rel-Dihydroaltersolanol A

ID: ALA2011664

PubChem CID: 57332240

Max Phase: Preclinical

Molecular Formula: C16H18O7

Molecular Weight: 322.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rel-Dihydroaltersolanol A | Dihydroaltersolanol|Rel-Dihydroaltersolanol A|CHEMBL2011664|CHEBI:226041|(2R,3R,4R,4aS,10R)-2,3,4,8,10-pentahydroxy-6-methoxy-3-methyl-2,4,4a,10-tetrahydroanthracen-9-one

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

Standard InChI:  InChI=1S/C16H18O7/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/h3-5,10,12,14-15,17-18,20-22H,1-2H3/t10-,12+,14+,15-,16-/m1/s1

Standard InChI Key:  MLOZPTTXVAPEPM-YXLJTMCISA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.6131   -2.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143   -3.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9042   -3.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9059   -2.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1951   -2.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1963   -3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842   -3.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4818   -2.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647   -2.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7678   -3.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549   -3.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -3.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488   -2.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3736   -3.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4594   -2.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200   -1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717   -1.5979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817   -1.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4869   -4.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3233   -2.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3235   -1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9045   -4.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.1861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  9 14  1  0
 10 11  2  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
  9 18  1  6
  9  8  1  0
  8 19  1  6
  9 10  1  0
  7 20  2  0
  5  4  2  0
  1 21  1  0
  4  1  1  0
 21 22  1  0
  5  6  1  0
  3 23  1  0
 14 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2011664

   Dihydroaltersolanol

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: 322.31

Molecular Weight (Monoisotopic): 322.1053

AlogP: -0.34

#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: 8.54

CX Basic pKa: ┄

CX LogP: -0.64

CX LogD: -0.67

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.48

Np Likeness Score: 2.41

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. 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