NP-MRD: Showing NP-Card for 3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside (NP0037681)

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Record Information

Version

2.0

Created at

2021-06-20 20:33:01 UTC

Updated at

2021-06-30 00:10:00 UTC

NP-MRD ID

NP0037681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside

Provided By

JEOL Database JEOL Logo

Description

3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside is found in Launaea arborescens. 3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside was first documented in 2008 (Bitam, F., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122333D          

 60 62  0  0  0  0            999 V2000
   -4.4689    3.3203    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    2.4613    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492    1.0945    2.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4812    0.6386    2.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706    0.4279    1.7299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    1.2235    1.4645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2707    0.6680    2.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    0.3488    1.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879   -0.2559    3.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    0.4818    0.6046 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4984   -0.7782   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7174   -1.4211   -0.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4046   -0.6601   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260   -1.2874   -1.8393 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3565   -0.3625   -2.8224 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3822   -0.3605    3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 28  1  0  0  0  0
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  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
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 12 21  1  0  0  0  0
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 21 19  1  0  0  0  0
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M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202122333D          

 60 62  0  0  0  0            999 V2000
   -4.4689    3.3203    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    2.4613    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0975    5.5663    1.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817    3.7392   -0.4011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1005    3.5571    0.6369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7468    2.6655    1.8411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3345    3.0468    4.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552    4.3145    3.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.1001    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.4881    3.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.3746    3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.3605    3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.2537    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.6344    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432   -1.5371    0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.4240   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320    0.6474   -2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -0.2739   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -1.7890   -3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -2.5283   -3.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -4.2361   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -3.8143   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765   -5.1942   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -2.7021   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -3.0559    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    1.5660   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.3652   -0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    3.2661    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    6.0858   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    5.4540    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    6.4551    2.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    2.8879   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343    4.5965   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974    4.5484    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    3.1618    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352    3.1308    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 28  1  0  0  0  0
 23 10  1  0  0  0  0
 10 11  1  0  0  0  0
 23 24  1  0  0  0  0
 10  8  1  0  0  0  0
  8  7  2  0  0  0  0
 25 24  2  0  0  0  0
  7  6  1  0  0  0  0
 30 29  1  0  0  0  0
 28 29  1  0  0  0  0
 30  6  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 30  2  1  0  0  0  0
 12 21  1  0  0  0  0
  8  9  1  0  0  0  0
 21 19  1  0  0  0  0
  2  1  2  3  0  0  0
 19 17  1  0  0  0  0
  3  4  2  0  0  0  0
 17 14  1  0  0  0  0
 25 26  1  0  0  0  0
 14 13  1  0  0  0  0
 26 27  1  0  0  0  0
 13 12  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
 12 11  1  0  0  0  0
 12 39  1  1  0  0  0
 17 44  1  6  0  0  0
 18 45  1  0  0  0  0
 19 46  1  1  0  0  0
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 21 48  1  6  0  0  0
 22 49  1  0  0  0  0
 15 41  1  0  0  0  0
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 23 50  1  0  0  0  0
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 10 38  1  1  0  0  0
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  7 34  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 30 60  1  1  0  0  0
  6 33  1  6  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 27 55  1  0  0  0  0
 16 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])/C([H])([H])[C@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])C([H])([H])C\1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O9/c1-10-7-15-13(11(2)20(27)28-15)5-3-12(8-22)4-6-14(10)29-21-19(26)18(25)17(24)16(9-23)30-21/h4,7,13-19,21-26H,2-3,5-6,8-9H2,1H3/b10-7-,12-4+/t13-,14-,15+,16+,17+,18-,19+,21+/m0/s1

> <INCHI_KEY>
LVLLXACEPRSSHZ-GNDYTOADSA-N

> <FORMULA>
C21H30O9

> <MOLECULAR_WEIGHT>
426.462

> <EXACT_MASS>
426.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.09463795034027

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,9S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-0.4662512226666658

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19990278602468

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210081692726908

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9710997476097876

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
105.6499

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,9S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.4689    3.3203    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2707    0.6680    2.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    0.3488    1.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879   -0.2559    3.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    0.4818    0.6046 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4984   -0.7782   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7174   -1.4211   -0.4338 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4046   -0.6601   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260   -1.2874   -1.8393 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3565   -0.3625   -2.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6738   -0.8212   -3.1052 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3338   -2.6550   -2.4801 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5434   -3.3139   -2.8715 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -3.5311   -1.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2112   -4.7626   -2.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -2.8048   -0.9845 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6929   -3.6100    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086    1.6024   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    3.0045    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919    3.9470    0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3046    5.3320    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    5.5663    1.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817    3.7392   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005    3.5571    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7468    2.6655    1.8411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3345    3.0468    4.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552    4.3145    3.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.1001    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.4881    3.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.3746    3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.3605    3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.2537    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.6344    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432   -1.5371    0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.4240   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320    0.6474   -2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -0.2739   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -1.7890   -3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -2.5283   -3.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -4.2361   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -3.8143   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765   -5.1942   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -2.7021   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -3.0559    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    1.5660   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.3652   -0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    3.2661    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    6.0858   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    5.4540    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    6.4551    2.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    2.8879   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343    4.5965   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974    4.5484    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    3.1618    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352    3.1308    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 28  1  0
 23 10  1  0
 10 11  1  0
 23 24  1  0
 10  8  1  0
  8  7  2  0
 25 24  2  0
  7  6  1  0
 30 29  1  0
 28 29  1  0
 30  6  1  0
 17 18  1  0
 19 20  1  0
 21 22  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 30  2  1  0
 12 21  1  0
  8  9  1  0
 21 19  1  0
  2  1  2  3
 19 17  1  0
  3  4  2  0
 17 14  1  0
 25 26  1  0
 14 13  1  0
 26 27  1  0
 13 12  1  0
 15 16  1  0
 14 15  1  0
 12 11  1  0
 12 39  1  1
 17 44  1  6
 18 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  6
 22 49  1  0
 15 41  1  0
 15 42  1  0
 14 40  1  1
 23 50  1  0
 23 51  1  0
 10 38  1  1
 24 52  1  0
  7 34  1  0
 29 58  1  0
 29 59  1  0
 28 56  1  0
 28 57  1  0
 30 60  1  1
  6 33  1  6
  9 35  1  0
  9 36  1  0
  9 37  1  0
  1 31  1  0
  1 32  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 16 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.469   3.320   3.597  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.932   2.461   2.722  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.449   1.095   2.521  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.481   0.639   2.977  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.571   0.428   1.730  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.399   1.224   1.464  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.271   0.668   2.296  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.004   0.349   1.951  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.888  -0.256   3.017  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.699   0.482   0.605  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.498  -0.778  -0.055  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.717  -1.421  -0.434  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.405  -0.660  -1.425  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.626  -1.287  -1.839  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.356  -0.363  -2.822  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.674  -0.821  -3.105  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.334  -2.655  -2.480  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.543  -3.314  -2.872  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.570  -3.531  -1.486  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.211  -4.763  -2.130  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.325  -2.805  -0.985  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.693  -3.610   0.022  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.309   1.602  -0.385  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.376   3.005   0.164  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.592   3.947   0.166  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.305   5.332   0.694  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.097   5.566   1.845  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.982   3.739  -0.401  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.100   3.557   0.637  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.747   2.666   1.841  0.00  0.00           C+0
HETATM   31  H   UNK     0      -5.335   3.047   4.194  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.055   4.314   3.731  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.205   1.100   0.402  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.565   0.488   3.331  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.769   0.375   3.177  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.382  -0.361   3.983  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.221  -1.254   2.714  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.768   0.634   0.818  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.343  -1.537   0.461  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.279  -1.424  -0.966  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.432   0.647  -2.405  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.803  -0.274  -3.764  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.613  -1.789  -3.259  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.730  -2.528  -3.388  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.274  -4.236  -3.071  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.219  -3.814  -0.648  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.577  -5.194  -1.522  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.600  -2.702  -1.801  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.033  -3.056   0.377  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.019   1.566  -1.223  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.642   1.365  -0.866  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.350   3.266   0.580  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.543   6.086  -0.064  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.748   5.454   0.973  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.866   6.455   2.164  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.003   2.888  -1.088  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.234   4.596  -1.039  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.397   4.548   1.005  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.985   3.162   0.119  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.935   3.131   2.412  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    3   30    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    7   30    5   33                                             
CONECT    7    8    6   34                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   35   36   37                                             
CONECT   10   23   11    8   38                                             
CONECT   11   10   12                                                       
CONECT   12   21   13   11   39                                             
CONECT   13   14   12                                                       
CONECT   14   17   13   15   40                                             
CONECT   15   16   14   41   42                                             
CONECT   16   15   43                                                       
CONECT   17   18   19   14   44                                             
CONECT   18   17   45                                                       
CONECT   19   20   21   17   46                                             
CONECT   20   19   47                                                       
CONECT   21   22   12   19   48                                             
CONECT   22   21   49                                                       
CONECT   23   10   24   50   51                                             
CONECT   24   23   25   52                                                  
CONECT   25   28   24   26                                                  
CONECT   26   25   27   53   54                                             
CONECT   27   26   55                                                       
CONECT   28   25   29   56   57                                             
CONECT   29   30   28   58   59                                             
CONECT   30   29    6    2   60                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

RDKit          3D

60 62  0  0  0  0  0  0  0  0999 V2000
   -4.4689    3.3203    3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    2.4613    2.7217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4492    1.0945    2.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4812    0.6386    2.9769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706    0.4279    1.7299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3990    1.2235    1.4645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2707    0.6680    2.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    0.3488    1.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8879   -0.2559    3.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    0.4818    0.6046 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4984   -0.7782   -0.0546 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4046   -0.6601   -1.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3565   -0.3625   -2.8224 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5704   -3.5311   -1.4860 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.3255   -2.8048   -0.9845 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6929   -3.6100    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086    1.6024   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762    3.0045    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919    3.9470    0.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3046    5.3320    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    5.5663    1.8455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817    3.7392   -0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005    3.5571    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7468    2.6655    1.8411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3345    3.0468    4.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552    4.3145    3.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    1.1001    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.4881    3.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7690    0.3746    3.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -0.3605    3.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2209   -1.2537    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.6344    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432   -1.5371    0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -1.4240   -0.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4320    0.6474   -2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -0.2739   -3.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6126   -1.7890   -3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7297   -2.5283   -3.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -4.2361   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2190   -3.8143   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765   -5.1942   -1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -2.7021   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0329   -3.0559    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0194    1.5660   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6417    1.3652   -0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499    3.2661    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431    6.0858   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    5.4540    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    6.4551    2.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035    2.8879   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2343    4.5965   -1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974    4.5484    1.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    3.1618    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352    3.1308    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 28  1  0
 23 10  1  0
 10 11  1  0
 23 24  1  0
 10  8  1  0
  8  7  2  0
 25 24  2  0
  7  6  1  0
 30 29  1  0
 28 29  1  0
 30  6  1  0
 17 18  1  0
 19 20  1  0
 21 22  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 30  2  1  0
 12 21  1  0
  8  9  1  0
 21 19  1  0
  2  1  2  3
 19 17  1  0
  3  4  2  0
 17 14  1  0
 25 26  1  0
 14 13  1  0
 26 27  1  0
 13 12  1  0
 15 16  1  0
 14 15  1  0
 12 11  1  0
 12 39  1  1
 17 44  1  6
 18 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  6
 22 49  1  0
 15 41  1  0
 15 42  1  0
 14 40  1  1
 23 50  1  0
 23 51  1  0
 10 38  1  1
 24 52  1  0
  7 34  1  0
 29 58  1  0
 29 59  1  0
 28 56  1  0
 28 57  1  0
 30 60  1  1
  6 33  1  6
  9 35  1  0
  9 36  1  0
  9 37  1  0
  1 31  1  0
  1 32  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 16 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₉

Average Mass

426.4620 Da

Monoisotopic Mass

426.18898 Da

IUPAC Name

(3aS,9S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

Traditional Name

(3aS,9S,11aR)-6-(hydroxymethyl)-10-methyl-3-methylidene-9-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])/C([H])([H])[C@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])C([H])([H])C\1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H30O9/c1-10-7-15-13(11(2)20(27)28-15)5-3-12(8-22)4-6-14(10)29-21-19(26)18(25)17(24)16(9-23)30-21/h4,7,13-19,21-26H,2-3,5-6,8-9H2,1H3/b10-7-,12-4+/t13-,14-,15+,16+,17+,18-,19+,21+/m0/s1

InChI Key

LVLLXACEPRSSHZ-GNDYTOADSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Launaea arborescens	JEOL database	Bitam, F., et al, Phytochem. 69, 2984 (2008)

Chemical Taxonomy

Classification

Not classified

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	-0.66	ALOGPS
logP	-0.47	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.65 m³·mol⁻¹	ChemAxon
Polarizability	44.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Bitam, F., et al. (2008). Bitam, F., et al, Phytochem. 69, 2984 (2008). Phytochem..

Showing NP-Card for 3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside (NP0037681)

MOL for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

3D MOL for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

3D SDF for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

3D-SDF for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

PDB for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

3D PDB for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

SMILES for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

INCHI for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

Structure for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)

3D Structure for NP0037681 (3beta,14-dihydroxycostunolide-3-O-beta-D-glycopyranoside)