NP-MRD: Showing NP-Card for genameside A (NP0028808)

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Record Information

Version

2.0

Created at

2021-06-19 20:35:52 UTC

Updated at

2021-06-29 23:55:48 UTC

NP-MRD ID

NP0028808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

genameside A

Provided By

JEOL Database JEOL Logo

Description

genameside A is found in Genipa americana. genameside A was first documented in 2005 (Ono, M., et al.). Based on a literature review very few articles have been published on Genameside A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122353D          

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     RDKit          3D

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M  END


  Mrv1652306192122353D          

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   -5.3711    3.6829    2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5379    4.2484    1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2018    1.7758    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7237    1.2268    2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0220    1.0620    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5425   -1.0381    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.9457    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -2.2540   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.3134   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -0.4972   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    0.9552    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635    2.5532    0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0589   -0.4243    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937    0.0385    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    1.4438    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3212    1.8175    3.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  6  1  0  0  0  0
  3  4  2  0  0  0  0
 22 23  1  0  0  0  0
 26 28  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 26 21  1  0  0  0  0
  6  5  2  0  0  0  0
 22 47  1  1  0  0  0
 21 22  1  0  0  0  0
 21 46  1  1  0  0  0
  8  9  1  0  0  0  0
 22  5  1  0  0  0  0
 10 19  1  0  0  0  0
 19 17  1  0  0  0  0
 17 15  1  0  0  0  0
 15 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 24 25  1  0  0  0  0
 13 14  1  0  0  0  0
 21  8  1  0  0  0  0
  2  1  1  0  0  0  0
  5  3  1  0  0  0  0
 26 27  1  1  0  0  0
  8  7  1  0  0  0  0
 28 29  1  0  0  0  0
 12 13  1  0  0  0  0
 10  9  1  0  0  0  0
  8 34  1  6  0  0  0
  6 33  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 24 50  1  1  0  0  0
 25 51  1  0  0  0  0
 28 53  1  0  0  0  0
 28 54  1  0  0  0  0
 10 35  1  6  0  0  0
 15 40  1  1  0  0  0
 16 41  1  0  0  0  0
 17 42  1  6  0  0  0
 18 43  1  0  0  0  0
 19 44  1  1  0  0  0
 20 45  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 12 36  1  6  0  0  0
 14 39  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 27 52  1  0  0  0  0
 29 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]3([H])C([H])([H])[C@@]([H])(O[H])[C@@](O[H])(C([H])([H])O[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

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

> <INCHI_KEY>
DPORNVNPTRLCKZ-RNLJPYGHSA-N

> <FORMULA>
C17H26O12

> <MOLECULAR_WEIGHT>
422.383

> <EXACT_MASS>
422.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.17731290273336

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-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

> <ALOGPS_LOGP>
-2.50

> <JCHEM_LOGP>
-3.7822760450000006

> <ALOGPS_LOGS>
-0.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.691750840949794

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.082122866576931

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192899

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
90.18539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-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

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    1.1683   -3.4477   -4.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103   -2.7637   -3.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -2.7414   -3.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -3.2425   -4.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -2.0095   -2.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707   -1.9158   -2.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904   -1.2877   -1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7310   -0.4011   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5282   -0.0952    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5164    0.8910    0.6339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8795    2.1620    0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072    3.2150    0.2074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9859    4.4957    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953    4.2981   -0.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8519    3.3619    1.3204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8267    4.3495    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5516    2.0195    1.5542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4253    2.1400    2.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5323    0.9059    1.7885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2303   -0.3432    1.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218   -1.0543    0.2674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5844   -1.4719   -0.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2139   -0.2099   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    0.6849   -0.0865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4865    1.8816   -0.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -0.1464    1.0269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5777   -0.9978    1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    0.6863    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    1.3633    2.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2453   -3.4071   -3.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614   -4.4979   -4.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -2.9555   -5.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -2.3581   -2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    0.5113   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0173    0.6256   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826    2.9781   -0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    4.7550    0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    5.3406   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555    3.4487   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    3.6829    2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5379    4.2484    1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2018    1.7758    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7237    1.2268    2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0220    1.0620    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5425   -1.0381    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.9457    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -2.2540   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.3134   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -0.4972   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    0.9552    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635    2.5532    0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0589   -0.4243    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937    0.0385    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    1.4438    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3212    1.8175    3.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  7  6  1  0
  3  4  2  0
 22 23  1  0
 26 28  1  0
 23 24  1  0
 24 26  1  0
 26 21  1  0
  6  5  2  0
 22 47  1  1
 21 22  1  0
 21 46  1  1
  8  9  1  0
 22  5  1  0
 10 19  1  0
 19 17  1  0
 17 15  1  0
 15 12  1  0
 12 11  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 19 20  1  0
 24 25  1  0
 13 14  1  0
 21  8  1  0
  2  1  1  0
  5  3  1  0
 26 27  1  1
  8  7  1  0
 28 29  1  0
 12 13  1  0
 10  9  1  0
  8 34  1  6
  6 33  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  1
 25 51  1  0
 28 53  1  0
 28 54  1  0
 10 35  1  6
 15 40  1  1
 16 41  1  0
 17 42  1  6
 18 43  1  0
 19 44  1  1
 20 45  1  0
 13 37  1  0
 13 38  1  0
 12 36  1  6
 14 39  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 52  1  0
 29 55  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.168  -3.448  -4.175  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.510  -2.764  -3.108  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.841  -2.741  -3.217  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.489  -3.243  -4.123  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.434  -2.010  -2.069  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.771  -1.916  -2.023  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.490  -1.288  -1.042  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.731  -0.401  -0.201  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.528  -0.095   0.948  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.516   0.891   0.634  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.880   2.162   0.527  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.807   3.215   0.207  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.986   4.496   0.029  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.995   4.298  -0.984  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.852   3.362   1.320  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.827   4.349   0.987  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.552   2.019   1.554  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.425   2.140   2.688  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.532   0.906   1.789  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.230  -0.343   1.900  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.422  -1.054   0.267  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.584  -1.472  -0.958  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.214  -0.210  -1.336  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.235   0.685  -0.087  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.487   1.882  -0.376  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.440  -0.146   1.027  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.578  -0.998   1.607  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.020   0.686   2.174  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.064   1.363   2.828  0.00  0.00           O+0
HETATM   30  H   UNK     0       2.245  -3.407  -3.990  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.861  -4.498  -4.205  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.963  -2.955  -5.131  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.438  -2.358  -2.756  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.532   0.511  -0.775  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.017   0.626  -0.307  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.283   2.978  -0.754  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.456   4.755   0.951  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.614   5.341  -0.268  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.555   3.449  -0.779  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.371   3.683   2.253  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.538   4.248   1.652  0.00  0.00           H+0
HETATM   42  H   UNK     0      -7.202   1.776   0.705  0.00  0.00           H+0
HETATM   43  H   UNK     0      -7.724   1.227   2.878  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.022   1.062   2.747  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.543  -1.038   1.864  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.657  -1.946   0.866  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.118  -2.254  -0.637  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.220   0.313  -2.197  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.236  -0.497  -1.611  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.268   0.955   0.160  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.164   2.553   0.255  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.059  -0.424   2.239  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.494   0.039   2.919  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.731   1.444   1.842  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.321   1.817   3.600  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    6   22    3                                                  
CONECT    6    7    5   33                                                  
CONECT    7    6    8                                                       
CONECT    8    9   21    7   34                                             
CONECT    9    8   10                                                       
CONECT   10   19   11    9   35                                             
CONECT   11   12   10                                                       
CONECT   12   15   11   13   36                                             
CONECT   13   14   12   37   38                                             
CONECT   14   13   39                                                       
CONECT   15   17   12   16   40                                             
CONECT   16   15   41                                                       
CONECT   17   19   15   18   42                                             
CONECT   18   17   43                                                       
CONECT   19   10   17   20   44                                             
CONECT   20   19   45                                                       
CONECT   21   26   22   46    8                                             
CONECT   22   23   47   21    5                                             
CONECT   23   22   24   48   49                                             
CONECT   24   23   26   25   50                                             
CONECT   25   24   51                                                       
CONECT   26   28   24   21   27                                             
CONECT   27   26   52                                                       
CONECT   28   26   29   53   54                                             
CONECT   29   28   55                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    6                                                            
CONECT   34    8                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    1.1683   -3.4477   -4.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5103   -2.7637   -3.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8410   -2.7414   -3.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892   -3.2425   -4.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -2.0095   -2.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7707   -1.9158   -2.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904   -1.2877   -1.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7310   -0.4011   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5282   -0.0952    0.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5164    0.8910    0.6339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8795    2.1620    0.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072    3.2150    0.2074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9859    4.4957    0.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9953    4.2981   -0.9839 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8267    4.3495    0.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5516    2.0195    1.5542 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4253    2.1400    2.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5323    0.9059    1.7885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2303   -0.3432    1.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218   -1.0543    0.2674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5844   -1.4719   -0.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2139   -0.2099   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    0.6849   -0.0865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4865    1.8816   -0.3759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -0.1464    1.0269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5777   -0.9978    1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    0.6863    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    1.3633    2.8277 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2453   -3.4071   -3.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614   -4.4979   -4.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -2.9555   -5.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4382   -2.3581   -2.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    0.5113   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0173    0.6256   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2826    2.9781   -0.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    4.7550    0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    5.3406   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5555    3.4487   -0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3711    3.6829    2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5379    4.2484    1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2018    1.7758    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7237    1.2268    2.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0220    1.0620    2.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5425   -1.0381    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570   -1.9457    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -2.2540   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2200    0.3134   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -0.4972   -1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    0.9552    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635    2.5532    0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0589   -0.4243    2.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937    0.0385    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    1.4438    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3212    1.8175    3.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  7  6  1  0
  3  4  2  0
 22 23  1  0
 26 28  1  0
 23 24  1  0
 24 26  1  0
 26 21  1  0
  6  5  2  0
 22 47  1  1
 21 22  1  0
 21 46  1  1
  8  9  1  0
 22  5  1  0
 10 19  1  0
 19 17  1  0
 17 15  1  0
 15 12  1  0
 12 11  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 19 20  1  0
 24 25  1  0
 13 14  1  0
 21  8  1  0
  2  1  1  0
  5  3  1  0
 26 27  1  1
  8  7  1  0
 28 29  1  0
 12 13  1  0
 10  9  1  0
  8 34  1  6
  6 33  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  1
 25 51  1  0
 28 53  1  0
 28 54  1  0
 10 35  1  6
 15 40  1  1
 16 41  1  0
 17 42  1  6
 18 43  1  0
 19 44  1  1
 20 45  1  0
 13 37  1  0
 13 38  1  0
 12 36  1  6
 14 39  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 52  1  0
 29 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆O₁₂

Average Mass

422.3830 Da

Monoisotopic Mass

422.14243 Da

IUPAC Name

methyl (1S,4aS,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-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,4aS,6R,7S,7aS)-6,7-dihydroxy-7-(hydroxymethyl)-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

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]3([H])C([H])([H])[C@@]([H])(O[H])[C@@](O[H])(C([H])([H])O[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

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

InChI Key

DPORNVNPTRLCKZ-RNLJPYGHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Genipa americana	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 53, 1342 (2005)

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
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-0.49	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	40.18 Å³	ChemAxon
Number of Rings	3	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

9865061

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11690334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono, M., et al. (2005). Ono, M., et al, Chem. Pharm. Bull. 53, 1342 (2005). Chem. Pharm. Bull..

Showing NP-Card for genameside A (NP0028808)

MOL for NP0028808 (genameside A)

3D MOL for NP0028808 (genameside A)

3D SDF for NP0028808 (genameside A)

3D-SDF for NP0028808 (genameside A)

PDB for NP0028808 (genameside A)

3D PDB for NP0028808 (genameside A)

SMILES for NP0028808 (genameside A)

INCHI for NP0028808 (genameside A)

Structure for NP0028808 (genameside A)

3D Structure for NP0028808 (genameside A)