(3aS,11S,11aR)-5,10,11-trihydroxy-7-methoxy-3a-methyl-3a,4,11,11a-tetrahydroanthra[2,3-d][1,3]dioxole-2,6,9-trione

ID: ALA4550515

PubChem CID: 155555316

Max Phase: Preclinical

Molecular Formula: C17H14O9

Molecular Weight: 362.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)c2c(O)c3c(c(O)c2C1=O)C[C@]1(C)OC(=O)O[C@@H]1[C@H]3O

Standard InChI:  InChI=1S/C17H14O9/c1-17-4-5-8(14(22)15(17)25-16(23)26-17)13(21)9-6(18)3-7(24-2)12(20)10(9)11(5)19/h3,14-15,19,21-22H,4H2,1-2H3/t14-,15+,17-/m0/s1

Standard InChI Key:  LUTOKTZSZLWHOP-UXLLHSPISA-N

Molfile:  

 
     RDKit          2D

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    8.5846   -3.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2009   -4.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2023   -2.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954   -3.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4974   -3.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8001   -2.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0898   -3.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878   -3.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919   -4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9086   -3.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9069   -3.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -4.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172   -2.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7874   -5.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8039   -1.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3847   -2.6361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -1.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -1.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -5.0983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6143   -5.0947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267   -3.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -3.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1071   -4.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1052   -2.7967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5334   -2.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3279   -4.6849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4018   -3.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2 11  2  0
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  3  5  1  0
  4  5  2  0
  4  9  1  0
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  6  7  1  0
  7  8  2  0
  8  9  1  0
 10 11  1  0
 10 13  1  0
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 12 22  1  0
 21 13  1  0
  9 14  2  0
  6 15  2  0
  7 16  1  0
 16 17  1  0
  3 18  1  0
  2 19  1  0
 12 20  1  1
 21 22  1  0
 22 23  1  0
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  1 24  1  0
 21 24  1  0
 21 25  1  1
 22 26  1  1
  1 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550515

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 362.29

Molecular Weight (Monoisotopic): 362.0638

AlogP: 0.89

#Rotatable Bonds: 1

Polar Surface Area: 139.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.21

CX Basic pKa: ┄

CX LogP: 1.71

CX LogD: 1.65

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: 2.71

References

1. Hou XM, Wang CY, Gerwick WH, Shao CL..  (2019)  Marine natural products as potential anti-tubercular agents.,  165  [PMID:30685527] [10.1016/j.ejmech.2019.01.026]

Source

Source(1):

• Scientific Literature