NP-MRD: Showing NP-Card for 10-p-cis-coumaroyl-1S-dihydromonotropein (NP0032686)

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Record Information

Version

2.0

Created at

2021-06-19 23:25:29 UTC

Updated at

2021-06-30 00:02:02 UTC

NP-MRD ID

NP0032686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-p-cis-coumaroyl-1S-dihydromonotropein

Provided By

JEOL Database JEOL Logo

Description

10-P-cis-Coumaroyl-1S-dihydromonotropein 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. 10-p-cis-coumaroyl-1S-dihydromonotropein is found in Vaccinium macrocarpon. 10-p-cis-coumaroyl-1S-dihydromonotropein was first documented in 2007 (PMID: 17269823). Based on a literature review very few articles have been published on 10-p-cis-Coumaroyl-1S-dihydromonotropein.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101253D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101253D          

 68 71  0  0  0  0            999 V2000
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    2.1386    1.3685   -4.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4527   -0.7394   -5.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7313   -1.9520   -0.3548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5594   -2.3217   -1.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7650   -2.3756    1.8195 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.0888    0.4506    3.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.3622    2.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -0.6396    1.1800 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.7213    2.2440   -3.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8277   -2.6451    1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.7170    2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -0.4654    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0663   -0.2375    4.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8407    1.0689    3.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1866   -2.6928   -2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3523   -1.2266   -3.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129   -2.7371   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    0.1464   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7736   -0.6855    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5929   -1.1141    1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9617    1.0880    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0037    1.1804    0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    0.8362    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    0.2172   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
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 34 36  1  0  0  0  0
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  2  3  1  0  0  0  0
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  8  9  1  0  0  0  0
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 15 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2(O[H])C([H])([H])OC(=O)C(\[H])=C(\[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O13/c26-9-16-19(29)20(30)21(31)24(37-16)38-23-18-14(15(10-35-23)22(32)33)7-8-25(18,34)11-36-17(28)6-3-12-1-4-13(27)5-2-12/h1-6,10,14,16,18-21,23-24,26-27,29-31,34H,7-9,11H2,(H,32,33)/b6-3-/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1

> <INCHI_KEY>
DQMJTGHIDOKZGT-ZCIFOOIUSA-N

> <FORMULA>
C25H30O13

> <MOLECULAR_WEIGHT>
538.502

> <EXACT_MASS>
538.168641026

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.706440074949256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7R,7aS)-7-hydroxy-7-({[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}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-carboxylic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-0.35627443099999984

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.397942673531546

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.135722663121764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601928367

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
125.60340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7R,7aS)-7-hydroxy-7-({[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}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-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    4.1998    0.5992   -1.3131 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3596    0.3831   -2.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0639    1.3804   -3.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1386    1.3685   -4.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    0.3243   -4.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527   -0.7394   -5.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -1.7406   -5.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7335   -1.6771   -4.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6167   -2.6864   -5.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0520   -0.6161   -4.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076    0.3841   -3.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -0.7374   -2.2859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970   -1.8010   -1.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7313   -1.9520   -0.3548 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5594   -2.3217   -1.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7650   -2.3756    1.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065   -0.8595    1.6075 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2904   -0.1073    2.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    0.1241    3.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1822    0.7689    4.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790   -0.4790    3.5987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.4506    3.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.3622    2.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -0.6396    1.1800 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6128   -1.1559   -0.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1929   -2.9038   -2.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2419   -1.3166   -0.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3853    0.7363    1.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    0.2330    0.9957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6947    0.5280    2.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092   -0.7106    0.5387 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7213    2.2440   -3.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    2.2135   -4.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -0.8014   -5.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416   -2.5718   -6.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9737   -2.7099   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8629   -1.6712   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4194   -1.6360   -1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1154   -3.5244    1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6394   -3.8694    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8277   -2.6451    1.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3511   -2.7170    2.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -0.4654    1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0663   -0.2375    4.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8407    1.0689    3.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1497   -1.6055    1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0903   -1.7356    0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8992   -2.6493   -0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1866   -2.6928   -2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3523   -1.2266   -3.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129   -2.7371   -2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    0.1464   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7736   -0.6855    0.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5929   -1.1141    1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9617    1.0880    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0037    1.1804    0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    0.8362    2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    0.2172   -0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  1  0
 28 29  1  0
 29 32  1  0
 32 34  1  0
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 15 48  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       4.200   0.599  -1.313  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.360   0.383  -2.175  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.064   1.380  -3.227  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.139   1.369  -4.199  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.149   0.324  -4.458  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.453  -0.739  -5.316  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.508  -1.741  -5.550  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.734  -1.677  -4.928  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.617  -2.686  -5.173  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.052  -0.616  -4.088  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.108   0.384  -3.847  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.617  -0.737  -2.286  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.897  -1.801  -1.357  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.731  -1.952  -0.355  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.559  -2.322  -1.076  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.041  -3.058   0.661  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.765  -2.376   1.819  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.607  -0.860   1.607  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.290  -0.107   2.860  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.317   0.124   3.894  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.182   0.769   4.918  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.479  -0.479   3.599  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.089   0.451   3.056  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.021   0.362   2.207  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.110  -0.640   1.180  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.821  -0.282   0.155  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.130  -0.818   0.343  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.613  -1.156  -0.962  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.930  -1.729  -0.944  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.259  -2.117  -2.391  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.193  -2.904  -2.944  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.943  -0.732  -0.380  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.242  -1.317  -0.292  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.493  -0.286   1.012  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.385   0.736   1.484  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.053   0.233   0.996  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.695   0.528   2.353  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.509  -0.711   0.539  0.00  0.00           C+0
HETATM   39  H   UNK     0       3.721   2.244  -3.160  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.083   2.213  -4.883  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.424  -0.801  -5.799  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.742  -2.572  -6.209  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.333  -2.673  -4.501  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.026  -0.546  -3.618  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.361   1.206  -3.181  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.974  -2.710  -1.965  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.863  -1.671  -0.857  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.419  -1.636  -1.761  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.115  -3.524   1.023  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.639  -3.869   0.232  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.828  -2.645   1.815  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.351  -2.717   2.776  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.541  -0.465   1.187  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.066  -0.238   4.346  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.841   1.069   3.913  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.150  -1.605   1.631  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.090  -1.736   0.943  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.899  -2.649  -0.345  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.187  -2.693  -2.457  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.352  -1.227  -3.021  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.413  -2.737  -2.370  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.023   0.146  -1.032  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.774  -0.686   0.236  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.593  -1.114   1.725  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.962   1.088   2.294  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.004   1.180   0.445  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.764   0.836   2.335  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.655   0.217  -0.027  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   12    1    3                                                  
CONECT    3    4    2   39                                                  
CONECT    4    3    5   40                                                  
CONECT    5    6    4   11                                                  
CONECT    6    5    7   41                                                  
CONECT    7    6    8   42                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   43                                                       
CONECT   10    8   11   44                                                  
CONECT   11   10    5   45                                                  
CONECT   12    2   13                                                       
CONECT   13   12   14   46   47                                             
CONECT   14   16   38   15   13                                             
CONECT   15   14   48                                                       
CONECT   16   17   14   49   50                                             
CONECT   17   18   16   51   52                                             
CONECT   18   19   38   17   53                                             
CONECT   19   18   23   20                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   54                                                       
CONECT   23   24   19   55                                                  
CONECT   24   25   23                                                       
CONECT   25   38   24   26   56                                             
CONECT   26   25   27                                                       
CONECT   27   28   36   26   57                                             
CONECT   28   27   29                                                       
CONECT   29   28   32   30   58                                             
CONECT   30   29   31   59   60                                             
CONECT   31   30   61                                                       
CONECT   32   29   34   33   62                                             
CONECT   33   32   63                                                       
CONECT   34   32   36   35   64                                             
CONECT   35   34   65                                                       
CONECT   36   34   27   37   66                                             
CONECT   37   36   67                                                       
CONECT   38   25   18   14   68                                             
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    6                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   29                                                            
CONECT   59   30                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   34                                                            
CONECT   65   35                                                            
CONECT   66   36                                                            
CONECT   67   37                                                            
CONECT   68   38                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

RDKit          3D

68 71  0  0  0  0  0  0  0  0999 V2000
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    1.7313   -1.9520   -0.3548 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7650   -2.3756    1.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
10-p-trans-Coumaroyl-1S-dihydromonotropein	MeSH

Chemical Formula

C₂₅H₃₀O₁₃

Average Mass

538.5020 Da

Monoisotopic Mass

538.16864 Da

IUPAC Name

(1S,4aS,7R,7aS)-7-hydroxy-7-({[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}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-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])O[C@@]([H])(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@@]2([H])[C@]1([H])C([H])([H])C([H])([H])[C@]2(O[H])C([H])([H])OC(=O)C(\[H])=C(\[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C25H30O13/c26-9-16-19(29)20(30)21(31)24(37-16)38-23-18-14(15(10-35-23)22(32)33)7-8-25(18,34)11-36-17(28)6-3-12-1-4-13(27)5-2-12/h1-6,10,14,16,18-21,23-24,26-27,29-31,34H,7-9,11H2,(H,32,33)/b6-3-/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1

InChI Key

DQMJTGHIDOKZGT-ZCIFOOIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, 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
Vaccinium macrocarpon	JEOL database	Turner, A., et al, J. Nat. Prod. 70, 253 (2007)

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
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Oxane
Monocyclic benzene moiety
Monosaccharide
Dicarboxylic acid or derivatives
Benzenoid
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Acetal
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.23	ALOGPS
logP	-0.36	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.6 m³·mol⁻¹	ChemAxon
Polarizability	51.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17267202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16109817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Turner A, Chen SN, Nikolic D, van Breemen R, Farnsworth NR, Pauli GF: Coumaroyl iridoids and a depside from cranberry (Vaccinium macrocarpon). J Nat Prod. 2007 Feb;70(2):253-8. doi: 10.1021/np060260f. Epub 2007 Feb 2. [PubMed:17269823 ]
Turner, A., et al. (2007). Turner, A., et al, J. Nat. Prod. 70, 253 (2007). J. Nat. Prod..

Showing NP-Card for 10-p-cis-coumaroyl-1S-dihydromonotropein (NP0032686)

MOL for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

3D MOL for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

3D SDF for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

3D-SDF for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

PDB for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

3D PDB for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

SMILES for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

INCHI for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

Structure for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)

3D Structure for NP0032686 (10-p-cis-coumaroyl-1S-dihydromonotropein)