NP-MRD: Showing NP-Card for (1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid (NP0255108)

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Record Information

Version

1.0

Created at

2022-09-07 19:28:45 UTC

Updated at

2022-09-07 19:28:45 UTC

NP-MRD ID

NP0255108

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid

Description

(1S,2S,4R,4aS,5R,8aS)-1-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalene-2-carboxylic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid is found in Tinospora cordifolia. Based on a literature review very few articles have been published on (1S,2S,4R,4aS,5R,8aS)-1-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalene-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221282D          

 41 44  0  0  1  0            999 V2000
   -0.1960   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  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
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    1.4072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4222    1.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0795    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474    2.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    3.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    2.8397    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
    3.8545    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 29 38  1  0  0  0  0
 38 39  1  1  0  0  0
 27 40  1  0  0  0  0
 10 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  6  0  0  0
M  END


  Mrv1652309072221282D          

 41 44  0  0  1  0            999 V2000
   -0.1960   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862   -2.1387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1808   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   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  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  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
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098    1.4072    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4222    1.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0795    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474    2.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794    3.2769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    2.8397    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
    3.8545    0.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 29 38  1  0  0  0  0
 38 39  1  1  0  0  0
 27 40  1  0  0  0  0
 10 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255108

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(O)CCC[C@H]2[C@](C)(C[C@H](O)C3=COC=C3)[C@@](O)(C[C@@H](O[C@@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]3O)[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O14/c1-24(9-14(29)13-6-8-39-12-13)16-5-4-7-26(36,23(35)38-3)25(16,2)17(10-27(24,37)22(33)34)41-21-20(32)19(31)18(30)15(11-28)40-21/h6,8,12,14-21,28-32,36-37H,4-5,7,9-11H2,1-3H3,(H,33,34)/t14-,15-,16-,17+,18-,19+,20+,21-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
QHRCDTOIELUASN-KZKLWCDVSA-N

> <FORMULA>
C27H40O14

> <MOLECULAR_WEIGHT>
588.603

> <EXACT_MASS>
588.241805968

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.59460364644224

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,4aS,5R,8aS)-1-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalene-2-carboxylic acid

> <JCHEM_LOGP>
-1.4915571796666685

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.745654809983199

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.985542988582381

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835441423658

> <JCHEM_POLAR_SURFACE_AREA>
236.80999999999995

> <JCHEM_REFRACTIVITY>
134.86180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,4aS,5R,8aS)-1-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid

> <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      -0.366  -2.545   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.161  -3.992   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.204  -5.707   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.657  -4.260   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.872   2.627   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.388   2.894   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.882   3.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.345   3.699   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.768   5.127   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.948   6.117   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.254   5.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.195   0.677   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.175   0.142   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.712  -2.485   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   40                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   40                                                  
CONECT   11   10   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   11   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   40                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   29   39                                                  
CONECT   39   38                                                            
CONECT   40   27   10    5   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4R,4AS,5R,8as)-1-[(2S)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-decahydronaphthalene-2-carboxylate	Generator

Chemical Formula

C₂₇H₄₀O₁₄

Average Mass

588.6030 Da

Monoisotopic Mass

588.24181 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(O)CCC[C@H]2[C@](C)(C[C@H](O)C3=COC=C3)[C@@](O)(C[C@@H](O[C@@H]3O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]3O)[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C27H40O14/c1-24(9-14(29)13-6-8-39-12-13)16-5-4-7-26(36,23(35)38-3)25(16,2)17(10-27(24,37)22(33)34)41-21-20(32)19(31)18(30)15(11-28)40-21/h6,8,12,14-21,28-32,36-37H,4-5,7,9-11H2,1-3H3,(H,33,34)/t14-,15-,16-,17+,18-,19+,20+,21-,24-,25-,26-,27+/m0/s1

InChI Key

QHRCDTOIELUASN-KZKLWCDVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tinospora cordifolia	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
Diterpenoid
Clerodane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Methyl ester
Tertiary alcohol
Cyclic alcohol
Heteroaromatic compound
Furan
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Carboxylic acid
Acetal
Oxacycle
Aromatic alcohol
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-1.5	ChemAxon
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	236.81 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	134.86 m³·mol⁻¹	ChemAxon
Polarizability	57.59 Å³	ChemAxon
Number of Rings	4	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

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

163185892

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid (NP0255108)

MOL for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

3D MOL for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

3D SDF for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

3D-SDF for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

PDB for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

3D PDB for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

SMILES for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

INCHI for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

Structure for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)

3D Structure for NP0255108 ((1s,2s,4r,4as,5r,8as)-1-[(2s)-2-(furan-3-yl)-2-hydroxyethyl]-2,5-dihydroxy-5-(methoxycarbonyl)-1,4a-dimethyl-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydronaphthalene-2-carboxylic acid)