Altersolanol B

ID: ALA2011669

Cas Number: 22350-90-9

PubChem CID: 161389

Max Phase: Preclinical

Molecular Formula: C16H16O6

Molecular Weight: 304.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Altersolanol B | Dactylarin|Altersolanol B|22350-90-9|(2R,3S)-2,3,8-trihydroxy-6-methoxy-3-methyl-2,4-dihydro-1H-anthracene-9,10-dione|3,7-dihydroxy-3',5-dimethoxy-5'-methylspiro[3H-1-benzofuran-2,4'-cyclohexa-2,5-diene]-1'-one|CHEMBL2011669|SCHEMBL23522406|DTXSID70176887|(2S,3R)-1,2,3,4-Tetrahydro-2,3,5-trihydroxy-7-methoxy-2-methyl-9,10-anthracenedione|CHEBI:219051|AKOS040745714|9,10-Anthracenedione, 1,2,3,4-tetrahydro-2,3,5-trihydroxy-7-methoxy-2-methyl-, (2S-cis)-|(2R, 3S)-2, 3, 8-trihydroxyShow More⌵

Canonical SMILES:  COc1cc(O)c2c(c1)C(=O)C1=C(C[C@@H](O)[C@@](C)(O)C1)C2=O

Standard InChI:  InChI=1S/C16H16O6/c1-16(21)6-10-8(5-12(16)18)15(20)13-9(14(10)19)3-7(22-2)4-11(13)17/h3-4,12,17-18,21H,5-6H2,1-2H3/t12-,16+/m1/s1

Standard InChI Key:  AAHQQIFXAQHGBD-WBMJQRKESA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.3800   -2.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3788   -3.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0889   -3.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0871   -2.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7978   -2.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7966   -3.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5088   -3.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5112   -2.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2280   -2.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2249   -3.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9379   -3.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6585   -3.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6616   -2.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9441   -2.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3663   -3.8130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4521   -2.7774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8725   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5112   -1.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5061   -4.6225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6701   -2.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6699   -1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0886   -4.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  2  3  1  0
  3  6  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1  2  2  0
 12 15  1  6
  5  8  1  0
 13 16  1  6
  6  7  1  0
 13 17  1  0
  7 10  1  0
  8 18  2  0
  9  8  1  0
  7 19  2  0
  9 10  2  0
  1 20  1  0
  5  4  2  0
 20 21  1  0
  4  1  1  0
  3 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2011669

   ALTERSOLANOL B

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: 304.30

Molecular Weight (Monoisotopic): 304.0947

AlogP: 0.98

#Rotatable Bonds: 1

Polar Surface Area: 104.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.17

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.65

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.71

Np Likeness Score: 2.31

References

1. Zheng CJ, Shao CL, Guo ZY, Chen JF, Deng DS, Yang KL, Chen YY, Fu XM, She ZG, Lin YC, Wang CY..  (2012)  Bioactive hydroanthraquinones and anthraquinone dimers from a soft coral-derived Alternaria sp. fungus.,  75  (2): [PMID:22276679] [10.1021/np200766d]

2. Ondeyka J, Buevich AV, Williamson RT, Zink DL, Polishook JD, Occi J, Vicente F, Basilio A, Bills GF, Donald RG, Phillips JW, Goetz MA, Singh SB..  (2014)  Isolation, structure elucidation, and biological activity of altersolanol P using Staphylococcus aureus fitness test based genome-wide screening.,  77  (3): [PMID:24428261] [10.1021/np400759f]

3. Zhou XM, Zheng CJ, Chen GY, Song XP, Han CR, Li GN, Fu YH, Chen WH, Niu ZG..  (2014)  Bioactive anthraquinone derivatives from the mangrove-derived fungus Stemphylium sp. 33231.,  77  (9): [PMID:25136754] [10.1021/np500340y]

4. Takahashi JA, Barbosa BVR, Lima MTNS, Cardoso PG, Contigli C, Pimenta LPS..  (2021)  Antiviral fungal metabolites and some insights into their contribution to the current COVID-19 pandemic.,  46  [PMID:34438338] [10.1016/j.bmc.2021.116366]

Source

Source(1):

• Scientific Literature