altertoxin I

ID: ALA521470

Cas Number: 56258-32-3

PubChem CID: 104860

Max Phase: Preclinical

Molecular Formula: C20H16O6

Molecular Weight: 352.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Altertoxin I | Altertoxin I|56258-32-3|Altertoxin l|(12S,12aS,12bR)-4,9,12,12b-tetrahydroxy-2,11,12,12a-tetrahydro-1H-perylene-3,10-dione|Altertoxin-I|altertoxin-1|CCRIS 2190|3,10-Perylenedione, 1,2,11,12,12a,12b-hexahydro-1,4,9,12a-tetrahydroxy-, (1S,12aR,12bS)-|CHEMBL521470|SCHEMBL22837286|DTXSID40971689|CHEBI:226199|HY-N6724|1,2,7,8,12b-pentahydro-1,4,6b,10-tetrahydroxyperylene-3,9-dione|BDBM50479261|AKOS040740694|BA162708|Altertoxin I 10 microg/mL in Acetonitrile|CS-0085164|1,4,9,12a-TetrahyShow More⌵

Canonical SMILES:  O=C1C[C@H](O)[C@@H]2c3c(ccc(O)c31)-c1ccc(O)c3c1[C@@]2(O)CCC3=O

Standard InChI:  InChI=1S/C20H16O6/c21-10-3-1-8-9-2-4-11(22)17-12(23)5-6-20(26,18(9)17)19-14(25)7-13(24)16(10)15(8)19/h1-4,14,19,21-22,25-26H,5-7H2/t14-,19+,20-/m0/s1

Standard InChI Key:  GJIALGLHOBXNAT-KPOBHBOGSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   -3.9223   -6.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235   -7.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2094   -8.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2112   -6.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -8.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232   -9.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9237  -10.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095  -10.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -6.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932   -7.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -8.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -7.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0665   -6.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -6.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -8.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4909   -9.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4906  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7776  -10.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632  -10.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -9.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697   -8.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932   -8.5618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -8.9719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -5.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900   -5.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079  -11.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7784  -11.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 16  1  0
  6  7  1  0
  1  2  2  0
  7  8  2  0
  8 17  1  0
 16  5  1  0
  3  5  1  0
 15 20  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 11 15  1  0
  9 10  1  0
 11 21  1  6
  9  4  2  0
 15 22  1  1
  4  1  1  0
 20 23  1  1
  4 24  1  0
  2  3  1  0
 14 25  2  0
  5  6  2  0
  8 26  1  0
  3 10  2  0
 18 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA521470

   ALTERTOXIN 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: 352.34

Molecular Weight (Monoisotopic): 352.0947

AlogP: 1.97

#Rotatable Bonds: ┄

Polar Surface Area: 115.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.24

CX Basic pKa: ┄

CX LogP: 1.88

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 2.08

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. Chen JL, Sperry J, Ip NY, Brimble MA.  (2011)  Natural products targeting telomere maintenance,  2  (4): [10.1039/C0MD00241K]

4. Bashyal BP, Wellensiek BP, Ramakrishnan R, Faeth SH, Ahmad N, Gunatilaka AA..  (2014)  Altertoxins with potent anti-HIV activity from Alternaria tenuissima QUE1Se, a fungal endophyte of Quercus emoryi.,  22  (21): [PMID:25260957] [10.1016/j.bmc.2014.08.039]

5. Zhao DL, Cao F, Wang CY, Yang LJ, Shi T, Wang KL, Shao CL, Wang CY..  (2019)  Alternatone A, an Unusual Perylenequinone-Related Compound from a Soft-Coral-Derived Strain of the Fungus Alternaria alternata.,  82  (11): [PMID:31659905] [10.1021/acs.jnatprod.9b00905]

6. Geris R, Pinho MA, Boffo EF, Simpson TJ..  (2022)  Naturally Occurring Partially Reduced Perylenequinones from Fungi.,  85  (9.0): [PMID:36098709] [10.1021/acs.jnatprod.2c00368]

Source

Source(1):

• Scientific Literature