NP-MRD: Showing NP-Card for (2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol (NP0160063)

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Record Information

Version

2.0

Created at

2022-09-02 17:55:45 UTC

Updated at

2022-09-02 17:55:45 UTC

NP-MRD ID

NP0160063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol

Description

(R)-1-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-3-octanol belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol is found in Crescentia cujete. Based on a literature review very few articles have been published on (R)-1-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-3-octanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219552D          

 30 31  0  0  1  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7550   -5.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945   -7.1795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6482   -7.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -7.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1916   -8.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -7.0080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4744   -7.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 66 67  0  0  0  0  0  0  0  0999 V2000
    6.5880    3.4111    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2295    2.7759   -0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7467    2.4151   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4734    1.4582    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124    1.1233    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5948    0.4944   -0.7110 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3360   -0.6837   -0.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1520    0.0053   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7276   -0.6255   -1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410   -1.1348   -1.8167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8154   -2.1178   -0.9151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2520   -3.2704   -1.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7211   -4.2586   -0.7451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9288   -4.8641   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4967   -5.8924   -0.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749   -3.9968    0.6472 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4012   -4.8687    1.5369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555   -2.6147    1.1697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7330   -2.3537    2.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9283   -1.6726    0.0131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8391   -0.3652    0.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8629    0.4482   -0.1405 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3497    1.4580   -0.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272    2.5418   -0.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2405    2.6496    0.7005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2796    3.4106    1.1706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    3.1793    1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081    4.4665    0.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696    1.1850    1.0839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7122    0.9226    1.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6890    3.6973    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839    4.3222    0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1427    2.6735    1.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766    1.8559   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3233    3.5375   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002    3.3695   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4058    1.9678   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0209    0.5024    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8416    1.8354    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    0.4134    1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    2.0144    0.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573    1.1451   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0222   -1.3917   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719   -0.6631    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204    0.9021   -0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710   -1.3826   -2.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7666    0.1877   -2.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -2.3048   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9616   -5.0984   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6218   -4.0093   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5406   -5.1571   -2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9656   -6.5185   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -4.2355    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -5.7984    1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7918   -2.5788    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9994   -3.2251    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006   -1.8858   -0.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896   -0.0892   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7421    3.4113   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2190    2.3052   -1.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9989    4.1314    1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    2.5370    0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8144    3.1725    2.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006    4.4786   -0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673    0.9951    1.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964    1.6571    1.8389 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  7  1  0
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  8  9  1  0
  9 10  1  0
 10 11  1  0
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 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 20 11  1  0
 29 22  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  6
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 11 48  1  1
 13 49  1  1
 14 50  1  0
 14 51  1  0
 15 52  1  0
 16 53  1  6
 17 54  1  0
 18 55  1  1
 19 56  1  0
 20 57  1  6
 22 58  1  6
 24 59  1  0
 24 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  1
 30 66  1  0
M  END


  Mrv1652309022219552D          

 30 31  0  0  1  0            999 V2000
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7550   -5.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945   -7.1795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6482   -7.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -7.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1916   -8.5772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -7.0080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4744   -7.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 27  1  6  0  0  0
 27 28  1  0  0  0  0
 25 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0160063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@@H](O)CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1OC[C@](O)(CO)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H36O11/c1-2-3-4-5-11(22)6-7-27-17-15(14(24)13(23)12(8-20)29-17)30-18-16(25)19(26,9-21)10-28-18/h11-18,20-26H,2-10H2,1H3/t11-,12-,13-,14+,15-,16+,17-,18+,19-/m1/s1

> <INCHI_KEY>
HTBXZRUTMUOBOY-BSZVCDTPSA-N

> <FORMULA>
C19H36O11

> <MOLECULAR_WEIGHT>
440.486

> <EXACT_MASS>
440.225761979

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.23971326602848

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3R)-3-hydroxyoctyl]oxy}oxane-3,4-diol

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-1.9232506326666658

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.651296916163076

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.807435899210756

> <JCHEM_PKA_STRONGEST_BASIC>
-2.717033753598537

> <JCHEM_POLAR_SURFACE_AREA>
178.53

> <JCHEM_REFRACTIVITY>
101.24830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3R)-3-hydroxyoctyl]oxy}oxane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002 -10.780   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.743 -10.924   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.773 -12.068   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.003 -13.402   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.410 -14.028   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.527 -14.866   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.558 -16.011   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.497 -13.082   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.352 -14.112   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   25   22   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(R)-1-[(2-O-D-Apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]-3-octanol	Generator
(R)-1-[(2-O-D-Apio-β-D-furanosyl-β-D-glucopyranosyl)oxy]-3-octanol	Generator

Chemical Formula

C₁₉H₃₆O₁₁

Average Mass

440.4860 Da

Monoisotopic Mass

440.22576 Da

IUPAC Name

(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3R)-3-hydroxyoctyl]oxy}oxane-3,4-diol

Traditional Name

(2R,3S,4S,5R,6R)-5-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3R)-3-hydroxyoctyl]oxy}oxane-3,4-diol

CAS Registry Number

Not Available

SMILES

CCCCC[C@@H](O)CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1OC[C@](O)(CO)[C@H]1O

InChI Identifier

InChI=1S/C19H36O11/c1-2-3-4-5-11(22)6-7-27-17-15(14(24)13(23)12(8-20)29-17)30-18-16(25)19(26,9-21)10-28-18/h11-18,20-26H,2-10H2,1H3/t11-,12-,13-,14+,15-,16+,17-,18+,19-/m1/s1

InChI Key

HTBXZRUTMUOBOY-BSZVCDTPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Crescentia cujete	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Oxane
Tertiary alcohol
Oxolane
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.3	ALOGPS
logP	-1.9	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.81	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	101.25 m³·mol⁻¹	ChemAxon
Polarizability	46.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101939202

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol (NP0160063)

MOL for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

3D MOL for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

3D SDF for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

3D-SDF for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

PDB for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

3D PDB for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

SMILES for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

INCHI for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

Structure for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)

3D Structure for NP0160063 ((2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol)