NP-MRD: Showing NP-Card for 12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate (NP0295283)

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Record Information

Version

2.0

Created at

2022-09-10 04:11:21 UTC

Updated at

2022-09-10 04:11:21 UTC

NP-MRD ID

NP0295283

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate

Description

12-(Benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]Heptacosan-2-yl benzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 12-(Benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]Heptacosan-2-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500052D          

 72 80  0  0  0  0            999 V2000
    7.5649  -12.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1861  -12.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9831  -12.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7047  -11.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4625  -12.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2142  -11.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9726  -12.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6911  -11.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4321  -12.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1249  -11.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8488  -12.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4990  -11.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1739  -12.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8419  -11.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3489  -12.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1669  -12.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0910  -11.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9297  -12.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6458  -12.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5854  -12.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2510  -12.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0714  -12.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0133  -12.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6737  -13.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1545  -14.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1388  -13.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9098  -14.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4096  -13.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8255  -12.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3694  -12.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3123  -11.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4001  -12.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5903  -12.8873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9818  -11.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0837  -10.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.4491  -10.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8844   -9.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5089   -9.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3548   -9.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9975  -10.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.9535  -11.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7234  -12.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4076  -13.1170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1576  -10.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3158   -9.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.7842   -9.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3491   -8.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5247   -8.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7889   -7.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4044   -7.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8442   -6.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6686   -6.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0531   -7.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6133   -7.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9387  -10.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7097  -11.0611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0287  -11.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2045  -10.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0706  -14.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3305  -15.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9513  -14.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  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  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 16 17  2  0  0  0  0
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 22 23  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
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 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
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 30 40  1  0  0  0  0
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 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
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 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 26 52  1  0  0  0  0
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 43 54  1  0  0  0  0
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 42 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 20 68  1  0  0  0  0
 68 69  1  0  0  0  0
 28 70  1  0  0  0  0
 70 71  2  0  0  0  0
 70 72  1  0  0  0  0
M  END

     RDKit          3D

154162  0  0  0  0  0  0  0  0999 V2000
   -4.2686    4.8942    2.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228    3.8494    2.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8934    0.3806    1.1186 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.5211    1.7276    0.2034 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7888    1.0088   -0.6705 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1446   -1.1175   -0.3153 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171500052D          

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 20 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
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 30 40  1  0  0  0  0
 23 40  1  0  0  0  0
 40 41  1  0  0  0  0
 26 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 26 52  1  0  0  0  0
 52 53  1  0  0  0  0
 43 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 58 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 60 65  1  0  0  0  0
 56 66  1  0  0  0  0
 42 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 20 68  1  0  0  0  0
 68 69  1  0  0  0  0
 28 70  1  0  0  0  0
 70 71  2  0  0  0  0
 70 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0295283

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OCC12OC1C1C3OC45OC3(CC(OC(=O)C3=CC=CC=C3)C1(O4)C1C(C(C)C(OC(=O)C3=CC=CC=C3)C1(O)C2O)C(C)CCCCCCC5O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C59H82O13/c1-6-7-8-9-10-11-12-13-14-15-16-17-28-35-45(61)66-37-56-51(69-56)47-50-55(38(2)3)36-44(67-52(62)41-30-23-20-24-31-41)58(47)48-46(39(4)29-22-18-19-27-34-43(60)59(70-50,71-55)72-58)40(5)49(57(48,65)54(56)64)68-53(63)42-32-25-21-26-33-42/h20-21,23-26,30-33,39-40,43-44,46-51,54,60,64-65H,2,6-19,22,27-29,34-37H2,1,3-5H3

> <INCHI_KEY>
WHZROJXHMHIRRT-UHFFFAOYSA-N

> <FORMULA>
C59H82O13

> <MOLECULAR_WEIGHT>
999.292

> <EXACT_MASS>
998.5755427

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
154

> <JCHEM_AVERAGE_POLARIZABILITY>
113.90394344137191

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate

> <ALOGPS_LOGP>
6.78

> <JCHEM_LOGP>
12.555574778666667

> <ALOGPS_LOGS>
-6.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.642572176720499

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.05377701443988

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8130556474002324

> <JCHEM_POLAR_SURFACE_AREA>
179.81

> <JCHEM_REFRACTIVITY>
268.8046

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.55e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      14.121 -23.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.281 -22.635   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.768 -23.143   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.115 -22.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.530 -23.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.933 -22.284   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.349 -22.997   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.690 -22.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.073 -22.922   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.367 -22.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.718 -22.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.931 -21.833   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.191 -22.775   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.438 -21.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.385 -23.078   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.912 -22.898   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      33.770 -21.365   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      35.335 -23.554   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.672 -22.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.426 -22.422   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      37.802 -23.830   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      39.333 -23.666   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.091 -23.661   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.324 -25.056   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      41.355 -26.547   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      41.326 -25.437   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      42.765 -26.724   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      43.698 -25.422   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      44.474 -24.051   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      43.623 -22.756   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      45.383 -22.076   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      46.990 -22.129   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      47.803 -20.821   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      47.716 -23.487   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      49.255 -23.538   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      49.981 -24.896   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      49.168 -26.204   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      47.629 -26.153   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      46.903 -24.795   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      41.813 -22.801   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      40.302 -24.056   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      41.033 -21.210   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      39.356 -20.208   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      38.025 -19.153   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      36.305 -19.767   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      38.984 -17.464   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      40.150 -17.074   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      41.729 -17.236   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      42.929 -18.698   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      43.326 -20.329   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      42.847 -21.961   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      42.417 -23.818   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      43.694 -24.485   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      39.494 -18.782   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      37.923 -17.795   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      40.995 -18.748   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      42.530 -17.596   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      41.718 -16.055   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      40.180 -15.995   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      42.539 -14.752   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      41.821 -13.389   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      42.642 -12.087   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      44.181 -12.146   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      44.899 -13.508   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      44.078 -14.811   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      40.952 -20.302   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      42.391 -20.647   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      39.254 -21.104   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      37.715 -20.490   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      44.932 -26.746   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      45.417 -28.291   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      46.576 -26.739   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   68                                             
CONECT   21   20   22                                                       
CONECT   22   21   20   23                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   41   52                                             
CONECT   27   26   28                                                       
CONECT   28   27   24   29   70                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   30   23   41   42                                             
CONECT   41   40   26                                                       
CONECT   42   40   43   66                                                  
CONECT   43   42   44   54                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   26   53                                                  
CONECT   53   52                                                            
CONECT   54   43   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   66                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   60                                                       
CONECT   66   56   42   67   68                                             
CONECT   67   66                                                            
CONECT   68   66   20   69                                                  
CONECT   69   68                                                            
CONECT   70   28   71   72                                                  
CONECT   71   70                                                            
CONECT   72   70                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  160    0
END

View in JSmol

Synonyms

Value	Source
12-(Benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1,.1,.0,.0,.0,]heptacosan-2-yl benzoic acid	Generator
12-(Benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoic acid	Generator

Chemical Formula

C₅₉H₈₂O₁₃

Average Mass

999.2920 Da

Monoisotopic Mass

998.57554 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OCC12OC1C1C3OC45OC3(CC(OC(=O)C3=CC=CC=C3)C1(O4)C1C(C(C)C(OC(=O)C3=CC=CC=C3)C1(O)C2O)C(C)CCCCCCC5O)C(C)=C

InChI Identifier

InChI=1S/C59H82O13/c1-6-7-8-9-10-11-12-13-14-15-16-17-28-35-45(61)66-37-56-51(69-56)47-50-55(38(2)3)36-44(67-52(62)41-30-23-20-24-31-41)58(47)48-46(39(4)29-22-18-19-27-34-43(60)59(70-50,71-55)72-58)40(5)49(57(48,65)54(56)64)68-53(63)42-32-25-21-26-33-42/h20-21,23-26,30-33,39-40,43-44,46-51,54,60,64-65H,2,6-19,22,27-29,34-37H2,1,3-5H3

InChI Key

WHZROJXHMHIRRT-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Glycidol ester
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
1,3-dioxepane
Ortho ester
Fatty acid ester
Carboxylic acid orthoester
Dioxepane
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Meta-dioxane
Tertiary alcohol
Meta-dioxolane
Cyclic alcohol
Secondary alcohol
Orthocarboxylic acid derivative
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
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	6.78	ALOGPS
logP	12.56	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	179.81 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	268.8 m³·mol⁻¹	ChemAxon
Polarizability	113.9 Å³	ChemAxon
Number of Rings	9	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

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DrugBank ID

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Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

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Chemspider ID

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KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

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PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for 12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate (NP0295283)

MOL for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

3D MOL for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

3D SDF for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

3D-SDF for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

PDB for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

3D PDB for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

SMILES for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

INCHI for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

Structure for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)

3D Structure for NP0295283 (12-(benzoyloxy)-9-[(hexadecanoyloxy)methyl]-10,11,22-trihydroxy-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl benzoate)