NP-MRD: Showing NP-Card for (1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate (NP0255727)

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Record Information

Version

2.0

Created at

2022-09-07 20:18:46 UTC

Updated at

2022-09-07 20:18:46 UTC

NP-MRD ID

NP0255727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate

Description

(1R,3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,23S,25R)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate is found in Pimelea linifolia. Based on a literature review very few articles have been published on (1R,3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,23S,25R)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072222182D          

 49 56  0  0  1  0            999 V2000
    1.4156   -0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -1.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071   -2.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596   -1.2279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6513   -2.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0021   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -1.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388   -1.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1327   -0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252    0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9649    1.2504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6334    0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    1.4711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0826    2.2503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5376    2.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150    2.2019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9822    3.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219    3.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1426    4.2490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    4.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4294    5.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278    5.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8189    5.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    4.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131    4.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    1.3978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7785    1.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345    1.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7314    1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172    0.3239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1398    0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9501    0.0757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141   -0.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7893   -0.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9425   -0.4915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5590   -1.2692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5689   -1.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739    0.0657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5357    0.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.5183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2198   -0.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464    0.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    0.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    0.9329    0.0000 C   0  0  2  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  6  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  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 37 36  1  1  0  0  0
 33 37  1  0  0  0  0
 38 37  1  1  0  0  0
 38 39  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  1  0  0  0
  6 40  1  1  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  4 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 41 48  1  1  0  0  0
  6 48  1  0  0  0  0
 41 49  1  0  0  0  0
 49 16  1  6  0  0  0
 29 49  1  0  0  0  0
M  END


  Mrv1652309072222182D          

 49 56  0  0  1  0            999 V2000
    1.4156   -0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -1.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071   -2.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596   -1.2279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6513   -2.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261   -1.3825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0021   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342   -1.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388   -1.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1327   -0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252    0.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    1.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9649    1.2504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6334    0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    1.4711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0826    2.2503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5376    2.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150    2.2019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9822    3.0656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219    3.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1426    4.2490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    4.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4294    5.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278    5.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8189    5.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    4.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131    4.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    1.3978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7785    1.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345    1.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7314    1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172    0.3239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1398    0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9501    0.0757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6141   -0.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7893   -0.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9425   -0.4915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5590   -1.2692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5689   -1.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3739    0.0657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5357    0.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0820   -0.5183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2198   -0.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464    0.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    0.8803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.4982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    0.9329    0.0000 C   0  0  2  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  6  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  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 37 36  1  1  0  0  0
 33 37  1  0  0  0  0
 38 37  1  1  0  0  0
 38 39  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  1  0  0  0
  6 40  1  1  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
  4 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 41 48  1  1  0  0  0
  6 48  1  0  0  0  0
 41 49  1  0  0  0  0
 49 16  1  6  0  0  0
 29 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255727

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)[C@H]3[C@H]1[C@H](C)CCCCCCC[C@@]14O[C@@H]5[C@H]([C@@H]6O[C@]6(CO)[C@H]2O)[C@@]3(C[C@@H](OC(C)=O)[C@@]5(O1)C(C)=C)O4

> <INCHI_IDENTIFIER>
InChI=1S/C38H50O11/c1-20(2)38-25(44-23(5)40)18-34-27-30-35(19-39,46-30)33(42)37(43)28(34)26(22(4)29(37)45-32(41)24-15-11-9-12-16-24)21(3)14-10-7-6-8-13-17-36(48-34,49-38)47-31(27)38/h9,11-12,15-16,21-22,25-31,33,39,42-43H,1,6-8,10,13-14,17-19H2,2-5H3/t21-,22+,25-,26+,27+,28+,29+,30+,31-,33-,34-,35+,36+,37-,38+/m1/s1

> <INCHI_KEY>
HSGSKBLDWJUNKU-YMCXTYKYSA-N

> <FORMULA>
C38H50O11

> <MOLECULAR_WEIGHT>
682.807

> <EXACT_MASS>
682.33531243

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
71.90441936318551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,23S,25R)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1^{4,23}.1^{5,23}.0^{1,6}.0^{7,9}.0^{11,25}]heptacosan-12-yl benzoate

> <JCHEM_LOGP>
4.636891961000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.576038364764258

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.289586104542687

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1494108817880546

> <JCHEM_POLAR_SURFACE_AREA>
153.51000000000002

> <JCHEM_REFRACTIVITY>
172.878

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,23S,25R)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1^{4,23}.1^{5,23}.0^{1,6}.0^{7,9}.0^{11,25}]heptacosan-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.642  -1.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.926  -3.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.066  -5.023   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.591  -2.292   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.949  -4.029   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.275  -2.581   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.737  -3.296   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.304  -2.671   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.819  -3.093   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.248  -1.646   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.838  -0.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.980   1.350   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.112   2.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.668   2.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.916   1.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.199   2.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.754   4.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.737   5.453   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.308   4.110   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.433   5.722   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.321   7.319   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.866   7.931   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.628   8.252   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.268   9.749   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.385  10.810   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.862  10.372   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.222   8.875   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.105   7.815   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.735   2.609   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.920   3.690   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.211   2.067   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.699   2.722   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.739   0.605   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.461   0.753   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.974   0.141   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.480  -0.745   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.940  -0.712   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.359  -0.917   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.643  -2.369   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.662  -3.559   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.298   0.123   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.733   0.324   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.886  -0.968   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.277  -0.712   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.207   0.532   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.545   0.630   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       2.415   1.643   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       5.193  -0.930   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.425   1.741   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   39   43                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   40   48                                             
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   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   49                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   19   30   31   49                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   36   37                                             
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37                                                       
CONECT   37   36   33   38                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38    4   40                                                  
CONECT   40   39    6                                                       
CONECT   41   38   42   48   49                                             
CONECT   42   41   43                                                       
CONECT   43   42    4   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   41    6                                                       
CONECT   49   41   16   29                                                  
MASTER        0    0    0    0    0    0    0    0   49    0  112    0
END

View in JSmol

Synonyms

Value	Source
(1R,3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,23S,25R)-3-(Acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1,.1,.0,.0,.0,]heptacosan-12-yl benzoic acid	Generator

Chemical Formula

C₃₈H₅₀O₁₁

Average Mass

682.8070 Da

Monoisotopic Mass

682.33531 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)[C@H]3[C@H]1[C@H](C)CCCCCCC[C@@]14O[C@@H]5[C@H]([C@@H]6O[C@]6(CO)[C@H]2O)[C@@]3(C[C@@H](OC(C)=O)[C@@]5(O1)C(C)=C)O4

InChI Identifier

InChI=1S/C38H50O11/c1-20(2)38-25(44-23(5)40)18-34-27-30-35(19-39,46-30)33(42)37(43)28(34)26(22(4)29(37)45-32(41)24-15-11-9-12-16-24)21(3)14-10-7-6-8-13-17-36(48-34,49-38)47-31(27)38/h9,11-12,15-16,21-22,25-31,33,39,42-43H,1,6-8,10,13-14,17-19H2,2-5H3/t21-,22+,25-,26+,27+,28+,29+,30+,31-,33-,34-,35+,36+,37-,38+/m1/s1

InChI Key

HSGSKBLDWJUNKU-YMCXTYKYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pimelea linifolia	LOTUS Database	35616633

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
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1,3-dioxepane
Ortho ester
Carboxylic acid orthoester
Dioxepane
Benzenoid
Monocyclic benzene moiety
Meta-dioxane
Dicarboxylic acid or derivatives
Tertiary alcohol
Meta-dioxolane
Cyclic alcohol
Secondary alcohol
Orthocarboxylic acid derivative
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Primary alcohol
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	4.64	ChemAxon
pKa (Strongest Acidic)	12.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	172.88 m³·mol⁻¹	ChemAxon
Polarizability	71.9 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163036382

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate (NP0255727)

MOL for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

3D MOL for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

3D SDF for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

3D-SDF for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

PDB for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

3D PDB for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

SMILES for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

INCHI for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

Structure for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)

3D Structure for NP0255727 ((1r,3r,4s,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,23s,25r)-3-(acetyloxy)-10,11-dihydroxy-9-(hydroxymethyl)-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-12-yl benzoate)