NP-MRD: Showing NP-Card for [(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate (NP0265834)

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Record Information

Version

2.0

Created at

2022-09-08 09:57:55 UTC

Updated at

2022-09-08 09:57:55 UTC

NP-MRD ID

NP0265834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate

Description

5Alpha-Lupane-20(29)-ene-3beta,28-diol 3-(4-hydroxy-cis-cinnamate) 28-palmitate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. [(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate is found in Diospyros maritima. Based on a literature review very few articles have been published on 5alpha-Lupane-20(29)-ene-3beta,28-diol 3-(4-hydroxy-cis-cinnamate) 28-palmitate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211572D          

 60 65  0  0  1  0            999 V2000
   -1.2240   -4.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602   -5.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999   -6.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1433   -5.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7670   -5.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733   -5.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862   -4.4540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0964   -4.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6365   -3.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4466   -4.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166   -4.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867   -3.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968   -3.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3369   -3.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1471   -3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6871   -2.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4973   -2.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0374   -2.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8475   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3876   -1.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1977   -1.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4678   -2.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9277   -3.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1977   -3.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6576   -4.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9277   -5.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4081   -3.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7078   -3.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -2.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5859   -2.1425    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9359   -1.3954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4079   -2.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7579   -1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1080   -0.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6360    0.0987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9861    0.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    0.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581    1.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2800    0.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1020    0.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    1.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741    1.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6241    1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    2.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5022    3.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3302    2.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801    1.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141    0.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    0.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -0.7187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3580   -0.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7080   -1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -2.2129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9425   -1.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643   -4.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  2  0  0  0  0
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 46 47  1  0  0  0  0
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 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  2  0  0  0  0
 45 51  1  0  0  0  0
 39 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 52 55  1  0  0  0  0
 35 55  1  0  0  0  0
 55 56  1  6  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 34 58  1  0  0  0  0
 29 58  1  0  0  0  0
 58 59  1  6  0  0  0
 31 60  1  0  0  0  0
 60  4  1  6  0  0  0
  7 60  1  0  0  0  0
M  END

     RDKit          3D

146151  0  0  0  0  0  0  0  0999 V2000
   -0.3742    5.0372   -2.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2811    3.9059   -1.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710    3.2396   -3.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    3.2671   -0.6370 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1201    3.0231   -0.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    1.4976   -0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034    1.0982    0.1588 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3223    1.6543    1.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4442    1.3167    2.1869 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9132    0.2212    2.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990   -0.8096    2.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    0.1620    3.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2231   -0.7459    2.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562   -0.3889    1.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1546    0.9998    1.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5084    1.3636   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3138   -1.9478   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4282   -3.3321   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4837   -2.3191   -0.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4359    0.6969    0.4486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8754    1.2043    1.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2730    1.4360   -0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6474   -0.5322   -1.0059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8719   -1.0826   -1.4184 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1605   -1.6319   -3.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3517   -2.1840   -3.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082211572D          

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M  END
> <DATABASE_ID>
NP0265834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC[C@]12CC[C@H]([C@@H]1[C@H]1CC[C@@H]3[C@@]4(C)CC[C@H](OC(=O)\C=C/C5=CC=C(O)C=C5)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C55H86O5/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-48(57)59-39-55-36-31-43(40(2)3)50(55)44-28-29-46-52(6)34-33-47(60-49(58)30-25-41-23-26-42(56)27-24-41)51(4,5)45(52)32-35-54(46,8)53(44,7)37-38-55/h23-27,30,43-47,50,56H,2,9-22,28-29,31-39H2,1,3-8H3/b30-25-/t43-,44+,45-,46+,47-,50+,52-,53+,54+,55+/m0/s1

> <INCHI_KEY>
BNIWLFQIYHLZHJ-WPHHMZNCSA-N

> <FORMULA>
C55H86O5

> <MOLECULAR_WEIGHT>
827.288

> <EXACT_MASS>
826.647525869

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
146

> <JCHEM_AVERAGE_POLARIZABILITY>
103.93919758320256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
15.818654622999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398614366561935

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9547318749588785

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
247.82300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.285  -8.826   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.232  -9.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.680 -11.424   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.268  -9.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.432 -10.610   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.750  -9.814   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.401  -8.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.913  -8.605   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.921  -7.441   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.434  -7.732   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.938  -9.187   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.442  -6.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.954  -6.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.962  -5.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.474  -5.986   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.483  -4.822   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.995  -5.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.003  -3.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.515  -4.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.523  -3.076   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.036  -3.367   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.540  -4.822   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.532  -5.986   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.036  -7.441   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.028  -8.605   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.532 -10.060   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.282  -7.051   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.629  -5.657   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.094  -5.525   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.975  -4.262   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.213  -6.788   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.321  -6.657   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.975  -5.262   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.094  -3.999   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.747  -2.605   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.628  -3.868   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.281  -2.473   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.935  -1.079   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.054   0.184   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.707   1.579   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.242   1.710   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.895   3.105   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.123   0.447   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -7.657   0.578   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -8.311   1.973   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -9.845   2.104   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -10.498   3.499   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -9.617   4.762   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0     -10.271   6.156   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -8.083   4.630   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -7.430   3.236   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.520   0.053   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -1.657   1.587   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.033   0.454   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.866  -1.342   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.668  -1.473   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.322  -2.868   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       0.441  -4.131   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       1.759  -3.335   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       0.867  -8.183   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   60                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   27   60                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    7   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   58                                             
CONECT   30   29                                                            
CONECT   31   29   32   60                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   58                                                  
CONECT   35   34   36   37   55                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   52                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   51                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   45                                                       
CONECT   52   39   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   35   56                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   34   29   59                                             
CONECT   59   58                                                            
CONECT   60   31    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   60    0  130    0
END

View in JSmol

Synonyms

Value	Source
5a-Lupane-20(29)-ene-3b,28-diol 3-(4-hydroxy-cis-cinnamate) 28-palmitate	Generator
5a-Lupane-20(29)-ene-3b,28-diol 3-(4-hydroxy-cis-cinnamic acid) 28-palmitic acid	Generator
5alpha-Lupane-20(29)-ene-3beta,28-diol 3-(4-hydroxy-cis-cinnamic acid) 28-palmitic acid	Generator
5Α-lupane-20(29)-ene-3β,28-diol 3-(4-hydroxy-cis-cinnamate) 28-palmitate	Generator
5Α-lupane-20(29)-ene-3β,28-diol 3-(4-hydroxy-cis-cinnamic acid) 28-palmitic acid	Generator

Chemical Formula

C₅₅H₈₆O₅

Average Mass

827.2880 Da

Monoisotopic Mass

826.64753 Da

IUPAC Name

[(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-5-yl]methyl hexadecanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@]12CC[C@H]([C@@H]1[C@H]1CC[C@@H]3[C@@]4(C)CC[C@H](OC(=O)\C=C/C5=CC=C(O)C=C5)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2)C(C)=C

InChI Identifier

InChI=1S/C55H86O5/c1-9-10-11-12-13-14-15-16-17-18-19-20-21-22-48(57)59-39-55-36-31-43(40(2)3)50(55)44-28-29-46-52(6)34-33-47(60-49(58)30-25-41-23-26-42(56)27-24-41)51(4,5)45(52)32-35-54(46,8)53(44,7)37-38-55/h23-27,30,43-47,50,56H,2,9-22,28-29,31-39H2,1,3-8H3/b30-25-/t43-,44+,45-,46+,47-,50+,52-,53+,54+,55+/m0/s1

InChI Key

BNIWLFQIYHLZHJ-WPHHMZNCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diospyros maritima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid ester
Steroid
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	15.82	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	247.82 m³·mol⁻¹	ChemAxon
Polarizability	103.94 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	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

8899503

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10724170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate (NP0265834)

MOL for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D MOL for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D SDF for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D-SDF for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

PDB for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D PDB for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

SMILES for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

INCHI for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

Structure for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D Structure for NP0265834 ([(1r,3as,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-9-{[(2z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)