[(2R,3R,4S,5S,6R)-6-[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexoxy]-3,4,5-tri(propanoyloxy)tetrahydropyran-2-yl]methyl propanoate

ID: ALA4744013

PubChem CID: 162647101

Max Phase: Preclinical

Molecular Formula: C24H40O15

Molecular Weight: 568.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)OC[C@H]1O[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO)[C@@H](OC(=O)CC)[C@@H](OC(=O)CC)[C@@H]1OC(=O)CC

Standard InChI:  InChI=1S/C24H40O15/c1-5-15(28)34-11-14-21(37-16(29)6-2)22(38-17(30)7-3)23(39-18(31)8-4)24(36-14)35-10-13(27)20(33)19(32)12(26)9-25/h12-14,19-27,32-33H,5-11H2,1-4H3/t12-,13-,14-,19-,20-,21-,22+,23+,24-/m1/s1

Standard InChI Key:  UJESJMHNLHRYBK-ZTTPAZJSSA-N

Molfile:  

 
     RDKit          2D

 39 39  0  0  0  0  0  0  0  0999 V2000
    6.0670  -13.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0670  -14.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764  -15.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4858  -14.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4858  -13.9624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764  -13.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971  -15.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764  -16.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3558  -15.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7764  -12.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540  -13.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4883  -12.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1980  -16.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9061  -16.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9070  -17.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6151  -17.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6160  -18.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6134  -16.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1997  -17.6449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3224  -17.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3241  -18.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250  -19.6856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9087  -18.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1949  -12.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9037  -12.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1929  -13.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6104  -12.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3531  -12.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450  -12.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604  -12.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9377  -12.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485  -14.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9404  -15.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6494  -13.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331  -14.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0687  -16.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0687  -17.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610  -16.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6533  -16.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  1
  3  8  1  1
  2  9  1  1
  6 10  1  1
  1 11  1  6
 10 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  1
 15 19  1  6
 16 20  1  6
 17 21  1  0
 21 22  1  0
 17 23  1  1
 12 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 11 28  1  0
 28 29  1  0
 28 30  2  0
 29 31  1  0
  9 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
  8 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4744013

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 568.57

Molecular Weight (Monoisotopic): 568.2367

AlogP: -1.92

#Rotatable Bonds: 16

Polar Surface Area: 224.81

Molecular Species: NEUTRAL

HBA: 15

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.59

CX Basic pKa: ┄

CX LogP: -0.93

CX LogD: -0.93

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.10

Np Likeness Score: 1.30

References

1. Tsutsui N,Tanabe G,Ikeda N,Okamura S,Ogawa M,Miyazaki K,Kita A,Sugiura R,Muraoka O.  (2016)  Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 4: Role of acyl side chains on d-mannose.,  121  [PMID:27243802] [10.1016/j.ejmech.2016.05.034]

Source

Source(1):

• Scientific Literature