altersolanol L

ID: ALA551302

PubChem CID: 42639666

Max Phase: Preclinical

Molecular Formula: C16H20O7

Molecular Weight: 324.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Altersolanol L | altersolanol L|SCHEMBL904385|CHEMBL551302|CHEBI:203731|(2R,3R,4R,4aS,9aS,10R)-2,3,4,8,10-pentahydroxy-6-methoxy-3-methyl-1,2,4,4a,9a,10-hexahydroanthracen-9-one

Canonical SMILES:  COc1cc(O)c2c(c1)[C@H](O)[C@@H]1[C@H](C[C@@H](O)[C@@](C)(O)[C@@H]1O)C2=O

Standard InChI:  InChI=1S/C16H20O7/c1-16(22)10(18)5-8-12(15(16)21)14(20)7-3-6(23-2)4-9(17)11(7)13(8)19/h3-4,8,10,12,14-15,17-18,20-22H,5H2,1-2H3/t8-,10+,12-,14-,15+,16+/m0/s1

Standard InChI Key:  NDGIDBHYSCKXJM-CBDPYCFPSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.4262  -13.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250  -14.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1391  -14.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1373  -13.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8521  -13.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8555  -14.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5701  -14.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5633  -13.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2825  -13.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2832  -14.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9943  -14.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7092  -14.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7086  -13.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9930  -13.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5588  -12.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5741  -15.5662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1397  -15.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7122  -13.0971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7120  -12.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2751  -12.6723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2751  -15.1451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.1152  -12.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5023  -13.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4228  -14.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9912  -12.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  8 15  1  6
  5  8  1  0
  7 16  2  0
  6  7  1  0
  3 17  1  0
  7 10  1  0
  1 18  1  0
  9  8  1  0
 18 19  1  0
  9 10  1  0
  9 20  1  6
  5  4  2  0
 10 21  1  1
  4  1  1  0
 13 22  1  0
  5  6  1  0
 13 23  1  6
 12 24  1  6
  2  3  1  0
 14 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA551302

   ALTERSOLANOL L

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: 324.33

Molecular Weight (Monoisotopic): 324.1209

AlogP: -0.26

#Rotatable Bonds: 1

Polar Surface Area: 127.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: -0.64

CX LogD: -0.68

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 2.56

References

1. Debbab A, Aly AH, Edrada-Ebel R, Wray V, Müller WE, Totzke F, Zirrgiebel U, Schächtele C, Kubbutat MH, Lin WH, Mosaddak M, Hakiki A, Proksch P, Ebel R..  (2009)  Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium.,  72  (4): [PMID:19271717] [10.1021/np8004997]

2. 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]

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]

Source

Source(1):

• Scientific Literature