Sinugyrosanolide A

ID: ALA3127575

PubChem CID: 76314712

Max Phase: Preclinical

Molecular Formula: C19H22O5

Molecular Weight: 330.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC(=O)C[C@H]2C(=O)[C@@H]3[C@@H]4C(=C[C@@H]12)C(=O)O[C@@H]4C[C@]3(C)O

Standard InChI:  InChI=1S/C19H22O5/c1-8(2)10-4-9(20)5-12-11(10)6-13-15-14(24-18(13)22)7-19(3,23)16(15)17(12)21/h6,10-12,14-16,23H,1,4-5,7H2,2-3H3/t10-,11-,12+,14+,15+,16-,19-/m0/s1

Standard InChI Key:  YJJAMYDPWUFEHG-LSEBWTMBSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    7.2553   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -5.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -5.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -5.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -4.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0089   -3.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3533   -4.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6270   -5.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4518   -5.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -4.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910   -5.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0699   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7255   -5.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4847   -4.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7341   -5.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0897   -7.2914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -6.2243    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -3.7493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768   -5.1876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987   -4.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -6.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -7.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2553   -7.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385   -3.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6137   -3.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5702   -3.3630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9014   -3.6002    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8020   -5.2074    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 11 15  1  0
 14 16  2  0
 15  1  1  0
  2 16  1  0
 13 17  2  0
  2 18  1  1
  1 19  1  1
 10 20  1  1
  5 21  2  0
  3 22  1  1
 22 23  2  0
 22 24  1  0
  7 25  1  0
  7 26  1  6
 15 27  2  0
 11 28  1  1
  9 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3127575

   (1R,3R,7R,8S,13R,15S,16R)-15-hydroxy-15-methyl-7-prop-1-en-2-yl-12-oxatetracyclo[8.5.1.03,8.013,16]hexadec-9-ene-2,5,11-trione

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: 330.38

Molecular Weight (Monoisotopic): 330.1467

AlogP: 1.60

#Rotatable Bonds: 1

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.13

CX LogD: 1.13

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: 2.61

References

1. Cheng SY, Shih NL, Chuang CT, Chiou SF, Yang CN, Wang SK, Duh CY..  (2014)  Sinugyrosanolide A, an unprecedented C-4 norcembranoid, from the Formosan soft coral Sinularia gyrosa.,  24  (6): [PMID:24529868] [10.1016/j.bmcl.2014.01.073]

Source

Source(1):

• Scientific Literature