(10R)10-C-(4-O-benzoyl-alpha-arabinopyranosyl)-1,8-dihydroxy-3-methylanthracen-9(10H)-one

ID: ALA471183

PubChem CID: 44575608

Max Phase: Preclinical

Molecular Formula: C28H26O8

Molecular Weight: 490.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Picramnioside H | PICRAMNIOSIDE H|CHEMBL471183

Canonical SMILES:  Cc1cc(O)c2c(c1)[C@H](C[C@H]1OC[C@@H](OC(=O)c3ccccc3)[C@@H](O)[C@@H]1O)c1cccc(O)c1C2=O

Standard InChI:  InChI=1S/C28H26O8/c1-14-10-18-17(16-8-5-9-19(29)23(16)27(33)24(18)20(30)11-14)12-21-25(31)26(32)22(13-35-21)36-28(34)15-6-3-2-4-7-15/h2-11,17,21-22,25-26,29-32H,12-13H2,1H3/t17-,21-,22-,25-,26-/m1/s1

Standard InChI Key:  HQLGEJWTJQYJJK-AHVPVAHRSA-N

Molfile:  

     RDKit          2D

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    9.6849    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3997    0.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3979    2.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1133    1.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1121    0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8251    0.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8274    2.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5449    1.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5433    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.9701    0.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9678    1.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2549    2.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2529    2.9835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6850    0.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8274    2.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3955    2.9836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8245   -0.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3979   -0.3185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6853   -0.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6804   -1.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3944   -1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1133   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8276   -1.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1042    0.1000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3910   -2.7925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9641   -1.9616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2515   -1.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5351   -1.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2552   -0.7209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8227   -1.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1068   -1.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1027   -2.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8203   -3.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5332   -2.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 10  1  0
  4 18  1  0
  9  8  1  0
  7 19  1  6
  5  4  2  0
 19 20  1  0
 20 21  1  0
  4  1  1  0
  9 10  2  0
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 22 23  1  0
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  2  3  1  0
 20 27  1  1
 12 13  1  0
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  3  6  2  0
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  1  2  2  0
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  5  8  1  0
 33 34  1  0
 12 16  1  0
 34 35  2  0
  6  7  1  0
 35 36  1  0
  8 17  2  0
 36 37  2  0
 37 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA471183

   PICRAMNIOSIDE H

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: 490.51

Molecular Weight (Monoisotopic): 490.1628

AlogP: 2.82

#Rotatable Bonds: 4

Polar Surface Area: 133.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.49

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 5.15

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.41

Np Likeness Score: 1.40

References

1. Diaz F, Chai HB, Mi Q, Su BN, Vigo JS, Graham JG, Cabieses F, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD..  (2004)  Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.,  67  (3): [PMID:15043409] [10.1021/np030479j]

Source

Source(1):

• Scientific Literature