NP-MRD: Showing NP-Card for alatoside F (NP0042678)

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Record Information

Version

2.0

Created at

2021-06-21 00:16:56 UTC

Updated at

2021-06-30 00:17:54 UTC

NP-MRD ID

NP0042678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alatoside F

Provided By

JEOL Database JEOL Logo

Description

2-[(6R,8aS)-3-Oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6alpha-yl]propenoic acid beta-D-glucopyranosyl ester belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. alatoside F is found in Laggera alata. alatoside F was first documented in 2013 (Wang, G.-C., et al.). Based on a literature review very few articles have been published on 2-[(6R,8aS)-3-Oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6alpha-yl]propenoic acid beta-D-glucopyranosyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102163D          

 59 61  0  0  0  0            999 V2000
   -0.9780    1.4180   -3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    1.0021   -2.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.9149   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289    3.0871   -0.9386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    1.2730    0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479    2.0714    1.4851 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4049    1.3276    2.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897    1.9838    3.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4022    1.1339    4.6205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6701    0.9664    3.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.1344    4.3399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8512    2.8209    5.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907    2.9189    3.3753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1263    2.9659    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    2.2991    1.9757 C   0  0  1  0  0  0  0  0  0  0  0  0
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 23 22  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
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 13 14  1  0  0  0  0
  9 10  1  0  0  0  0
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  2  1  2  3  0  0  0
 11 13  1  0  0  0  0
  2  3  1  0  0  0  0
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 24 25  2  0  0  0  0
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  1 30  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102163D          

 59 61  0  0  0  0            999 V2000
   -0.9780    1.4180   -3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    1.0021   -2.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5806   -1.4194   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.1166   -1.4303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9034    0.8302   -4.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212    2.3572   -3.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    3.0217    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    2.9609    3.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698    1.6025    5.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    0.1338    4.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.6755    3.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3526    1.1502    4.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821    3.0355    5.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    3.9644    3.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757    3.3165    3.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    1.3416    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    3.3608    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.6876   -2.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -1.5604   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5847   -1.0889   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545   -3.4423   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -3.0744   -2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -1.3946    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.1994    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838   -3.1344    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -4.2550   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -4.7107   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3438   -3.6682    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537   -4.8519   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    0.5148   -2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386   -0.7466   -3.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6300   -0.3973   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978    0.3096   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    0.6309   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0  0  0  0
 24 26  1  0  0  0  0
 26 28  2  0  0  0  0
 20 22  1  0  0  0  0
 20 28  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  1  0  0  0  0
  6  5  1  0  0  0  0
 20 19  1  0  0  0  0
 28 29  1  0  0  0  0
 29 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 16  1  0  0  0  0
 20 21  1  1  0  0  0
 26 27  1  0  0  0  0
 13 14  1  0  0  0  0
  9 10  1  0  0  0  0
 17  2  1  0  0  0  0
 23 24  1  0  0  0  0
  2  1  2  3  0  0  0
 11 13  1  0  0  0  0
  2  3  1  0  0  0  0
 13 15  1  0  0  0  0
 24 25  2  0  0  0  0
  3  5  1  0  0  0  0
 15  6  1  0  0  0  0
  3  4  2  0  0  0  0
 11 12  1  0  0  0  0
  8  9  1  0  0  0  0
 12 38  1  0  0  0  0
 11 37  1  1  0  0  0
  6 32  1  6  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  8 33  1  6  0  0  0
 15 41  1  1  0  0  0
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 13 39  1  6  0  0  0
 14 40  1  0  0  0  0
 10 36  1  0  0  0  0
 23 53  1  0  0  0  0
 23 54  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
 17 43  1  6  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 21 50  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC(=O)C(=C([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C2([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O8/c1-10(12-4-6-21(3)7-5-14(23)11(2)13(21)8-12)19(27)29-20-18(26)17(25)16(24)15(9-22)28-20/h12,15-18,20,22,24-26H,1,4-9H2,2-3H3/t12-,15-,16-,17+,18-,20+,21+/m1/s1

> <INCHI_KEY>
RFPMNQJMSCFDTL-BECYNZDRSA-N

> <FORMULA>
C21H30O8

> <MOLECULAR_WEIGHT>
410.463

> <EXACT_MASS>
410.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.751646967836315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]prop-2-enoate

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.9653260446666663

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194438838059284

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195722992084562

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938228984556

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
102.02739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -0.9780    1.4180   -3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4049    1.3276    2.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897    1.9838    3.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4022    1.1339    4.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6701    0.9664    3.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.1344    4.3399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8512    2.8209    5.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907    2.9189    3.3753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1263    2.9659    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    2.2991    1.9757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5937    3.1757    1.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3484   -0.3028   -1.9455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -1.3877   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.6967   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -2.5709   -0.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8577   -2.3084    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254   -3.9346   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -3.8822   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5951   -2.8271   -1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866   -2.9842   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -1.5414   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296   -0.4840   -2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.4194   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.1166   -1.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034    0.8302   -4.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212    2.3572   -3.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    3.0217    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    2.9609    3.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698    1.6025    5.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    0.1338    4.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.6755    3.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3526    1.1502    4.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821    3.0355    5.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    3.9644    3.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757    3.3165    3.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    1.3416    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    3.3608    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.6876   -2.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -1.5604   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5847   -1.0889   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545   -3.4423   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -3.0744   -2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -1.3946    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.1994    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838   -3.1344    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -4.2550   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -4.7107   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3438   -3.6682    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537   -4.8519   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    0.5148   -2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386   -0.7466   -3.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6300   -0.3973   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978    0.3096   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    0.6309   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 24 26  1  0
 26 28  2  0
 20 22  1  0
 20 28  1  0
  6  7  1  0
  7  8  1  0
  8 11  1  0
  6  5  1  0
 20 19  1  0
 28 29  1  0
 29 17  1  0
 17 18  1  0
 18 19  1  0
 15 16  1  0
 20 21  1  1
 26 27  1  0
 13 14  1  0
  9 10  1  0
 17  2  1  0
 23 24  1  0
  2  1  2  3
 11 13  1  0
  2  3  1  0
 13 15  1  0
 24 25  2  0
  3  5  1  0
 15  6  1  0
  3  4  2  0
 11 12  1  0
  8  9  1  0
 12 38  1  0
 11 37  1  1
  6 32  1  6
  9 34  1  0
  9 35  1  0
  8 33  1  6
 15 41  1  1
 16 42  1  0
 13 39  1  6
 14 40  1  0
 10 36  1  0
 23 53  1  0
 23 54  1  0
 22 51  1  0
 22 52  1  0
 29 58  1  0
 29 59  1  0
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
  1 30  1  0
  1 31  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.978   1.418  -3.188  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.427   1.002  -2.032  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.588   1.915  -0.866  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.929   3.087  -0.939  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.333   1.273   0.290  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.348   2.071   1.485  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.405   1.328   2.453  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.490   1.984   3.730  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.402   1.134   4.620  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.670   0.966   3.980  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.905   2.134   4.340  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.851   2.821   5.590  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.791   2.919   3.375  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.126   2.966   3.905  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.800   2.299   1.976  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.594   3.176   1.156  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.348  -0.303  -1.946  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.399  -1.388  -1.159  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.387  -2.697  -1.172  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.850  -2.571  -0.665  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.858  -2.308   0.859  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.525  -3.935  -0.949  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.031  -3.882  -0.803  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.595  -2.827  -1.716  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.687  -2.984  -2.262  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.830  -1.541  -1.890  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.630  -0.484  -2.604  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.581  -1.419  -1.379  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.790  -0.117  -1.430  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.903   0.830  -4.098  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.521   2.357  -3.265  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.168   3.022   1.296  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.970   2.961   3.586  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.570   1.603   5.594  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.984   0.134   4.775  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.467   0.676   3.071  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.353   1.150   4.526  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.782   3.035   5.807  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.460   3.964   3.325  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.676   3.317   3.173  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.334   1.342   1.997  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.116   3.361   0.319  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.448  -0.688  -2.973  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.385  -1.560  -1.609  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.585  -1.089  -0.123  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.155  -3.442  -0.575  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.386  -3.074  -2.204  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.318  -1.395   1.128  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.877  -2.199   1.246  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.384  -3.134   1.401  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.296  -4.255  -1.976  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.119  -4.711  -0.289  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.344  -3.668   0.223  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.454  -4.852  -1.090  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.195   0.515  -2.554  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.739  -0.747  -3.662  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.630  -0.397  -2.165  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.798   0.310  -0.421  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.268   0.631  -2.068  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2   17    1    3                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    7    5   15   32                                             
CONECT    7    6    8                                                       
CONECT    8    7   11    9   33                                             
CONECT    9   10    8   34   35                                             
CONECT   10    9   36                                                       
CONECT   11    8   13   12   37                                             
CONECT   12   11   38                                                       
CONECT   13   14   11   15   39                                             
CONECT   14   13   40                                                       
CONECT   15   16   13    6   41                                             
CONECT   16   15   42                                                       
CONECT   17   29   18    2   43                                             
CONECT   18   17   19   44   45                                             
CONECT   19   20   18   46   47                                             
CONECT   20   22   28   19   21                                             
CONECT   21   20   48   49   50                                             
CONECT   22   23   20   51   52                                             
CONECT   23   22   24   53   54                                             
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   24   28   27                                                  
CONECT   27   26   55   56   57                                             
CONECT   28   26   20   29                                                  
CONECT   29   28   17   58   59                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
   -0.9780    1.4180   -3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270    1.0021   -2.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5876    1.9149   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9289    3.0871   -0.9386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    1.2730    0.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3479    2.0714    1.4851 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4049    1.3276    2.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897    1.9838    3.7302 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4022    1.1339    4.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6701    0.9664    3.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.1344    4.3399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8512    2.8209    5.5903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907    2.9189    3.3753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1263    2.9659    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    2.2991    1.9757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5937    3.1757    1.1562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3484   -0.3028   -1.9455 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3993   -1.3877   -1.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867   -2.6967   -1.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8496   -2.5709   -0.6646 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8577   -2.3084    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254   -3.9346   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -3.8822   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5951   -2.8271   -1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866   -2.9842   -2.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -1.5414   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296   -0.4840   -2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -1.4194   -1.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.1166   -1.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9034    0.8302   -4.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212    2.3572   -3.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    3.0217    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    2.9609    3.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698    1.6025    5.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    0.1338    4.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4667    0.6755    3.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3526    1.1502    4.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821    3.0355    5.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    3.9644    3.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757    3.3165    3.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3345    1.3416    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    3.3608    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4480   -0.6876   -2.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -1.5604   -1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5847   -1.0889   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545   -3.4423   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -3.0744   -2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3182   -1.3946    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.1994    1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838   -3.1344    1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -4.2550   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1189   -4.7107   -0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3438   -3.6682    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537   -4.8519   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1946    0.5148   -2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7386   -0.7466   -3.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6300   -0.3973   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978    0.3096   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    0.6309   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 24 26  1  0
 26 28  2  0
 20 22  1  0
 20 28  1  0
  6  7  1  0
  7  8  1  0
  8 11  1  0
  6  5  1  0
 20 19  1  0
 28 29  1  0
 29 17  1  0
 17 18  1  0
 18 19  1  0
 15 16  1  0
 20 21  1  1
 26 27  1  0
 13 14  1  0
  9 10  1  0
 17  2  1  0
 23 24  1  0
  2  1  2  3
 11 13  1  0
  2  3  1  0
 13 15  1  0
 24 25  2  0
  3  5  1  0
 15  6  1  0
  3  4  2  0
 11 12  1  0
  8  9  1  0
 12 38  1  0
 11 37  1  1
  6 32  1  6
  9 34  1  0
  9 35  1  0
  8 33  1  6
 15 41  1  1
 16 42  1  0
 13 39  1  6
 14 40  1  0
 10 36  1  0
 23 53  1  0
 23 54  1  0
 22 51  1  0
 22 52  1  0
 29 58  1  0
 29 59  1  0
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(6R,8AS)-3-oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6a-yl]propenoate b-D-glucopyranosyl ester	Generator
2-[(6R,8AS)-3-oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6a-yl]propenoic acid b-D-glucopyranosyl ester	Generator
2-[(6R,8AS)-3-oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6alpha-yl]propenoate beta-D-glucopyranosyl ester	Generator
2-[(6R,8AS)-3-oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6α-yl]propenoate β-D-glucopyranosyl ester	Generator
2-[(6R,8AS)-3-oxo-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-6α-yl]propenoic acid β-D-glucopyranosyl ester	Generator

Chemical Formula

C₂₁H₃₀O₈

Average Mass

410.4630 Da

Monoisotopic Mass

410.19407 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-2-yl]prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-[(2R,4aS)-4a,8-dimethyl-7-oxo-1,2,3,4,5,6-hexahydronaphthalen-2-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC(=O)C(=C([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C2([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C21H30O8/c1-10(12-4-6-21(3)7-5-14(23)11(2)13(21)8-12)19(27)29-20-18(26)17(25)16(24)15(9-22)28-20/h12,15-18,20,22,24-26H,1,4-9H2,2-3H3/t12-,15-,16-,17+,18-,20+,21+/m1/s1

InChI Key

RFPMNQJMSCFDTL-BECYNZDRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laggera alata	JEOL database	Wang, G.-C., et. al, Phytochem. 96, 201 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Cyclohexenone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Ketone
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Aldehyde
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.4	ALOGPS
logP	0.97	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.03 m³·mol⁻¹	ChemAxon
Polarizability	42.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

102125246

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, G.-C., et al. (2013). Wang, G.-C., et. al, Phytochem. 96, 201 (2013). Phytochem..

Showing NP-Card for alatoside F (NP0042678)

MOL for NP0042678 (alatoside F)

3D MOL for NP0042678 (alatoside F)

3D SDF for NP0042678 (alatoside F)

3D-SDF for NP0042678 (alatoside F)

PDB for NP0042678 (alatoside F)

3D PDB for NP0042678 (alatoside F)

SMILES for NP0042678 (alatoside F)

INCHI for NP0042678 (alatoside F)

Structure for NP0042678 (alatoside F)

3D Structure for NP0042678 (alatoside F)