NP-MRD: Showing NP-Card for methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate (NP0209931)

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Record Information

Version

2.0

Created at

2022-09-05 07:32:17 UTC

Updated at

2022-09-05 07:32:17 UTC

NP-MRD ID

NP0209931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate

Description

Clandonoside II belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate is found in Caryopteris clandonensis. methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate was first documented in 2000 (PMID: 11014270). Based on a literature review very few articles have been published on Clandonoside II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052209322D          

 29 30  0  0  1  0            999 V2000
   -0.4444   -1.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -1.1921    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
   -1.5180   -0.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6358   -0.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    0.5230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744    1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    0.9907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2546    0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048    0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    1.4584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1567    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7334    2.1807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5520    2.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    2.4330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1525    3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    2.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    1.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1758    0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    0.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4459   -0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    0.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763   -0.2566    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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 18  1  1  0  0  0
  9 21  1  0  0  0  0
 13 21  1  0  0  0  0
  7 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
    2.9015    0.3608    5.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727   -0.0213    4.2492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8942   -0.8560    3.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0803   -1.1812    2.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070   -1.2472    2.3201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3864   -0.8269    3.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -0.4471    1.0043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5522   -0.6033    0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568    0.2635    0.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5718    0.0481    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2737   -1.1494    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.4142   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346   -0.3954   -1.3777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6403   -0.9626   -2.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4064    0.7587   -1.2734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6126    0.5067   -1.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6665    1.9242   -1.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2345    1.5080   -2.0081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2865    2.5881   -1.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    1.3263   -3.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541    0.1850   -1.3110 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6126   -0.9303    0.1687 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6824   -0.1402   -0.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5921    0.4359   -1.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668    1.2071   -1.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982   -0.8361   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0874   -0.2364   -0.2229 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205   -2.2168    0.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3551   -2.8854    0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398    0.1478    6.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -0.1771    4.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0444    1.4540    4.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6820   -2.3127    2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -1.2368    4.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594    0.5772    1.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750    1.3068    0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4632   -1.8424    1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983   -2.3197   -0.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -0.3652   -3.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6514    1.0163   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1842   -0.0766   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1393    2.1323   -2.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7804    2.8503   -1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211    3.2960   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142    2.1357   -1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903    3.2104   -0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377    1.7294   -3.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -0.4570   -1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584    0.8048    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6325   -0.3669   -2.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719    1.1459   -1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9431    1.7157   -0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5485   -3.4678   -0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1546   -2.1144    0.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4462   -3.5485    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  1  0
 26 27  2  0
 26 23  1  0
 23 24  1  0
 24 25  1  0
 23 22  1  0
 22  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  6
 18 21  1  0
  7  5  1  0
  5  6  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
 21  9  1  0
 21 13  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 23 49  1  1
 24 50  1  0
 24 51  1  0
 25 52  1  0
  7 35  1  1
  9 36  1  1
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  1
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  6
  5 33  1  6
  6 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309052209322D          

 29 30  0  0  1  0            999 V2000
   -0.4444   -1.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -1.1921    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
   -1.5180   -0.2254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6358   -0.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    0.5230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744    1.1466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845    0.9907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2546    0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048    0.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3347    1.4584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1567    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7334    2.1807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5520    2.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    2.4330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1525    3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190    2.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246    1.6143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1758    0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    0.0552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4459   -0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    0.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0662   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763   -0.2566    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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 18  1  1  0  0  0
  9 21  1  0  0  0  0
 13 21  1  0  0  0  0
  7 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209931

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O12/c1-16(23)6-9(19)17(24)4-5-27-15(11(16)17)29-14(10(20)13(22)26-3)28-8(7-18)12(21)25-2/h4-5,8-11,14-15,18-20,23-24H,6-7H2,1-3H3/t8-,9-,10-,11-,14+,15+,16+,17-/m1/s1

> <INCHI_KEY>
CNNYMNKPTOVMNY-AQCYEJSWSA-N

> <FORMULA>
C17H26O12

> <MOLECULAR_WEIGHT>
422.383

> <EXACT_MASS>
422.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.53056479952461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-[(1S,2S)-1-{[(1S,4aS,5R,7S,7aR)-4a,5,7-trihydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate

> <JCHEM_LOGP>
-3.318509415333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.840915419607178

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.968563105563877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.046591416816045

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
91.10549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(1S,2S)-1-{[(1S,4aS,5R,7S,7aR)-4a,5,7-trihydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.830  -3.389   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.838  -2.225   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.834  -0.421   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.179  -0.479   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.187  -1.643   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.683   0.976   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.326   2.140   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.838   1.849   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.342   0.394   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.854   0.103   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.862   1.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.358   2.722   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.893   2.591   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.102   4.071   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.630   4.261   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.050   5.195   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.655   4.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.151   5.997   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.156   4.192   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.846   3.013   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.195   1.267   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.203   0.103   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.699  -1.352   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.707  -2.516   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.715   0.394   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.219   1.849   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.723  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.236  -0.479   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                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18    9   13                                                  
CONECT   22    7   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₁₂

Average Mass

422.3830 Da

Monoisotopic Mass

422.14243 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](CO)O[C@@H](O[C@@H]1OC=C[C@@]2(O)[C@H](O)C[C@](C)(O)[C@@H]12)[C@H](O)C(=O)OC

InChI Identifier

InChI=1S/C17H26O12/c1-16(23)6-9(19)17(24)4-5-27-15(11(16)17)29-14(10(20)13(22)26-3)28-8(7-18)12(21)25-2/h4-5,8-11,14-15,18-20,23-24H,6-7H2,1-3H3/t8-,9-,10-,11-,14+,15+,16+,17-/m1/s1

InChI Key

CNNYMNKPTOVMNY-AQCYEJSWSA-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
Caryopteris x clandonensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Sugar acid
Glyceric_acid
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Dicarboxylic acid or derivatives
Methyl ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036915

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

101084572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hannedouche S, Stanislas E, Moulis C, Fouraste I: Iridoids from Caryopteris x clandonensis. Phytochemistry. 2000 Aug;54(8):807-9. doi: 10.1016/s0031-9422(00)00069-8. [PubMed:11014270 ]
LOTUS database [Link]

Showing NP-Card for methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate (NP0209931)

MOL for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

3D MOL for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

3D SDF for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

3D-SDF for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

PDB for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

3D PDB for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

SMILES for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

INCHI for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

Structure for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)

3D Structure for NP0209931 (methyl (2r)-2-[(1s,2s)-1-{[(1s,4as,5r,7s,7ar)-4a,5,7-trihydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-2-hydroxy-3-methoxy-3-oxopropoxy]-3-hydroxypropanoate)