(+/-)-1,2-bis[5-(E)-hept-5-ene-1,3-diynylthiophen-2-yl]-2-hydroxypentane-1,4-dione

ID: ALA496243

PubChem CID: 16083190

Max Phase: Preclinical

Molecular Formula: C27H20O3S2

Molecular Weight: 456.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: xanthopappin C | XANTHOPAPPIN C|CHEMBL496243|1,2-bis[5-( e )-hept-5-ene-1,3-diynylthiophen-2-yl]-2-hydroxypentane-1,4-dione|1,2-bis[5-[(E)-hept-5-en-1,3-diynyl]thiophen-2-yl]-2-hydroxypentane-1,4-dione

Canonical SMILES:  C/C=C/C#CC#Cc1ccc(C(=O)C(O)(CC(C)=O)c2ccc(C#CC#C/C=C/C)s2)s1

Standard InChI:  InChI=1S/C27H20O3S2/c1-4-6-8-10-12-14-22-16-18-24(31-22)26(29)27(30,20-21(3)28)25-19-17-23(32-25)15-13-11-9-7-5-2/h4-7,16-19,30H,20H2,1-3H3/b6-4+,7-5+

Standard InChI Key:  YIPZRWXKZQNUSS-YDFGWWAZSA-N

Molfile:  

     RDKit          2D

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   18.2357    1.7064    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5658    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8984    1.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7411    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9161    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0911    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2661    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4411    1.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0297    0.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2047    0.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.4958    3.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3208    3.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9083    2.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1917    2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5013    3.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3159    1.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1408    1.9228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4796    2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7627    2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4843    3.4791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
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  3  4  1  0
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  8  9  3  0
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  4  5  2  0
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  9 10  1  0
 20 21  3  0
  5  1  1  0
 21 22  1  0
 10 11  2  0
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  1  2  1  0
 23 24  1  0
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 17 25  1  0
 13 14  1  0
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  2  6  1  0
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  6  7  3  0
 28 29  2  0
  2  3  2  0
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  7  8  1  0
 30 31  1  0
 14 15  2  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA496243

   XANTHOPAPPIN C

Molecule Features

Natural Product: No

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: 456.59

Molecular Weight (Monoisotopic): 456.0854

AlogP: 4.72

#Rotatable Bonds: 5

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.57

CX Basic pKa: ┄

CX LogP: 6.84

CX LogD: 6.84

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 1.35

References

1. Tian Y, Wei X, Xu H..  (2006)  Photoactivated insecticidal thiophene derivatives from Xanthopappus subacaulis.,  69  (8): [PMID:16933888] [10.1021/np060209b]

Source

Source(1):

• Scientific Literature