Ent-Shiraiachrome A

ID: ALA4796095

PubChem CID: 102374213

Max Phase: Preclinical

Molecular Formula: C30H26O10

Molecular Weight: 546.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1c(O)c2c(=O)cc(OC)c3c4c(OC)cc(=O)c5c(O)c(OC)c6c(c(c1C[C@@](C)(O)[C@@H]6C(C)=O)c23)c54

Standard InChI:  InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3/t25-,30-/m1/s1

Standard InChI Key:  VANSZAOQCMTTPB-FYBSXPHGSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   32.8280   -4.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1222   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8325   -5.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9993   -3.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2849   -2.9715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5680   -3.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8673   -2.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1424   -3.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1424   -4.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5680   -4.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8682   -4.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2831   -7.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9607   -6.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5905   -5.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8682   -5.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1510   -5.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1510   -6.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8552   -7.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5726   -6.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3213   -4.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9993   -4.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7843   -4.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3213   -5.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9607   -5.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7593   -5.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2839   -2.1502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7106   -2.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4188   -3.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8683   -2.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4307   -4.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7229   -4.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4402   -5.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7315   -5.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2505   -7.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8490   -7.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6207   -7.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6088   -7.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3368   -6.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1272   -7.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1257   -6.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
 21  4  1  0
  4  5  2  0
  5  6  1  0
 10  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 11  1  0
 20 10  1  0
 10 11  1  0
 11 15  2  0
 23 14  2  0
 19 12  2  0
 12 13  1  0
 13 24  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 14  1  0
 20 21  2  0
 21 22  1  0
 20 23  1  0
 22  2  1  0
 23 24  1  0
  2 25  1  0
 24 25  1  0
  5 26  1  0
  4 27  1  0
 27 28  1  0
  7 29  2  0
  9 30  1  0
 30 31  1  0
 16 32  1  0
 32 33  1  0
 12 34  1  0
 18 35  2  0
 13 36  1  0
 36 37  1  0
 25 38  1  6
 38 39  2  0
 38 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796095

   Ent-shiraiachrome A

Molecule Features

Natural Product: Yes

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: 546.53

Molecular Weight (Monoisotopic): 546.1526

AlogP: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 148.82

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.14

CX Basic pKa: 3.65

CX LogP: 2.55

CX LogD: 1.99

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: 1.45

References

1. Al Subeh ZY,Raja HA,Monro S,Flores-Bocanegra L,El-Elimat T,Pearce CJ,McFarland SA,Oberlies NH.  (2020)  Enhanced Production and Anticancer Properties of Photoactivated Perylenequinones.,  83  (8): [PMID:32786877] [10.1021/acs.jnatprod.0c00492]

Source

Source(1):

• Scientific Literature