(-)-(10E,15S)-6-chloro-10(11)-dehydrocurvularin

ID: ALA4105086

PubChem CID: 60159010

Max Phase: Preclinical

Molecular Formula: C16H17ClO5

Molecular Weight: 324.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CCC/C=C/C(=O)c2c(cc(O)c(Cl)c2O)CC(=O)O1

Standard InChI:  InChI=1S/C16H17ClO5/c1-9-5-3-2-4-6-11(18)14-10(8-13(20)22-9)7-12(19)15(17)16(14)21/h4,6-7,9,19,21H,2-3,5,8H2,1H3/b6-4+/t9-/m0/s1

Standard InChI Key:  UQSXUWXEMMUFMK-DNQSNQRASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    9.5696   -5.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2799   -4.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9905   -5.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7091   -4.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7126   -3.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5696   -3.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9981   -3.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0087   -2.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2967   -2.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5739   -2.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557   -4.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8584   -3.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1460   -3.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4308   -3.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4322   -4.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1450   -5.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5705   -6.0111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7296   -2.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8613   -2.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1460   -6.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7145   -3.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -5.1908    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12  6  1  0
 11  1  1  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  7  1  0
  6 10  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  1 17  2  0
  8 18  1  1
 10 19  2  0
 16 20  1  0
 14 21  1  0
 15 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4105086

   6-Chloro-10,11-dehydrocurvularin

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: 324.76

Molecular Weight (Monoisotopic): 324.0765

AlogP: 3.15

#Rotatable Bonds: ┄

Polar Surface Area: 83.83

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.50

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 2.96

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: 2.13

References

1. Bashyal BP, Wijeratne EM, Tillotson J, Arnold AE, Chapman E, Gunatilaka AA..  (2017)  Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus.,  80  (2): [PMID:28139929] [10.1021/acs.jnatprod.6b00960]

Source

Source(1):

• Scientific Literature