NP-MRD: Showing NP-Card for 4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one (NP0247777)

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Record Information

Version

2.0

Created at

2022-09-07 09:44:53 UTC

Updated at

2022-09-07 09:44:53 UTC

NP-MRD ID

NP0247777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one

Description

Caseariaside D belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one is found in Casearia sylvestris. Based on a literature review very few articles have been published on Caseariaside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211442D          

 43 47  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3731   -2.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5925   -1.9275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2600   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1446   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8896   -0.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0405   -1.3144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2120   -0.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 27 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END

     RDKit          3D

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   -1.1893    0.8366    0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843   -0.6307    0.3375 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2047   -0.9779   -0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1849   -1.4152    0.5580 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3551   -0.6508    0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2344   -0.9460    1.4799 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3751    0.0453    1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0638   -0.0284    0.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146    0.8743    0.1838 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0668    1.7572   -0.8671 O   0  0  0  0  0  0  0  0  0  0  0  0
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 37 80  1  0
M  END


  Mrv1652309072211442D          

 43 47  0  0  1  0            999 V2000
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    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3731   -2.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5925   -1.9275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2600   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1446   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8896   -0.5298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0405   -1.3144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2120   -0.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 27 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0247777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)[C@H](CC[C@@H](O[C@@H]3O[C@H](CO[C@@H]4OC[C@](O)(CO)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C2=C)[C@@]1(C)CCC1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O12/c1-16-7-9-30(4)17(2)19(5-6-21(30)29(16,3)10-8-18-11-22(33)39-12-18)42-27-25(36)24(35)23(34)20(43-27)13-40-28-26(37)31(38,14-32)15-41-28/h11,16,19-21,23-28,32,34-38H,2,5-10,12-15H2,1,3-4H3/t16-,19-,20-,21-,23-,24+,25-,26+,27-,28-,29+,30+,31-/m1/s1

> <INCHI_KEY>
UKQPKSUMKQCUJM-KWFXHBRWSA-N

> <FORMULA>
C31H48O12

> <MOLECULAR_WEIGHT>
612.713

> <EXACT_MASS>
612.314576986

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
64.93839618416982

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{2-[(1S,2R,4aR,6R,8aR)-6-{[(2R,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
0.8184725129999992

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.704894779973696

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.471517782705886

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
150.80269999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-[(1S,2R,4aR,6R,8aR)-6-{[(2R,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.163  -4.612   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -9.669  -4.932   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.439  -3.598   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -11.685  -4.503   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -11.470  -2.454   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.994  -0.989   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.409  -2.454   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.729  -0.947   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.798   2.627   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.788   3.807   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.415   5.301   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.721   6.117   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.829   7.653   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.901   5.127   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.324   3.699   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   13   10   18                                                  
CONECT   18   17                                                            
CONECT   19    7   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    5   24                                                  
CONECT   24   23                                                            
CONECT   25    3   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   42                                                  
CONECT   28   27   29   30   38                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   32                                                       
CONECT   38   28   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41    2   27   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈O₁₂

Average Mass

612.7130 Da

Monoisotopic Mass

612.31458 Da

IUPAC Name

4-{2-[(1S,2R,4aR,6R,8aR)-6-{[(2R,3R,4S,5S,6R)-6-({[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)[C@H](CC[C@@H](O[C@@H]3O[C@H](CO[C@@H]4OC[C@](O)(CO)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C2=C)[C@@]1(C)CCC1=CC(=O)OC1

InChI Identifier

InChI=1S/C31H48O12/c1-16-7-9-30(4)17(2)19(5-6-21(30)29(16,3)10-8-18-11-22(33)39-12-18)42-27-25(36)24(35)23(34)20(43-27)13-40-28-26(37)31(38,14-32)15-41-28/h11,16,19-21,23-28,32,34-38H,2,5-10,12-15H2,1,3-4H3/t16-,19-,20-,21-,23-,24+,25-,26+,27-,28-,29+,30+,31-/m1/s1

InChI Key

UKQPKSUMKQCUJM-KWFXHBRWSA-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
Casearia sylvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Disaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Oxolane
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Primary 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	0.82	ChemAxon
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	150.8 m³·mol⁻¹	ChemAxon
Polarizability	64.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

44477873

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one (NP0247777)

MOL for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

3D MOL for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

3D SDF for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

3D-SDF for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

PDB for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

3D PDB for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

SMILES for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

INCHI for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

Structure for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)

3D Structure for NP0247777 (4-{2-[(1s,2r,4ar,6r,8ar)-6-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-5h-furan-2-one)