(1S,4S,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-11a-(acetoxymethyl)-5b,8,8,13a-tetramethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[2,1-c]furan-1,4-diyl diacetate

ID: ALA577464

PubChem CID: 25158707

Max Phase: Preclinical

Molecular Formula: C31H46O7

Molecular Weight: 530.70

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 12-deacetoxy-23-O-acetoxyheteronemin | CHEMBL577464|12-deacetoxy-23-O-acetoxyheteronemin|BDBM50480798

Canonical SMILES:  CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3C[C@H](OC(C)=O)C4=CO[C@@H](OC(C)=O)[C@@H]4[C@@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C31H46O7/c1-18(32)36-17-31-12-8-11-28(4,5)23(31)9-13-29(6)24(31)10-14-30(7)25(29)15-22(37-19(2)33)21-16-35-27(26(21)30)38-20(3)34/h16,22-27H,8-15,17H2,1-7H3/t22-,23-,24-,25-,26+,27-,29+,30-,31+/m0/s1

Standard InChI Key:  WKNPZHVTIXXKDH-NXZGYMOBSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
    7.4208   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4208   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1329   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8449   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8459   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5570   -2.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2715   -1.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5549   -0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2701   -0.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2780    0.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9932    0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9830   -0.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6919   -0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4156   -0.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7123    0.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4233    0.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0501    0.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7265    1.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8996    1.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4733    2.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8718    3.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4453    3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6967    3.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7042    0.0250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417   -2.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -1.2000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8375    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5483    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1194    0.4394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2625    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9875    1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9750   -1.2125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5375   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1249   -0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8444   -0.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5538   -0.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8545    0.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1120    1.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3939    1.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8228    1.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 16 20  1  0
  3  6  1  0
 20 21  1  6
  5  4  1  0
 21 22  1  0
  5  6  1  0
 22 23  1  0
  9 29  1  0
 22 24  2  0
 10 13  1  0
 16 25  1  6
 12 11  1  0
  6 26  1  6
 11 29  1  0
  9 27  1  6
 12 13  1  0
  5 28  1  1
  1  2  1  0
 28 30  1  0
  1  4  1  0
 10 31  1  1
  2  3  1  0
 12 32  1  1
 12 16  1  0
 13 33  1  6
 13 14  1  0
  3 34  1  0
 14 15  1  0
  3 35  1  0
 15 17  1  0
 15 36  1  1
 16 17  1  0
 36 37  1  0
  5  9  1  0
 37 38  1  0
  6  7  1  0
 37 39  2  0
  7  8  1  0
 30 40  1  0
  8 10  1  0
 40 41  1  0
  9 10  1  0
 40 42  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA577464

   12-deacetoxy-23-O-acetoxyheteronemin

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: 530.70

Molecular Weight (Monoisotopic): 530.3244

AlogP: 5.95

#Rotatable Bonds: 4

Polar Surface Area: 88.13

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.39

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: 2.75

References

1. Song J, Jeong W, Wang N, Lee HS, Sim CJ, Oh KB, Shin J..  (2008)  Scalarane sesterterpenes from the sponge Smenospongia sp.,  71  (11): [PMID:18973387] [10.1021/np8003694]

2. Hahn D, Won DH, Mun B, Kim H, Han C, Wang W, Chun T, Park S, Yoon D, Choi H, Nam SJ, Ekins M, Chin J, Kang H..  (2013)  Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp.,  23  (8): [PMID:23489626] [10.1016/j.bmcl.2013.02.061]

Source

Source(1):

• Scientific Literature