NP-MRD: Showing NP-Card for 3-(Z)-caffeoyllupeol (NP0027879)

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Record Information

Version

2.0

Created at

2021-06-19 19:55:04 UTC

Updated at

2021-06-29 23:54:17 UTC

NP-MRD ID

NP0027879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(Z)-caffeoyllupeol

Provided By

JEOL Database JEOL Logo

Description

3-(Z)-caffeoyllupeol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-(Z)-caffeoyllupeol is found in Betula ermani and Bruguiera parviflora. 3-(Z)-caffeoyllupeol was first documented in 2005 (PMID: 15635238). Based on a literature review very few articles have been published on 3-(Z)-caffeoyllupeol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121553D          

 99104  0  0  0  0            999 V2000
    0.9122   -3.5335    4.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -3.9673    3.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524   -4.2939    2.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -4.1605    2.9828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7814   -5.6660    2.7886 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2632   -5.8267    1.3369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7071   -4.4169    0.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1208   -4.1591    1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -4.1737   -0.5885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9087   -2.6782   -0.9190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8986   -1.7124   -0.2002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4842   -1.9865   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164   -2.0649    1.3437 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1865   -1.1615    2.0703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1087    0.3294    1.8803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2506    0.7465    0.3987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3407    2.3213    0.1556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5540    2.9532    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    2.9930    0.7284 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1420    4.4464    0.3034 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1248    4.6204   -1.2146 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2300    6.0267   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    6.5582   -1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221    5.9605   -1.3653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    7.9957   -1.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4988    8.9057   -1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772    8.6951   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    8.9827   -1.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471    8.8013   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740    8.3401    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    8.1553    1.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    8.0659    1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8465    7.6127    2.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367    8.2484    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604    4.0389   -1.8833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0764    4.0722   -3.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    4.9330   -1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426    2.5512   -1.4034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5006    1.7902   -2.0790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3827    0.2800   -1.8446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3223   -0.1464   -0.3513 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7505    0.0754    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695   -3.5749    1.5565 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0044   -3.3011    5.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503   -3.3972    5.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -4.2579    3.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312   -3.5787    2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -5.3002    2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433   -3.7170    3.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626   -6.3357    2.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2998   -1.3828   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427   -1.8109   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -3.0254   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -1.8506    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2104   -1.3775    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1530   -1.3597    3.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070    0.8811    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0128    0.5748    2.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.4918   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271    2.4091    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9371    2.9641    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    2.4253    0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013    4.8019    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    5.0995    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918    4.0910   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3316    8.3149   -2.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    9.9266   -1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    9.3365   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9280    7.8324    2.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0754    7.4509    2.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    8.0414    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3701    5.0723   -3.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264    3.8075   -3.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8732    3.3799   -3.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3117    4.4647   -1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996    5.8890   -2.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248    5.1784   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699    2.0475   -1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4756    2.1581   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4782    1.9399   -3.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213   -0.2170   -2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4804   -0.0406   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.5603   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3639   -3.8323    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 99104  0  0  0  0  0  0  0  0999 V2000
    0.9122   -3.5335    4.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -3.9673    3.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4482   -4.1605    2.9828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7814   -5.6660    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -5.8267    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071   -4.4169    0.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1208   -4.1591    1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -4.1737   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192121553D          

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 13 43  1  0  0  0  0
 29 28  2  0  0  0  0
 28 27  1  0  0  0  0
 11 10  1  0  0  0  0
 32 33  1  0  0  0  0
 10  9  1  0  0  0  0
 30 31  1  0  0  0  0
 39 92  1  0  0  0  0
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 40 95  1  0  0  0  0
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 15 68  1  0  0  0  0
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 42 96  1  0  0  0  0
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 33 83  1  0  0  0  0
 31 82  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(\C([H])=C(\[H])C(=O)O[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@]3([H])[C@@]5([H])[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]43C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C39H56O4/c1-24(2)26-15-18-36(5)21-22-38(7)27(34(26)36)11-13-31-37(6)19-17-32(35(3,4)30(37)16-20-39(31,38)8)43-33(42)14-10-25-9-12-28(40)29(41)23-25/h9-10,12,14,23,26-27,30-32,34,40-41H,1,11,13,15-22H2,2-8H3/b14-10-/t26-,27+,30-,31+,32-,34+,36+,37-,38+,39+/m0/s1

> <INCHI_KEY>
NIKLINODNHPPMX-JPXCXHODSA-N

> <FORMULA>
C39H56O4

> <MOLECULAR_WEIGHT>
588.873

> <EXACT_MASS>
588.417860283

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
69.19100819769896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
7.53

> <JCHEM_LOGP>
9.874806555666666

> <ALOGPS_LOGS>
-6.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612464945867803

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208619942595545

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283760827585149

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
174.43780000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.69e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 99104  0  0  0  0  0  0  0  0999 V2000
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 13 64  1  1
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 28 80  1  0
 33 83  1  0
 31 82  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       0.912  -3.534   4.976  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.877  -3.967   3.703  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.152  -4.294   2.973  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.448  -4.160   2.983  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.781  -5.666   2.789  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.263  -5.827   1.337  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.707  -4.417   0.926  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.121  -4.159   1.508  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.725  -4.174  -0.589  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.909  -2.678  -0.919  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.899  -1.712  -0.200  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.484  -1.986  -0.888  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.816  -2.065   1.344  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.187  -1.161   2.070  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.109   0.329   1.880  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.251   0.747   0.399  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.341   2.321   0.156  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.554   2.953   0.880  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.946   2.993   0.728  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.142   4.446   0.303  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.125   4.620  -1.215  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.230   6.027  -1.521  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.471   6.558  -1.544  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.522   5.960  -1.365  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.442   7.996  -1.885  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.499   8.906  -1.591  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.277   8.695  -0.808  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.967   8.983  -1.389  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.147   8.801  -0.664  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.074   8.340   0.642  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.227   8.155   1.349  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.844   8.066   1.233  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.847   7.613   2.524  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.337   8.248   0.521  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.160   4.039  -1.883  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.076   4.072  -3.420  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.391   4.933  -1.627  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.343   2.551  -1.403  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.501   1.790  -2.079  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.383   0.280  -1.845  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.322  -0.146  -0.351  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.751   0.075   0.232  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.570  -3.575   1.557  0.00  0.00           C+0
HETATM   44  H   UNK     0       0.004  -3.301   5.524  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.850  -3.397   5.505  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.023  -4.258   3.638  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.331  -3.579   2.165  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.114  -5.300   2.546  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.243  -3.717   3.598  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.063  -6.336   2.984  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.578  -5.955   3.485  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.426  -6.167   0.715  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.059  -6.574   1.253  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.472  -3.138   1.341  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.850  -4.830   1.038  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.176  -4.340   2.586  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.534  -4.748  -1.056  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.799  -4.540  -1.046  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.940  -2.422  -0.672  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.832  -2.557  -2.007  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.300  -1.383  -0.488  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.443  -1.811  -1.967  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.807  -3.025  -0.786  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.787  -1.851   1.802  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.210  -1.377   1.747  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.153  -1.360   3.146  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.707   0.881   2.358  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.013   0.575   2.446  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.716   0.492  -0.054  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.827   2.409   1.787  0.00  0.00           H+0
HETATM   71  H   UNK     0      -1.359   3.974   1.217  0.00  0.00           H+0
HETATM   72  H   UNK     0      -2.443   3.013   0.251  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.937   2.964   1.824  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.830   2.425   0.410  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.101   4.802   0.701  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.397   5.099   0.769  0.00  0.00           H+0
HETATM   77  H   UNK     0       1.992   4.091  -1.635  0.00  0.00           H+0
HETATM   78  H   UNK     0       3.332   8.315  -2.420  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.635   9.927  -1.943  0.00  0.00           H+0
HETATM   80  H   UNK     0      -1.028   9.336  -2.416  0.00  0.00           H+0
HETATM   81  H   UNK     0      -3.112   9.013  -1.114  0.00  0.00           H+0
HETATM   82  H   UNK     0      -2.928   7.832   2.222  0.00  0.00           H+0
HETATM   83  H   UNK     0       0.075   7.451   2.789  0.00  0.00           H+0
HETATM   84  H   UNK     0       1.298   8.041   0.981  0.00  0.00           H+0
HETATM   85  H   UNK     0       0.370   5.072  -3.759  0.00  0.00           H+0
HETATM   86  H   UNK     0      -0.826   3.808  -3.979  0.00  0.00           H+0
HETATM   87  H   UNK     0       0.873   3.380  -3.713  0.00  0.00           H+0
HETATM   88  H   UNK     0      -2.312   4.465  -1.987  0.00  0.00           H+0
HETATM   89  H   UNK     0      -1.300   5.889  -2.155  0.00  0.00           H+0
HETATM   90  H   UNK     0      -1.525   5.178  -0.573  0.00  0.00           H+0
HETATM   91  H   UNK     0       0.570   2.047  -1.766  0.00  0.00           H+0
HETATM   92  H   UNK     0      -2.476   2.158  -1.750  0.00  0.00           H+0
HETATM   93  H   UNK     0      -1.478   1.940  -3.163  0.00  0.00           H+0
HETATM   94  H   UNK     0      -2.221  -0.217  -2.347  0.00  0.00           H+0
HETATM   95  H   UNK     0      -0.480  -0.041  -2.373  0.00  0.00           H+0
HETATM   96  H   UNK     0      -3.497  -0.560  -0.250  0.00  0.00           H+0
HETATM   97  H   UNK     0      -2.811  -0.105   1.307  0.00  0.00           H+0
HETATM   98  H   UNK     0      -3.122   1.085   0.068  0.00  0.00           H+0
HETATM   99  H   UNK     0       0.364  -3.832   1.042  0.00  0.00           H+0
CONECT    1    2   44   45                                                  
CONECT    2    4    1    3                                                  
CONECT    3    2   46   47   48                                             
CONECT    4    5   43    2   49                                             
CONECT    5    6    4   50   51                                             
CONECT    6    7    5   52   53                                             
CONECT    7    9   43    6    8                                             
CONECT    8    7   54   55   56                                             
CONECT    9    7   10   57   58                                             
CONECT   10   11    9   59   60                                             
CONECT   11   41   13   12   10                                             
CONECT   12   11   61   62   63                                             
CONECT   13   14   11   43   64                                             
CONECT   14   13   15   65   66                                             
CONECT   15   16   14   67   68                                             
CONECT   16   15   41   17   69                                             
CONECT   17   38   19   18   16                                             
CONECT   18   17   70   71   72                                             
CONECT   19   17   20   73   74                                             
CONECT   20   19   21   75   76                                             
CONECT   21   20   35   22   77                                             
CONECT   22   21   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26   78                                                  
CONECT   26   25   27   79                                                  
CONECT   27   26   34   28                                                  
CONECT   28   29   27   80                                                  
CONECT   29   30   28   81                                                  
CONECT   30   32   29   31                                                  
CONECT   31   30   82                                                       
CONECT   32   34   30   33                                                  
CONECT   33   32   83                                                       
CONECT   34   27   32   84                                                  
CONECT   35   38   21   36   37                                             
CONECT   36   35   85   86   87                                             
CONECT   37   35   88   89   90                                             
CONECT   38   17   39   35   91                                             
CONECT   39   38   40   92   93                                             
CONECT   40   39   41   94   95                                             
CONECT   41   11   40   16   42                                             
CONECT   42   41   96   97   98                                             
CONECT   43    7    4   13   99                                             
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    3                                                            
CONECT   47    3                                                            
CONECT   48    3                                                            
CONECT   49    4                                                            
CONECT   50    5                                                            
CONECT   51    5                                                            
CONECT   52    6                                                            
CONECT   53    6                                                            
CONECT   54    8                                                            
CONECT   55    8                                                            
CONECT   56    8                                                            
CONECT   57    9                                                            
CONECT   58    9                                                            
CONECT   59   10                                                            
CONECT   60   10                                                            
CONECT   61   12                                                            
CONECT   62   12                                                            
CONECT   63   12                                                            
CONECT   64   13                                                            
CONECT   65   14                                                            
CONECT   66   14                                                            
CONECT   67   15                                                            
CONECT   68   15                                                            
CONECT   69   16                                                            
CONECT   70   18                                                            
CONECT   71   18                                                            
CONECT   72   18                                                            
CONECT   73   19                                                            
CONECT   74   19                                                            
CONECT   75   20                                                            
CONECT   76   20                                                            
CONECT   77   21                                                            
CONECT   78   25                                                            
CONECT   79   26                                                            
CONECT   80   28                                                            
CONECT   81   29                                                            
CONECT   82   31                                                            
CONECT   83   33                                                            
CONECT   84   34                                                            
CONECT   85   36                                                            
CONECT   86   36                                                            
CONECT   87   36                                                            
CONECT   88   37                                                            
CONECT   89   37                                                            
CONECT   90   37                                                            
CONECT   91   38                                                            
CONECT   92   39                                                            
CONECT   93   39                                                            
CONECT   94   40                                                            
CONECT   95   40                                                            
CONECT   96   42                                                            
CONECT   97   42                                                            
CONECT   98   42                                                            
CONECT   99   43                                                            
MASTER        0    0    0    0    0    0    0    0   99    0  208    0
END

RDKit          3D

99104  0  0  0  0  0  0  0  0999 V2000
    0.9122   -3.5335    4.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767   -3.9673    3.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524   -4.2939    2.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -4.1605    2.9828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7814   -5.6660    2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632   -5.8267    1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071   -4.4169    0.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1208   -4.1591    1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -4.1737   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9087   -2.6782   -0.9190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986   -1.7124   -0.2002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4842   -1.9865   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8164   -2.0649    1.3437 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1865   -1.1615    2.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087    0.3294    1.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.7465    0.3987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3407    2.3213    0.1556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5540    2.9532    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    2.9930    0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420    4.4464    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248    4.6204   -1.2146 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2300    6.0267   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    6.5582   -1.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221    5.9605   -1.3653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    7.9957   -1.8850 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4988    8.9057   -1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772    8.6951   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    8.9827   -1.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471    8.8013   -0.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740    8.3401    0.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    8.1553    1.3490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    8.0659    1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8465    7.6127    2.5240 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3367    8.2484    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1604    4.0389   -1.8833 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0764    4.0722   -3.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    4.9330   -1.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426    2.5512   -1.4034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5006    1.7902   -2.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    0.2800   -1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223   -0.1464   -0.3513 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7505    0.0754    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695   -3.5749    1.5565 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0044   -3.3011    5.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503   -3.3972    5.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -4.2579    3.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312   -3.5787    2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138   -5.3002    2.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2433   -3.7170    3.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626   -6.3357    2.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5781   -5.9548    3.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259   -6.1674    0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0589   -6.5741    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4718   -3.1378    1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8503   -4.8295    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -4.3395    2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341   -4.7483   -1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -4.5404   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399   -2.4218   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317   -2.5569   -2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2998   -1.3828   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427   -1.8109   -1.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8070   -3.0254   -0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -1.8506    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2104   -1.3775    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1530   -1.3597    3.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7070    0.8811    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0128    0.5748    2.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.4918   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271    2.4091    1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595    3.9743    1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4432    3.0127    0.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371    2.9641    1.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    2.4253    0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013    4.8019    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    5.0995    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918    4.0910   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3316    8.3149   -2.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6351    9.9266   -1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    9.3365   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117    9.0128   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4782    1.9399   -3.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213   -0.2170   -2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4804   -0.0406   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.5603   -0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8114   -0.1054    1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1216    1.0850    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3639   -3.8323    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₅₆O₄

Average Mass

588.8730 Da

Monoisotopic Mass

588.41786 Da

IUPAC Name

(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(1R,2R,5R,8R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-yl (2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C([H])=C(\C([H])=C(\[H])C(=O)O[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@]3([H])[C@@]5([H])[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]43C([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C39H56O4/c1-24(2)26-15-18-36(5)21-22-38(7)27(34(26)36)11-13-31-37(6)19-17-32(35(3,4)30(37)16-20-39(31,38)8)43-33(42)14-10-25-9-12-28(40)29(41)23-25/h9-10,12,14,23,26-27,30-32,34,40-41H,1,11,13,15-22H2,2-8H3/b14-10-/t26-,27+,30-,31+,32-,34+,36+,37-,38+,39+/m0/s1

InChI Key

NIKLINODNHPPMX-JPXCXHODSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Betula ermani	Plant	KNApSAcK
Bruguiera parviflora	JEOL database	Chumkaew, P., et al, Chem. Pharm. Bull. 53, 95 (2005)

Chemical Taxonomy

Classification

Not classified

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	7.53	ALOGPS
logP	9.87	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	174.44 m³·mol⁻¹	ChemAxon
Polarizability	69.19 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

C00031552

Chemspider ID

9961317

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65549

Good Scents ID

Not Available

References

General References

Chumkaew P, Kato S, Chantrapromma K: A new triterpenoid ester from the fruits of Bruguiera parviflora. Chem Pharm Bull (Tokyo). 2005 Jan;53(1):95-6. doi: 10.1248/cpb.53.95. [PubMed:15635238 ]
Chumkaew, P., et al. (2005). Chumkaew, P., et al, Chem. Pharm. Bull. 53, 95 (2005). Chem. Pharm. Bull..

Showing NP-Card for 3-(Z)-caffeoyllupeol (NP0027879)

MOL for NP0027879 (3-(Z)-caffeoyllupeol)

3D MOL for NP0027879 (3-(Z)-caffeoyllupeol)

3D SDF for NP0027879 (3-(Z)-caffeoyllupeol)

3D-SDF for NP0027879 (3-(Z)-caffeoyllupeol)

PDB for NP0027879 (3-(Z)-caffeoyllupeol)

3D PDB for NP0027879 (3-(Z)-caffeoyllupeol)

SMILES for NP0027879 (3-(Z)-caffeoyllupeol)

INCHI for NP0027879 (3-(Z)-caffeoyllupeol)

Structure for NP0027879 (3-(Z)-caffeoyllupeol)

3D Structure for NP0027879 (3-(Z)-caffeoyllupeol)