(2S,3S,3aR,4S,6S,6aR,6bS,9aR,10aS)-4-Acetoxy-6-(butyryloxy)-6a-hydroxy-1,4,6b,8-tetramethyl-2-{[(Z)-2-methylbut-2-enoyl]oxy}-2,3,3a,4,5,6,6a,6b,9a,10a-decahydroazuleno[5',4':4,5]furo[2,3-d]-oxazol-3-yl Octanoate

ID: ALA2332551

PubChem CID: 71655741

Max Phase: Preclinical

Molecular Formula: C36H53NO11

Molecular Weight: 675.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(/C)C(=O)O[C@H]1C(C)=C2[C@H]([C@@H]1OC(=O)CCCCCCC)[C@@](C)(OC(C)=O)C[C@H](OC(=O)CCC)[C@@]1(O)[C@H]2O[C@H]2N=C(C)O[C@]21C

Standard InChI:  InChI=1S/C36H53NO11/c1-10-13-14-15-16-18-26(40)44-30-28-27(21(5)29(30)45-32(41)20(4)12-3)31-36(42,35(9)33(46-31)37-22(6)47-35)24(43-25(39)17-11-2)19-34(28,8)48-23(7)38/h12,24,28-31,33,42H,10-11,13-19H2,1-9H3/b20-12-/t24-,28+,29-,30-,31-,33+,34-,35+,36+/m0/s1

Standard InChI Key:  SQMJSIKUOUSKGN-HQNXNICLSA-N

Molfile:  

     RDKit          2D

 51 54  0  0  0  0  0  0  0  0999 V2000
    1.6740  -14.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885  -13.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6740  -14.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029  -14.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885  -12.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1029  -14.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8173  -13.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4621  -14.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247  -14.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543  -13.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7363  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028  -15.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7117  -14.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5422  -14.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0679  -15.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8907  -16.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1484  -16.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3911  -16.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8230  -16.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9405  -16.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3239  -13.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2530  -14.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474  -13.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9590  -12.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5302  -12.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7161  -16.0290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1324  -15.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9574  -15.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7237  -14.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3737  -14.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1986  -14.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5322  -13.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162  -12.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5252  -11.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2912  -12.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238  -15.3822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752  -11.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0502  -11.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6342  -10.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092  -10.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932  -10.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5682  -10.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4459  -17.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0463  -17.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2345  -17.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1352  -18.2032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8858  -18.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0453  -19.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405  -17.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5582  -16.0438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017  -17.3820    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  2  4  1  0
  2  5  1  0
  4  6  2  0
  4  7  1  0
  8  7  1  6
  9 12  2  0
  8  9  1  0
 13 10  1  0
 10  8  1  0
  9 11  1  0
 12 13  1  0
 13 14  1  0
 12 18  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  0
 17 18  1  0
 44 17  1  0
 18 19  1  0
 19 45  1  0
 17 20  1  1
 14 21  1  0
 14 22  1  1
 22 23  1  0
 23 24  2  0
 23 25  1  0
 16 26  1  6
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 10 32  1  1
 32 33  1  0
 33 34  2  0
 33 35  1  0
 13 36  1  1
 35 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 44 45  1  0
 43 44  1  0
 45 46  1  0
 46 47  2  0
 47 43  1  0
 47 48  1  0
 44 49  1  1
 18 50  1  6
 45 51  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2332551

   [(1S,4S,5S,6R,7S,9S,10R,11S,15R)-7-acetyloxy-9-butanoyloxy-10-hydroxy-3,7,11,13-tetramethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-12,16-dioxa-14-azatetracyclo[8.6.0.02,6.011,15]hexadeca-2,13-dien-5-yl] octanoate

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: 675.82

Molecular Weight (Monoisotopic): 675.3619

AlogP: 5.18

#Rotatable Bonds: 13

Polar Surface Area: 156.25

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.66

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: ┄

Heavy Atoms: 48

QED Weighted: 0.09

Np Likeness Score: 1.95

References

1. Paulsen ES, Villadsen J, Tenori E, Liu H, Bonde DF, Lie MA, Bublitz M, Olesen C, Autzen HE, Dach I, Sehgal P, Nissen P, Møller JV, Schiøtt B, Christensen SB..  (2013)  Water-mediated interactions influence the binding of thapsigargin to sarco/endoplasmic reticulum calcium adenosinetriphosphatase.,  56  (9): [PMID:23574308] [10.1021/jm4001083]

Source

Source(1):

• Scientific Literature