NP-MRD: Showing NP-Card for methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0328295)

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Record Information

Version

2.0

Created at

2022-09-12 11:38:19 UTC

Updated at

2022-09-12 11:38:19 UTC

NP-MRD ID

NP0328295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Hastatoside belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Penstemon nitidus, Penstemon pachyphyllus, Penstemon secundiflorus, Verbena hastata and Verbena officinalis. methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate was first documented in 2019 (PMID: 31148270). Based on a literature review a small amount of articles have been published on hastatoside (PMID: 33260609) (PMID: 31769179) (PMID: 31121915).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213382D          

 28 30  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  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  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    6.2585    2.3509   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0933    1.7007   -0.4618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990    2.3597    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    3.6114    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8296    1.6134    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7592    2.2517    0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    1.4235    1.3677 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2697    0.3372    0.5571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6075    0.7504   -0.4247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    0.1977   -0.2152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1293   -0.6381   -1.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -1.1454   -1.4431 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8698   -1.0346   -2.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1478   -1.5827   -2.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708   -0.6943   -0.4403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0873   -1.3694    0.7628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3005    0.7834   -0.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9476    1.5105   -1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840    1.2446    0.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7693    1.7500    1.3742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532   -0.4162   -0.0131 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5002   -1.8202    0.5938 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5814   -2.6345   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748   -1.5067    2.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -0.3568    1.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    0.0806    2.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656    0.1374    0.4587 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8209   -0.4213   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4075    2.0440   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1145    1.9373   -0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1839    3.4547   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224    3.3267    1.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -0.3299    1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -0.4283    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -2.2681   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8659    0.0143   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315   -1.6059   -3.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2764   -2.3237   -2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3757   -0.9481   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612   -1.1553    1.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9102    0.9249    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6044    0.9368   -1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064    2.0969   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240    0.9546    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805   -0.5235   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925   -2.2806    0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159   -2.5851    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463   -2.3462   -1.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -3.7296   -0.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0118   -1.1410    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626   -2.3683    2.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7475   -0.1397   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  6
 27  5  1  0
 19 10  1  0
 27 21  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  8 33  1  1
 10 34  1  1
 12 35  1  1
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  0
 17 41  1  1
 18 42  1  0
 19 43  1  6
 20 44  1  0
 21 45  1  6
 22 46  1  1
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 28 52  1  0
M  END


  Mrv1652309122213382D          

 28 30  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    0.0000 O   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  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  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)CC(=O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1

> <INCHI_KEY>
PRZVXHGUJJPSME-CZMSZWGTSA-N

> <FORMULA>
C17H24O11

> <MOLECULAR_WEIGHT>
404.368

> <EXACT_MASS>
404.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.341804142888094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.9379771826666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.330320726633815

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.646672450084402

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760198322

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
87.58839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.455  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    5   21   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₁₁

Average Mass

404.3680 Da

Monoisotopic Mass

404.13186 Da

IUPAC Name

methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)CC(=O)[C@]12O

InChI Identifier

InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1

InChI Key

PRZVXHGUJJPSME-CZMSZWGTSA-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
Penstemon nitidus	LOTUS Database	35616633
Penstemon pachyphyllus	LOTUS Database	35616633
Penstemon secundiflorus	LOTUS Database	35616633
Verbena hastata	LOTUS Database	35616633
Verbena officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Cyclic alcohol
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Methyl ester
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Polyol
Acetal
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Carbonyl group
Organic oxygen compound
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	-1.9	ChemAxon
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.59 m³·mol⁻¹	ChemAxon
Polarizability	38.34 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010576

Chemspider ID

34997604

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92043450

PDB ID

Not Available

ChEBI ID

178050

Good Scents ID

rw1815021

References

General References

Kubica P, Szopa A, Kokotkiewicz A, Miceli N, Taviano MF, Maugeri A, Cirmi S, Synowiec A, Gniewosz M, Elansary HO, Mahmoud EA, El-Ansary DO, Nasif O, Luczkiewicz M, Ekiert H: Production of Verbascoside, Isoverbascoside and Phenolic Acids in Callus, Suspension, and Bioreactor Cultures of Verbena officinalis and Biological Properties of Biomass Extracts. Molecules. 2020 Nov 28;25(23):5609. doi: 10.3390/molecules25235609. [PubMed:33260609 ]
Gibitz-Eisath N, Eichberger M, Gruber R, Seger C, Sturm S, Stuppner H: Towards eco-friendly secondary plant metabolite quantitation: Ultra high performance supercritical fluid chromatography applied to common vervain (Verbena officinalis L.). J Sep Sci. 2020 Feb;43(4):829-838. doi: 10.1002/jssc.201900854. Epub 2019 Dec 17. [PubMed:31769179 ]
Liu X, Zhang H, Xu J, Gong S, Han Y, Zhang T, Liu C: Identification of absorbed components and their metabolites in rat plasma after oral administration of Shufeng Jiedu capsule using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2019 Oct 15;33(19):1494-1501. doi: 10.1002/rcm.8498. [PubMed:31148270 ]
Lara-Issasi G, Salgado C, Pedraza-Chaverri J, Medina-Campos ON, Morales A, Aguila MA, Aviles M, Rivero-Cruz BE, Navarro V, Rios-Gomez R, Aguilar MI: Antimicrobial, Antioxidant Activities, and HPLC Determination of the Major Components of Verbena carolina (Verbenaceae). Molecules. 2019 May 22;24(10):1970. doi: 10.3390/molecules24101970. [PubMed:31121915 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0328295)

MOL for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0328295 (methyl (1s,4ar,7s,7ar)-4a-hydroxy-7-methyl-5-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)