NP-MRD: Showing NP-Card for methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0203407)

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Record Information

Version

2.0

Created at

2022-09-04 22:51:31 UTC

Updated at

2022-09-04 22:51:31 UTC

NP-MRD ID

NP0203407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Lamalbid 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,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Lamium album, Lamium amplexicaule, Lamium purpureum, Phlomis rigida and Phlomoides tuberosa. methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate was first documented in 2010 (PMID: 20656306). Based on a literature review a small amount of articles have been published on Lamalbid (PMID: 30366450) (PMID: 29584748) (PMID: 32283643).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200512D          

 29 31  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  1  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
    1.7798    1.0799    0.0000 C   0  0  2  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
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  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
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    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  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -5.3379    2.9027    2.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2285    2.5903    1.5838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0169    1.3361    1.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8503    0.4347    1.3374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600    1.0248    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9840    1.9658   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9087    1.6372   -0.8805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2712    0.3877   -0.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4560    0.5310    0.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119    0.3453    0.3506 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2475   -0.7413    1.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5413   -1.1163    0.7981 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3044   -1.4680    2.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6021   -1.8448    1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3049   -0.1401   -0.0193 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1638   -0.4244   -1.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454    1.2938    0.2831 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9950    1.8555    1.1347 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6365    1.5404    0.7795 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1158    2.7276    0.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2324   -0.7440   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6653   -0.3210   -0.3259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1977   -0.4935   -1.7312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5678   -0.4228   -1.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679   -1.8961   -2.0529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2616   -2.8637   -1.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -1.7342   -1.6226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4586   -1.2469   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -3.0026   -1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5094    3.9971    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1967    2.4533    3.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2401    2.4661    1.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    2.9589    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678    0.1545   -1.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9962    0.1212   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -2.0698    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455   -0.5755    2.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024   -2.2641    2.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1075   -2.0370    2.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4015   -0.3244    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4177    0.3636   -1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1362    1.8661   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427    1.3361    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    1.5983    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3915    3.0246    0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825   -1.3328    0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.0563    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6597    0.1958   -2.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8836   -1.2638   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7310   -2.1085   -3.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0886   -2.5364   -0.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6262   -1.4049   -2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511   -1.8347   -3.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7545   -0.2008   -3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1391   -3.6396   -1.8673 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
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  1
 22  5  1  0
 19 10  1  0
 27 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  8 34  1  6
 10 35  1  6
 12 36  1  6
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  1
 16 41  1  0
 17 42  1  6
 18 43  1  0
 19 44  1  1
 20 45  1  0
 21 46  1  1
 22 47  1  1
 23 48  1  6
 24 49  1  0
 25 50  1  6
 26 51  1  0
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
M  END


  Mrv1652309052200512D          

 29 31  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  1  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
    1.7798    1.0799    0.0000 C   0  0  2  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
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  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
    1.1726   -0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429   -1.0637    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  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0203407

> <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]1[C@H](O)[C@H](O)[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O12/c1-17(25)8-7(10(20)13(17)23)5(14(24)26-2)4-27-15(8)29-16-12(22)11(21)9(19)6(3-18)28-16/h4,6-13,15-16,18-23,25H,3H2,1-2H3/t6-,7-,8-,9-,10+,11+,12-,13+,15+,16+,17-/m1/s1

> <INCHI_KEY>
HHDWDLBSGSYIQQ-GNDDPXJISA-N

> <FORMULA>
C17H26O12

> <MOLECULAR_WEIGHT>
422.383

> <EXACT_MASS>
422.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.915055951963595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,5S,6S,7R,7aS)-5,6,7-trihydroxy-7-methyl-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>
-3.732315955333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.78633389236105

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.122156606793048

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601928963

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
89.92619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <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       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       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.189  -1.518   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.627  -1.986   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   22                                                  
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    5   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    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)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]1[C@H](O)[C@H](O)[C@]2(C)O

InChI Identifier

InChI=1S/C17H26O12/c1-17(25)8-7(10(20)13(17)23)5(14(24)26-2)4-27-15(8)29-16-12(22)11(21)9(19)6(3-18)28-16/h4,6-13,15-16,18-23,25H,3H2,1-2H3/t6-,7-,8-,9-,10+,11+,12-,13+,15+,16+,17-/m1/s1

InChI Key

HHDWDLBSGSYIQQ-GNDDPXJISA-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
Lamium album	LOTUS Database	35616633
Lamium amplexicaule	LOTUS Database	35616633
Lamium purpureum	LOTUS Database	35616633
Phlomis rigida	LOTUS Database	35616633
Phlomoides tuberosa	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
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Polyol
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
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

C00010589

Chemspider ID

10272896

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Czerwinska ME, Swierczewska A, Granica S: Bioactive Constituents of Lamium album L. as Inhibitors of Cytokine Secretion in Human Neutrophils. Molecules. 2018 Oct 25;23(11):2770. doi: 10.3390/molecules23112770. [PubMed:30366450 ]
Fuji Y, Uchida A, Fukahori K, Chino M, Ohtsuki T, Matsufuji H: Chemical characterization and biological activity in young sesame leaves (Sesamum indicum L.) and changes in iridoid and polyphenol content at different growth stages. PLoS One. 2018 Mar 27;13(3):e0194449. doi: 10.1371/journal.pone.0194449. eCollection 2018. [PubMed:29584748 ]
Czerwinska ME, Kalinowska E, Popowski D, Bazylko A: Lamalbid, Chlorogenic Acid, and Verbascoside as Tools for Standardization of Lamium album Flowers-Development and Validation of HPLC-DAD Method. Molecules. 2020 Apr 9;25(7):1721. doi: 10.3390/molecules25071721. [PubMed:32283643 ]
Li H, Yang SQ, Wang H, Tian J, Gao WY: Biosynthesis of the iridoid glucoside, lamalbid, in Lamium barbatum. Phytochemistry. 2010 Oct;71(14-15):1690-4. doi: 10.1016/j.phytochem.2010.06.019. Epub 2010 Jul 23. [PubMed:20656306 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0203407)

MOL for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0203407 (methyl (1s,4as,5s,6s,7r,7as)-5,6,7-trihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate)