NP-MRD: Showing NP-Card for 9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate (NP0189442)

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Record Information

Version

2.0

Created at

2022-09-04 05:55:24 UTC

Updated at

2022-09-04 05:55:25 UTC

NP-MRD ID

NP0189442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate

Description

8-(Acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]Octadecan-9-yl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate is found in Jungermannia exsertifolia. 8-(Acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]Octadecan-9-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508522D          

 54 62  0  0  0  0            999 V2000
   -0.0723    0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950    0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    0.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681    1.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326    1.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245    1.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9822    0.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292    0.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2661    0.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1884    0.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186    1.7861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391    2.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    3.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328    2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116    0.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756   -0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9164   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763   -1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8108   -1.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932   -0.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270   -1.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1389   -2.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -1.6529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590   -1.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -2.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943   -2.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -3.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6090   -3.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8936   -3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277   -4.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978   -3.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3202   -2.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -3.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -2.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3310   -1.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6220   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978   -1.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086   -2.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -2.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383   -2.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -4.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9230   -5.2787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780   -4.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7360   -5.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435   -0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642    0.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3290   -0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321   -1.4704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336    1.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4859    1.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9001    2.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8967    0.6696    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 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
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 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  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 26 42  1  0  0  0  0
 30 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 28 45  1  0  0  0  0
 45 46  2  0  0  0  0
 24 47  1  0  0  0  0
  7 47  1  0  0  0  0
 47 48  1  0  0  0  0
  3 48  1  0  0  0  0
 47 49  1  0  0  0  0
  2 49  1  0  0  0  0
 49 50  2  0  0  0  0
 15 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
M  END

     RDKit          3D

116124  0  0  0  0  0  0  0  0999 V2000
    1.8356   -2.2302   -4.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367   -1.5578   -3.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0121   -0.7911   -2.0644 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3118   -1.3222   -1.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0203   -0.1828    0.4365 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5244   -0.0028    1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0568   -0.0189    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -1.0986    2.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1780    1.3300    2.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3007    2.0549    1.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374    1.1100    1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5166   -0.0380    0.2773 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7877   -1.2730    0.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762    0.1455   -1.1942 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8568    0.1844   -1.6423 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0233    0.9952   -0.8982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1413    0.4181   -0.4585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0506    0.2611    0.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307   -0.6977    1.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6077   -1.1497    3.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4750    1.9771   -2.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2886    2.7954   -2.2776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0981    1.8051   -2.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788    1.1550   -0.8789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5001    2.4424   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8498    2.9282    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8601    0.7063    2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
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 44104  1  0
M  END


  Mrv1533004161508522D          

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M  END
> <DATABASE_ID>
NP0189442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC3(C(OC4CC5CC6(CCC7C(C)(C)CCCC7(C)C46)C(=O)C5=C)OC(O)C4C(C)(C)CC(OC(C)=O)C(OC(C)=O)C4(C)C33OC3C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H62O10/c1-21-25-16-27(31-40(9)14-11-13-38(5,6)29(40)12-15-42(31,18-25)33(21)47)52-37-43-19-26(22(2)34(43)48)17-30-44(43,54-30)41(10)32(36(49)53-37)39(7,8)20-28(50-23(3)45)35(41)51-24(4)46/h22,25-32,35-37,49H,1,11-20H2,2-10H3

> <INCHI_KEY>
HJZKIIZGWSZZFE-UHFFFAOYSA-N

> <FORMULA>
C44H62O10

> <MOLECULAR_WEIGHT>
750.97

> <EXACT_MASS>
750.434298196

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
81.82090061177006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-9-yl acetate

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
6.669274362666665

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.83609787374103

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.0788991178514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8538013937401545

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
195.50080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.75e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.135   0.494   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.484   0.245   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.591   1.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.674   2.548   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.101   2.109   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.952   1.937   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.567   0.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.961   0.097   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.097   1.604   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.818   1.376   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.501   3.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.913   4.968   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.808   6.040   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.394   5.388   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.355   1.274   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.034  -0.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.177  -1.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.596  -2.246   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.980  -3.095   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.641  -1.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.957  -2.677   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.726  -4.169   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.477  -3.085   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.217  -2.175   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.636  -2.788   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.789  -4.428   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.283  -5.108   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.385  -6.724   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.004  -6.793   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.668  -7.005   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.238  -7.706   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.116  -6.938   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.121  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.464  -4.637   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.972  -6.091   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.984  -4.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.485  -3.097   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.161  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.183  -3.062   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.203  -4.602   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.526  -3.814   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.565  -5.362   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.445  -8.493   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       1.723  -9.854   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.066  -8.308   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.107  -9.442   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.188  -0.681   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.480   0.097   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.481  -1.030   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       1.553  -2.745   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      10.516   2.589   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.107   2.586   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      12.880   3.917   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      12.874   1.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   49                                                  
CONECT    3    2    4   48                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8   47                                             
CONECT    8    7    9   10   20                                             
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   51                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17    8   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   47                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   42                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   45                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   42   43                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   26   30                                                  
CONECT   43   30   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   28   46                                                  
CONECT   46   45                                                            
CONECT   47   24    7   48   49                                             
CONECT   48   47    3                                                       
CONECT   49   47    2   50                                                  
CONECT   50   49                                                            
CONECT   51   15   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  124    0
END

View in JSmol

Synonyms

Value	Source
8-(Acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0,.0,]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0,.0,.0,]octadecan-9-yl acetic acid	Generator
8-(Acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-9-yl acetic acid	Generator

Chemical Formula

C₄₄H₆₂O₁₀

Average Mass

750.9700 Da

Monoisotopic Mass

750.43430 Da

IUPAC Name

8-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-9-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2CC3(C(OC4CC5CC6(CCC7C(C)(C)CCCC7(C)C46)C(=O)C5=C)OC(O)C4C(C)(C)CC(OC(C)=O)C(OC(C)=O)C4(C)C33OC3C2)C1=O

InChI Identifier

InChI=1S/C44H62O10/c1-21-25-16-27(31-40(9)14-11-13-38(5,6)29(40)12-15-42(31,18-25)33(21)47)52-37-43-19-26(22(2)34(43)48)17-30-44(43,54-30)41(10)32(36(49)53-37)39(7,8)20-28(50-23(3)45)35(41)51-24(4)46/h22,25-32,35-37,49H,1,11-20H2,2-10H3

InChI Key

HJZKIIZGWSZZFE-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

Species Name	Source	Reference
Jungermannia exsertifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Oxepane
Dicarboxylic acid or derivatives
Carboxylic acid ester
Hemiacetal
Ketone
Ether
Oxirane
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	4.3	ALOGPS
logP	6.67	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	195.5 m³·mol⁻¹	ChemAxon
Polarizability	81.82 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

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

73999139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate (NP0189442)

MOL for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

3D MOL for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

3D SDF for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

3D-SDF for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

PDB for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

3D PDB for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

SMILES for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

INCHI for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

Structure for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)

3D Structure for NP0189442 (9-(acetyloxy)-4-hydroxy-6,6,10,16-tetramethyl-17-oxo-2-({5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl}oxy)-3,12-dioxapentacyclo[13.2.1.0¹,¹¹.0⁵,¹⁰.0¹¹,¹³]octadecan-8-yl acetate)