alternariol 5-O-methyl ether

ID: ALA483526

Cas Number: 23452-05-3

PubChem CID: 5360741

Product Number: S22154, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H12O5

Molecular Weight: 272.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alternariol 5-O-Methyl Ether | Alternariol monomethyl ether|23452-05-3|Djalonensone|26894-49-5|Alternariol-9-methyl ether|Alternariol monomethylether|Alternariol methyl ether|3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one|alternariol 5-O-methyl ether|3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one|3,7-Dihydroxy-9-methoxy-1-methyl-6H-dibenzo(b,d)pyran-6-one|CHEMBL483526|Y79STA800H|6H-DIBENZO(b,d)PYRAN-6-ONE, 3,7-DIHYDROXY-9-METHOXY-1-METHYL-|NSC638262|Alternariol monomethyl etherShow More⌵

Canonical SMILES:  COc1cc(O)c2c(=O)oc3cc(O)cc(C)c3c2c1

Standard InChI:  InChI=1S/C15H12O5/c1-7-3-8(16)4-12-13(7)10-5-9(19-2)6-11(17)14(10)15(18)20-12/h3-6,16-17H,1-2H3

Standard InChI Key:  LCSDQFNUYFTXMT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    8.0124  -11.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1853  -11.4499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1708  -12.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7665  -12.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9439  -12.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193  -12.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9235  -13.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7524  -13.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167  -12.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9915  -12.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3878  -13.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2092  -13.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6325  -12.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2338  -12.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6587  -11.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6104  -14.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4375  -10.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6921  -12.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1577  -14.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1844  -15.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  9 10  2  0
  3 10  1  0
 10 11  1  0
  9  1  1  0
 11 12  2  0
  1  2  1  0
 12 13  1  0
  3  4  1  0
 13 14  2  0
 14  9  1  0
  3  8  2  0
 14 15  1  0
  4  5  2  0
 12 16  1  0
  5  6  1  0
  1 17  2  0
  6  7  2  0
  6 18  1  0
  7  8  1  0
  8 19  1  0
 16 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA483526

   Alternariol monomethyl ether

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: 272.26

Molecular Weight (Monoisotopic): 272.0685

AlogP: 2.67

#Rotatable Bonds: 1

Polar Surface Area: 79.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.71

CX Basic pKa: ┄

CX LogP: 3.32

CX LogD: 3.15

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.53

Np Likeness Score: 1.25

References

1. Aly AH, Edrada-Ebel R, Indriani ID, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Proksch P, Ebel R..  (2008)  Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense.,  71  (6): [PMID:18494522] [10.1021/np070447m]

2. 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]

3. Kellogg JJ, Todd DA, Egan JM, Raja HA, Oberlies NH, Kvalheim OM, Cech NB..  (2016)  Biochemometrics for Natural Products Research: Comparison of Data Analysis Approaches and Application to Identification of Bioactive Compounds.,  79  (2): [PMID:26841051] [10.1021/acs.jnatprod.5b01014]

4. Lai D, Wang A, Cao Y, Zhou K, Mao Z, Dong X, Tian J, Xu D, Dai J, Peng Y, Zhou L, Liu Y..  (2016)  Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22.,  79  (8): [PMID:27441892] [10.1021/acs.jnatprod.6b00327]

5. Baek SC, Ryu HW, Kang MG, Lee H, Park D, Cho ML, Oh SR, Kim H..  (2018)  Selective inhibition of monoamine oxidase A by chelerythrine, an isoquinoline alkaloid.,  28  (14): [PMID:29925480] [10.1016/j.bmcl.2018.06.023]

6. Baek SC, Lee HW, Ryu HW, Kang MG, Park D, Kim SH, Cho ML, Oh SR, Kim H..  (2018)  Selective inhibition of monoamine oxidase A by hispidol.,  28  (4): [PMID:29395970] [10.1016/j.bmcl.2018.01.049]

7. Carter AC, King JB, Mattes AO, Cai S, Singh N, Cichewicz RH..  (2019)  Natural-Product-Inspired Compounds as Countermeasures against the Liver Carcinogen Aflatoxin B₁.,  82  (6): [PMID:31136174] [10.1021/acs.jnatprod.9b00290]

8. van Stuijvenberg J, Proksch P, Fritz G..  (2020)  Targeting the DNA damage response (DDR) by natural compounds.,  28  (4): [PMID:31980363] [10.1016/j.bmc.2019.115279]

9. Manzoor S, Hoda N..  (2020)  A comprehensive review of monoamine oxidase inhibitors as Anti-Alzheimer's disease agents: A review.,  206  [PMID:32942081] [10.1016/j.ejmech.2020.112787]

Source

Source(1):

• Scientific Literature