NP-MRD: Showing NP-Card for (2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate (NP0167972)

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Record Information

Version

2.0

Created at

2022-09-03 03:39:50 UTC

Updated at

2022-09-03 03:39:50 UTC

NP-MRD ID

NP0167972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate

Description

(2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-decahydronaphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position. (2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate is found in Eschenbachia blinii. Based on a literature review very few articles have been published on (2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-decahydronaphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205392D          

 52 54  0  0  1  0            999 V2000
  -16.4328   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7111    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3033   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -3.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532   -4.4774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7904   -5.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -4.5061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1414   -5.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2670   -3.8353    0.0000 O   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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 44 43  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  1  0  0  0
M  END

     RDKit          3D

130132  0  0  0  0  0  0  0  0999 V2000
   13.1874    2.1539   -3.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8157    0.7882   -3.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9141    0.3065   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1050   -0.5966   -0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6948   -0.7041   -1.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9899    0.6260   -1.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9034    1.3146    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2564    0.7052    1.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8337    0.3358    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2933   -0.6517    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7807   -0.8707    0.7176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0217    0.3662    0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530    0.2882    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0059   -0.2542    1.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537   -1.6922    2.2452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5590   -1.9656    3.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -2.5850    1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -2.3053    1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900   -2.7633    0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -1.5218    2.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -1.1961    2.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4528   -0.4912    1.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    0.7236    1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    1.5198    2.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2370    1.8961    3.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819    1.2973    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622    1.6164   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8685    0.4370    1.0540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2340   -0.3363    2.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1339    0.2402    2.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2262   -0.4451    1.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5454    0.0759    0.8655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6258   -1.9161    1.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7695   -1.5925   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4157   -1.5862   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1372   -0.2177   -1.2821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9396   -0.2232   -2.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2134    0.0598   -2.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5375   -0.6594   -3.1594 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2711    0.1878   -4.2850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9742    1.3920   -4.0881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4664    1.1736   -4.2854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1830    1.4527   -3.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6493   -0.3288   -4.5187 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.0237   -0.5545   -4.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0121   -1.0146   -3.3308 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1798   -2.3943   -3.5380 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5437    0.0057    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9487    0.1200    2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8541    2.2884   -1.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152    2.4549    0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8070    1.6100   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2794   -0.8319    1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
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 51129  1  1
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M  END


  Mrv1652309032205392D          

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 16 18  1  0  0  0  0
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 51 52  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0167972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCC[C@@H](O)CC(=O)OC\C=C(/CO)CC[C@H]1[C@@](C)(CC[C@H]2C(C)(C)CCC[C@]12C)O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C43H78O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-20-33(45)29-37(47)50-28-24-32(30-44)21-22-36-42(4)26-19-25-41(2,3)35(42)23-27-43(36,5)52-40-39(49)38(48)34(46)31-51-40/h24,33-36,38-40,44-46,48-49H,6-23,25-31H2,1-5H3/b32-24-/t33-,34+,35+,36-,38+,39-,40+,42+,43-/m1/s1

> <INCHI_KEY>
OCSCUKHGZXPCFA-BQRCDTPTSA-N

> <FORMULA>
C43H78O9

> <MOLECULAR_WEIGHT>
739.088

> <EXACT_MASS>
738.564584092

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
89.55213052448269

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-decahydronaphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate

> <ALOGPS_LOGP>
7.08

> <JCHEM_LOGP>
8.349857337333335

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.385991324271178

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.244541240307884

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7338229039375923

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
206.49280000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1H-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0     -30.675  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -29.341  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -28.007  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -26.674  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -25.340  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -24.006  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -22.673  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.339  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.184   1.273   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.194   2.987   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.944  -4.440   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.300  -5.692   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.116  -6.998   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.393  -8.358   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.209  -9.664   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       2.854  -8.411   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.131  -9.771   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       0.498  -7.159   0.000  0.00  0.00           O+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   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   41                                                  
CONECT   30   29   31   32   38                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   30   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   29   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   51                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

View in JSmol

Synonyms

Value	Source
(2Z)-3-{2-[(1R,2R,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-decahydronaphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoic acid	Generator

Chemical Formula

C₄₃H₇₈O₉

Average Mass

739.0880 Da

Monoisotopic Mass

738.56458 Da

IUPAC Name

(2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-decahydronaphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate

Traditional Name

(2Z)-3-{2-[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-2-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1H-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3R)-3-hydroxyoctadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC[C@@H](O)CC(=O)OC\C=C(/CO)CC[C@H]1[C@@](C)(CC[C@H]2C(C)(C)CCC[C@]12C)O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C43H78O9/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-20-33(45)29-37(47)50-28-24-32(30-44)21-22-36-42(4)26-19-25-41(2,3)35(42)23-27-43(36,5)52-40-39(49)38(48)34(46)31-51-40/h24,33-36,38-40,44-46,48-49H,6-23,25-31H2,1-5H3/b32-24-/t33-,34+,35+,36-,38+,39-,40+,42+,43-/m1/s1

InChI Key

OCSCUKHGZXPCFA-BQRCDTPTSA-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
Eschenbachia blinii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Wax monoesters

Alternative Parents

Substituents

Wax monoester skeleton
Labdane diterpenoid
Diterpenoid
Long chain fatty alcohol
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Beta-hydroxy acid
Hydroxy acid
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	7.08	ALOGPS
logP	8.35	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	206.49 m³·mol⁻¹	ChemAxon
Polarizability	89.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10232859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21602022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate (NP0167972)

MOL for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

3D MOL for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

3D SDF for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

3D-SDF for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

PDB for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

3D PDB for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

SMILES for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

INCHI for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

Structure for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)

3D Structure for NP0167972 ((2z)-3-{2-[(1r,2r,4as,8as)-2,5,5,8a-tetramethyl-2-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}-hexahydro-1h-naphthalen-1-yl]ethyl}-4-hydroxybut-2-en-1-yl (3r)-3-hydroxyoctadecanoate)