PMID:31927314] [10.1016/j.ejmech.2020.112034]

7. Jiwacharoenchai N, Saruengkhanphasit R, Niwetmarin W, Seetaha S, Choowongkomon K, Ruchirawat S, Eurtivong C..  (2022)  Discovery of potent antiproliferative agents from selected oxygen heterocycles as EGFR tyrosine kinase inhibitors from the U.S. National Cancer Institute database by in silico screening and bioactivity evaluation.,  58  [PMID:34995690] [10.1016/j.bmcl.2021.128524]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays